Home Vacation Rentals By Owner In Holmes Beach, FL

Showing 300 Of 1242 Vacation Rentals
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$623.77

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Private Vacation Home

One Of The Most Unique Homes in Anna Maria Island

Holmes Beach, Florida, United States

Property SummarybrbrProperty Ref: AMI_5002R | Happy Place | 5601 Flotilla Dr, Holmes Beach, Fl *Minimum of 30 Nights Requiredbrbr*This 5 bed home (5002) is also listed as a 6 bed option with an adjoining in-law suite (5000).brbrHighlightsbrbrBacks onto canalbrHuge 0.5 acre lotbr7-minute walk to the beachbrClose to restaurants and grocery storesbrbrWelcome to Happy Place, a ground level 4 bedroom 3.5 bathroom recently updated home with 75 ft of canal. frontage. Located just 0.4 miles from the white sandy beaches of the Gulf of Mexico. surrounded by tropical landscaping. This home has all the essentials for a fabulous vacation. There is a fully equipped kitchen with stainless steel appliances. There is a bistro table set for two guests. After a long day of fun at the beach and watch your favorite show on the large flat screen TV and fall asleep to the sound of the nearby palm trees swaying. The bedroom has a smart TV and King bed with Tuft & Needle mattress, the bathroom has a walk-in shower.brbrOverlooking the dock is the second story boat house bar along with a seating area overlooking the pool where you can relax with a book whilst you see the sun go down in the distance.brbrMany rooms open out to the beautiful pool area with large 24' x 32' deep pool. The boat house is one feature that makes this home so unique.brbrNestled on the fringe of the deep water canal. Nearly 4,500 sq.ft the home surrounds pool &,soothing waterfall, The kitchen offers an oven, dishwasher, two 48 cubic ft. refrigerators, double oven, 3 x beverage fridges.brbrThe exceptionally over-sized master suite makes a bold statement at approx.1600 sq.ft. with large closet, sitting area, laundry & master en-suite with a 5'x9' walk-in shower & tub.brbrSet on a large corner lot with lush foliage, circular paver drive & quintessential curbside appeal; home is only 7 houses out of the canal to Tampa Bay!brbrStroll to the beach each evening to watch the amazing Anna Maria Island sunsets.brbrEverything you could want is in close proximity, including the beach, restaurants, and shopping centers, and up the street is an Anna Maria Island trolley stop that can take you and your guests anywhere you like on this coastal 7-mile island.brbrHolmes Beach, nestled on Anna Maria Island in Florida, is a charming coastal destination that perfectly balances natural beauty and a laid-back vibe. Known for its pristine white-sand beaches and crystal-clear waters, it offers visitors a serene escape from the hustle of everyday life. Holmes Beach stretches along the central part of the island, making it an ideal spot to enjoy the tranquil Gulf of Mexico.brbrThe beach itself is a paradise for relaxation and recreation, with plenty of opportunities for swimming, sunbathing, and shell collecting. Its gentle waves and family-friendly atmosphere make it an excellent choice for visitors of all ages. Beyond the beach, the area boasts a selection of quaint shops, locally-owned restaurants, and casual beach bars that highlight the island's laid-back charm. Whether you're savoring fresh seafood, biking along the scenic pathways, or catching a breathtaking sunset over the Gulf, Holmes Beach provides an idyllic setting for a quintessential Florida getaway.brbrOne of the best features of this home is the location, you can walk to restaurants such as The Ugly Grouper, The Chateau, Isola Bella Italian Eatery, Breakfast At Victoria's, Minnie's Beach Cafe, Pizzano's Pizza, AMI Mediterranean Express and more such as Blueberries Cafe, Anna Maria Island Coffee Shack, Scott's Deli and Small Town Creamer Ice Cream store.brbrYou can also walk to bars such as The Doctors Offce, The Feckled Fin, D'Coy Ducks, Duffy's Tavern, Fifty Three Fifty The Pourhouse & Hurricane Hanks. You can also walk to AMI Health & Fitness Gym, the soccer field, playground, pickle ball and tennis courts, skate park and public boat ramp.brbrThere is a free shuttle and the Monkey Bus if you would like to check out bars and restaurant's outside of Holmes Beach.brbrProperty SummarybrbrGeneralbrbrComplimentary high-speed wireless internetbrSmoke-free and pet-free for your comfortbrTowels and linens are providedbrFully equipped kitchenbrKeyless entrybrbrLiving Area/KitchenbrbrSmart TVbrSofabrDeskbrbrBedroom/Bed SizesbrbrBedroom 1 - King + Full/Full (bunk)brBedroom 2 - KingbrBedroom 3 - KingbrBedroom 4 - Full/Full (bunk)brBedroom 5 - Queen/Twin (bunk) (Bonus suite, separate access from pool area)brbrPool AreabrbrTable with seatingbrScreen enclosurebrJacuzzi Hot TubbrbrWhy book this rental brProfessionally managed to offer you superior, personalized service.brNo hassle with key pick-up! Drive straight to your vacation rental!brDetailed guest information guide provided within each property.brbrTerms And Conditions:brCity of Holmes Beach Vacation Rental License: VRC25-000018brMax Occupancy: 10 Guests | Max Vehicles: 5brMinimum of one month (30 days) rental.brThe boat lift has a boat on and is not for guest use.brThis property is managed by Florida Vacation Homes, a vacation rental management company.brQuiet Hours: 10 p.m. - 7 a.m. - please Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.brThis home does not provide access to a garage.brCheck-in time is 4:00 pmbrCheck-out time is 10:00 ambrAll properties are non-smoking and no pets are allowedbrTax is not included in nightly ratesbrThere is a one-time departure cleaning fee for all staysbrA Limited Damage Protection (LDP) fee will be required to cover any reported accidental damage to this property and its contentsbrMid stay leaning service is NOT included but please ask for a quotebrFinal payment due 45 days prior to your arrivalbrTravel insurance is highly recommended if making a reservation for dates in hurricane season (Jun 1st to Nov 30th).brRed Tide - Please stay informed about red tide to ensure a safe and enjoyable stay on Anna Maria Island. What It Is: Red tide refers to algal blooms that can produce toxins affecting marine life and may cause respiratory irritation in humans. Occurrence: While red tide is a natural phenomenon in Florida's Gulf Coast, its presence and intensity can vary. Guests are advised to avoid swimming in affected waters, especially if they have respiratory conditions. It's also recommended to stay indoors if experiencing irritation.brThe guest making the reservation must be 25 years of age or older. Persons under 25 to are not allowed to occupy a property unless accompanied by someone over 25 years of age.brBookings made within 30 days of the arrival date must verify ID before the access information is released. The credit/debit card used for payment must be shown along with a valid driving license or passport in the same name as the card. As well as a utility bill with the same address as the card billing address. Pre-Paid cards are not accepted. If an alternative payment method cannot be used the booking will be canceled.brPlease note it is not permitted to host parties or group events such as weddings in this vacation home.brThis property has exterior security cameras.brThe enclosed pool area is not indoors, there is a screen above so the pool deck area can get dusty and require occasional sweeping or hosing down.brA rental agreement must be signed by the lead guest making the reservation, along with a full list of guest names that will be staying in the propertybrWe use a third party to verify identification and fraud risk, based on the findings we could cancel the reservation.brDriveway has on-site parking for a maximum of 5 cars
Bed 5

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Bath 4

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Sleep 10

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Exceptional(15)

$368.27

/ Nightly
Private Vacation Home

Home with heated pool, spa, games, walk to beach

Holmes Beach, Florida, United States

Escape to this modern 2BR/2BA beachside retreat on Anna Maria Island. Enjoy a sunlit open-concept living area with coastal décor and a fully equipped kitchen with stainless appliances. After a day in the sun, relax in two tranquil bedrooms, including a master suite. A dedicated workspace keeps you connected, and families will love the convenience of an in-unit washer and dryer plus a high chair for little ones.brRental Certificate: VRC22-000002brbrDiscover your personal slice of paradise at this modern 2-bedroom, 2-bathroom beachside retreat. Step into a sunlit, open-concept living space where coastal chic design meets modern comfort, creating a bright and welcoming atmosphere for your stay.brbrKey Features:br **Fully Equipped Kitchen: The stylish kitchen features stainless steel appliances, perfect for preparing everything from quick beach snacks to full family dinners.brbr **Comfortable Bedrooms: Unwind in one of two tranquil bedrooms, including a master suite, providing flexible and restful sleeping arrangements.brbr **Dedicated Workspace: Need to stay productive A dedicated workspace provides a quiet spot to connect and focus.brbr **Convenience: The home includes an in-unit, full-size washer and dryer.brbr **Family-Friendly: A high chair is available for our youngest guests.brbrYour private getaway includes full access to the entire home and a variety of amenities designed for relaxation and fun. Two Parking spaces are also available for guest use directly under the unit.brbrYou will have access to:br* The entire 2-bedroom, 2-bathroom private home.brbr* A private patio complete with comfortable outdoor seating and a BBQ grill for evening cookouts.brbr* A shared community pool and a bubbling hot tub, located just steps from your door.brbr* Beach essentials, including a wagon, towels, chairs, umbrellas, and sand toys.brbr* A convenient outdoor shower to rinse off after a day at the beach.brbr* A complimentary EV charger to keep your vehicle ready for island adventures.brbrWe respect our guests` privacy and aim to provide a seamless, independent stay. We will not be on the property during your visit but are readily available via phone or the messaging app should you need any assistance or have questions.brbr**Welcome to the Tranquil Holmes Beach Neighborhood on Anna Maria Island!**brbrOur charming Airbnb is nestled in the heart of Holmes Beach, a serene and picturesque neighborhood on the beautiful Anna Maria Island. With its laid-back atmosphere and pristine beaches, this coastal haven promises a truly unforgettable vacation experience.brbr**The Neighborhood:**brHolmes Beach exudes a classic beach town vibe, offering a perfect blend of relaxation and local charm. You`ll find friendly locals, quaint shops, and delightful restaurants within walking distance, making it easy to immerse yourself in the island`s warm hospitality and vibrant culture.brbr**Holmes Beach:**brJust steps away from our Airbnb, you`ll discover the breathtaking Holmes Beach. Sink your toes into the soft, white sand and relish the gentle Gulf breeze as you bask in the sun or take leisurely strolls along the shoreline. The crystal-clear waters beckon you to swim, paddleboard, or simply unwind in the tranquility of the island paradise.brbr**Local Attractions:**brBeyond the beach, you`ll find a plethora of activities to enjoy. Rent a bike or a golf cart to explore the island`s hidden gems, including the historic Anna Maria City Pier and the iconic Bean Point Beach. For the nature enthusiasts, visit the Leffis Key Preserve or the Robinson Preserve to experience the island`s lush wildlife and scenic trails.brbr**Dining and Shopping:**brSavor the island`s flavors by indulging in fresh seafood at local restaurants, or treat yourself to some delectable ice cream as you explore the charming shops along the way. You`ll find everything you need within reach to ensure a comfortable and enjoyable stay.brbr**Unwind in our Cozy Airbnb:**brOur inviting Airbnb offers a cozy retreat after a day of island adventures. Relax on the private patio, take a refreshing dip in the pool, or simply unwind in the comfortable living space. With [number of bedrooms] charming bedrooms and [number of bathrooms] luxurious bathrooms, our home provides all the comforts you need for a memorable stay.brbr**Book Your Island Getaway:**brEscape to our serene Holmes Beach neighborhood on Anna Maria Island and experience the magic of a true beachside escape. Whether you`re seeking relaxation, exploration, or a bit of both, our Airbnb promises an exceptional stay in this tropical paradise. Reserve your dates now and let the island adventure begin!brbrYou can get around using the free trolley (runs every 20 minutes), golf carts, bikes, walking or car! The island is 7 miles long and this unit is right in the center of it! There are two trolley stops (one on either side of the street).brbr**Starter Supplies:** We provide a starter kit of amenities (shampoo, soap, toilet paper, etc.) to get you settled in for your first few days. For longer stays, you may wish to pick up additional supplies for the remainder of your visit.brbr** Also provided at no cost: wagon, beach chairs, beach towels, umbrellas, sand toys.brbr**Rental Certificate:** City of Holmes Beach Vacation Rental Certificate: VRC22-000002brNo parties. No pets of any kind allowed on premises. Any additional visitors must be disclosed prior to arrival as there are strict occupancy rules on AMI which must be adhered to. br===========================================================================================================================================================================brSEO Keywords (for search indexing only – guests may ignore):brAnna Maria Island, AMI, Holmes Beach, luxury rental, heated pool, pool home, walk to beach, steps to beach, Gulf of Mexico, beach getaway, waterfront oasis, sunrise views, dolphin watching, outdoor dining, boutique shopping, Pine Avenue, Bean Point, Sandbar Restaurant, island restaurants, waterfront dining, beach vacation, family-friendly rental, couples retreat, romantic getaway, girls trip, sports fishing, snorkeling, clear blue water, white sand, tropical escape, coastal chic, modern coastal, full kitchen, smart TVs, fast Wi-Fi, work from beach, remote work friendly, private backyard, outdoor grilling, poolside lounging, resort alternative, upscale Airbnb, VRBO rental, weekly rental, Florida vacation rental, luxury stay, heated pool year-round, private patio, golf cart friendly, beach cruiser bikes, kid friendly, quiet neighborhood, walkable location, boat-friendly, bay access, paradise rental, waterfront views, vacation home, island retreat, AMI rental, Tampa Bay area, Sarasota getaway.
Bath 2

Bath

Sleep 6

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Exceptional(38)

$797.78

/ Nightly
Private Vacation Home

Spectacular BEACH to BAY VIEWS ELEVATOR PRIVATE HEATED POOL

Holmes Beach, Florida, United States

NO CAR NEEDED! TWO MASTER SUITES! Modern home within walking distance to Beach, Bay, Historic Bridge Street, pier, restaurants, shops, ice cream, mini golf, fishing, water sports, this location has it all! You will absolutely love the convenience here! Enjoy our beautiful beaches, watch sunsets and sunrises from your balconies or enjoying the heated pool. We are the second house from the beach 50 yards and your toes will be in the sand. Clean quiet street but close enough to walk anywhere.brThe spacebrThe house is a 4-bedroom, 3.5 bath with 2 master bedroom suites each having a private full bathroom, double sinks, granite counters, tiled walk in shower with glass doors, and walk in closet. Third bedroom has 2 single beds and shared bathroom with the fourth bedroom that has bunk beds. Jack & Jill bathroom also has double sinks, granite counters, tub/shower combination, beautiful tile with that beachy feel.brOur unit is spacious, clean, bright with an open concept. The kitchen has granite counters, beautiful cabinetry, and supplies for all your cooking needs. Full size refrigerator, flat top stove, microwave, K cup coffee maker. The living room has plenty of seating, flat screen TV and a queen pullout sofa bed. The walk-out balcony off living room has beach and bay views. Elevator to all floors, 2 car garage, private washer and dryer in the unit. The PRIVATE pool is heated with full covered patio, table, chairs, gas grill, flat screen TV. Ping Pong Table brWe supply all linens, bath towels, 1 roll of toilet paper per bathroom, 10 beach chairs, 10 beach towels. Pack and Play booster seat brWe also own the adjoining house that has the same floor plan and is also available to rent. Double your space for the family get together's .brCome and enjoy our house and see what our area has to offer. Gulf breezes and salt air are awaiting... thanks for looking at our happy place.
Bed 5

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Bath 3

Bath

Sleep 10

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Exceptional(2)

$1253.01

/ Nightly
Private Vacation Home

Grains of Sand by Beach Boutique Rentals

Holmes Beach, Florida, United States

Grains of Sand is a stunning custom home located directly across from the beautiful Gulf of Mexico. This home boasts almost 3000 square feet of living space making it the perfect choice for a large family vacation. brbr*Features include* brbr* Amazing almost Gulf front location br* Heated saltwater pool with waterfall featurebr* Pool Chiller for the hot summer monthsbr* Rooftop deck with sweeping water views br* 4 king bedrooms each w/ ensuite bathbr* Bonus room w/ twin trundle beds br* Indoor/outdoor living on all 3 levels br* Elevatorbr* Patio dining for 6, plus lounge area br* Outdoor TV, refrigerator, bar and ping pongbr* Beach chairs, umbrella, and cart br* Home gymbr* Across the street from the beach!brbrPrepare yourself to be amazed by the ultimate splendor that awaits you at Grains of Sand. As you walk through the door and head upstairs you will arrive in the grand living and dining space. The ultra modern, yet warm and welcoming living room is sure to please all the senses with multiple doors opening to the outdoor deck and balcony. This home is just steps from the gulf and you can see the gulf and beautiful sunsets from the balconies and rooftop. brbrThe kitchen features state of the art appliances and a huge island with breakfast bar seating. Your seating options also include the large, custom dining table with plenty of room for eight or more. Enjoy the marvelous sunsets with a cocktail in hand on the balcony overlooking Gulf Drive. The side deck also includes a cozy pub table for two.brbrBack inside and down the hall of this main level you will find two king master bedroom suites. Each bedroom offers TV and beautiful custom tile showers. A convenient half bathroom and full laundry facilities complete this level.brbrAt the top of the stairs - or an elevator^ ride up - on the third floor you will find the super fun bonus room. This spacious loft makes a great place to hang out or can even function as a 5th bedroom. There are two twin beds with trundles and cable TV. Kids will love the funky surf vibe! This area has yet another balcony with relaxing Adirondack chairs and full views of sunset and the beautiful Gulf waters.brbrThrough the sliding barn door you will enter another king master suite with access to the balcony. This bedroom features a huge ensuite master bathroom with double vanity, deep soaking tub and serene spa shower.brbrDown the hall and to the right takes you to the fourth king master suite. This room also has TV and the bathroom offers a tub/shower combo. Through the door outside you will see the spiral staircase which leads you up to the expansive roof deck. The deck offers sun loungers, Adirondack chairs and astounding sweeping views of the gulf from left to right!brbrThis home includes everything a family needs to pack light. The kitchen is stocked full of cookware and bakeware. The garage includes a double BOB stroller, puddle jumpers, life jackets, a portable cooler, tons of pool and beach toys and rafts, skim boards, boogie boards, a paddle board, and a heavy duty huge wagon to take everything you need with ease to and from the beach, which is just steps away!brbrLast but not least, this amazing home would not be complete without the private heated pool and spa. The pool patio includes an outdoor fridge so you can easily grab your favorite drinks while you lounge by the pool or play ping pong or backgammon. Colored LED lights will make your evening sparkle. Relax in the jetted hot tub/spa, grill a delicious meal or enjoy a game of ping pong in the covered lounge area. There is also an outdoor TV and bar for your entertainment. brbrBest of all is the gorgeous turquoise waters of the Gulf right outside your door. Simply cross the street and you are there, on the wide white sand beach, Grains of Sand is pure paradise.brbr^Please note that at the current time the elevator is out of service. Stairs are required to access the main living areas of the home.brbrPET POLICY:brbrWe are DOG FRIENDLY! A fee of $150 + tax is required in advance for each dog you are bringing.brbr2 pets maximum unless granted an exception. Weight limit of 75 lbs total for 1 pet or 120 lbs for 2 pets.brbrDue to property insurance policies and liability concerns NO dangerous breeds or aggressive animals are allowed. The following breeds (purebred or crossbred) are not permitted:brbrPit Bull, Akita, Rottweiler, German Shepherd, Siberian Husky, Malamute, Doberman Pinscher, Chows, Any Wolf-dog hybrid, Any other dog that has been known to have bitten anyonebrbrADDITIONAL INFORMATIONbrbrWe generally require a minimum stay during the high season. We are more flexible in the off season so please send us a message if your dates appear unavailable. We may be able to accommodate you!brbrHousekeeping will provide a starter supply of toilet paper, soap, and garbage bags but guests will likely need to replenish the supply during their stay.brbrOur cleaning fee includes a professional linen service. When you stay with us you can rest assured that you will have high quality linens such as those at a fine hotel. We also provide plenty of luxury bath and beach towels. brbrAnna Maria Island is a family community and the city imposes a strict noise ordinance. Please adhere to our good neighbor policy and observe the local quiet hours between 10 pm and 8 am. No loud music or use of the pool is allowed during these hours along with any other noise which may disturb the neighbors. brbrVRC20-000010brbrThis home provides off-street parking for up to 4 vehicles.brbrBooking Platform Note:brFor VRBO bookings, the reservation payment is processed by Beach Boutique Rentals and will appear as Beach Boutique Rentals on your credit card statement. VRBO also charges a separate service fee directly to the guest as a separate transaction.
Bed 4

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Bath 4

Bath

Sleep 8

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Exceptional(33)

$352.22

/ Nightly
Private Vacation Home

Summer Wind- An island getaway in the perfect location.

Holmes Beach, Florida, United States

Experience all the best elements of the perfect Island vacation in this well-appointed rental home. It is located just a short walk to the beach where you can enjoy Anna Maria Island's famous white sand, swim in the Gulf of Mexico and take in a technicolor sunset. brbrThe home's backyard is the perfect place to socialize. There is an outdoor wet bar, lounge area and BBQ grill. The heated pool features a sun shelf - perfect for sunbathing. If you'd rather overlook the action, there are front and rear balconies that round out the outdoor spaces. brbrThe home's interior is spacious with four bedrooms and two and a half baths, accommodating eight. The second floor has an open living and dining space with a large table for eight. Two of the bedrooms are on this floor. The large master suite and fourth bedroom are located on the third floor. brbrThis home offers all the components for a fun vacation with family or friends. And with its central Holmes Beach location, the home is the perfect place to enjoy Anna Maria Island and make memories that last a lifetime.brbrFloor 1 (ground)brOutdoor kitchen and lounge area with TVbrHeated pool brbrFloor 2 (main living level)brBedroom 1: Queen with TVbrBedroom 2: Two twin beds, one with trundle, and TV (3 twins total)brShared hallway bathroom with shower/tub combobrbrFloor 3brBedroom 3: King Mater with TV, private balcony, and ensuite bathroom with walk-in shower and soaking tubbrBedroom 4: Queen with TV and ensuite half bathbrbr***OVERCROWDING CONSEQUENCES***brMaximum occupancy of rental homes on Anna Maria Island are set by the Cities and are strictly enforced. An occupant is any person staying overnight, regardless of the number of nights. Due to recent issues of overcrowding in the area, if maximum occupancy is exceeded during your stay, a $1000 (one thousand dollar) overcrowding fee will be charged to the payment method on file and your party will be immediately evicted. We appreciate your understanding and cooperation to keep Anna Maria Island enjoyable for everyone.brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.brbr*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.brbrVRC19-000059
Bed 4

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Bath 2

Bath

Sleep 10

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Exceptional(56)

$244.11

/ Nightly
Private Vacation Home

Island Vibe 5: Close to Beach with Private Heated Pool

Holmes Beach, Florida, United States

Welcome to Island Vibe 5! This is a newly renovated 2-bedroom, 2-bathroom home with private, heated and cooled pool, tropical landscaping and a private back yard.brbr** If you're visiting AMI with another group, consider renting with attached duplex Island Vibe 6 (VRBO# 1930033) for a total of 4 bedrooms!brbrLocated on 63rd Street in Holmes Beach, this lovely property is convenient to the beach and in a very quiet Holmes Beach residential neighborhood. It has one shared wall with the unit next door. From here, it is just a short walk to the many shops and restaurants in downtown Holmes Beach, as well as the Island’s only dog park. It's mere steps from the northbound Anna Maria Island Trolley!brbrThis beautiful property will sleep 6 people with 1 King bed, 2 Twin beds that can convert to a second king, and 1 Queen sized sleeper sofa in the living room. You can park up to 2 cars in the driveway.brbrIn the backyard, you'll find a large open deck and a covered, shaded area overlooking the pool. There are solar lights and a pool light for enjoying the outdoors during those great Florida evenings.brbrYou'll never miss a moment of your favorite sporting event! We have a 55 television in the living room with a DVD player, a 50 television in the master bedroom, a 43 television in the second bedroom, AND even a 50 television on the outdoor patio!brbrConvenience for our guests is a priority for us! All of the TVs are smart TVs and have streaming television with the Spectrum App. A washer and dryer, wireless internet, cable television and free domestic long distance calling are all included! Additionally, if you're traveling with little ones or pets, we gladly provide an array of convenient items upon request. We have high-chairs, pack 'n plays, baby gates, fans, and dog crates so you can pack less and enjoy a worry-free family getaway. Just let us know what you need in advance so we can make sure it is ready for you at the property upon your arrival.brbrThere is plenty of opportunity for fun and games at Island Vibe 5. We have a storage shed on the property with a beach cart, beach toys, and lots of beach equipment. Additionally, there is a propane grill and outdoor propane fire pit.brbrWe are pet-friendly! Two pets are permitted with prior approval, signed Pet Addendum, and a $150.00 non-refundable pet fee (plus 13% tax).brbrWe treat for mosquitos from May through AugustbrbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.brbrNOISE ORDINANCE: Anna Maria Island has a zero tolerance policy for noise after 9 PM. Please show consideration for your neighbors. No loud music, parties or playing in pools after 9 PM. If a neighbor complains the Police Department has no choice but to file a complaint. Any tickets issued by the police department for noise violations will be the responsibility of the guest and may result in immediate eviction with no refunds of rent or deposits.brbrBy City Regulation, a 7 night minimum stay is required with a maximum occupancy of 6 persons. Violation of the occupancy limit may result in immediate eviction with no refunds of rent or deposits.brbrLicense #: VRC20-000096
Bed 2

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Bath 2

Bath

Sleep 6

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Exceptional(15)

$296.81

/ Nightly
Condo

Coconuts 116 - Anna Maria Island - Condo -1 Bedroom/ 1 Bath- maximum occupancy of 6 people. Distance to the Beach: 3 min walk Community pool.

Holmes Beach, Florida, United States

Coconuts 116 - Anna Maria Island - 1 Bedroom/ 1 Bath - maximum occupancy of 6 people. VRC21-000194br Distance to the Beach: 3 min walkbr Community Poolbr br Courtyard Condo Unit Layout:br Bedroom with 2 Queen bedsbr Hallway Bathroom with shower/tub combobr Queen sleeper sofa in the Living roombr br There are 3 buildings in this cozy complex. This condo is in the courtyard building, tucked away in the back corner of the complex, making it extra private, and still just a short walk to the beach.br Let the sounds of the calm waves will leave you feeling refreshed, rested, and recharged after your stay on Anna Maria Island. The private screened in lanai allows you to feel the breeze while enjoying a meal or morning coffee. br br The property is centrally located in the City of Holmes Beach. Enjoy many activities on your visit; swimming, snorkeling, beautiful sunsets, fishing, boating, sunset dining, picnicking, shopping, watching wildlife, golfing, bicycling, tennis, and more. Easily explore the island on the free trolley.br br At this time there is laundry facility on-site for guest use.br br Anna Maria Island is a tropical barrier island seven and one half miles long. Its fine white sugar sand beaches are open to the public with convenient accesses along the entire island. It is one of the finest beaches in the United States. Unlike some tourist areas of Florida that are typified by endless rows of high rise apartment buildings and hotels, Anna Maria is an island of homes and small resorts.br br Please Remember: You are vacationing in a residential area where homes are in close proximity to each other. Please be a good neighbor by keeping the noise to a respectful level during the day and night. A violation of the city's noise control ordinance shall subject the violator to the issuance of a notice of violation or citation. Noise is measured at the property line of the property generating the noise.br Amenities Include:br - # Bedrooms: 1br - Bed Sizes: 2 Queenbr - Sofa Sleeper: queen sofa sleeperbr - # Baths: 1br - Tub or Shower: tub/shower combobr - Balcony: screened lanaibr - Pool: communitybr - #of units in complex: 18br - BBQ Grill: community charcoalbr - Square Feet: 780br - Floor Number: ground levelbr - Distance to Beach: 50 yardsbr - Internet: wifibr - View: courtyardbr - washer dryer: on-site coin operatebr - Dishwasher: yesbr - Maximum Persons: 6br - TV: 2br - Phone: yesbr - Hairdryer: yesbr - Type of Parking: openbr - Coffee maker: yes- Keurigbr - Blender: yes
Bed 1

Bed

Bath 1

Bath

Sleep 4

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Exceptional(4)

$491.72

/ Nightly
Private Vacation Home

Cheeky Chateau: Cozy Retreat with Pool, Steps to Beach!

Holmes Beach, Florida, United States

Welcome to your island getaway at the Cheeky Chateau in Holmes Beach! This cozy retreat on Anna Maria Island is your ticket to relaxation and fun in the sun. With 4 bedrooms, 3 bathrooms, and a bonus room leading to the pool area, there's plenty of space for you and your loved ones to spread out and unwind. Enjoy lazy afternoons lounging by the pool in your private backyard oasis.brbrInside, the tastefully designed interior creates a welcoming atmosphere for your vacation. Whip up delicious meals in the fully equipped kitchen. With two screened lanais and a sunroom, there's no shortage of space to enjoy the island breeze. brbrWhen you're ready to explore, you'll find yourself just a short stroll away from the pristine beaches of the Gulf of Mexico. Spend your days swimming, sunbathing, or trying your hand at exciting water sports. And with charming cafes, restaurants, shops, and parks nearby, there's always something new to discover. Whether you're seeking adventure or relaxation, Cheeky Chateau offers everything you need for an unforgettable island vacation.brbrFloor 2 (main living level)brBedroom 1: Queen bedbrHall bath with walk-in showerbrLiving room, kitchen, dining room, sun porchbrbrFloor 3brBedroom 2: King master with TV, ensuite bathroom with walk-in shower and jet tub, and direct balcony accessbrBedroom 3: Queen bed with TV brBedroom 4: Twin over twin bunk bedbrHall bath with tub/showerbrLaundry in hallbrbrPETS: Please note this property is NOT pet friendly. brbrPARKING: 4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.brbr***OVERCROWDING CONSEQUENCES***brMaximum occupancy of rental homes on Anna Maria Island are set by the Cities and are strictly enforced. An occupant is any person staying overnight, regardless of the number of nights. Due to recent issues of overcrowding in the area, if maximum occupancy is exceeded during your stay, a $1000 (one thousand dollar) overcrowding fee will be charged to the payment method on file and your party will be immediately evicted. We appreciate your understanding and cooperation to keep Anna Maria Island enjoyable for everyone.brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.brbr*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.brbrNOTE: For security and insurance purposes, there are exterior-only video cameras on the premises.brbrVRC24-000050
Bed 4

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Bath 3

Bath

Sleep 8

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Exceptional(4)

$252.24

/ Nightly
Condo

Beachview 5 · Two Kings · 2-Min Walk to Gulf

Holmes Beach, Florida, United States

2BR · 2BA · Sleeps 4 · Two King Beds · 2-Min Walk to Manatee Beach · Heated Pool · Dual Screened Lanais · In-Unit Laundry · Publix & CVS Across the Street · Two Covered Parking Spaces · 1,131 Sq FtbrbrTwo minutes from Manatee Public Beach via the 38th Street path — lifeguards, volleyball courts, restrooms, and beachfront food service when you get there. Publix grocery and CVS pharmacy are directly across the street. The free Anna Maria Island trolley stops at both Publix and Manatee Beach, running the full length of the island from Bradenton Beach through Holmes Beach to Anna Maria City. Guests who stay at Beachview #5 consistently arrive, park, and don't need their car again until checkout.brbrThe condo is 1,131 square feet with an open floor plan — spacious for two couples or a small family. Both bedrooms have king beds, positioned on opposite sides of the unit for privacy. The primary suite has an en-suite bath with walk-in shower and access to the garden-view screened lanai. The guest bedroom has its own flat-screen TV, access to a second full bathroom with tub and shower, and direct access to the pool-view screened lanai. The living room opens to the garden-view lanai through sliding doors — a natural extension of the indoor space for morning coffee or evening drinks.brbrThe pool-view lanai overlooks the heated community pool. The garden-view lanai houses a private in-unit laundry closet with full-size washer and dryer — no shared laundry room, no coin machines, no scheduling around other guests.brbrThe kitchen has granite countertops, stainless appliances, and a breakfast bar. Dining table seats six. High-speed WiFi, smart TVs throughout, and central AC replaced August 2025. A ground-level secure storage closet is available for beach gear — bikes, chairs, coolers — so the unit stays uncluttered.brbrTwo assigned covered parking spaces are included under the building.brbrBeachview #5 requires a one-week minimum stay. Not pet-friendly. Second-floor unit via exterior stairs — no elevator. brbr*Final payments are due 60 days prior to arrival payable by personal check or Echeck (which will incur a $1.00 processing fee) we do takebrcredit cards for final payment with a 3% fee on the balance due.brVirtual Tour Url: https://my.matterport.com/show/ m=xP9KX7gC1gE&mls=1
Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps

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$502.34

/ Nightly
Private Vacation Home

Under the Foxtails by Beach Boutique Rentals

Holmes Beach, Florida, United States

Welcome to Under the Foxtails, a freshly renovated beach escape offering the perfect blend of comfort, style, and sunshine.brbr*Features include* brbr* Private heated pool with covered patiobr* Ground-level conveniencebr* 3 bedrooms and 3 full bathroomsbr* Primary suite with king bed and ensuite bathbr* Second bedroom with king bedbr* Third bedroom with twin bunk beds – perfect for kidsbr* Vaulted ceilings and skylightsbr* Outdoor area with gas grill and ping pongbr* Lounge chairs by the poolbr* Washer and dryerbr* Beach chairs, umbrella, and cartbr* Small dog friendly!brbrStep inside this stunning coastal retreat, completely renovated from top to bottom for Fall 2025. Every inch of the home has been refreshed with designer finishes, natural textures, and a warm, beach-modern aesthetic that perfectly balances sophistication and comfort.brbrThe open-concept living area features vaulted ceilings, skylights, and soft natural light that fills the space from every direction. The spacious living room is furnished with super-comfy seating and a soothing neutral palette, creating a perfect spot to unwind after a day in the sun.brbrThe all-new kitchen is both beautiful and functional, showcasing crisp white cabinetry paired with warm lower cabinets, sleek quartz countertops, and modern stainless appliances. A farmhouse sink and gold accents add charm, while the thoughtful design keeps everything within easy reach.brbrEnjoy memorable meals in the bright dining room for six, surrounded by windows and coastal-inspired décor. For more casual moments, the breakfast nook for two provides a cozy space for coffee or an intimate bite. At the front of the home, a stylish sitting room for four offers an inviting place to relax or enjoy conversation in the afternoon light.brbrEach bedroom is designed as a serene retreat, complete with plush new furnishings, soft linens, and calming tones. The three full bathrooms each feature fresh tilework and custom details - from the curved glass-block shower to modern fixtures and calming green hues that tie the home’s natural style together.brbrOutside, your private backyard oasis offers a sparkling heated pool, lush tropical landscaping, and a shaded patio with ping pong table and gas grill.brbrNestled in the heart of Holmes Beach, Under the Foxtails is just a short stroll from the beach, local shops, and island favorites like Frecked Fin Irish Pub,The Feast, Hurricane Hanks, and Island Creamery.brbrPET POLICY:brbrWe are DOG FRIENDLY! At this home a fee of $150 + tax is required in advance for each dog you are bringing.brbr2 pets maximum unless granted an exception. Weight limit of 25 lbs maximum per pet.brbrDue to property insurance policies and liability concerns NO dangerous breeds or aggressive animals are allowed. The following breeds (purebred or crossbred) are not permitted:brbrPit Bull, Akita, Rottweiler, German Shepherd, Siberian Husky, Malamute, Doberman Pinscher, Chows, Any Wolf-dog hybrid, Any other dog that has been known to have bitten anyonebrbrADDITIONAL INFORMATION brbrWe generally require a minimum stay of 7 nights with Saturday check-in during the high season. We are more flexible in the off season so please send us a message if your dates appear unavailable. We may be able to accommodate you! brbrHousekeeping will provide a starter supply of toilet paper, soap, and garbage bags but guests will likely need to replenish the supply during their stay. brbrAnna Maria island is a family community and the city imposes a strict noise ordinance. Please adhere to our good neighbor policy and observe the local quiet hours between 10 pm and 8 am. No loud music or use of the pool is allowed during these hours along with any other noise which may disturb the neighbors.brbrVRC25-000123br brThis home provides off-street parking for up to 3 vehicles.brbrBooking Platform Note:brFor VRBO bookings, the reservation payment is processed by Beach Boutique Rentals and will appear as Beach Boutique Rentals on your credit card statement. VRBO also charges a separate service fee directly to the guest as a separate transaction.
Bed 3

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Bath 3

Bath

Sleep 6

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Exceptional(2)

$387.05

/ Nightly
Private Vacation Home

North Beach Paradise by Duncan Real Estate

Holmes Beach, Florida, United States

Welcome to North Beach Paradise - a 3BD/2BA Key West, Island style townhouse on Holmes Beach! It's located in a quiet and peaceful residential area just a half block from the pristine Anna br Maria Island beaches. North Beach Paradise is just a few steps to the main free trolley line that can take you anywhere you want to go on this beautiful 7 mile island.br br When entering North Beach Paradise, you walk up a short flight of stairs to the main level or take the elevator from the garage level to the first floor. This story features a large open plan living area with lots of natural light, a beautiful primary bedroom with a Queen size bed with walk in closet and Jack and Jill bathroom. The well equipped kitchen with granite counter tops includes all appliances like Keurig and drip coffee maker and the washer and dryer are also located here. Step outside onto the large, shaded and screened in lanai off the kitchen to enjoy the tropical breezes or have al fresco meals at the outdoor dining area. There is an additional deck off the living room to soak up the sun. br This home feature another story which has a queen guest bedroom, the third bedroom with two twin beds and a shared hall bathroom with a walk-in shower. br br The downstairs double garage accommodates extra room for parking. You will find your beach gear including beach wagon and chairs.br br HIGHLIGHTSbr br 1152 sq. ft.br Elevatorbr Double garagebr 967 sq. ft. of deck spacebr Shared heated community pool (40x16 ft)br Centrally located near Holmes Beach Plaza br 0.3 miles from bay access br 0.1 miles from beach accessbr br BEDROOMSbr br Sleeps 6br Primary Bedroom: Queenbr Second Bedroom: Queenbr Third Bedroom: Twinsbr br BATHROOMSbr br Primary Bathroom: Walk-in Shower br Second Bathroom: Shower/Tub Combo br br EXTERIORbr br North Beach Village features a shared, heated 40 ft. by 16 ft. community pool in the center of the complex. Enjoy a swim surrounded by tropical landscaping!br There is a gas grill by the ground level covered outdoor area in the back of the house.br br br br br br br br br br br br br br br br br br br br br br Please keep in mind that you are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.br br VRC23-000065br Amenities Include:br - Bedroom 1 Queenbr - Bedroom 2 Queenbr - Bedroom 3 2 Twinsbr - Bathroom 1 Shower/Tubbr - Bathroom 2 Walk-in showerbr - Hot Waterbr - Elevator Ybr - Central A Cbr - Cental Heatbr - Free Parkingbr - Parking Spots 2br - Garagebr - Self Check Inbr - Keyless Entrybr - Bath Towelsbr - Beach Towelsbr - Quality Linensbr - Hair Dryerbr - Hangersbr - Refrigeratorbr - Ice Makerbr - Stovebr - Ovenbr - Cookwarebr - Toasterbr - Blenderbr - Keurigbr - Drip Coffee makerbr - Dishwasherbr - Microwavebr - Garbage disposalbr - Dining Tablebr - High Speed WIFIbr - TV 3br - Cable Channelsbr - Washerbr - Dryerbr - Ironbr - Ironing Boardbr - Cleaning Kitbr - First Aid Kitbr - Fire Extinguisherbr - Smoke Alarmbr - Carbon Monoxide Alarmbr - Shared Pool Ybr - Pool Dimensions 40X16br - Sun Loungersbr - Screened Lanaibr - Balconybr - Outdoor Diningbr - Outdoor Showerbr - Propane Grillbr - Beach Amenitiesbr - Exterior Outletbr - Duncan Emerald Club
Bed 3

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Bath 2

Bath

Sleep 6

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Exceptional(31)

$320.55

/ Nightly
Cottage

Stay at Sun Daze: Private Pool, 3 Minutes to the Beach!

Holmes Beach, Florida, United States

Sun Daze by Anna Maria Island Accommodations brVRC16-000103 brbrWelcome to Sun Daze by Anna Maria Island Accommodations, a bright and inviting two-bedroom, two-bathroom villa perfectly located in the heart of Holmes Beach. This newly remodeled charming coastal retreat is just a three-minute walk to the beach and steps from local shops, restaurants, and trolley stop. Ideal for families or small groups, Sun Daze blends comfort, style, and convenience for a truly effortless Anna Maria Island vacation. brbrHighlights br• 3-minute walk to the beach br• 2 Bedrooms / 2 Bathrooms br• 1 King bed, 1 Queen bed, 1 Queen sleeper sofa br• Private heated pool br• BBQ grill and outdoor dining area br• Outdoor shower br• Washer and dryer br• 2 parking spaces brbrYour private outdoor oasis awaits! The heated pool is surrounded by lush tropical landscaping, creating a serene backdrop for swimming, lounging, and enjoying the sunshine. Fire up the BBQ grill and gather around for outdoor meals or evening cookouts. The outdoor shower offers a convenient way to rinse off after a day at the beach, completing the perfect setup for relaxed island living. brbrInside, Sun Daze features an open concept layout designed for easy living. The cozy living room offers plush seating, TV, and plenty of natural light for relaxing after beach days. The fully equipped kitchen boasts stainless steel appliances, granite countertops, and all the cookware essentials needed to prepare family favorites. The dining area provides space to share meals and plan your next Anna Maria Island adventure. brbrEach bedroom is beautifully designed to ensure a restful night’s sleep. The primary bedroom includes a king bed, TV, and private ensuite bathroom with a walk-in shower. The second bedroom features a queen bed and cheerful coastal decor. A queen sleeper sofa in the living area provides additional sleeping space for guests. Both bathrooms are modern and well-appointed, offering comfort and convenience for your stay. brbrRoom Details br• Primary Bedroom: King bed, ensuite bathroom with walk-in shower br• Second Bedroom: Queen bed br• Living Room: Queen sleeper sofa br• Hall bath features a shower-tub combo brbrWith two parking spaces, washer and dryer, and close proximity to both the beach and Holmes Beach’s local shops and restaurants, this villa is perfectly situated for exploring Anna Maria Island. Walk to the shore for a morning swim, hop on the trolley for a pleasing island ride, or unwind poolside in your own private retreat. brbrCombining modern updates with Old Florida charm, Sun Daze by Anna Maria Island Accommodations is your home away from home on the Gulf Coast. Whether you’re swimming in your private pool, enjoying sunset strolls along the beach, or relaxing with loved ones, this villa makes every day feel like vacation. brBook your stay today and experience the laid-back island lifestyle of Anna Maria Island! brbr br- brThis home is managed by Anna Maria Island Accommodations, an Anna Maria Island property management company. brbrThere are no pets allowed in this home. brbr2 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease see our Anna Maria Island Accommodations Rental Policies for full details. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.
Bed 2

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Bath 2

Bath

Sleep 4

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Exceptional(41)

$1110.23

/ Nightly
Private Vacation Home

Poseidons Palace! Family Fun and Gulf Views!

Holmes Beach, Florida, United States

Poseidons Palace by Anna Maria Island Accommodations brVRC16-000122 brbrWelcome to Poseidons Palace, an extraordinary eight bedroom, five and a half bath vacation retreat just a two-minute walk from the beach. Designed with families and groups in mind, this spacious home features a resort style backyard with a private pool and spa, a rooftop deck with stunning views, and endless entertainment options including a game room, outdoor bar, and indoor shuffleboard, ping pong and pool table. Find beach access a short stroll away, shopping, dining, and the Anna Maria Island trolley stop just steps away. brbrHighlights br-2-minute walk to Holmes beach br-8 Bedrooms / 5.5 Bathrooms br-Private pool with spa br-Rooftop deck br-Outdoor bar with fridge and TV br-Pool table, ping pong, and indoor shuffleboard br-Covered patio with dining area and BBQ grill br-Beach chairs and wagon included br-Washer and dryer br-5 Parking spots brbrThe private backyard oasis is made for entertainment and relaxation. Swim in the heated pool, soak in the spa, or enjoy drinks at the built-in Tiki swim-up table. A covered patio offers a full outdoor bar with seating, TV, and fridge, plus a large dining area for freshly grilled meals. For added fun, the game room is equipped with a pool table, ping pong, and shuffleboard. After a day in the sun, head up to the rooftop deck for breathtaking sunsets over the Gulf. brbrInside, the open concept living space is filled with nautical charm and natural light. Relax in the cozy seating area with a large TV or cook in the chef’s kitchen with stainless steel appliances, essential cookware, and a large island with seating for six. Gather everyone around the formal dining table or open the doors to enjoy seamless indoor-outdoor living. brbrWith eight beautifully decorated bedrooms, there’s plenty of space for everyone to rest comfortably. Three primary bedrooms feature king beds and ensuite bathrooms with walk-in showers, while three guest rooms offer queen beds. Two bunk bedrooms provide fun sleeping spaces for kids or teens. Two additional hall bathrooms; one with a shower-tub combo, one with a walk-in shower; ensure convenience for larger groups. brbrRoom Details br-Primary Bedroom, 2nd floor: King bed, ensuite bathroom with walk-in shower br-Second Bedroom, 2nd floor: King bed, ensuite bathroom with walk-in shower br-Third Bedroom, 3rd floor: King bed, balcony, ensuite bathroom with walk-in shower br-Fourth Bedroom, 3rd floor: Queen bed br-Fifth Bedroom, 3rd floor: Queen bed br-Sixth Bedroom, 3rd floor: Queen bed br-Seventh Bedroom, 3rd floor: Twin-over-Twin bunk bed br-Eighth Bedroom, 3rd floor: Twin-over-Twin bunk bed br-Bonus, Living Room: Queen Sleeper Sofa brbrPoseidons Palace includes a washer and dryer, multiple balconies with seating, and plenty of storage throughout. Guests will love the easy walk to the beach and the close proximity to restaurants, shops, and historic attractions along Anna Maria Island. Beach chairs and a wagon are provided to make beach days effortless. brbrPoseidons Palace has everything you need for an unforgettable island escape. With luxury amenities, endless entertainment, and the Gulf just steps away, your perfect Anna Maria Island adventure begins here. Book your stay today! brbr- brNo pets of any kind are allowed in this home. brbr5 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrThis home is managed by Anna Maria Island Accommodations, an Anna Maria Island property management company. Please see our Anna Maria Island Accommodations Rental Policies for full details. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.
Bed 8

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Bath 5

Bath

Sleep 16

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Exceptional(3)

$501.15

/ Nightly
Private Vacation Home

Gorgeous Home with a Pool, Outdoor Lounge, and Elevator! Near Beach and Dining

Holmes Beach, Florida, United States

Ohana by Anna Maria Island Accommodations brbrExperience the perfect family vacation at Ohana, a stunning four-bedroom, three and a half bath home just a three-minute walk from the white sands and turquoise waters of Holmes Beach! This beautifully furnished home features a private pool shaded by graceful palms, an outdoor kitchen with a bar and grill, a ping-pong table, and an outdoor TV, creating an outdoor oasis for fun, relaxation, and island memories. Located near shops, galleries, and waterfront dining, Ohana offers easy access to everything Anna Maria Island has to offer, beaches, watercraft, and adventure!brbrHighlights br• 3-minute walk to Holmes Beachbr• 4 Bedroom / 3.5 Bathbr• 2 Kings, 1 queen, 2 twin beds, sleeper sofabr• Private pool br• Outdoor kitchen and grill br• Outdoor dining br• Ping pong tablebr• Elevator br• Short walk or bike ride to shops, restaurants, parks, and local water activitiesbr• 3 Parking SpacesbrbrEnjoy outdoor living at its best with your private pool, shaded by lush palms, and a deck area perfect for lounging, dining, or sunset cocktails. The outdoor kitchen includes a propane grill, mini fridge, and bar, ideal for summer cookouts and gathering. Pass hours in the game room with ping pong, lounge at the outdoor TV, or explore nearby water activities, parks, and local dining. With walking or biking distance to the beach and shops, every day offers new adventures and relaxation in paradise.brbrInside, the home features a bright, coastal-inspired open layout. The kitchen boasts stainless steel appliances, a granite island with barstools, and all essentials for island dining. The chic wicker dining table seats six comfortably, perfect for family dinners or casual gatherings. The spacious living room with plush sofas and a smart TV invites lounging after fun days at the beach, with large sliding doors opening onto the balcony and outdoor space.br brRetreat to the primary bedroom on the second floor, featuring a king bed, a private balcony, and a luxurious ensuite with a walk-in shower, double vanity, and a soaking tub, a perfect oasis after a day of water adventures. The second bedroom, with its king bed and balcony access, also has an ensuite bathroom with a walk-in shower. The third bedroom offers a queen bed, while the fourth bedroom has two twin beds, each with easy access to the hall bathroom with a shower/tub combo. For added convenience, there is a washer and dryer, and a cozy den or sitting area with a desk and sleeper sofa for larger groups or extra guests.brbrRoom Details br• Primary Bedroom (2nd floor): King bed, private balcony, ensuite bathroombr• Second Bedroom (3rd floor): King bed, private balcony, ensuite bathroom br• Third Bedroom (3rd floor): Queen bed br• Fourth Bedroom (3rd floor): Two twin bedsbr• Den: Sleeper SofabrbrBook Ohana today and enjoy a luxurious, fun-filled Gulf Coast retreat. With stunning views, outdoor amenities, and prime proximity to beaches, shops, and waterfront dining, this home offers everything for an unforgettable Anna Maria Island escape. Reserve your dates now and start creating lifelong memories!brbrbr-brThere are no pets allowed in this home.brbr3 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrThis home is managed by Anna Maria Island Accommodations Accommodations, an Anna Maria Island property management company.brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age.brbrPlease see our Anna Maria Island Accommodations Accommodations Rental Policies for full details.brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.
Bed 4

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Bath 3

Bath

Sleep 8

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Exceptional(32)

$1482.06

/ Nightly
Private Vacation Home

Near the Beach with Balconies and Tiki Bar!

Holmes Beach, Florida, United States

Two Pina Coladas by Anna Maria Island Accommodations brVRC16-000094 brbrWelcome to Two Pina Coladas by Anna Maria Island Accommodations, a luxurious six bedroom, four and a half bath home just one block from the Gulf beaches of Holmes Beach. Designed for large families and groups, this coastal gem combines resort style amenities, peeks of the Gulf from the balconies, and a backyard paradise built for fun. With a private heated pool, hot tub, tiki bar, and game room, every day here feels like an island celebration. brbrHighlights br• 1-minute walk to the beach br• 6 Bedrooms / 4.5 Bathrooms br• Private heated pool and hot tub br• Swim-up tiki table and covered tiki bar with TV br• Game room with Ping Pong, Foosball, Putting Green and Galaxia arcade br• Gas grill and outdoor dining area br• Balconies with partial Gulf views br• Washer and dryer br• Pet friendly with host approval br• 4 parking spaces brbrYour private backyard oasis is the heart of Two Pina Coladas. Enjoy the tropically landscaped pool and hot tub, complete with a swim-up tiki for poolside refreshments. Gather under the covered tiki bar, featuring a flat-screen TV, comfortable seating, and a gas grill for island style cookouts. Whether you’re lounging in the sun, watching the game outdoors, or challenging friends to a round of Ping Pong or Foosball, every corner invites relaxation and fun. brbrInside, the open living area welcomes you with soft coastal decor and plenty of space for everyone to unwind. The living room features plush seating, a large TV and Wi-Fi. The fully equipped kitchen offers granite countertops, stainless steel appliances, and ample space for group cooking, while the dining area sets the scene for shared family meals and easy conversation after a day in the sun. brbrEach of the six bedrooms is thoughtfully appointed with a TV and plenty of storage. Two king suites feature private ensuite bathrooms, while two additional king bedrooms share a Jack and Jill bathroom. A twin bedroom and a twin trundle bedroom provide flexible sleeping arrangements, perfect for kids or extra guests. The bathrooms are modern and bright, featuring walk-in showers, granite finishes, and coastal touches that add to the relaxing atmosphere. brbrRoom Details br• Primary Bedroom (3rd Floor): King bed, TV, ensuite bathroom br• Second Bedroom (3rd Floor): King bed, TV, ensuite bathroom br• Third Bedroom (3rd Floor): Two Twin beds, TV, shared bathroom br• Fourth Bedroom (3rd Floor): Twin Trundle bed, TV, shared bathroom br• Fifth Bedroom (2nd Floor): King bed, TV, Jack-and-Jill bathroom br• Sixth Bedroom (2nd Floor): King bed, TV, Jack-and-Jill bathroom brbrGuests can spend time in the ground-floor game room, featuring classic and arcade favorites, or take a short stroll to the island trolley for effortless access to Anna Maria Island’s shops, restaurants, and beaches. Within minutes, you can enjoy local dining spots, boutique shopping, and the sparkling Gulf waters that make the Florida coast so memorable. brbrBlending luxury, location, and laid-back island style, Two Pina Coladas by Anna Maria Island Accommodations is the ultimate vacation retreat for families and large groups. With its private pool, outdoor tiki bar, and close proximity to the beach, this home captures everything that makes Anna Maria Island special. brBook your stay today and experience the tropical magic of Two Pina Coladas! brbr- br*Please note: 4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrThis home is managed by AMI Accommodations, an Anna Maria Island property management company. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease see our AMI Accommodations Rental Policies for full details. brbrPlease Remember: brbrYou are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.
Bed 6

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Bath 4

Bath

Sleep 12

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$751.5

/ Nightly
Private Vacation Home

Stunning Home with Pool, Tiki Bar, and Game Room! 2 Minute Walk to Beach

Holmes Beach, Florida, United States

Margarita-Ville by Anna Maria Island Accommodations br121 46th Street, Holmes Beach, FL 34217brVRC16-000136brbrExperience the ultimate island escape at Margarita-Ville, a stunning six-bedroom, four and a half bath vacation home designed for large families or groups seeking a memorable getaway! Just a two-minute walk from the beach, this beautifully landscaped estate offers glimpses of the water from balconies, your private pool with a spa, a Tiki bar, outdoor TV, and ample outdoor dining and lounging areas, perfect for relaxing days and lively evenings. Located near locally owned shops, waterfront restaurants, and just a short walk to the trolley stop, Margarita-Ville blends convenience with elegance for an unforgettable Anna Maria Island vacation!brbrHighlights br• 2-minute walk to Manatee Public Beach br• 6 Bedroom / 4.5 Bathsbr• 4 Kings, 1 Queen, 1 twin with trundle, 1 Queen sleeper sofabr• Private heated pool and spabr• Elevator accessbr• Tiki bar with an outdoor TVbr• Outdoor dining space and BBQ grillbr• Foosball and pool table br• Short walk or trolley ride to shops, waterfront restaurants, and local attractions br• 4 Parking Spacesbr brUnwind in your personal aquatic oasis, relax in the private heated pool, soak in the spa and enjoy the Florida sun. Gather under the covered Tiki bar with a TV and plenty of seating or fire up the BBQ grill for casual family dinners or sunset parties. Enjoy the lush backyard in your secluded retreat or play a game of pool or foosball, easily accessible to the outdoors.brbrInside, the welcoming layout features a large flat-screen HDTV, plush seating, and serene island decor. The kitchen boasts stainless steel appliances, granite countertops, and an island with seating for four. Seamlessly connecting with a formal dining table for eight, ideal for family meals or entertaining indoors. The open floor plan encourages everyone to gather comfortably, whether indoors or outside on the patio.brbrRelax in the primary bedroom, located on the third floor, with a king-sized bed, private balcony, and ensuite bathroom with a walk-in shower. Three additional bedrooms, one on the second floor and two on the third floor, include king beds, each with their own flat-screen TV and luxurious linens, two with en-suite bathrooms and walk-in showers. On the third floor, find the fifth bedroom with a stunning queen bed, while the final bedroom offers a twin bed plus a twin trundle, ideal for kids or additional guests. The living room offers a queen sleeper sofa for more space. The hall bathroom features a walk-in shower, and a half bath and laundry room add convenience to your stay.brbrRoom Details br• Primary Bedroom (3rd floor): King bed, ensuite with walk-in shower br• Second Bedroom (3rd floor): King bed, ensuite with walk-in shower br• Third Bedroom (2nd floor): King bed, ensuite with walk-in shower br• Fourth Bedroom (2nd floor): King bed, ensuite with walk-in shower br• Fifth Bedroom (3rd floor): Queen bedbr• Sixth Bedroom (3rd floor): Twin bed with twin trundlebr• Living Room: Queen sleeper sofabrbrBook Margarita-Ville today and enjoy a luxurious home in the heart of Anna Maria Island. Whether you are floating in the pool, exploring nearby beaches and restaurants, or enjoying breathtaking sunsets, this home has everything you need for an unforgettable Gulf Coast vacation. Reserve your dates now and start creating lifelong island memories!brbrbr-brThis home is managed by Anna Maria Island Accommodations, an Anna Maria Island property management company.brbrThere are no pets allowed in this home.brbr4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Anna Maria Island Accommodations Rental Policies for full details.brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.
Bed 6

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Bath 4

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Sleep 12

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Exceptional(24)

$779.05

/ Nightly
Private Vacation Home

Sea Oats: Anna Maria Island Family Retreat with Pool Just Steps from the Beach!

Holmes Beach, Florida, United States

Sea Oats by Anna Maria Island Accommodations brVRC16-000115 brbrWelcome to Sea Oats by Anna Maria Island Accommodations, a stunning six bedroom, four and a half bathroom home designed for the ultimate island getaway. Located just four houses from the beach, this luxury retreat offers the perfect mix of coastal comfort and resort-style amenities. Families and friends will love being just a one-minute walk to the Gulf, near local restaurants, shops, and the free trolley stop, ensuring that every day is filled with ease and adventure. brbrHighlights br• 1-minute walk to the beach br• 6 Bedrooms / 4.5 Bathrooms br• Private heated pool with in-ground spa br• Outdoor kitchen with grill, sink, and refrigerator br• Built-in tiki bar and covered patio with TV br• Elevator access br• Washer and dryer br• 4 parking spaces brbrThe outdoor living space at Sea Oats feels like your own private resort. Take a dip in the heated pool with spa, mix drinks at the tiki bar, or grill up fresh seafood in the outdoor kitchen, complete with a sink, refrigerator, and prep area. The covered patio includes a TV, comfortable seating, and plenty of shade for laid-back afternoons. Whether you’re dining outdoors or relaxing after a beach day, this backyard oasis sets the stage for unforgettable memories. brbrInside, this elegant coastal home welcomes you with bright, open spaces and inviting style. The living room features plush seating and a TV, perfect for family movie nights. The fully equipped kitchen includes stainless steel appliances, a large island with bar seating, and all the essentials for preparing group meals. Gather around the dining table for shared meals, laughter, and conversation after a day on the sand. brbrEvery bedroom in Sea Oats is designed for relaxation and convenience, each with its own TV and storage. The primary suite is a serene retreat, complete with a private balcony, king bed, and ensuite bathroom featuring a double vanity and walk-in shower. The second bedroom connects to a jack-and-jill bathroom shared with the bunk room, making it ideal for families. The third bedroom includes a queen bed and private ensuite bath, while two additional king bedrooms on the second floor share a jack-and-jill bathroom. For extra guests, the living room offers a queen sleeper sofa. brbrRoom Details br• Primary Bedroom (3rd Floor): King bed, ensuite bathroom with double vanity and walk-in shower, balcony access br• Second Bedroom (3rd Floor): King bed, jack-and-jill bathroom with shower-tub combo br• Third Bedroom (3rd Floor): Queen bed, ensuite bathroom with walk-in shower br• Fourth Bedroom (2nd Floor): King bed, jack-and-jill bathroom with walk-in shower br• Fifth Bedroom (2nd Floor): King bed, jack-and-jill bathroom with walk-in shower br• Sixth Bedroom (3rd Floor): Twin-over-Full bunk bed, jack-and-jill bathroom with shower-tub combo br• Living Room (2nd Floor): Queen sleeper sofa brbrGuests can take advantage of the private elevator, washer and dryer, and ample parking for up to four vehicles. The home’s central Holmes Beach location makes it easy to walk to nearby dining, boutique shopping, and beach access points. Explore the island using the Anna Maria Island trolley, visit local attractions, or simply spend your days lounging by the pool and enjoying the relaxed Gulf Coast lifestyle. brbrWith its luxurious features, prime location, and family-friendly layout, Sea Oats by Anna Maria Island Accommodations offers the best of Anna Maria Island living. Whether you’re soaking in the spa, cooking in the outdoor kitchen, or walking to the beach for sunset, every moment here is designed for comfort and connection. brBook your stay today and start making lifelong memories at Sea Oats! brbr- brThis home is managed by Anna Maria Island Accommodations, an Anna Maria Island property management company. brbrThere are no pets allowed in this home. brbr4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our AMI Accommodations Rental Policies for full details. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.
Bed 6

Bed

Bath 4

Bath

Sleep 12

Sleeps

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