Florida South-West Vacation Rentals - 267 Properties

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

    City : Anna Maria
    Bedrooms : 6
    Bathrooms : 3
    Pool Pets OK

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

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

    City : Sanibel
    Bedrooms : 4
    Bathrooms : 4

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

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

    City : Sanibel
    Bedrooms : 4
    Bathrooms : 2
    Pool

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

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

    City : Holmes Beach
    Bedrooms : 3
    Bathrooms : 2.5

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

  5. 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...

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

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

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

  7. 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...

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

    City : Sanibel
    Bedrooms : 3
    Bathrooms : 2

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

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

    City : Anna Maria
    Bedrooms : 3
    Bathrooms : 2
    Pool

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

  10. Sleeps 8, $350 to $535/night

    City : Holmes Beach
    Bedrooms : 4
    Bathrooms : 4
    Pool

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

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

    City : Sanibel
    Bedrooms : 3
    Bathrooms : 2

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

  12. Sleeps 10, $340 to $645/night

    City : Anna Maria
    Bedrooms : 4
    Bathrooms : 3

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

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

    City : Bradenton Beach
    Bedrooms : 2
    Bathrooms : 2

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

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

    City : Anna Maria
    Bedrooms : 4
    Bathrooms : 3
    Pool Pets OK

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

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

    City : Holmes Beach
    Bedrooms : 3
    Bathrooms : 2.5
    Pool

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

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

    City : Bradenton Beach
    Bedrooms : 2
    Bathrooms : 2

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

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

    City : Sanibel
    Bedrooms : 3
    Bathrooms : 3

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

  18. Sleeps 10, $310 to $655/night

    City : Anna Maria
    Bedrooms : 4
    Bathrooms : 2
    Pool

    Adorable and quaint old-Florida style seasonal vacation cottage. (4)...

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

    City : Holmes Beach
    Bedrooms : 4
    Bathrooms : 3

    One of the appeals of island life is simplicity. We love our days...

  20. 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...

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

    City : Anna Maria
    Bedrooms : 3
    Bathrooms : 4
    Pool

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

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

    City : Sanibel
    Bedrooms : 2
    Bathrooms : 2

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

  23. Sleeps 6, ~$295/night

    City : Bradenton Beach
    Bedrooms : 3
    Bathrooms : 3
    Pool

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

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

    City : Nokomis
    Bedrooms : 3
    Bathrooms : 2

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

  25. Sleeps 12, $290 to $565/night

    City : Holmes Beach
    Bedrooms : 5
    Bathrooms : 3
    Pool Pets OK

    "Forever Flip Flops" welcomes you to this recently re-done and...

  26. Sleeps 6, $290 to $625/night

    City : Holmes Beach
    Bedrooms : 3
    Bathrooms : 2.5

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

  27. Sleeps 8, $285 to $465/night

    City : Holmes Beach
    Bedrooms : 3
    Bathrooms : 2.5

    This vacation rental is exactly what you’ve been dreaming of –...

  28. Sleeps 6, $280 to $560/night

    City : Anna Maria
    Bedrooms : 3
    Bathrooms : 2

    There’s a certain Florida way of life. It’s about knowing you...

  29. Sleeps 6, $270 to $500/night

    City : Sanibel
    Bedrooms : 2
    Bathrooms : 2

    Sundial Beach Resort and Spa unit Q204 is a spacious and beautifully...

  30. Sleeps 12, $270 to $750/night

    City : Holmes Beach
    Bedrooms : 5
    Bathrooms : 4
    Pool

    Light and bright coastal duplex-style home perfect for larger...