Florida South-West Vacation Rentals - 304 Properties

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  1. Sleeps 21, $660 to $1060/night

    City : Bradenton Beach
    Bedrooms : 8
    Bathrooms : 7
    Pool

    This Bradenton Beach vacation home is actually two rentals in one,...

  2. Sleeps 16, $525 to $1495/night

    City : Anna Maria
    Bedrooms : 6
    Bathrooms : 3
    Pool Hot Tub

    Grande Haven is a spectacular example of high architecture, fine...

  3. Sleeps 9, $515 to $1020/night

    City : Sanibel
    Bedrooms : 4
    Bathrooms : 4

    Sandals is an ultra-exclusive direct gulf front townhome "community"...

  4. Sleeps 12, $475 to $575/night

    City : Sanibel
    Bedrooms : 4
    Bathrooms : 2
    Pool

    Rendezvous by the Sea is a beautiful Sanibel Island vacation home...

  5. Sleeps 10, $465 to $990/night

    City : Holmes Beach
    Bedrooms : 5
    Bathrooms : 4
    Pool

    Brand new 5 bedroom 4 bathroom vacation home in Holmes Beach, just...

  6. Sleeps 6, $410 to $585/night

    City : Holmes Beach
    Bedrooms : 3
    Bathrooms : 2.5
    Pool

    On Anna Maria Island, there are no high rise hotels. Life is better...

  7. Sleeps 12, $385 to $850/night

    City : Holmes Beach
    Bedrooms : 6
    Bathrooms : 4
    Pool Pets OK

    Key Lime Cottages 202 & 204  welcomes you to this recently re-done...

  8. Sleeps 8, $375 to $585/night

    City : Anna Maria
    Bedrooms : 4
    Bathrooms : 2
    Pool Hot Tub Pets OK

      Welcome to the Dolphin/Heron. This quaint duplex with each unit...

  9. Sleeps 10, $370 to $605/night

    City : Anna Maria
    Bedrooms : 4
    Bathrooms : 2.5

      Anna Maria Island is Old Florida – we take things a little...

  10. Sleeps 6, $365 to $725/night

    City : Sanibel
    Bedrooms : 3
    Bathrooms : 2
    Pool

    Luxurious direct gulf front penthouse at Junonia. Junonia 301 is a...

  11. Sleeps 8, $350 to $525/night

    City : Anna Maria
    Bedrooms : 3
    Bathrooms : 2
    Pool Hot Tub

    Paradise Pointe, located in the quiet north end of beautiful Anna...

  12. Sleeps 8, $350 to $550/night

    City : Holmes Beach
    Bedrooms : 4
    Bathrooms : 4
    Hot Tub

    Brand new  to our rentals- Catchin' Rays is only steps to the sugar...

  13. Sleeps 8, $340 to $545/night

    City : Sanibel
    Bedrooms : 3
    Bathrooms : 2
    Pool

    Gulf view three bedroom, two bathroom Sundial Beach Resort condo....

  14. Sleeps 10, $340 to $625/night

    City : Anna Maria
    Bedrooms : 4
    Bathrooms : 3

    Get comfortable on the coveted north end of Anna Maria. This serene...

  15. Sleeps 4, $340 to $535/night

    City : Bradenton Beach
    Bedrooms : 2
    Bathrooms : 2
    Pool Hot Tub

    Sunsets, shimmering gulf waters, and sand between your toes are all...

  16. Sleeps 10, $340 to $540/night

    City : Anna Maria
    Bedrooms : 4
    Bathrooms : 3
    Pool Hot Tub

    Spacious and elegant home idyllic for your holiday sejourn. (4)...

  17. Sleeps 14, $330 to $660/night

    City : Holmes Beach
    Bedrooms : 6
    Bathrooms : 3.5
    Pool

    Entertain family and friends with a private swimming pool area....

  18. Sleeps 11, $330 to $530/night

    City : Bradenton Beach
    Bedrooms : 4
    Bathrooms : 3.5
    Pool

    This Bradenton Beach vacation home provides you and your family or...

  19. Sleeps 10, $330 to $530/night

    City : Bradenton Beach
    Bedrooms : 4
    Bathrooms : 3.5
    Pool

    This home provides you with your own private pool. It has virtually...

  20. Sleeps 6, $330 to $665/night

    City : Holmes Beach
    Bedrooms : 3
    Bathrooms : 2.5
    Pool Hot Tub

      Some of the most popular vacation rentals on Anna Maria Island...

  21. Sleeps 4, $325 to $410/night

    City : Bradenton Beach
    Bedrooms : 2
    Bathrooms : 2
    Pool Hot Tub

      Spectacular, direct gulf front condo with an enviable Gulf front...

  22. Sleeps 6, $320 to $430/night

    City : Sanibel
    Bedrooms : 3
    Bathrooms : 3

    Enjoy your Island retreat in this three bedroom and three bathroom...

  23. Sleeps 12, $315 to $430/night

    City : Bradenton Beach
    Bedrooms : 6
    Bathrooms : 3
    Pool

    Includes swimming pool and partial views of the gulf, and only 1/2...

  24. Sleeps 10, $310 to $605/night

    City : Anna Maria
    Bedrooms : 4
    Bathrooms : 2
    Pool

      Adorable beach cottage rental so close to the beach you can smell...

  25. Sleeps 14, $305 to $645/night

    City : Holmes Beach
    Bedrooms : 4
    Bathrooms : 3
    Pool

    We know a thing or two about luxury on Anna Maria Island, and we...

  26. Sleeps 8, $300 to $400/night

    City : Cape Coral
    Bedrooms : 5
    Bathrooms : 3
    Pool

    8-room villa 300 m2, very nice furnishings: living room with...

  27. Sleeps 8, $300 to $535/night

    City : Anna Maria
    Bedrooms : 3
    Bathrooms : 4
    Pool Hot Tub

    3 Bedroom, 4 Bath (sleeps 8)- "HoneyWood House"  Living at the...

  28. Sleeps 6, ~$295/night

    City : Bradenton Beach
    Bedrooms : 3
    Bathrooms : 3
    Pool

    4-room terraced house 113 m2, on the upper floor, spacious and...

  29. Sleeps 8, $295 to $515/night

    City : Sanibel
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Sundial Beach Resort, unit T201 is a second floor, gulf view condo....

  30. Sleeps 8, $295 to $330/night

    City : Nokomis
    Bedrooms : 3
    Bathrooms : 2

    Located on the ground floor, this deluxe three-bedroom/two bath...