Vacation Condo Rentals By Owner In Holmes Beach, FL

Comfortable family-friendly condo close to everything on Anna Maria.

Holmes Beach, Florida, United States

This stylish coastal getaway at Sandy Pointe is a spacious 2-bedroom condo, centrally located on Anna Maria close to shops and restaurants and a short walk from the beach. The condo is decorated to a high standard with a well-equipped kitchen, washer and dryer, dishwasher, flat-panel TVs, and unlimited hi-speed WiFi. The screened-in balcony affords comprehensive views over the natural mangrove preserve which ensures tranquility and relaxation.brbrSandy Pointe has a large swimming pool and a community launch for kayaking in the secluded bays around Palma Sola.

2

Bed

2

Bath

6

Sleeps

$269.66

/ Nightly

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Charming island condo with heated pool near beach & trolley

Holmes Beach, Florida, United States

Bay Dr 106brbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWelcome to your charming island retreat in Holmes Beach, FL! This delightful condo is just five blocks from the pristine shores of Anna Maria Island, making it the perfect getaway for beach lovers and nature enthusiasts alike. With a shared heated pool and easy access to the island's highlights, you can enjoy the best of both relaxation and adventure during your stay.brbrNestled in the heart of the island, this condo is a stone's throw from Grassy Point Nature Preserve, where you can immerse yourself in the beauty of 34 acres of scenic wetlands and mangroves. Take a leisurely stroll or hop on the free island trolley to discover local favorites like Holmes Beach Plaza, Peaches, and Old Hamburg Schnitzelhaus. With two covered parking spaces, exploring the area is a breeze.brbrAfter a sun-soaked day, unwind by the heated community pool or relax on the second-floor screened lanai, which offers serene views of the preserve. Inside, the condo features a cozy living area equipped with a flat-screen TV and free WiFi, perfect for unwinding after a day of adventure. The well-equipped kitchen provides ample counter space and everything you need to prepare delicious meals, best enjoyed at the dining table with tranquil nature views.brbrWhether you're here for beach days, wildlife watching, or simply to embrace the island lifestyle, this dog-friendly condo is the ideal place to settle in and savor all that Anna Maria Island has to offer. Book your stay today and experience the charm of island living!brbrThis property has a 7-night stay requirement. However, select properties have the flexibility for shorter stays. Let us do the searching for you! brPlease note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!brCity of Holmes Beach VRC17-000019brHeated Pools may not be available if temperatures drop below 65 degreesbrWe will not be accepting payments for pool heat for the months of May through October.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.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. No more dogs are allowed.brParking notes: There is free parking available for 2 vehicles.brThis rental is located on floor 2.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 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

2

Bed

2

Bath

6

Sleeps

$271.75

/ Nightly

Condo

5400 - Condo 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. 55+

Holmes Beach, Florida, United States

Bed

Bath

Sleeps

$370.57

/ Nightly

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Anna Maria Island Direct Beachfront Condo- Awesome View and Amazing Sunsets

Holmes Beach, Florida, United States

brView dolphins, terns, gulls, sandpipers, and other shorebirds from your 22 foot wide screened lanai. Walk directly out to the beach. In summertime manatees often swim past in shallow water.brbrBecome one with nature as soothing ocean waves gently lap and crash against our beach shoreline, whispering in your ears.brbrSee extraordinary sunsets almost every evening.brbrBreathtaking sunsets, strolls along the white, sandy beach, and the direct Gulf view are only a few of the perks of spending your vacation in this comfortable beachfront condo. Savor the warm, salty breeze as you relax on the lanai overlooking the Gulf of Mexico. Soak up the sun and listen to the waves in a lounge chair or build sandcastles on the beach.brbrThis comfortably appointed two-bedroom, two-bath + den direct Gulf front condo is in a small 12-unit complex - no crowds, just a quiet, peaceful beach with sea oats, dolphins, terns, gulls, pelicans shorebirds, sometimes a few old-time fishing boats, and even a few rare shorebirds such as American Oyster Catchers or Black Skimmers.brbrWhen you take a break from the beach, you can appreciate the spacious living room and fully equipped kitchen with granite countertops. Or cozy up with a book in the den.brbrEnjoy meals indoors from your dining area with exquisite Gulf Views. Step onto the lanai for even better views or outdoor dining beachside. brbrThe two bedroom suites, each with a dressing area, bathroom, and street-side balcony, are the perfect place to rest after a long day in the sun. brbrThe master bedroom suite has a queen-size bed, TV and a desk for your computer. brbrThe second bedroom suite has two twin beds and a TV. brbrThe lovely den has a full- size sleeper sofa, a comfortable armchair and a flat-screen TV on the wall.brbrProfessional linen service provides the bed and bath linens as well as beach towels. brbrVRC-16-000037 - Local ordinances require guest stays of at least 7 nights. brbrMax 2 Vehicles allowed onsite. One assigned parking Space. Additional parking on first come basis. brbrNoise Notice as required by The City of Holmes Beach:brYou 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.

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Bath

Sleeps

$197.75

/ Nightly

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Sandy Point get away on AMI excellent location

Holmes Beach, Florida, United States

Quiet location, removed from the street, turn down the drive & crossover wooden bridge and arrive at Sandy Pointe Condominiums 26 units. The unit over looks the pool. close to shopping & free public bus all within waliking distance. the complex is next to a nature preserve( Grassy Point), Quite location away from street traffic and noise. VRC License # 22-000222

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Bath

Sleeps

$372.22

/ Nightly

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AMI Dreaming: Gulf View Condo, Steps to the Beach, Resort Pool by Anna Maria Life Vacation Rentals

Holmes Beach, Florida, United States

AMI Dreaming by Anna Maria Life Vacation Rentalsbr4200 Gulf Dr #105, Holmes Beach, FL 34217brbrWhat You'll Love About This Home:brLocation! On the Beach! Next to Manatee Public Beach!br2 bedrooms / 2 Bathroomsbr1 King, Twin over Double Bunkbed, Queen Sofa BedbrHeated Resort PoolbrPool LoungersbrElevator in Building (2nd Floor Condo)brOpen Air Balcony With Patio Furniture to Enjoy the Gulf ViewsbrCovered Patio Dining for 6brProfessional Linen Service, Washer & DryerbrComplimentary WIFIbrBeach Towels & Beach ChairsbrParking for 2 Cars in Covered LotbrbrDetails:brWith an excellent location at the Gulf Sands condo resort and amazing gulf views, AMI Dreaming will wake you up to the beach lifestyle and the shimmering turquoise waters of the Gulf of Mexico.brbrThe living area is a comfortable spot for the family to gather. Open the sliding glass doors to let the sea breeze in. The gulf facing balcony features patio dining for four and offers amazing views.brbrThe master bedroom includes a king bed, en suite bathroom and gulf views. The guest room has a set of twin over double bunk beds. A queen sofa bed in the living room adds another sleeping option. Each bedroom includes crisp linens and plush towels in the bathrooms from our professional linen service. Your guests will stay connected with complimentary WIFI and enjoy all of the comforts of home, including a washer and dryer.brbrThe condo resort pool and spa are steps from the sand. Relax in a pool lounger and enjoy the island breezes of paradise.brbrYour reservation also includes two covered parking spaces beneath the building.brbrAMI Dreaming is easy walking distance to Publix, restaurants, Manatee Public beach, and the free island trolley, which travels the entire length of the 7 miles of the island. Hop on and off at your leisure and explore shopping, dining and the beaches. The perfect location for your next beach vacation!brbrBedroom 1 - King Bed, Ensuite Bathroom, TVbrBedroom 2 - Twin over Double Bunkbed, TVbrQueen Sofa Bed in the Living RoombrbrPlease note:brPets are not allowed in this home.brAmenities are subject to change.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. The minimum requirement for this home is no less than seven nights. The maximum occupancy is six.brbrVRC19-000072brbrIMPORTANT INFORMATION: brbrYour booking is with Anna Maria Life Vacation Rentals. We will send you check-in instructions 14 days prior to your arrival date. We will send you our rental agreement in an electronic signature document. Please review and return to us by following the instructions.brbr** Your signed rental agreement must be returned in order to receive your check-in details. brbrVRBO BOOKINGSbrbrAnna Maria Life Vacation Rentals will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee. brbrYour final balance is due 60 days prior to your arrival date. We will send you a final payment reminder 90 days prior to arrival. We do not automatically charge your card for your final balance. brbrThe instructions for making your final payment will be included in your final payment reminder.brbrPlease review the cancellation policy prior to booking. brbrGOOGLE VACATION RENTAL BOOKINGSbrbrYour payment is due in full at the time of booking and the final balance information above does not apply to your reservation. brbrGolf Cart DEAL ALERT!!! brReserve now a street legal GOLF CART from Fun & More Rentals! 4, 6 or 8 passenger gas or electric carts to choose.brFUN way to explore the island for the entire family.brMention Anna Maria Life Vacation Rentals and receive this VIP deal!brwww.FunAndMoreRentals.combr941-462-2719

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Sleeps

$933.22

/ Nightly

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Beachfront Condo with Pool

Holmes Beach, Florida, United States

Located on beautiful Anna Maria Island, La Plage 10 is one of only six units on the Island that have a full beachfront view and a beach facing pool. Experience a luxurious beach vacation with over 2300 hundred square feet of gorgeous living space and an expansive balcony overlooking the pool, beach and the gorgeous Florida Gulf sunset.brThe Kitchen is stocked with essential cookware. You can enjoy dining in the dining room or on the balcony with gorgeous sunsets.brNo events or partiesbrNo pets

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Bath

Sleeps

$216.33

/ Nightly

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West Bay Cove 216 · Pool Views · 30-Night Min · Renovated 2026

Holmes Beach, Florida, United States

VRC20-000192brbr2BR · 2BA · Sleeps 4 · 30-Night Minimum · Two Heated Pools · Tennis Court · 5-Min Walk to Manatee Beach · Condo Application Required · 2 Parking Spaces · Completely renovated in 2026brbrImportant before booking: West Bay Cove 216 requires a minimum stay of 30 nights and a condo application — contact IVP to start the process before booking.brbrA two-bedroom condo in the heart of Holmes Beach with two heated pools, a tennis court, and a 5-minute walk to Manatee Beach on the Gulf. Publix, CVS, shops, and restaurants are all within easy walking distance. The free Anna Maria Island trolley stops nearby — a car is not needed for daily island life.brbrTwo bedrooms sleep four. The primary suite has a king bed. The guest bedroom has two twin beds. Two full bathrooms. Flat-screen TVs in the living room and primary bedroom. High-speed WiFi included.brbrWest Bay Cove 216 requires a 30-night minimum stay with parking for two vehicles. Condo application required. Not 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

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Bath

Sleeps

$157.94

/ Nightly

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West Bay Cove 226 · Kayak Launch · For Sale

Holmes Beach, Florida, United States

VRC20-000180brbr1BR · 1BA · Sleeps 6 · 30-Night Minimum · Kayak & Paddleboard Launch · Two Heated Pools · Tennis Court · 5-Min Walk to Manatee Beach · Condo Application Required · For Sale — Showings with 24-Hr Notice · 2 Parking SpacesbrbrImportant before booking: West Bay Cove 226 is currently listed for sale. Occasional showings may be scheduled during your stay with a minimum of 24 hours notice. If that's a concern, worth knowing before you book.brbrAlso before booking: West Bay Cove 226 requires a minimum stay of 30 nights and a condo application — contact IVP to start the process before booking.brbrA one-bedroom condo in Holmes Beach with a kayak and paddleboard launch located in the northeast corner of the property — direct water access for guests who want to explore Anna Maria Sound without leaving the complex. Two heated pools, a tennis court, and an outdoor sitting area are also available within the community.brbrThe unit sleeps six with a queen bed in the primary bedroom, a sofa sleeper, and bunk beds — a practical configuration for a small family or mixed group staying a month or longer. Flat-screen TVs in the living room and bedroom. High-speed WiFi included.brbrManatee Beach on the Gulf is a 5-minute walk. Publix, CVS, shops, and restaurants are all within easy walking distance. The free Anna Maria Island trolley stops nearby — a car is not needed for daily island life.brbrWest Bay Cove 226 requires a 30-night minimum stay with parking for two vehicles. Condo application required. Not 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

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Bath

Sleeps

$349.97

/ Nightly

Condo

Ocean Front ~ No Streets To Cross! Come And Enjoy A Memorable Beach Vacation!

Holmes Beach, Florida, United States

This complex at 7100 Gulf Drive is well managed, impeccably maintained and has a reputation of being one of the island's best! brbrEnjoy the white sandy beach directly in front of the complex, soak in the recently renovated community pool, or play a game of tennis (courts have lights). The complex is on the island's free trolley route and there is a stop just up the street on 78th and Gulf Drive. The trolley makes it easy to hit up the local shops, grab a bite to eat or to just sit and enjoy the scenery as you travel the length of the island. brbrThis 2nd floor, end unit has two bedrooms, two bathrooms and is fully furnished. The condo was updated with new flooring, granite countertops, area rugs & some new furniture in December of 2021. The main/master bedroom has a king sized bed and attached bathroom. This bathroom was renovated in October of 2019. The second bedroom is furnished with two twin sized beds and offers quick access to the second bathroom. Televisions are located in the master bedroom and living room. The kitchen is well-equipped with everything you need for basic cooking. The private terrace offers a glimpse of the Gulf of Mexico and is perfect for eating breakfast or enjoying a glass of wine in the evening! We have beach chairs for you to use. If you need additional chairs, you can ask the onsite property manager.brbrThe complex has a laundry room, so it's possible to do your laundry on site. The unit has one reserved parking spot, but additional parking is available.br

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Bath

Sleeps

$497.13

/ Nightly

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Cool Breeze by Beach Boutique Rentals

Holmes Beach, Florida, United States

Looking for the ultimate beachfront vacation experience Look no further than Cool Breeze, a stunningly remodeled 2 bedroom, 2 bathroom condo rental in Holmes Beach!brbr*Features include* brbr* Beachfront condo complex br* 2 full bedrooms and 2 bathroomsbr* Modern kitchenbr* Balcony with full beach viewbr* Plenty of room to sleep 6br* Washing machine in unitbr* Public laundry room with pay washer/dryerbr* Beautiful heated community pool^br* Tennis and Pickleball courtsbr* Premier Holmes Beach locationbr* One (1) assigned parking space brbrLocated in a small complex right on the beach, this spacious and beautifully appointed condo boasts everything you need to make your stay comfortable, luxurious, and unforgettable. From the stunning gulf views to the community pool just steps away, you'll find yourself surrounded by the very best that Anna Maria Island has to offer.brbrInside, you'll find modern and comfortable furnishings, as well as all of the amenities you need to make your stay as enjoyable as possible. From a fully equipped kitchen to high-speed internet and cable TV in every room, you'll have everything you need to feel right at home.brbrCool Breeze features two bedrooms and two full bathrooms ensuring that you and your guests have plenty of space to relax and unwind. The master suite features a king bed and attached private bath. The second bedroom also offers a king bed and shares the hallway bathroom. With the bonus den that includes a queen bed, this condo can sleep up to 6 people comfortably. Please note this den is separated from the main living area by a privacy curtain.brbrOf course, the real star of the show is the breathtaking beachfront location. Whether you're relaxing on your private balcony with table for two or taking a dip in the community pool, you'll enjoy views of the beautiful Gulf waters. With direct access to the beach, you can spend your days swimming, sunbathing, or simply strolling along the sand. (Please see important pool disclaimer below.)brbrDon't miss out on the chance to experience the very best of Anna Maria Island beachfront living. Choose Cool Breeze and start planning your dream vacation!brbr^IMPORTANT: When the air temperature drops below 70 degrees the HOA will close the pool with the solar cover. Unfortunately this is the decision of the HOA and Beach Boutique Rentals has no control over the issue. Additionally the HOA has the right to close the pool for any reason and Beach Boutique Rentals has no control over this decision.brbr* Please note this condo allows 1 assigned parking space and additional guest parking is available on a first come, first served basis. Please keep in mind that if the elevator becomes inoperable for any reason, the stairs will be only way to access the unit.brbrADDITIONAL 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. brbrVRC23-000039 brbrThis 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.

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Bath

Sleeps

$221.97

/ Nightly

Condo

West Bay Point Moorings 42 - Condo 2 Bedroom/ 2 Bath , maximum occupancy of 6 people.

Holmes Beach, Florida, United States

West Bay Point Moorings 42 - Anna Maria Island - Condo 2 Bedroom/ 2 Bath , maximum occupancy of 6 people. VRC#20-000124br Distance to the Beach: 7 blocksbr Community pool.br Please ask for Long-term specials. br br Relax and enjoy the tranquility of West Bay Point Moorings with its panoramic view of Tampa Bay. br Your vantage point for these spectacular views is a condo located in the unique Anna Maria Island resort style complex of West Bay Point & Mooring, tucked away in the City of Holmes Beach.br br br Your remodeled and spacious Island retreat hosts a coastal flair throughout with master and guest bedrooms featuring luxury linens and en suite baths. Open your floor-to-ceiling rear slider doors and a soft breeze will flow through your master suite and beyond! The gourmet kitchen with its full array of items and view-line of the waterfront will enhance your cooking experiences. br br In addition, you will enjoy the complex's amenities that include lush tropical landscaping, a heated swimming pool, and tennis courts.br *This condo association does not permit motorcycles, trailers, large trucks, or RV parking on their property.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 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 propertybr Amenities Include:br - # Bedrooms: 2br - Bed Sizes: King, Kingbr - Sofa Sleeper: trundle bed in guestbr - # Baths: 2br - Tub or Shower: t/sh and showerbr - Balcony: Deckbr - Pool: 2 Community poolbr - Pool Heat Avail: Yesbr - #of units in complex: 6br - Tennis: Yesbr - Square Feet: 1458br - Floor Number: groundbr - Distance to Beach: 7 BLOCKSbr - Internet: wifibr - View: Bayoubr - washer dryer: yesbr - Dishwasher: yesbr - Boat Dock: Yesbr - Maximum Persons: 6br - TV: yesbr - Phone: yesbr - Hairdryer: yesbr - Type of Parking: open

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Bath

Sleeps

$315.07

/ Nightly

Condo

Happy, Beachy Holmes Beach Condo Tennis, Heated Pool, Elevator Anna Maria Island

Holmes Beach, Florida, United States

Just Bring You to this beautifully appointed bright beach condo. Feel the island vibe with modern beachy furniture with comfortable beds just steps from beach with elevator, 2 bedrooms, 2 bathrooms, 2 porches (1 screened-in), 3 bikes and everything (really, everything!) you need for a happy, relaxing beach getaway! Rest by the beach or pool and take an elevator to your modern cottage-style beach condo with washer-dryer, dishwasher, a Guest Room with 1 Full and 1 Twin bed and a Master Bedroom with 1 super comfortable King bed. Park easily in your spot in the covered garage. On beach side of Gulf Drive, so you don't even have to cross the street and you are toes-in-the-sand in minutes! Our porch looks out to trees on the side of the building. Walk down and take a short well-manicured path to beach. Well-maintained heated pool and tennis courts. Close to stores (Publix, CVS), restaurants (like Hurricane Hanks, The Sandbar, Blue Marlin, The Waterfront, The Beach House, our faves!) and minutes to walk to *FREE* trolley stop (runs until 10p). Enjoy 3 Flat screen TVS - 1 per bedroom and 1 in living room, all with Cable. Free WiFi. Fresh furnishings, towels (bath and pool towels) and bedding. Guest Bathroom Reno completed December 2025 ; Brand new Washer / Dryer December 2025. Master Bedroom Reno Jan 2022. We are available by text, phone and email to answer any of your Qs at any time. We love it here on AMI, and you will too! Great for couples and families (supplied with a pack and play, board games and a bin of toys) and perfect for celebrating anniversaries and birthdays - we've hosted many Anniversary and Birthday celebrations! 1 Labeled 103 parking spot, Additional Guest parking spots. Please Note Per Holmes Beach: 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. LICENSE # VRC17-000175

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Bath

Sleeps

$266.95

/ Nightly

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Palm Isle Village 3208 - Charming Beachside Condo | Island Real Estate

Holmes Beach, Florida, United States

Disclaimer: Discoloration in the pool is from staining, not dirt or debris in the pool, and the pool is safe and clean for swimming.brbrUnwind in island comfort at Palm Isle Village 3208, a beautifully maintained 2-bedroom, 1-bath condo just steps from the beach on the Gulf side of Holmes Beach. This inviting rental offers a peaceful setting, Gulf views from the private balcony, and access to a shared pool, all within walking distance of shops, dining, and local attractions.brbrPerfect for couples or small families, this home comfortably sleeps up to 4 guests. The spacious primary bedroom features a king bed, while the guest room includes a queen bed, providing a restful space to relax after long days in the sun.brbrStart your mornings with coffee on the private patio, then head out to explore the nearby white-sand beaches, just across the street. Prefer a slower pace Hop on the free Anna Maria Island trolley to enjoy car-free access to Bradenton Beach, Pine Avenue, and beyond.brbrInside, the condo is filled with natural light and decorated with coastal-inspired touches. The fully equipped kitchen has everything you need for at-home meals, and the breakfast bar doubles as a convenient workspace. With free WiFi, central air conditioning, a private washer/dryer, and parking for two vehicles, every detail is covered.brbrAfter a day of adventure, cool off in the shared pool, fire up the gas grill for a BBQ dinner, or stroll to the beach to catch a stunning sunset over the Gulf.brbr*Disclaimer: Please note that the widow watch for this unit is currently under repair and is not accessible until further notice. We apologize for any inconvenience and appreciate your understanding as we work to restore safe access.*brbrIMPORTANT INFORMATION:brYour booking is with Island Real Estate Vacations. We will send you check-in instructions 30 days prior to your arrival date. Please review the cancellation policy prior to booking. Island Real Estate Vacations will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee.brbrPayment of reservation deposit is considered acceptance of all terms regardless of signature status of contract. Guest is responsible for adhering to the rental terms andbrbrdates. Any error on Guest’s part is not the responsibility of the agent. Sub-leasing of your vacation rental is strictly prohibited. A mid-stay clean and charge equal to the standard cleaning fee are required for all stays 21 nights or longer. By providing your phone number, you agree to receive text messages from our company. Message and data rates may apply. Message frequency varies.brbrYour final balance is due 60 days prior to your arrival date. Please note unless alternative arrangements are made, the bank account or credit card on file will be charged your remaining balance automatically at 60 days. If you do not wish to pay with the bank account or credit card on file, please reach out to pay several days in advance of 60 days prior to your arrival. If you initially paid with an eCheck and received the booking incentive, please remember future payments must also be made with an eCheck. Thank you for choosing eCheck to help reduce the cost of business. Please note the eCheck payment option cannot be used within 14 days of arrival. Any refunds on checks and echecks will be delayed at least 14 days after deposit or until funds are verified.brbr*Please Note: This is a non-smoking complex. Smoking is not permitted anywhere on the property, including balconies, patios, and common areas.*brbrAnna Maria Island’s noise ordinance aims to ensure citizens can enjoy a peaceful environment. The ordinance applies to all areas of the city, including public and private property, and places of business. It defines noise as any sound that annoys or disturbs a reasonable person of ordinary sensibilities or causes or tends to cause an adverse physical or psychological effect on such reasonable person. The noise ordinance limits the maximum permissible noise levels to:brbr7 AM–10 PM: 65 decibels: (Consistently shouting in the pool exceeds 65 decibels)brbr10 PM–7 AM: 50 decibels: (An audible conversation from 50’ or 15 meters away exceeds 50 decibels)brbrThe ordinance also prohibits plainly audible noise, which refers to any sound that can be clearly heard by a person using their normal hearing faculties. This means that a person can still be in violation if the noise can be easily heard by responding officers from a distance of 100 feet from the property line. Fines for excessive noise can range from $100 to $1,000.brbrAll our properties provide luxury linens for you to enjoy during your stay.brbrVRC25-000048

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Sleeps

$237.08

/ Nightly

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Beachfront Complex: Enjoy Amenities, Beach Gear and Beach Access!

Holmes Beach, Florida, United States

The Twins Hideaway at Sun Plaza West by Anna Maria Island Accommodations brVRC20-000171brbrDiscover your ultimate beach vacation at The Twins Hideaway at Sun Plaza West, a beautifully updated two-bedroom, two-bath condo nestled directly in Holmes Beach on Anna Maria Island! Just steps from the stunning Gulf beaches, this oceanfront residence offers a perfect blend of relaxation and activity, with access to a community pool, tennis court, and nearby shops and dining. The outdoor amenities and scenic water views make this the ideal island retreat for families and friends!brbrHighlights br• Oceanfront Condobr• Direct Access to Holmes Beach br• 2 Bedroom / 2 Bathbr• 1 King, 1 Queen Bed, 1 Twin-over-twin Bunkbr• Community poolbr• Tennis court (equipment provided)br• Beach chairs and cart provided br• Private washer and dryer br• 2 Parking SpacesbrbrEnjoy outdoor living by the shared pool or on the sugar-white sands of Holmes Beach. Both the pool area and the tennis court offer perfect settings for outdoor fun, relaxation, and friendly competition. Take a short walk or trolley ride to explore nearby shops, restaurants, and water activities such as kayaking, paddle boarding, and fishing.brbrInside, the condo features a bright and modern design with a seamless flow between living, dining, and outdoor space. The updated kitchen boasts sleek stainless-steel appliances, including a refrigerator, stove, and oven, with island seating for quick meals or snacks. The dining area comfortably accommodates four, perfect for family dinners or game nights. brbrRelax in the primary bedroom, which provides a tranquil atmosphere with a king-sized bed, a TV, and ensuite bathroom with a walk-in shower. The second bedroom offers a comfortable queen bed, and a twin-over-twin bunk for guests or children, with a nearby hall bathroom with a shower and tub combo. A convenient washer and dryer are included for easy laundry days.brbrRoom Details br• Primary Bedroom: King bed, ensuite with walk-in shower br• Second Bedroom: Queen bed, Twin-over-Twin bunk bed brbrBook The Twins Hideaway today and enjoy a memorable island vacation in beautiful Anna Maria. Whether relaxing by the water, exploring local hotspots, or soaking in breathtaking views, this condo provides everything you need for a fun-filled getaway. Reserve your dates now and start creating lifelong beach memories!brbrbr-brThis home is managed by Anna Maria Island Accommodations, an Anna Maria Island property management company. brbrThis property does not allow pets of any kind. brbr2 cars maximum are able to park at this home, a designated spot will be provided. 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.

2

Bed

2

Bath

6

Sleeps

$231.21

/ Nightly

Condo

Beachfront Balcony, Cozy Escape

Holmes Beach, Florida, United States

Mermaid’s Retreat by Anna Maria Island Accommodations brbrWelcome to Mermaid’s Retreat, a bright and inviting two-bedroom, one-bath Holmes Beach vacation rental by Anna Maria Island Accommodations, perfectly positioned just steps from the sugar-white sands of the Gulf of Mexico. This charming upper-level condo offers the ultimate Anna Maria Island beach escape, featuring serene coastal vibes, effortless beach access with no roads to cross, and a peaceful location close to local shops, cafes, and island favorites. Ideal for couples or small families, you’ll love waking up to Gulf breezes and spending your days soaking in the laid-back island lifestyle. brbrHighlights br• Directly across the street from Holmes Beach br• 2 Bedrooms / 1.5 Bathrooms br• Wraparound balcony br• Washer and Dryer br• Quiet Street near shops, restaurants, and grocery stores br• Short walk to Grassy Pointe Preserve br• Near Anna Maria Island trolley stop br• Pet friendly with host approval br• 2 Parking spots brbrOutside, the wraparound balcony invites you to enjoy sea breezes, sunshine, and peekaboo Gulf views. Perfect place for sipping your morning coffee or enjoying sunset cocktails. Stroll across the calm street to the beach or hop on the free island trolley and explore new avenues of Anna Maria Island, your island escape awaits. brbrStep inside to find a bright and breezy interior with coastal decor and an open layout that makes you feel right at home. The living area offers a cozy spot to relax after beach days, with plenty of space to lounge, read, or stream your favorite shows. The updated kitchen features countertops, stainless steel appliances, and everything you need to prepare casual meals or quick bites before heading out to explore. brbrEnter the luxurious primary bedroom to find a queen bed, a workspace area with a desk, large sliding glass doors opening to a balcony, and an ensuite bathroom with shower and tub combination. The second bedroom features a queen bed, coastal decor, and an ensuite half bathroom. An in-unit washer and dryer are included to keep your island gear fresh. brbrRoom Details br• Primary Bedroom: Queen bed, ensuite bathroom with walk-in shower br• Second Bedroom: Queen bed, ensuite half bathroom brbrLocated in a central part of Holmes Beach, Mermaid’s Retreat places you just minutes from everything. Walk to Grassy Pointe Preserve for a peaceful nature stroll, stock up at nearby Publix, or explore local restaurants and shops all within walking distance. When you're ready to venture out, hop on the free Anna Maria Island Trolley, just steps from your door, and tour the island’s scenic 7-mile stretch. brbrBook your stay at Mermaid’s Retreat today and experience the best of Anna Maria Island. brbr- brThis 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. brbrWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. Weight limit of 50lbs max total for 1 or 2 dogs combined. No dangerous breeds allowed. See our Anna Maria Island Accommodations Policies for full details. 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 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.

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Bath

Sleeps

$696.35

/ Nightly

Condo

New! Beachfront Paradise! ~Heated Pool! Top Floor

Holmes Beach, Florida, United States

Summary:brbr Welcome to Coconuts 109 – Your Luxurious Gulf-Front Getaway brbrThis second-level, direct Gulf-front retreat offers breathtaking views and unbeatable beach access. Sleep soundly in a king bed or queen sleeper with premium linens. Enjoy a fully stocked kitchen, in-unit washer/dryer, walk-in shower with toiletries, and open living space with Gulf views. Relax on the screened balcony, unwind by the shared heated pool, and grill poolside—perfect for a serene beach escape! ️✨brbrbrbrThe Space:brbr Welcome to Coconuts 109 – Your Luxurious Gulf-Front Getaway brbrbrbr✅ VRC #: VRC16-000668brbrbrbrStep into paradise at Coconuts 109, a beautifully appointed second-level, direct Gulf-front retreat offering breathtaking views, unbeatable beach access, and effortless coastal luxury. Perfect for couples, small families, or anyone craving a serene seaside escape, this elegant one-bedroom residence comfortably sleeps up to four guests.brbrbrbr✨ Rest Easy in Coastal ComfortbrbrUnwind in the tranquil king bedroom featuring a premium luxury king mattress and plush down pillows for a blissful night’s sleep. Additional guests will enjoy the queen sleeper with a premium mattress. Drift off wrapped in hotel-quality linens from our professional linen service. Soft bath towels and beach towels are provided—so you can pack light and relax fully. ️ brbrbrbr Comfort & ConveniencebrbrThe modern bathroom boasts a sleek walk-in shower, stocked with shampoo, conditioner, and body wash. An in-unit washer and dryer, four luggage racks, dimmable lighting, and charming shiplap accents throughout add thoughtful touches that elevate your stay.brbrbrbr ️ Fully Stocked KitchenbrbrWhether you’re cooking a gourmet dinner or quick beach snacks, the kitchen has everything you need: stainless steel appliances, full-size fridge with filtered water and ice maker, oven, microwave, dishwasher, and essential cookware. Start your mornings with the drip/Keurig combo coffee maker. ☕ brbrbrbr Open Living with Stunning Gulf ViewsbrbrSoak in uninterrupted Gulf vistas from the open-concept kitchen, dining, and living areas. Relax on the queen sleeper sofa, stream your favorites on the large smart TV (also in the bedroom), and unwind after sun-filled days. ✨brbrbrbr Outdoor OasisbrbrStep onto your screened-in Gulf-front balcony, perfectly positioned above the beach. Sip morning coffee, dine al fresco, or watch spectacular sunsets. Enjoy two chaise loungers, a dining table with four chairs, and turtle-safe mood lighting for peaceful evenings. brbrbrbr ️ Resort-Style AmenitiesbrbrCool off in the shared heated pool, fire up the poolside BBQ grills, or lounge on the patio furniture for laid-back island moments. brbrWhether you’re celebrating a honeymoon, anniversary, birthday, or simply escaping for a weekend—or longer—Coconuts 109 delivers the perfect blend of luxury, comfort, and unforgettable Gulf-front beauty.brbrbrbr Book your beachfront escape today and make lasting memories at Coconuts 109!brbrbrbrGuest Access:brbrCoconuts features beautifully maintained shared grounds with lush tropical landscaping. During your stay, you’ll have access to a shared swimming pool and convenient propane barbecue grills—perfect for relaxing or enjoying a meal outdoors.brbrbrbrOther Things to Note:brbrFor your convenience, the home includes 2 beach chairs, , a beach umbrella, and all the bath towels, beach towels, and linens you'll need—everything ready for a relaxing stay!brbrbrbrInteraction with Guests:brbrIf you need anything during your stay, I’m here to help! You can call or text me directly on my cell. I’m available 24/7 to answer questions, offer local tips, or assist with anything that comes up. Your comfort is my priority!

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Bath

Sleeps

$260.38

/ Nightly

Condo

Latitude Adjustment by A Shore Thing Vacations

Holmes Beach, Florida, United States

Welcome to Latitude Adjustment! Escape to this tranquil 2-bedroom condo on beautiful Anna Maria Island, just a short walk from the beach! This inviting retreat offers a perfect blend of comfort and coastal charm. Relax on your private balcony with stunning views, perfect for sipping your morning coffee or unwinding after a day in the sun.brbr Property Highlights:br✨ 2 full bedrooms and 2 bathroomsbr✨ Beautiful scenery from nature preservebr✨ Fully equipped kitchenbr✨ Screened in balcony with room to dinebr✨ Easy Walk to the Anna Maria Island Beachesbr✨ Washer and dryer in unitbr✨ Plenty of room to sleep 4br✨ Beautiful heated community poolbr✨ Beach chairs, and umbrellasbrbrThis charming 2-bedroom condo on Anna Maria Island offers the perfect escape, complete with a private balcony to enjoy the warm Florida breezes. Located in a quiet area but close to the island’s beautiful beaches, this condo provides a cozy and convenient stay. This cozy retreat features a king bed in the primary bedroom and a queen bed in the secondary bedroom, offering comfort for all guests. The screened-in lanai overlooking the natural mangrove preserve is an amazing setting for morning coffee or evening cocktails. This condo also features a spacious living area with plenty of room to stretch out. Indoor or outdoor dining table for 4. Enjoy watching tv during your stay in either bedroom, or out in the living area! brbrWhether you’re strolling to the beach, exploring local shops, or simply enjoying the peaceful surroundings, this condo is your perfect getaway on Anna Maria Island!brbrThe community has a large heated pool for guests only. The covered parking space has room for two cars and there is additional parking for guests. brbrBeach chairs and an umbrella are available as well as beach and pool towels. This condo participates in our professional linen program so you can rest well in luxury.brbrPLEASE NOTE: The Sandy Pointe condo complex does not allow charging of electric vehicles including Teslas.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. Our 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 bath and beach towels.brbrVRC17-000018

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Bath

Sleeps

$295.43

/ Nightly

Condo

Steps to Beach - SunSet Azul by SeaBreeze Vacation

Holmes Beach, Florida, United States

Sunset Azul is a fully-updated 2 bedroom/1 bath gulf-side ground level villa on the southern end of Holmes Beach. It's quiet, yet close to shopping, restaurants and trolley stops. Best of all, this unit is only a few short steps to the white sandy beaches. This villa has a fully-equipped kitchen, granite countertops, stainless steel appliances, cozy living area and luxurious bedrooms, turnkey furnished in beautiful contemporary beach decor. Amenities also include heated pool, washer/dryer, cable TV, high-speed internet, A/C, and more. Everything you could ask for in the perfect beach vacation home, including a fabulous shared heated pool with waterfall for relaxing after a full day at the beach. Close to shops and restaurants. Each villa offers an outdoor private patio, lush tropical landscape. With the spacious common area providing a paver courtyard, charming handmade tiki hut and lush tropical gardens making the perfect setting for an unforgettable beach getaway. Just a 90 second walk from the sugary white sands of the Gulf beaches, the villas are a serene and relaxing retreat.brbrCancellation Policy - SeaBreeze Vacation has spent a great deal of time and effort into formulating a cancellation policy for you. SeaBreeze Vacation has the most flexible cancellation policy on the Island. You are allowed to cancel your reservation up to 14 days prior to check-in to receive a refund. Additional terms and conditions apply.brbrThis property participates in our Professional Linen Program. SeaBreeze Vacation strives to bring only the best quality experience to our guests. To do so, we provide a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you high quality linens that are in place and ready for your use upon your arrival. These high-quality linens are laundered in a commercial setting that uses only hypoallergenic, perfume & dye-free soaps assuring all of our guests a comfortable stay.brbrWith all SeaBreeze Vacation properties, we think of the little things to make your vacation special. Included to get you started are the following: brbrPer Guest: 1 Bath Towel, 1 Hand Towel, 1 Washcloth, 1 Pool/Beach TowelbrPer Full Bathroom: 2 Rolls of Toilet Paper, Hand Soap, Shower Products Set (including trial size shampoo, conditioner, shower gel, and body lotion), Cosmetic Cloth, Bath MatbrPer Kitchen: 2 Rolls of Paper Towels, Hand Soap, Dish Soap, Sponge, Dishwasher Pods (x4), Laundry Detergent Pods (x4), All-Purpose Disinfectant, Microfiber Cloth, 2 Kitchen TowelsbrbrWe also offer a range of supplemental services including pre-stock grocery shopping and babysitting. Need a pack and play or high chair, etc. These are available for a small additional fee and will be waiting in the home on your arrival.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.brbrCity of Holmes Beach Vacation Rental License: VRC19-000302brMax Occupancy: 6 Guests | Max Vehicles: 2brQuiet Hours: 10 p.m. - 7 a.m. - please respect our island communitybrMin stay requirements vary by city ordinance and are often 7 nights. Please contact our office with any questions.

2

Bed

1

Bath

6

Sleeps

$170.41

/ Nightly

Condo

Beachy Butterfly! Poolside Holmes Beach Stay!

Holmes Beach, Florida, United States

Beachy Butterfly by Anna Maria Vacations brCondo in Holmes Beach, Florida brVRC24-000089brbrWelcome to Beachy Butterfly, a charming two-bedroom, two-bath condo located in the heart of Holmes Beach on beautiful Anna Maria Island. Just a 8-minute walk to the pristine Gulf shoreline, this recently refreshed retreat offers guests access to a community pool, tennis and pickleball courts, and is within steps of local restaurants, a grocery store, and the Anna Maria Island trolley. Beachy Butterfly is the perfect choice for a relaxing island getaway! brbrHighlights br- 8-minute walk to Manatee Beach br- 2 Bedroom / 2 Bath br- 1 King, 2 Twin beds br- Community pool br- 2 workspaces with desks br- Community tennis and pickleball courts br- In-unit washer and dryer br- Near shopping and dining br- 3-minute walk to free trolley stop br- 1 Parking Space br- Pet friendly with host approval brbrSoak up the Florida sunshine at the community pool, surrounded by tropical landscaping and lounge seating. Enjoy a friendly match at the tennis and pickleball court, or unwind with a book in your private Florida room, overlooking the peaceful pool and garden area. With its convenient central location in Holmes Beach, this condo offers everything you need for a stress-free extended stay vacation on Anna Maria Island. brbrStep inside to find a bright, open concept living room with comfortable seating, TV, and large windows that fill the space with natural light. Just beyond the main living area is an additional sunlit sitting space, complete with a small table and chairs or a workspace overlooking the garden area. The fully equipped kitchen includes a refrigerator, stove, dishwasher, microwave, toaster, and Keurig coffee maker, making meal prep simple and convenient. The dining area seats six, creating a welcoming spot for family meals or game nights. For remote work, find a quiet area at one of the two workspaces with desks inside. brbrThe primary bedroom features a cozy king bed, ensuite bathroom with a walk-in shower, and a spacious walk-in closet. The second bedroom includes two twin beds, perfect for kids or guests, along with a private ensuite bathroom featuring a shower-tub combination and its own walk-in closet. Both rooms are decorated in soothing coastal tones that reflect the relaxed island vibe. brbrRoom Details br- Primary Bedroom: King bed, ensuite bathroom with walk-in shower br- Second Bedroom: Two twin beds, ensuite bathroom with shower-tub combination brbrEnjoy the simplicity of beach living with a grocery store, local shops, and restaurants such as Skinny's Place, just a short walk away. The Anna Maria Island Trolley makes exploring the island effortless, from boutique shopping on Pine Avenue to sunset dining at Bridge Street. With its family-friendly atmosphere and excellent location, Beachy Butterfly is perfect for long-term guests seeking comfort, convenience, and authentic island charm. brbrWith its inviting interiors, community amenities, and ideal Holmes Beach location, Beachy Butterfly by Anna Maria Vacations is the perfect home away from home for a peaceful island escape. Whether you’re lounging by the pool, strolling to the Gulf shore, or exploring the local shops and dining, this condo has everything you need for a memorable Anna Maria Island vacation. brbrBook your stay today and experience the laid-back coastal lifestyle of Holmes Beach! brbr- brThis home is managed by Anna Maria Vacations, an Anna Maria Island property management company. brbrWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. Weight limit of 50lbs max total for 1 or 2 dogs combined. No dangerous breeds allowed. See our Anna Maria Vacations Policies for full details. brbr1 reserved parking spot is provided. 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 Vacations 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.

2

Bed

2

Bath

4

Sleeps

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