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  1. APARTMENT
    Island House Beach Resort- Two-Bedroom Apartment

    Island House Beach Resort- Two-Bedroom Apartment

    Siesta Key, FL

    Island House Beach Resort - Siesta Key, Crescent Beach, Ground Floor unit! This unit is located at Island House Beach Resort on sunny Siesta Key. King, full, futon. It has a large living room, fully equipped kitchen, all appliances, dining area,...

    Pool
    FREE CANCELLATION

    $275 to $399/night

  2. CONDOMINIUM
    Shell Point Condo #54640

    Shell Point Condo #54640

    Holmes Beach, FL

    6300 Flotilla Drive, Holmes Beach, Anna Maria Island Shell Point Condominium #78 ... Nice 2 bedroom, 2 bath unit in quiet area. Condominium has 1 queen bed and 2 twin beds and a full kitchen. This complex offers tennis, heated pool, and covered...

    Pool
    FREE CANCELLATION
  3. COTTAGE
    203 76Th St- Upstairs Cottage #54631

    203 76Th St- Upstairs Cottage #54631

    Holmes Beach, FL

    Lime in De Coconut - Upstairs..... Adorable, one bedroom, one bath in a 2 unit cottage. Cheery beach decor and a shared heated pool in a tropically landscaped courtyard. Flat screen TV, wireless internet access, washer & dryer, and a gas grill...

    Pool
    FREE CANCELLATION

    $173 to $312/night

  4. HOUSE
    Mermaid Manor House #64483

    Mermaid Manor House #64483

    BRADENTON BEACH, FL

    Mermaid Manor - This is a unique waterfront complex directly on the Intracoastal Waterway. The main house has 3 bedroom/4 bath suites, granite and marble counters with back splashes throughout, teak flooring, multiple top-of-the-line ceiling fans....

    Pool
    FREE CANCELLATION

    $726 to $877/night

  5. CABIN
    604 N Shore Cabin #54645

    604 N Shore Cabin #54645

    Anna Maria, FL

    604 North Shore Drive, Anna Maria FL 34216 Unit 4 Still Water". Adorable, vintage 2 bedroom cottage on Lake La Vista located at the north end of the Island . Just 250 steps to the beach and just a short stroll to historic Pine Avenue for great...

    Pets OK
    FREE CANCELLATION

    $242 to $393/night

  6. HOUSE
    Shady Pines

    Shady Pines

    Englewood, FL

    Shady Pines in Englewood is as large a park at 1.3 acres. Shady Pines is laid out to be of maximum use, reminding you of an old Florida and the South of another era. She has waterfront views, large sweeping lawns, the mossy pines and palm trees, a...

    Pool

    $284 to $312/night

  7. HOUSE
    504 Bay Drive Upstairs House #54612

    504 Bay Drive Upstairs House #54612

    Bradenton Beach, FL

    504 Bay Drive South, Bradenton Beach, Anna Maria Island Dock on the Bay ... Exceptional direct bay front 2 bedroom, 1 bath. This is the upstairs of a two unit building that was just completely remodeled. New bathroom with deep jet tub and separate...

    Hot Tub
    FREE CANCELLATION

    $182 to $277/night

  8. HOTEL ROOM
    Bridge Villa 4 Bradenton Beach

    Bridge Villa 4 Bradenton Beach

    Bradenton Beach, FL

    Bridge Villa 4 Located on Bridge Street in the heart of Anna Maria Island, a block away from the Gulf of Mexico. You'll be sure to enjoy the convenience of watching the sunset, dining, shopping, and the island nightlife. This one bedroom corner unit...

    $144 to $203/night

  9. COTTAGE
    301 23rd St- Cha Cha Cottage #68392

    301 23rd St- Cha Cha Cottage #68392

    BRADENTON BEACH, FL

    Glimpses of the water are one of the special features from this adorable coastal cottage. Lives large is what you'll say as you enter the living area with lots of windows to let the outside in. Dining area off the perfectly appointed new kitchen....

    FREE CANCELLATION

    $173 to $346/night

  10. HOUSE
    Kendall Home #18672

    Kendall Home #18672

    Marco Island, FL

    This 4 bedroom plus den,3 bath air conditioned home is 300 yards from Tigertail beach. It has it's own private tennis court, bocce, basketball and shuffleboard courts. The oversized screened in lanai has a heated pool, Spa & summer kitchen. 12 ft....

    Pool
  11. HOUSE
    Whiteheart Home #65487

    Whiteheart Home #65487

    Marco Island, FL

    Marco Island is an affluent area of luxury real estate, gorgeous beaches, local shops and high-quality restaurants. It’s a little piece of paradise tucked off of the coast of the Sunshine State. Visitors looking to experience the slow-paced,...

    Pool Hot Tub

    $233 to $664/night

  12. HOUSE
    San Marco Home #62849

    San Marco Home #62849

    Marco Island, FL

    For the ultimate in waterfront living, look no further than this stunning four- bedroom home on Marco Island. From luxury furniture to modern architectural and design elements, this 2,781 square foot home is the perfect addition to a dream beach...

    Pool

    $359 to $833/night

  13. HOUSE
    Shenandoah Home #47311

    Shenandoah Home #47311

    Marco Island, FL

    Distance to Marco Island South Beach Entrance: 2.5 miles Distance to Tigertail Beach Entrance: 2.9 miles Distance to Private Residents' Beach (Monthly stay restriction): 1.2 miles Welcome to Marco Island and Shenandoah Ct.! This beautiful home...

    Pool

    $260 to $538/night

  14. HOUSE
    Sycamore Home #13070

    Sycamore Home #13070

    Marco Island, FL

    Distance to Marco Island South Beach Entrance: 1.2 miles Distance to Tigertail Beach Entrance: 2.7 miles Distance to Private Residents' Beach (Monthly stay restriction): 1 mile Experience Marco Island like a local by staying a week (or two) in this...

    Pool

    $251 to $530/night

  15. HOUSE
    Breakwater Home #54005

    Breakwater Home #54005

    Marco Island, FL

    From the moment you pull up to 1107 Breakwater Court, you’ll feel like you’ve been transported to a tropical island retreat. From the charming manatee mailbox to the lush landscaping and modern Florida-style architecture, this four-bedroom...

    Pool Hot Tub

    $448 to $1,166/night

  16. HOUSE
    Bald Eagle Home #62266

    Bald Eagle Home #62266

    Marco Island, FL

    400 Bald Eagle is an impressive three-bedroom home on Marco Island with large living spaces, private, elegant bathrooms, a gourmet kitchen and a private pool and shaded lanai that you’ll have to see to believe. Outside, this waterfront home is an...

    Pool

    $232 to $538/night

  17. HOUSE
    Rose Home #16347

    Rose Home #16347

    Marco Island, FL

    Distance to Marco Island South Beach Entrance: 3.7 miles Distance to Tigertail Beach Entrance: 1.9 miles Distance to Private Residents' Beach (Monthly stay restriction): 2 miles Stunning 4 bedroom 3 bath, waterfront home on Marco Island with heated...

    Pool

    $269 to $833/night

  18. HOUSE
    Wintergreen Home #61001

    Wintergreen Home #61001

    Marco Island, FL

    This stunning, four-bedroom home with a sparkling private pool, three elegant bathrooms, a fully furnished kitchen and two levels of luxurious living space. This modern waterfront home combines classic coastal flair with modern comforts and...

    Pool Hot Tub

    $502 to $968/night

  19. HOUSE
    Plantation Home #12955

    Plantation Home #12955

    Marco Island, FL

    Distance to Marco Island South Beach Entrance: 3.5 miles Distance to Tigertail Beach Entrance: 0.3 miles Distance to Private Residents' Beach (Monthly stay restriction): 1.7 miles Leave all your cares behind. Well appointed interior decorations and...

    Pool

    $260 to $582/night

  20. HOUSE
    Peach Home #62051

    Peach Home #62051

    Marco Island, FL

    Relax in an open, bright, and comfortable house with a large dock, screened-in lanai, and direct access to open water. This lovely home offers a Southern exposure so you can enjoy the sun most of the day on the dock and in the pool and spa or relax...

    Pool

    $448 to $833/night

  21. HOTEL ROOM
    Bridge Villa 2 Bradenton Beach

    Bridge Villa 2 Bradenton Beach

    Bradenton Beach, FL

    Bridge Villa 2 Located on Bridge Street in the heart of Anna Maria Island, a block away from the Gulf of Mexico. You'll be sure to enjoy the convenience of watching the sunset, dining, shopping, and the island nightlife. This one bedroom is equipped...

    $123 to $155/night

  22. HOUSE
    Colonial Ave 364 Home

    Colonial Ave 364 Home

    Marco Island, FL

    Distance to Tigertail Beach Entrance: 0.6 miles Distance to Residents' Beach Entrance (monthly stay restriction): 1.6 miles Distance to Marco Island South Beach Entrance: 2.0 miles 364 Colonial Ave is a beautiful three bedroom home that is perfect...

    Pool

    $269 to $493/night

  23. HOUSE
    Street South House #54586

    Street South House #54586

    Bradenton Beach, FL

    105 B 12th Street South, Bradenton Beach, Anna Maria Island Unit B - Front ... Lovely 2 bedroom, 1 bath unit within walking distance to both the beach and bay. Comfortably furnished with private, lushly landscaped courtyard. High speed internet,...

    Pool
    FREE CANCELLATION

    $156 to $277/night

  24. HOUSE
    Palm Cay 9 House #54482

    Palm Cay 9 House #54482

    Holmes Beach, FL

    Holmes Beach, Anna Maria Island Palm Cay # 9 ... Updated 1 bedroom, 1 bath unit located in small complex with heated pool located west of Gulf Drive just 2 houses to the beach for easy beach access. Enjoy peeks of the beach from the balcony....

    Pool
    FREE CANCELLATION

    $139 to $277/night

  25. HOUSE
    Street South House #54587

    Street South House #54587

    Bradenton Beach, FL

    105 A 12th Street South, Bradenton Beach, Anna Maria Island Unit A - Back ... Lovely 2 bedroom, 1 bath unit within walking distance to both beach and bay. Comfortably furnished with private, lushly landscaped courtyard. High speed internet, nice...

    Pool
    FREE CANCELLATION

    $156 to $277/night

  26. CONDOMINIUM
    Sunset Beach Condo #54455

    Sunset Beach Condo #54455

    Holmes Beach, FL

    2716 Gulf Drive, Holmes Beach, Anna Maria Island Sunset Beach Condo # 202 ... Direct gulf front 2 bedrooms, 2 bath unit with screened porches overlooking the beach. Smaller complex with lush landscaping, private pool, and covered parking. Amenities...

    Pool
    FREE CANCELLATION

    $234 to $363/night

  27. DUPLEX
    Vacationer's Duplex #54505

    Vacationer's Duplex #54505

    Holmes Beach, FL

    211 58th Street, Holmes Beach, Anna Maria Island Vacationer's Duplex ... Newly furnished, 2 bedroom, 2 bath elevated duplex located in a quiet residential neighborhood. Offers phone, cable, dishwasher, washer & dryer, microwave. Just one block from...

    Pets OK
    FREE CANCELLATION

    $148 to $260/night

  28. HOUSE
    Barefoot Villas W #54496

    Barefoot Villas W #54496

    Holmes Beach, FL

    Barefoot Villas West ... Adorable duplex located just steps to the beach. Each side has 2 bedrooms, 1 bath with open porches. Artistic decor, phone, cable, and microwave. Wonderful private outdoor shower with hot and cold water. Each side sleeps 4....

    Pets OK
    FREE CANCELLATION

    $151 to $260/night

  29. HOUSE
    Spinnaker Home #62228

    Spinnaker Home #62228

    Marco Island, FL

    Distance to Marco Island South Beach Entrance: 3.4 miles Distance to Tigertail Beach Entrance: 0.2 miles Distance to Private Residents' Beach (Monthly stay restriction): 1.7 miles Until you see this property for yourself, there truly is no way to...

    Pool

    $986 to $2,689/night

  30. HOUSE
    526 72nd St (2 Bedroom- Home)

    526 72nd St (2 Bedroom- Home)

    Holmes Beach, FL

    Gorgeous, recently renovated two bedroom, two bath canal front home. This ground level home located in Bay Palms Subdivision was just updated with brand new furnishings, paint and an updated kitchen and bathrooms. Very bright interior with tons of...

    FREE CANCELLATION

    $260 to $277/night