Vacation Rentals By Owner In Holmes Beach, FL

Forget everything around you and switch to vacation mode the moment you step foot onto this beachfront balcony. Located at the Playa Encantada condominium complex, this elevator accessible unit could not be any closer to the beautiful beach of Anna Maria Island.brbrOffering more than 1,700 square feet of living space, this 3 bedroom and 2 bathroom corner condo unit has plenty of natural light of living space, as well as unforgettable views from the balcony. Other amenities available exclusively to guests of Playa Encantada include a heated pool, hot tub, shuffleboard, tennis courts and sauna.brbrThe master bedroom has a king size bed, TV, and en-suite bathroom with walk-in shower. The second and third bedroom each have two single beds and share a hallway bathroom with a shower/ tub combination. The kitchen is very well stocked with everything you need to prepare anything from a light breakfast to a full family dinner. The living room has plenty of comfortable seating for everyone, a large smart TV and you can stay connected with free high speed Wi-Fi internet throughout the condo.brbrReserved parking for one vehicle is available inside the ground floor garage. Additional parking spaces are available marked as Guests.brbrVRC26-000013brMinimum Stay: 14 NightsbrMax Occupancy: 6 GuestsbrMaximum Parking: 2 VehiclesbrNoise Ordinance: The City of Holmes Beach has a noise ordinance with quiet hours from 10 PM to 7 AM, prohibiting unreasonable, loud, or excessive noise that disturbs the peace, with specific decibel limits (65 dBA daytime, 50 dBA nighttime) and fines for violations, enforced by code officers using noise meters.

Beachfront Condo with Stunning Ocean Views, Heavenly Sunsets, Large Balcony

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$871.01

We have found our perfect spot on the beach. After visited the resorts and beaches of Florida for many years we are here to stay: at Anna Maria Island. Unfortunately only for holidays - the rest of the time you can take advantage of it as a tenant. Three comfortable bedrooms, the master with a king-size bed and sea views, a queen in the second and the third with two queen beds. The two bathrooms have walk-in showers. Sliding doors in the living room and the kitchen take you directly to the deck and there you sit or lie virtually on the beach. Just down the stairs and into the clean and warm waters of the Gulf of Mexico. Almost every day you have the chance to discover dolphins. In only 500 meters you will find at Publix everything you need. Never forget the sunset with a drink on the terrace. Then you decide whether you want stay home for a steak on the Weber grill or dine out at the City Pier or one of the many other restaurants. In May 2011, we have renovated the house completely.

Comfortable vacation home directly on the beach and sunsets from the terrace

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$217.53

Anna Maria Island is a stunning destination in Florida, known for its serene atmosphere and easy accessibility. The island boasts breathtaking sunsets, gentle breezes from the Gulf of Mexico, and miles of pristine white sand beaches. This private and tranquil home, situated on the ground floor of a two-unit building, features two bedrooms with king-size beds, a full bath with tub and shower plus an additional half bath, a fully equipped kitchen, and a private screened in lanai. Recently renovated in the summer of 2025, it offers bright, airy spaces with fresh paint, and all-new furniture. Guests can unwind in the yard or on the lanai and enjoy evening strolls to the beach for sunset views. This is 1/2 of a duplex, the second unit is an apartment above the garage it is not on top of this unit. The adorable cottage-style duplex is within walking distance of the Gulf's beautiful beaches, village shops, restaurants, cafes, and a library. For added convenience, a free island trolley is available, and both Sarasota International Airport and Tampa International Airport are just 40 and 70 minutes away, respectively.

Terrific 2-bedroom house in Holmes Beach

Holmes Beach, Florida, United States

Bed

1

Bath

4

Sleeps

$306.27

Watch the world go by on AMI as you enjoy the sea breeze on your private front deck. Unwind in the hot tub after a day at the beach and be sure to catch the sunset over the gulf, there's nothing better than reflecting on your day as the sun eases below the horizon.brbrThis is a lovely split level home. Enter the home at the front deck with outdoor dining area, grill, and additional seating. Through the front door, step into the main open plan living area of the house. This space has two couches (one can be converted into a queen sized sleeper), a recliner, and large tv. It flows into the dining area with full sized dining table plus window seat as well as fully equipped kitchen. Bedrooms are a half story up from the main living area providing separation for the early birds and those who want to sleep in while on vacation.brbrUpstairs are two bedrooms, each with a king sized bed and tvs with Roku streaming devices. In the hallway between the two bedrooms is the primary full bathroom with tub and shower. Across the hall from the bathroom is the fully stocked linen closet with bath towels, beach towels, and select toiletries.brbrTake the short half-flight of steps down and you'll find a second living area, with a queen daybed and tv as well as bistro set. The downstairs living area opens with sliding glass windows out to the front of the house with a pair of bikes available as well as a storage chest full of beach chairs and life jackets to use with the paddle boards and kayaks under the patio. The downstairs living room connects to the second bathroom with shower at the back of the house as well as the washer and dryer. Through this bathroom is access to the back yard.brbrThe back yard has a bromine hot tub as well as additional seating and a pair of lounge chairs to enjoy the rear deck area. Relax in this tranquil space surrounded by the lush green palms.brbrThere is a games cabinet on the lower level of the home with assorted board games and puzzles as well as an assortment of toddler toys.brbrThis house is very child friendly but not baby proof. We have lots of amenities for babies/toddlers, but there are stairs and no baby gates. The baby items can be set up for you ahead of time, just message me, otherwise most of the baby gear is in the closet of the front bedroom so as to be out of the way for those without young children.brbrWe generally require a 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!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.

Destination Relaxation

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$508.12

Experience the serenity of our newly renovated, single-story sanctuary, nestled perfectly alongside an idyllic canal. This comfortable retreat, set in a tranquil area of AMI paradise, boasts a large private pool and a spacious floorplan to ensure utmost relaxation and rejuvenation. Enjoy three voluminous bedrooms, each complemented with a private, modern ensuite bathroom, offering plenty of space to unwind in style. Unleash your culinary creativity in the modern kitchen, bond in the cozy family room, or host a memorable dinner in the spacious dining area that effortlessly seats six. brbrFor the adventurous at heart, enjoy the option to dock your boat right in your backyard, an ideal base for exploring the mesmerizing beauty of Anna Maria Island`s waters. With the comfort of two king-sized and two queen-sized beds, our home is capable of pampering up to six guests, making it the perfect destination for a blissful family escape or an exciting rendezvous with friends. brbrPartake in the delicious local culinary scene, explore charming boutique shops, and soak up the breathtakingly beautiful white sand beaches and crystalline turquoise gulf waters that our location is celebrated for. Your unforgettable Anna Maria Island adventure awaits – secure your dream vacation today!brNo smoking of any kind, no pets, no parties or events allowed. Guest will be responsible for any and all damages to the property that they or their guests may incur. A signed Rental Agreement is required with your reservation. A complete list of House Rules will be available at the Rental Property.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.brbrMaximum Guests Allowed - 6brMaximum Parking - 5 VehiclesbrMinimum Stay - 28 DaysbrProperty License # - VRC25-00075

New Listing Discount! Beautifully renovated home w/pool on canal near beach!

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$483.15

VRC# 19-000218brbrCozy 'Day' Side Cottage is located in Holmes Beach on Anna Maria Island. It offers 2 bedrooms and 1 1/2 baths. This pet friendly cottage has everything you need to relax and enjoy the island life style! Open floor plan includes kitchen with new stainless steel appliances and table for 4. Updates include white cabinetry, granite counters and new food pantry. Light and bright, the Kitchen/Dining/Living room is full of windows and a sliding glass door to your own balcony, the perfect place for that first cup of coffee while enjoying the sun rise!brbrThere is also a covered patio with propane grill to prepare your meals while soaking in the heated pool. Our unique Salt water pool is always clear and pleasant! We have water toys, life jackets, floaties, etc to keep kids having fun! Adult supervision required while children are in pool area (gated and fenced).brbrIf you need a portacrib, highchair, just ask and we will do our best to provide it complimentary. brWe have a jogging stroller as well. brThis home provides adult bikes as well as a child's bike and a tricycle! While we have our bikes serviced and maintained, please use caution and stay with children as they operate bikes. Please report to our property manager anything needing repairs or adjustments. brbrTake a walk or bike ride (bikes included) around this beautiful area! One block away is an Island free trolley stop to take you throughout the island. A leisurely stroll, less than 3 short blocks, will take you to the 81st Street beach entrance where you can enjoy the sound of the waves and the soft white sand! This beach entrance has no parking and is only for those that can walk to it and remains less crowded. It's great for a quick walk to view the islands beautiful sunsets! Nearby 77th St. beach entrance offers some parking for golf carts and cars.brThere are days that you will feel that area of the beach is yours only! We have so much beach equipment you are welcome to use!brbrYour cottage is equipped with high speed wireless internet as well as Portable Roku for the 3 tv's in the unit. Also a Nintendo Switch with games and board games are here for your entertainment as well!brbrYour enjoyment is important to us so we have recently purchased all new mattresses and bedding to whisk you off to a great night sleep so you can awake refreshed and ready to enjoy your day on this picturesque island!brOur location provides a peaceful neighborhood and is suited for long term stays. You are welcome to bring your best furry friend with you! Inquire about pet policy and what items we keep for your dog (dogs only) to make their stay comfortable too!brbrMore reviews can be found on our listing brwww.vrbo.com/2047245br which is both sides together as that is how it's mostly rented.br

Villa

Cozy 'Day' Side Cottage with Heated Pool Pet Friendly No size restrictions

Holmes Beach, Florida, United States

Bed

1

Bath

4

Sleeps

$330.64

Steps to Holmes Beach! 3BR 2BA Beach Bungalow – Walk to Beach with Beach GearbrbrWelcome to your relaxing beach bungalow steps from the light sand and Caribbean-like water on Anna Maria Island. If you’re seeking a true “island vibe” experience, Island Soul Life is the bungalow that will call to your soul.brbrThis location is sought after because of its direct access to a more private section of the beach ushering you into the island vibe where getting your toes in the sand is simple, healing, and grounding.brbrThe spacebrIsland Soul Life Beach Bungalow provides you the peaceful atmosphere to enjoy unforgettable beach days filled with laughter, beautiful memories, and soaking in the best of what nature and Anna Maria Island freely gives.brbrEverything you need for the perfect beach vacation is at Island Soul Life Beach Bungalow, including beach gear and a fully stocked home.brbrThe LOCATION embodies the heart of Anna Maria Island and all it has to offer:br• Beach access across the street – 100 feetbr• Walking distance to the free island trolley stops – 0.2 milebr• Close to Bridge Street’s shops, restaurants, nightlife, and bayfront living – 1.7 milesbr• Close to Anna Maria shops, restaurants, beachside yoga, and more – 3.7 milesbr• A morning stroll leads to close cafes – 0.4 milebr• Publix grocery store – 0.7 milebrbrRequirements (City of Holmes Beach Land Development Code):br• 7-day minimum staybr• Occupancy: 6 personsbrbrThe Space:br3 Bedrooms / 2 Bathrooms – ideal for families, small groups, couples or individualsbr• Primary Bedroom: King bed + en-suite bathbr• Guest Bedroom 1: Queen with smart TVbr• Guest Bedroom 2: Twin trundle bed and deskbr• Extra self-inflating twin air bedbr• Bright, open living space with smart TVbr• Fully stocked kitchenbr• Dining area for shared meals and game nightbr• Designated work spacebr• Washer/Dryer conveniently located in the hallwaybr• Wifi + Smart TVs for streaming and remote workbr• Outdoor, screened deck with dining table & chairsbr• Outdoor showerbr• Parking for 3 vehiclesbr• Professionally cleaned and sanitizedbrbrBeach Gear Included: beach chairs, towels, wagons, umbrellas, small coolerbrbrExtras: Dream On Me travel playard, games, and booksbrbrOutdoor Living:br• Screened outdoor deck with dining table & chairsbr• Outdoor seatingbr• Grill (charcoal and propane)brbrLicense # VRC24-000056brbr“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” (Chapter 4-14, City of Holmes Beach Municipal Code).brbrPet Fee with Approval: $150 taxable pet fee, if pet is approved.brbrProximity to popular destinations:br• Beach Access – 100 feetbr• Free Trolley Stops (2) – 0.2 milesbr• Anna Maria - Pine St – 3.7 milesbr• Bridge St - Bradenton Beach – 1.7 milesbr• Sarasota Airport (SRQ) – 15 milesbr• Tampa Airport (TPA) – 53 milesbr• Busch Gardens – 61 milesbr• Disney World – 93 milesbr• Universal Studios and SeaWorld – 118 milesbrbrGuest accessbrGuests have access to the full house and surrounding yard space (not fully fenced).brbrOther things to notebrFront door code provided for easy check-in and check-out.

Steps to Beach - Prime Location Beach Bungalow – Beach Gear

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$202.15

2BR · 2BA · Sleeps 4 · 30-Night Minimum · Pool & Sound Views · Murphy Bed Office · Granite Kitchen · Two Heated Pools · Tennis Court · Bayfront Grilling Area · Condo Application Required · 2 Parking SpacesbrbrImportant before booking: West Bay Cove 242 requires a minimum stay of 30 nights and a condo application — contact IVP to start the process before booking.brbrA completely renovated two-bedroom condo with pool and Anna Maria Sound views — second floor, quiet community, and a setup that works particularly well for guests who need to work while they're here. The second bedroom is configured as a proper office with a Murphy bed that folds down when sleeping space is needed — a desk, full work-from-home setup, and a real bed when the occasion calls for it.brbrThe kitchen opens directly into the living and dining area — granite countertops, stainless appliances, and enough cabinet space for a month of serious cooking. The windows look out over the pool and water. The dining table seats four and doubles as a workspace for guests who need more than one screen.brbrThe primary suite has a king bed, ensuite bathroom, and the same pool and bay views. Two heated pools and tennis courts are available within the community. The bayfront area has grills and Adirondack seating where guests naturally gather for sunsets. Manatee Beach is a 5-minute walk. Publix and CVS are directly across the street. The free Anna Maria Island trolley stops nearby.brbrWest Bay Cove 242 requires a 30-night minimum stay with parking for two vehicles. Condo application required. brbrNot pet-friendly.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

West Bay Cove 242 · Murphy Bed Office · Pool

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$504.98

Whether you're here for long beach days, sunset strolls, or cruising the island, Groovy Guava makes island life feel effortless.brbr*Features Include* brbr* Private heated pool br* Pool loungers br* Private back patio with outdoor dining br* Propane grill br* Washer and dryer br* 2 bedrooms, 2 full bathrooms br* Ground floor and easily accessible br* 1/2 block to the beach! br* Complimentary 6-seat street legal golf cart for stays through November 28, 2026br* Beach chairs, umbrella and cart brbrSpecial Notice: Complimentary 6-seat street legal golf cart included with all stays through November 28, 2026! Cruise to the beach, restaurants, and island shops with ease while this exclusive perk is still available.brbrWelcome to Groovy Guava, a bright and cheerful island retreat just half a block from the powder-white beaches of Anna Maria Island. This charming two-bedroom half-duplex offers the perfect mix of laid-back beach living and private outdoor space, complete with your own heated pool. brbrInside, Groovy Guava feels welcoming and comfortable with an open living space and a fully equipped kitchen that makes vacation dining easy. Enjoy casual breakfasts before heading to the beach or gather around the dining table after a day of island adventures.brbrWhen you're ready to explore, you are within easy walking distance to some of the island’s favorite spots including The Feast, Freckled Fin, Island Creamery, Hurricane Hanks, and more.brbrStep outside and you’ll discover your own private tropical escape. The fenced backyard is surrounded by lush landscaping and features a sparkling heated pool, perfect for cooling off after a day at the beach. Fire up the grill and enjoy alfresco dining on the patio before heading out to catch one of Anna Maria Island’s famous sunsets.brbrAt the end of the day, retreat to the comfortable primary bedroom featuring a king bed and a private ensuite bathroom with walk-in shower. The guest bedroom offers a queen bed and a Twin XL bed, making it perfect for additional guests or kids. A second full bathroom with tub is located just off the hallway.brbrWith its unbeatable location, private pool, and fun island touches, Groovy Guava is the perfect home base for a relaxed and memorable Anna Maria Island getaway.brbrIf you need space for a larger group of friends or family we are happy to also offer Beach Daze, the other side of this duplex, right next door! brbrPET POLICY:brbrWe are DOG FRIENDLY! A fee of $150 + tax is required in advance for each dog you are bringing.brbr1 pet maximum unless granted an exception. Weight limit of 75 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. brbrVRC16-000148 brbr This home provides off-street parking for up to 2 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.

Groovy Guava by Beach Boutique Rentals

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$479.88

Whether you're spending your days at the beach or relaxing poolside in your private backyard oasis, Beach Daze makes it easy to settle into vacation mode the moment you arrive.brbr*Features Include* brbr* Private heated pool br* Pool loungers br* Beach chairs, umbrella and cart br* Private back patio with outdoor dining br* Propane grill br* Washer and dryer br* 2 bedrooms, 2 full bathrooms br* Ground floor and easily accessible br* Complimentary 6-seat street legal golf cart for stays through November 28, 2026br* Beach chairs, umbrella and cartbrbrSpecial Notice: Complimentary 6-seat street legal golf cart included with all stays through November 28, 2026! Cruise to the beach, restaurants, and island shops with ease while this exclusive perk is still available.brbrWelcome to Beach Daze, a bright and breezy island retreat just half a block from the powder-white beaches of Anna Maria Island. This charming two-bedroom half-duplex offers the perfect blend of comfort, convenience, and laid-back coastal living, complete with a private heated pool.brbrInside, Beach Daze feels welcoming and comfortable with an open living space and a fully equipped kitchen with eat-in dining area that makes vacation meals simple and stress-free. Enjoy casual breakfasts before heading to the beach or gather around the table after a day of island adventures.brbrWhen you are ready to explore, you will be within easy walking distance to some of Anna Maria Island’s favorite dining spots including The Feast, Freckled Fin, Island Creamery, Hurricane Hanks, and more.brbrStep outside and you will discover your own private tropical retreat. The fenced backyard is surrounded by lush landscaping and features a sparkling heated pool, perfect for cooling off after a sunny day on the sand. Fire up the grill and enjoy alfresco dining on the patio before a quick walk to the beach to catch one of Anna Maria Island’s legendary sunsets.brbrAt the end of the day, retreat to the comfortable primary bedroom featuring a king bed and a private ensuite bathroom with walk-in shower. The guest bedroom offers another king bed, creating a perfect setup for couples or small families traveling together. A second full bathroom with tub is conveniently located just off the hallway.brbrWith its unbeatable location, private pool, and easy island charm, Beach Daze is the perfect home base for a relaxed and memorable Anna Maria Island getaway.brbrIf you need space for a larger group of friends or family we are happy to also offer Groovy Guava, the other side of this duplex, right next door! brbrPET POLICY:brbrWe are DOG FRIENDLY! A fee of $150 + tax is required in advance for each dog you are bringing.brbr1 pet maximum unless granted an exception. Weight limit of 75 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.brbrVRC16-000176br brThis home provides off-street parking for up to 2 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.

Beach Daze by Beach Boutique Rentals

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$781.32

Discover this lovely 3-bedroom gem in Holmes Beach. Relax pool side in lush landscaping at our home just 1.5 blocks from gorgeous Holmes Beach. We offer 1 king bedroom with en suite bath and 2 queen bedrooms with adjacent bath on the second floor. Also on the second floor you’ll find a relaxing getaway second family room that includes a queen leather sleep sofa. The main floor boasts a huge great room with a large sectional sofa, dining room table with seating for 6, and tons of daylighting overlooking the pool. The huge covered deck also overlooks the pool and includes dinner seating for eight. With amenities like 5 flat screen smart TV’s, a gourmet kitchen, washing machine, dryer, AC, and WiFi, guests can enjoy a comfortable stay. We're available to answer any questions you have to ensure you enjoy an epic beach vacation on Anna Maria Island!

Playa Palma Private Pool Home 4 Minute Walk to Holmes Beach on AMI

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$906.18

Gulf Pearl by AMI Locals brVRC21-000130brbrWelcome to Gulf Pearl, an exquisite four-bedroom, three and a half bath vacation home on Anna Maria Island! This coastal paradise boasts a sparkling pool, relaxing in-ground spa, and an inviting backyard oasis with a tiki umbrella, poolside bar, and outdoor TV, the perfect setting to unwind, entertain, and soak up the warm island sun. Ideally located two minutes from Holmes Beach, Gulf Pearl offers the ultimate island escape with access to shopping, dining, parks, and endless beach adventures!brbrHighlights br• 2-minute walk to Holmes Beach br• 4 Bedroom / 3.5 Bathbr• 3 Kings, 2 Twin beds, 1 Queen sleeper sofabr• Heated pool and in-ground spa br• Poolside bar and ice maker br• BBQ grill br• Balconies br• In-unit washer and dryer br• 4 car parking br• Central location close to boutique shopping, restaurants, water sports, and parks brbrRelax in your tropical backyard oasis featuring a private heated pool, in-ground spa, and lounge chairs. The outdoor bar and TV create the perfect spot for sunset cocktails or game watching. Dining outdoors is easy with outdoor tables and a BBQ grill. Located just minutes from the Gulf beaches and attractions, and a short ride to shops and restaurants, Gulf Pearl is your ideal island retreat.brbrAscend the first flight of stairs into a bright, airy open floor plan filled with natural light. Large windows offer breathtaking tropical views and amplify the home's relaxed vibe. The living room boasts plush couches, an armchair, and a TV, perfect for unwinding after a day of sun and surf. The kitchen features stainless steel appliances, pots, pans, and utensils, making meal preparation effortless. Dining options include a stylish island bar and a rustic chic dining table, creating an inviting setting for family meals or friendly gatherings.brbrThe home features a primary suite furnished with a king bed, high-end decor, and a spacious ensuite bathroom with a double vanity and walk-in shower, offering privacy and comfort. The second bedroom offers a king bed, ensuite bathroom with a luxurious walk-in shower. The third bedroom has a coastal decor-inspired king bed, while the fourth bedroom is perfect for kids or extra guests with two twin beds. The hall bathroom with a shower/tub combo is shared by the third and fourth bedrooms. A half bath and a sleeper sofa on the second floor add extra space and convenience for all guests.brbrRoom Details br• Primary Bedroom (2nd floor): King bed, ensuite bathroom br• Second Bedroom (3rd floor): King bed, ensuite bathroom br• Third Bedroom (3rd floor): King bedbr• Fourth Bedroom (3rd floor): Two twin beds br• Bonus (2nd floor): Queen sleeper sofabrbrBook Gulf Pearl today and enjoy a luxurious, sun-filled vacation on Anna Maria Island! Whether lounging by the pool, exploring local hotspots, or relaxing on the beach, this home offers everything you need for a memorable getaway. Reserve now and start living your island dream!brbrbr-brThis home does not allow pets.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.brbrThis home is managed by AMI Locals, 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 Locals 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.

Dream Vacation Home with Pool and Spa! On the Beach Block

Holmes Beach, Florida, United States

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Bath

Sleeps

Select Dates for Price

Villa

Tropical Anna Maria Island Villa

Holmes Beach, Florida, United States

Privacy with close stroll to the beach! Beautiful Anna Maria Island Vacation Villa. Sleeps 6 in 3 bedrooms, with 2 full bathrooms and outdoor shower. Luxury at an affordable price. Private location with exotic, tropical landscaping and a nice variety of palm trees. Less than a 2 minute walk to the best white sand beach on Anna Maria Island. The nicest outdoor living spaces of any villa in the area. Screened lanai, plus 2 sun/shade decks that wrap completely around the house. Hi speed wifi works on screened Lanai and decks. Large flat screen TV's in Living room and master bedroom.brbrHeated community pool with less than 20 members, clean pool restrooms, and secure keyed access to pool. Pool is very secluded, but just a one minute walk from Villa.brbrHouse is located in a unique private location with very close proximity to beach. brbrBeach chairs, and more to make your vacation experience more like a visit to a tropical resort!brbrHouse was recently updated with fresh paint and furnishings. Decorated like a fine beach home, not a rental. Meticulously maintained. Quality appliances, well equipped kitchen, dining table for six indoors and another dining table on the screened Lanai.brbrWeber gas grill, wood floors, granite counters, designer furniture, Plus, an outdoor shower with hot and cold water to rinse off after a nice day at the beach, and much, much more.brbrThe Master Suite has a king bed with full bath in suite. Guest Suite #1 has a queen bed, guest suite #2 has a full sized bed. The 2 guest rooms share a full bath that is private, just a few steps from both rooms. House was decorated by a professional interior designer with an emphasis on Relax.....brbr10 cup traditional coffee maker, 4 slice toaster, and more.brbrHi Speed Wi-Fi, 65 inch-High-Definition TV.brbrTropical vacation villa on a private drive with just 6 homes. This home features the perfect combination of a secluded location, and being very, very close to the beach. A short walk on the beach to the Sandbar beachfront restaurant or Cafe on the Beach. Have breakfast, lunch or dinner with your toes in the sand!brbrAnna Maria Island is a very friendly place with some of the best beaches in Florida. Fine dining and family style restaurants are close by. Publix Supermarket is just a 4 minute drive by car. Great boutique shopping, sun bathing, fishing, boating, shelling and everything for your tropical island vacation are just moments from this special home.brbrFree trolley service is available to take you all over the island and Publix grocery store.brbrI hope you can come and visit my little piece of paradise in Holmes Beach on Anna Maria Island. Anna Maria Island was voted one of the best 30 islands in the World by Conde Nast Traveler Magazine in November 2014.brbrThis is the nicest home for the price in the area. Certainly one of the 3 nicest Villas in North Beach Village. The most private location, closest stroll to the beach in North Beach Village too. Amazing outdoor decks and screened porch areas to enjoy the Florida Island lifestyle!brbrThere isn't a nicer vacation home available on Anna Maria Island for this price. brbrMake this a beach vacation to remember in your Tropical Anna Maria Island Villa. Authentic Florida at its finest. brbrKeywords: Tropical Villa

Bed

Bath

Sleeps

$338.26

Blissful Beach RetreatbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWelcome to paradise by the beach! An opportunity like this doesn't come around often, as this home is located west of Gulf Drive and steps away from the Gulf of Mexico. The secluded location is away from the traffic noise and just steps to a private beach, so you will have your own sense of peace and quiet away from it all. The newly remodeled kitchen is absolutely adorable with bright accents and modern appliances, and a brand new Roman-style pool and spa await out back. The first floor features a separate bedroom and bath that would be ideal for elderly family members or teenagers who want a little separation from the adults upstairs. This beach shack is situated on an extra-large lot and has been owned by the same family for generations with much love. Relax on the front porch for morning coffee with Gulf breezes and then gather around the firepit in the evenings.brbrThings to KnowbrPool heat is included and maintained at 80°F. Additional pool heat to 85°F is available upon request for $32 per day plus tax. A 48 hour notice is required. Heat may not be available if temperatures drop below 65 degrees. We will not be accepting payments for pool heat for the months of May through OctoberbrSnowbird-friendlybrThis property has a 7-night stay requirement.brThis property's maximum occupancy is limited to 6 guests. brCode enforcement notification: 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.brbrParking notes: There is free parking available for 3 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

Updated Beach Escape with Private Pool, Spa & Fast WiFi - Walk to the Gulf

Holmes Beach, Florida, United States

Bed

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Sleeps

$393.42

Welcome to the Nautilus 103!brVRC25-000019brWe are 34 individually owned and uniquely decorated condominiums available for vacation rentals. We occupy one entire block right on the Gulf of Mexico on Anna Maria Island. No streets to cross to get to the beach here—just a few steps to our beautiful 7-mile white sand beach. Many visitors are content to while away the day under an umbrella, soaking up the sun and sea breeze.brbrTake a swim in our heated swimming pool or in the warm Gulf waters, or enjoy a game of tennis or pickleball. You can be as active as you'd like here, though a lazy day on the beach might make your vacation exactly what you're looking for!brbrThis inviting 2-bedroom, 2-bathroom downstairs poolside condominium comfortably accommodates up to 4 guests for a minimum of 7 night stay. Enjoy your morning coffee or evening dinner on your private outdoor patio, or explore the local restaurants for a wonderful variety of dining choices. From casual burgers to elegant bistros, breakfast, lunch, or dinner—you'll find plenty of delicious options on this charming island.brbrCome stay with us and discover what makes The Nautilus a perfect vacation destination. Take a leisurely walk, ride your bike, or hop on Anna Maria's free trolley service (trolley stop just one block away!) for sightseeing and shopping. Experience the laid-back island charm and natural beauty that make Anna Maria Island such a beloved getaway!brbrPROPERTY HIGHLIGHTSbrPrime Location: Wake up to ocean breezes and fall asleep to the sound of gentle waves. This oceanfront complex puts you mere steps from Anna Maria's renowned white sand beaches, where you can spend your days swimming, sunbathing, or searching for shells.brbrPoolside Convenience: Step directly from your front door onto the pool deck, making it easy to alternate between refreshing dips in the pool and relaxing ocean swims.brbrFully Equipped Kitchen: Prepare everything from morning coffee to gourmet meals in the well-appointed kitchen, perfect for enjoying fresh seafood or preparing beach picnics.brbrComfortable Accommodations: The property features two spacious bedrooms and two full bathrooms, providing ample space for families or friends to unwind after sun-soaked days.brbrPrivate Patio: Enjoy your morning coffee or evening cocktails in your own private outdoor space, where you can soak in the coastal atmosphere.brbrOn-Site Recreation: Stay active with the complex's private tennis/pickleball court, perfect for pickleball and tennis enthusiasts looking to add some friendly competition to their beach vacation.brbrFree Trolley Access: Explore the island with ease! The complimentary Anna Maria Island trolley stop is just one block away, providing convenient transportation to shops, restaurants, and attractions throughout the island.brbrProperty GuidelinesbrbrNoise Ordinance: 65 dB (7 AM-10 PM) | 50 dB (10 PM-7 AM)brProhibited: Trailers, boats, jet skis, smoking, illegal substancesbrPlease observe all posted Nautilus community rulesbrbrOnsite Laundry FacilitybrbrTHE ANNA MARIA EXPERIENCEbrAnna Maria Island is renowned for its laid-back island atmosphere, stunning sunsets, and sugar-sand beaches. From your doorstep, explore charming local restaurants, a range of unique shops, and endless water activities. Whether you're seeking adventure or relaxation, this oceanfront retreat provides the perfect base for your Florida beach getaway.brbrBook now and start counting down the days until your toes are in the sand!

Nautilus 103 by Nautilus Vacations-Beachfront Complex, Heated Pool, Racket Court

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$221.63

You'll feel like royalty when you check into this pristine two bedroom, two bath home tucked away in Key Royale on Anna Maria Island. Lovingly designed for comfortable living, this special home is the perfect place to relax and enjoy the pleasures of island life.brbrZoning in this area requires a minimum stay of one month, so you'll have plenty of time to settle in and get to know your surroundings. Once you've arrived, you'll realize no one wants to be here for less than a month anyway!brbrKey Royale is an island within an island, about as close as you can get to a private community in these parts. Anna Maria's only golf course is the centerpiece of the community, and gives the area its special cache. If you love to walk, you'll be able to step right out your front door and wander the warren of canal-side streets, past mansions on the Bay and other less-palatial but equally attractive homes lined up for your enjoyment. Because of its location tucked along the east side of Anna Maria Island, many visitors may never even know it's there, adding to the overall sense of privacy and seclusion.brbrA five-minute bike ride, however, will take you back to Gulf Drive and the free Island Trolley traveling north to the village of Anna Maria. Or head a little further west to catch the southbound trolley to restaurants, shopping, and various area attractions you won't want to miss during your visit. The beach, of course, stretches the length of the island, and you can access it wherever you like.brbrAt home you'll enjoy the large, open concept kitchen/dining/living space, with a spacious, well-equipped kitchen so enticing that even people who don't like to cook may feel tempted! There's also a wet bar with its own drinks, fridge next to the dining table, and views of the very large smart TV from every part of the room. Another comfy seating area is tucked away just beyond, perfect for a cozy chat with a friend or for reading while others are watching TV. Rounding out the amenities of the main living area is a hidden sleeping corner, where two additional guests can bunk down.brbrA full laundry room leads to a one-car garage, where you can stow your beach supplies or even plug in a golf cart.brbrBoth of the bedrooms are located along a hallway that sits off to the side as you enter the home. The primary bedroom features a king bed, smart TV, and ensuite bath, while the second bedroom features a queen bed. The second bathroom is located in the hallway between the two bedrooms, easily accessible to either the bedroom or the main living area. Both bathrooms feature walk-in showers.brbrAs inviting as the inside of the house is, you're also here to enjoy the Florida weather, and this is the place to do it! As you head out the back door you'll find a pergola, home to a gas grill and a dining table that seats four. It's a terrific spot to enjoy dining al fresco. But the amenities don't stop there! Around the corner you'll find a pavered patio area that's nothing short of a tropical oasis, with more dining options, chaises for sunning, and even a gas heater for chilly evenings, all tucked behind a privacy fence and lush landscaping for a real sense of solitude.brbrYou may bring along ONE canine companion weighing less than 25 pounds to Royale Retreat. Please inform the management company office when they contact you after booking. They'll add a non-refundable pet fee to the total price that was quoted to you. (Some breeds may be excluded due to insurance).brbrPlease note: This home sleeps a total of six people in one king bed, one queen bed, and one hideaway bed. The desk shown in these photos has since been replaced by the two-person hideaway bed. Occupancy limits are strictly enforced by the City of Holmes Beach.brbrOur Cancellation Policy: In order to protect our owners from loss of income, ALL MONIES PAID TOWARDS YOUR RESERVATION MAY BE NON-REFUNDABLE AFTER A CERTAIN DATE! FULL AND PARTIAL REFUNDS MAY BE GIVEN UNDER CERTAIN CONDITIONS. Ask our office for details, or check your rental agreement.brbrPer City of Holmes Beach code: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 property.brbrCity of Holmes Beach Vacation Rental License: VRC23-000108

BOOK THE MONTH FOR THE PRICE OF A WEEK!!! Spacious 2BR/2BA Home in Key Royale | Golf Community | 1-Month Minimum Stay

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$437.88

Coconuts Poolside #104 by AMI Locals brVRC16-000664 brbrWelcome to Coconuts Poolside #104! Enjoy the luxury of a dreamy one-bedroom, one-bathroom condo with direct access to the shared heated pool and just steps from the sands of Anna Maria Island beaches. Located in the heart of Holmes Beach, this modern ground-floor apartment combines cozy comfort, vibrant coastal decor, and ultimate convenience for your next island getaway. brbrHighlights br• Gulf-Front Condo br• 1 Bedroom / 1 Bath br• 1 King bed, 1 Queen Sleeper Sofa br• Direct Pool Access from Lanai br• Steps to the Beach br• Updated Furnishings br• Shared Heated Pool br• Lanai with Outdoor Seating br• Centrally Located Near Shops and Restaurants br• One Assigned Parking Spot brbrStart your mornings sipping coffee on the lanai, enjoying the island breeze and sounds of waves crashing just beyond the palm trees. The shared heated pool is perfect for cooling off between beach trips, just steps away, where sunsets are magical and relaxation comes naturally. Whether you’re reading a book on the lanai, lounging by the pool, or exploring the island, you’ll feel right at home in paradise. brbrInside, a bright and open concept living and dining area offers the perfect space to unwind after a day on the beach or by the pool. This condo is newly remodeled with stylish decor, modern furnishings, and thoughtful touches to make your stay extra special. The fully stocked kitchen has everything needed to prepare meals and snacks, including a breakfast bar for quick meals or additional seating. brbrEnter your private sanctuary in the primary bedroom, featuring a luxurious king bed and ample storage for your island gear. A hall bathroom includes a walk-in shower and space for all your essentials. The living room provides additional sleeping space with a queen sleeper sofa available for extra guests. brbrRoom Details br• Primary Bedroom: King bed br• Living Room: Queen sleeper sofa br• Hall Bathroom: Shower and tub combination brbrTake a short walk to nearby restaurants, local boutiques, a grocery store, and a surf shop or hop on the AMI trolley to explore even more of the island. The on-site laundry facility adds a touch of convenience to extended stays. brbrWhether you're planning a romantic getaway, a solo retreat, or a laid-back beach vacation, Coconuts Poolside #104 delivers the island charm you’ve been craving. brBook Your Beach Getaway Today! brbr- brThis home does not allow pets. brbrThis home is managed by AMI Locals, an Anna Maria Island property management company. brbr1 car maximum is 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 AMI Locals 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. brbr*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Beach Condo with Pool Near Holmes Beach!

Holmes Beach, Florida, United States

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Select Dates for Price

Looking for a beach vacation that can accommodate multiple groups This is the location for you! Turtle Beach is is the perfect combination of two properties that create the perfect setting for larger groups traveling together. The main property is an elevated three bedroom, 3 bathroom home with gulf views from every room and a private heated pool! brbrThe second property is a ground level two bed and two bathroom home with a large porch with beautiful gulf views that leads directly onto the white sandy beach. As an added bonus, a heated pool and hot tub have been added in late 2023. Each property includes a full kitchen, dining, and living room. brbrUnit 105: Beach LifebrSLEEPING ARRANGEMENTS (Sleeps 4):brPrimary Bedroom: KingbrSecond Bedroom: Two TwinsbrbrBATHROOMS:brPrimary En-Suite: Double Vanity Sink, Walk-in ShowerbrSecond Bathroom: Walk-in ShowerbrbrUnit 107: Turtle WatchbrSLEEPING ARRANGEMENTS (Sleeps 6):brPrimary Bedroom: KingbrSecond Bedroom: QueenbrThird Bedroom: Two TwinsbrbrBATHROOMS:brPrimary En-suite: Shower Tub CombobrSecond Bathroom: Shower Tub CombobrThird Bathroom: ShowerbrbrPETS: Dogs are allowed with prior approval. Must be a non-aggressive breed and well-trained. 2 dogs max. A $150 non-refundable pet fee applies per pet.brbrPARKING: 5 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.brbrVRC16-000688brVRC23-000083

Turtle Beach: 2 Homes, Sleeps 10, Gulf Front with 2 Pools!

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$1761.61

If your goal is to experience the best beach views that Anna Maria Island has to offer then look no further! This amazing 3 bedroom and 3 bathroom elevated home sits directly on the edge of the sands and overlooks the pristine Gulf beaches from every bedroom—not to mention the Gulf-facing private heated pool!brbrSit back and relax as you get to watch the sunset from the privacy of your own living room or step out to the open-air balcony. The Master suite offers a sweeping view of the Gulf waters from its large windows designed to offer the best sights of the world-renowned beaches. The second and third bedrooms also both offer fabulous Gulf views that just can’t be beaten!brbrHidden away off a quiet residential street on Holmes Beach, you are still just a short walk or bike ride away from the island’s only fully stocked grocery store, delicious local restaurants, and island boutiques. Come and get away from it all at the beautiful Turtle Watch! brbrDirect Gulf front elevated private home with private access to the beachbrPrivate heated pool facing the GulfbrGulf views from every bedroombrClose to local shops and restaurantsbrMaster suite has incredible beach viewsbrOpen air balcony from the living roombrOn our Professional Linen ProgrambrbrbrSLEEPING ARRANGEMENTS (Sleeps 6):brPrimary Bedroom: KingbrSecond Bedroom: QueenbrThird Bedroom: Two TwinsbrbrBATHROOMS:brPrimary En-suite: Shower Tub CombobrSecond Bathroom (Upstairs): Shower Tub CombobrThird Bathroom (Main Living Level): ShowerbrbrBEACH ACCESS: There is direct access to beach through gate in pool area.brbrPETS: Dogs are allowed with prior approval. Must be a non-aggressive breed and well-trained. 2 dogs max. A $150 non-refundable pet fee applies per pet.brbrPARKING: 2 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.brbrParking Spaces: Driveway underneath building and far east side of driveway. Please park where signs indicate. Leave driveway clear at all times.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.brbrVRC23-000083

Turtle Watch: *Gulf front *Heated Pool *Spectacular Views

Holmes Beach, Florida, United States

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