Florida South-West Vacation Rentals - 262 Properties

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  1. $715 to $890/night
    Bedrooms : 4
    Type : home

      Welcome to Sea Shell and Sunsets! Brand New Custom-built Island...

  2. $535 to $890/night
    Bedrooms : 3
    Type : cottage

      Luxury is here in this brand new direct gulf front three bedroom...

  3. $525 to $1425/night
    Bedrooms : 6
    Type : home

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

  4. $510 to $1155/night
    Bedrooms : 5
    Type : home

      Immaculate, stunning and spacious multi-level holiday island...

  5. $510 to $715/night
    Bedrooms : 3
    Type : condo

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

  6. $510 to $935/night
    Bedrooms : 4
    Type : condo

      Luxury at its finest with this stand-alone, spacious condo in all...

  7. $510 to $1155/night
    Bedrooms : 4
    Type : home

      Island Real Estate's rental program now presents Casa Bonita,...

  8. $435 to $1185/night
    Bedrooms : 8
    Type : home

    Enjoy this set of elevated vacation homes with two private lagoon...

  9. $435 to $890/night
    Bedrooms : 4
    Type : home

      Located at the prestigious north end of Anna Maria, Blue Waters...

  10. $420 to $1370/night
    Bedrooms : 6
    Type : home

      Luxurious custom built multi-level tropical oasis and pool...

  11. $420 to $1370/night
    Bedrooms : 5
    Type : home

    Magical and stunning vacation rental with an enviable backyard that...

  12. $410 to $560/night
    Bedrooms : 3
    Type : condo

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

  13. $395 to $555/night
    Bedrooms : 4
    Type : home

      Welcome to Casa Varadero a new ground level vacation rental home...

  14. $385 to $790/night
    Bedrooms : 6
    Type : home

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

  15. $380 to $685/night
    Bedrooms : 4
    Type : home

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

  16. $380 to $465/night
    Bedrooms : 4
    Type : home

      Coastal and spacious vacation paradise seasonal rental  (4)...

  17. $375 to $850/night
    Bedrooms : 4
    Type : home

      Welcome to Wind Song!  This is a brand new  single family home....

  18. $375 to $545/night
    Bedrooms : 4
    Type : home

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

  19. $360 to $1245/night
    Bedrooms : 5
    Type : home

      Immaculate and beachy, multi-level island vacation home.  (5)...

  20. $350 to $1220/night
    Bedrooms : 6
    Type : home

    A dream come true holiday oasis perfect for large families. (6)...

  21. $350 to $1220/night
    Bedrooms : 6
    Type : home

    Fantastic new private vacation rental home with outstanding Gulf...

  22. $350 to $735/night
    Bedrooms : 5
    Type : home

    Spacious, private vacation home that offers peeks of the gulf and...

  23. $350 to $500/night
    Bedrooms : 4
    Type : home

      Beautiful light, bright and beachy relaxing seasonal rental. (4)...

  24. $350 to $500/night
    Bedrooms : 3
    Type : home

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

  25. $350 to $535/night
    Bedrooms : 4
    Type : home

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

  26. $340 to $610/night
    Bedrooms : 3
    Type : condo

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

  27. $340 to $510/night
    Bedrooms : 2
    Type : condo

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

  28. $340 to $515/night
    Bedrooms : 4
    Type : home

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

  29. $340 to $685/night
    Bedrooms : 4
    Type : home

      There is getting away from it all and there’s completely...

  30. $335 to $535/night
    Bedrooms : 4
    Type : home

      Wash away the sand, salt, and stress with a luxurious vacation at...