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Properties Available 1137 properties available
Escape to Island Hideaway, a charming one-bedroom, one-bath home perfectly situated just a four-minute walk from Anna Maria Island’s stunning white sand beaches! This ground-level, fully accessible retreat boasts a private heated pool surrounded by lush tropical landscaping, making it an ideal romantic, small family, or solo escape. Enjoy a seclude
Island Hideaway
Condo
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.9 (60)
Palmetto Pointe by AMI Locals Vacation Rental License #VR19-000033 Welcome to Palmetto Pointe, a luxurious five bedroom, five and a half bath vacation home located just one block from Anna Maria Island Beach. This retreat features a rooftop deck with Gulf views, wraparound balconies, a large private pool with spa, and spacious bedroom suites; perfe
Palmetto Pointe
House
Bedrooms 5 bedrooms
Bathrooms 5 baths
HalfBathrooms 1 Half baths
Guests 8 guests
Rating 5 (31)
Off The Hook - B by Tropical Sands Accommodations Welcome to Off The Hook – B, your ideal sunny vacation getaway just minutes from the world famous Siesta Key Beach! This charming two-bedroom, one-bath duplex offers a delightful blend of comfort and convenience, just minutes from the beach and Siesta Key Village. Perfect for couples or families lo
Off The Hook - B
Duplex Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 (23)
Florida Fling by AMI Locals Vacation Rental License #DWE5105449Welcome to Florida Fling by AMI Locals, a breathtaking seven bedroom, seven and a half bath luxury home just a 1-minute walk to the pristine beaches of Anna Maria Island. Newly built and elegantly designed, this stunning retreat features a resort-style pool with in-ground spa, a rooftop
Florida Fling
House
Bedrooms 7 bedrooms
Bathrooms 7 baths
HalfBathrooms 1 Half baths
Guests 14 guests
Rating 5 (27)
Stars on the Water by AMI Locals Duplex in Holmes Beach, FloridaVRC21-000115Perfect for beach and bay lovers alike, Stars on the Water is a charming canal-front vacation home with a private dock, just a leisurely six-minute walk from Manatee Beach! This intimate two-bedroom, one-bath retreat offers stunning water views, a fully equipped kitchen, an
Stars on the Water
Duplex
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
Rating 4.9 (21)
Siesta Sun by Siesta Key Luxury Rental Properties Siesta Sun by Siesta Key Luxury Rental Properties is a stunning 3 bedroom, 3. and a half bath Siesta Key luxury rental located just a 1-minute walk to Siesta Key Beach. This elevated duplex offers beach views, a private rooftop deck with sweeping Gulf scenery, and a bright coastal interior perfect f
Siesta Sun
Duplex Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
HalfBathrooms 1 Half baths
Guests 10 guests
Rating 5 (51)
Marbella Villa Penthouse by AMI LocalsVacation Rental License #TPL25-000041, CND5105469Discover true coastal elegance at Marbella Villa Penthouse, a spectacular Gulf-front retreat nestled on Anna Maria Island! This three-bedroom, three-and-a-half-bath penthouse offers panoramic water vistas, luxurious finishes, and access to pristine beaches just s
Marbella Villa Penthouse
Condo
Bedrooms 3 bedrooms
Bathrooms 3 baths
HalfBathrooms 1 Half baths
Guests 8 guests
Home away from home- Home Away from Home -Sea Breeze 202 is a GOLD Tier corner two-bedroom, two-bath Gulf Front vacation rental located in Madeira Beach.. This spacious second floor vacation rental has a delightful décor and includes a private Gulf Front balcony with a view of our beautiful white sugar sand beach. Vacation rental 202 offers a full
Sea Breeze 202
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (40)
Casita West by Siesta Key Luxury Rental Properties Welcome to Casita West, a charming two-bedroom, one-bathroom Siesta Key beach bungalow located just one block from Siesta Key Beach with private beach access. This single story vacation rental offers relaxed coastal living with access to the Calini Beach Club Resort community pool, a shared patio w
Casita West
Duplex Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.9 (15)
A wonderful 2-bedroom/2-bath fully appointed condo nestled into a the only true resort on Siesta Key. Enjoy the state of the art fitness center, saunas/spas, 3 heated swimming pools, 8 tennis courts (2 converted for pickleball), shuffleboard, basketball/racquetball, tiki huts, grilling areas, 2 clubhouses, and if you like, Americas #1 beach is wait
Gulf and Bay Club- C702
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Jamaica Royale 085 by Tropical Sands AccommodationsWelcome to Jamaica Royale 085, a newly renovated two-bedroom, two-bath garden-view villa in the popular Jamaica Royale beachfront complex on Siesta Key. Featuring a bright, open layout and fresh coastal design, this modern retreat offers updated finishes, stylish furnishings, and all the comforts o
Jamaica Royale 085
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Upgraded and refurbished in 2013- Home away from home- Vacation Rental 213- GOLD rated, is a second-floor condo located in N Redington Beach. Living/dining room, three bedrooms and two full baths. Updated and fully equipped kitchen, complete with everything needed for at home dining. Living room and master bedroom with private Gulf front balcony di
Ram Sea 213
Condo
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.8 (44)

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