FEATURED FLORIDA SOUTH-WEST, FLORIDA STAYS

Vacation Rentals in Florida South-West, Florida

Every property is professionally managed with 24/7 guest support and a best-rate guarantee through RedAwning. Tap a card to check availability and book direct.

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BEDROOMS
SLEEPS
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Showing 63 of 63 properties

  1. Longboat Key
    Sunset Sanctuary

    CONDOMINIUM

    Sunset Sanctuary

    2 Bedrooms 2 Bathrooms 4 Guests

    Longboat Key, FL, Sunset Sanctuary vacation rental.

    Free cancellation · 24/7 support Book Now
  2. Longboat Key
    Decked Out on Marbury

    HOUSE

    Decked Out on Marbury

    4 Bedrooms 4.5 Bathrooms 10 Guests

    Longboat Key, FL, Decked Out on Marbury vacation rental.

    Pool Pets OK
    Free cancellation · 24/7 support Book Now
  3. Sarasota
    Coastal Cottage

    HOUSE

    Coastal Cottage

    2 Bedrooms 2 Bathrooms 6 Guests

    Sarasota, FL, Coastal Cottage vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  4. Siesta Key
    Sole Retreat

    CONDOMINIUM

    Sole Retreat

    2 Bedrooms 2 Bathrooms 6 Guests

    Siesta Key, FL, Sole Retreat vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  5. Sarasota
    Sunny Urban Escape

    HOUSE

    Sunny Urban Escape

    3 Bedrooms 2 Bathrooms 6 Guests

    Sarasota, FL, Sunny Urban Escape vacation rental.

    Free cancellation · 24/7 support Book Now
  6. Sarasota
    Casa de Flores

    HOUSE

    Casa de Flores

    4 Bedrooms 3 Bathrooms 9 Guests

    Sarasota, FL, Casa de Flores vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  7. Siesta Key
    The Windward House

    HOUSE

    The Windward House

    3 Bedrooms 2.5 Bathrooms 6 Guests

    Siesta Key, FL, The Windward House vacation rental.

    Pool Pets OK
    Free cancellation · 24/7 support Book Now
  8. Fort Myers
    Luxurious Waterfront Condo at Alta Mar

    CONDOMINIUM

    Luxurious Waterfront Condo at Alta Mar

    2 Bedrooms 2 Bathrooms 4 Guests

    Fort Myers, FL, Luxurious Waterfront Condo at Alta Mar vacation rental.

    Pool Hot Tub Pets OK
    Free cancellation · 24/7 support Book Now
  9. Sarasota
    Paradise Palace

    HOUSE

    Paradise Palace

    4 Bedrooms 2 Bathrooms 10 Guests

    Sarasota, FL, Paradise Palace vacation rental.

    Pool Pets OK
    Free cancellation · 24/7 support Book Now
  10. Siesta Key
    Turtle Beach Bliss

    CONDOMINIUM

    Turtle Beach Bliss

    2 Bedrooms 2 Bathrooms 4 Guests

    Siesta Key, FL, Turtle Beach Bliss vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  11. Cape Coral
    Waterfront Luxury Micro Resort Heated Salt Pool

    HOUSE

    Waterfront Luxury Micro Resort Heated Salt Pool

    4 Bedrooms 2 Bathrooms 10 Guests

    Cape Coral, FL, Waterfront Luxury Micro Resort Heated Salt Pool vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  12. Siesta Key
    Sandy Cove Oasis

    CONDOMINIUM

    Sandy Cove Oasis

    2 Bedrooms 2 Bathrooms 4 Guests

    Siesta Key, FL, Sandy Cove Oasis vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  13. Sarasota
    Coastal Moderne

    TOWNHOUSE

    Coastal Moderne

    2 Bedrooms 2.5 Bathrooms 6 Guests

    Sarasota, FL, Coastal Moderne vacation rental.

    Pets OK
    Free cancellation · 24/7 support Book Now
  14. Siesta Key
    Crescent Siesta Key Charmer

    CONDOMINIUM

    Crescent Siesta Key Charmer

    3 Bedrooms 2 Bathrooms 6 Guests

    Siesta Key, FL, Crescent Siesta Key Charmer vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  15. Longboat Key
    Just Beachy at Beach Castle #16

    CONDOMINIUM

    Just Beachy at Beach Castle #16

    2 Bedrooms 2 Bathrooms 6 Guests

    Longboat Key, FL, Just Beachy at Beach Castle #16 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  16. Sarasota
    Paradise Found

    HOUSE

    Paradise Found

    3 Bedrooms 3.5 Bathrooms 6 Guests

    Sarasota, FL, Paradise Found vacation rental.

    Pool Pets OK
    Free cancellation · 24/7 support Book Now
  17. Sarasota
    Cityscape Retreat

    TOWNHOUSE

    Cityscape Retreat

    2 Bedrooms 3.5 Bathrooms 6 Guests

    Sarasota, FL, Cityscape Retreat vacation rental.

    Hot Tub Pets OK
    Free cancellation · 24/7 support Book Now
  18. Sarasota
    The Beach House

    CONDOMINIUM

    The Beach House

    2 Bedrooms 2 Bathrooms 6 Guests

    Sarasota, FL, The Beach House vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  19. Siesta Key
    Siesta Beach Retreat

    TOWNHOUSE

    Siesta Beach Retreat

    2 Bedrooms 2 Bathrooms 6 Guests

    Siesta Key, FL, Siesta Beach Retreat vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  20. Fort Myers
    Relaxing 2BR Fort Myers Getaway Near Beaches

    APARTMENT

    Relaxing 2BR Fort Myers Getaway Near Beaches

    2 Bedrooms 2.5 Bathrooms 4 Guests

    Fort Myers, FL, Relaxing 2BR Fort Myers Getaway Near Beaches vacation rental.

    Pool Pets OK
    Free cancellation · 24/7 support Book Now
  21. Cape Coral
    Blue Oasis- Saltwater Pool, Dock, Dog-Friendly

    HOUSE

    Blue Oasis- Saltwater Pool, Dock, Dog-Friendly

    3 Bedrooms 3 Bathrooms 8 Guests

    Cape Coral, FL, Blue Oasis- Saltwater Pool, Dock, Dog-Friendly vacation rental.

    Pool Pets OK
    Free cancellation · 24/7 support Book Now
  22. Cape Coral
    Sleeps 16 plus Central Cape Coral Family Escape

    HOUSE

    Sleeps 16 plus Central Cape Coral Family Escape

    4 Bedrooms 2 Bathrooms 16 Guests

    Cape Coral, FL, Sleeps 16 plus Central Cape Coral Family Escape vacation rental.

    Free cancellation · 24/7 support Book Now
  23. Sarasota
    Sunshine Retreat

    HOUSE

    Sunshine Retreat

    4 Bedrooms 2 Bathrooms 8 Guests

    Sarasota, FL, Sunshine Retreat vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  24. Sarasota
    Uptown Oasis

    TOWNHOUSE

    Uptown Oasis

    3 Bedrooms 3.5 Bathrooms 8 Guests

    Sarasota, FL, Uptown Oasis vacation rental.

    Pets OK
    Free cancellation · 24/7 support Book Now
  25. Longboat Key
    Las Hermanas 2

    CONDOMINIUM

    Las Hermanas 2

    1 Bedroom 1 Bathroom 4 Guests

    Longboat Key, FL, Las Hermanas 2 vacation rental.

    Free cancellation · 24/7 support Book Now
  26. Siesta Key
    'Bout Time- Turtle Beach, Tennis, Heated Pool, Bay Views

    CONDOMINIUM

    'Bout Time- Turtle Beach, Tennis, Heated Pool, Bay …

    2 Bedrooms 2 Bathrooms 7 Guests

    Siesta Key, FL, 'Bout Time- Turtle Beach, Tennis, Heated Pool, Bay Views vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  27. Longboat Key
    Surf and Turf at Cedars East

    TOWNHOUSE

    Surf and Turf at Cedars East

    2 Bedrooms 2.5 Bathrooms 4 Guests

    Longboat Key, FL, Surf and Turf at Cedars East vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  28. Longboat Key
    Las Hermanas 1

    STUDIO

    Las Hermanas 1

    Studio 1 Bathroom 4 Guests

    Longboat Key, FL, Las Hermanas 1 vacation rental.

    Free cancellation · 24/7 support Book Now
  29. Longboat Key
    Serenity on Sutton

    TOWNHOUSE

    Serenity on Sutton

    2 Bedrooms 2 Bathrooms 4 Guests

    Longboat Key, FL, Serenity on Sutton vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  30. Longboat Key
    Buttonwood Bliss

    CONDOMINIUM

    Buttonwood Bliss

    2 Bedrooms 2 Bathrooms 4 Guests

    Longboat Key, FL, Buttonwood Bliss vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  31. Longboat Key
    Pura Vida at Beach Castle #15

    CONDOMINIUM

    Pura Vida at Beach Castle #15

    2 Bedrooms 2 Bathrooms 6 Guests

    Longboat Key, FL, Pura Vida at Beach Castle #15 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  32. Siesta Key
    Siesta Sea Gem

    CONDOMINIUM

    Siesta Sea Gem

    2 Bedrooms 1 Bathroom 4 Guests

    Siesta Key, FL, Siesta Sea Gem vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  33. Longboat Key
    Sunshine Cottage at Cedars

    CONDOMINIUM

    Sunshine Cottage at Cedars

    2 Bedrooms 2.5 Bathrooms 6 Guests

    Longboat Key, FL, Sunshine Cottage at Cedars vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  34. Sarasota
    Sarasota Solitude

    HOUSE

    Sarasota Solitude

    3 Bedrooms 2 Bathrooms 6 Guests

    Sarasota, FL, Sarasota Solitude vacation rental.

    Pool Pets OK
    Free cancellation · 24/7 support Book Now
  35. Siesta Key
    White Sands on Siesta

    CONDOMINIUM

    White Sands on Siesta

    1 Bedroom 1 Bathroom 2 Guests

    Siesta Key, FL, White Sands on Siesta vacation rental.

    Pool Pets OK
    Free cancellation · 24/7 support Book Now
  36. Longboat Key
    Las Hermanas 4

    STUDIO

    Las Hermanas 4

    Studio 1 Bathroom 2 Guests

    Longboat Key, FL, Las Hermanas 4 vacation rental.

    Free cancellation · 24/7 support Book Now
  37. Sarasota
    Urban Nest on 8th

    HOUSE

    Urban Nest on 8th

    4 Bedrooms 2 Bathrooms 9 Guests

    Sarasota, FL, Urban Nest on 8th vacation rental.

    Pets OK
    Free cancellation · 24/7 support Book Now
  38. Siesta Key
    Siesta Pearl

    CONDOMINIUM

    Siesta Pearl

    2 Bedrooms 2.5 Bathrooms 6 Guests

    Siesta Key, FL, Siesta Pearl vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  39. Siesta Key
    Hawk's Sea Nest

    CONDOMINIUM

    Hawk's Sea Nest

    2 Bedrooms 2 Bathrooms 6 Guests

    Siesta Key, FL, Hawk's Sea Nest vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  40. Sarasota
    Mauna Loa Hideaway

    HOUSE

    Mauna Loa Hideaway

    3 Bedrooms 3 Bathrooms 6 Guests

    Sarasota, FL, Mauna Loa Hideaway vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  41. Sarasota
    Tee Time on Breezemont

    HOUSE

    Tee Time on Breezemont

    3 Bedrooms 2 Bathrooms 6 Guests

    Sarasota, FL, Tee Time on Breezemont vacation rental.

    Pool Pets OK
    Free cancellation · 24/7 support Book Now
  42. Sarasota
    Sapphire Shores

    HOUSE

    Sapphire Shores

    3 Bedrooms 2 Bathrooms 7 Guests

    Sarasota, FL, Sapphire Shores vacation rental.

    Pool Pets OK
    Free cancellation · 24/7 support Book Now
  43. Sarasota
    Lazy Days at Waterside

    TOWNHOUSE

    Lazy Days at Waterside

    3 Bedrooms 2.5 Bathrooms 5 Guests

    Sarasota, FL, Lazy Days at Waterside vacation rental.

    Pets OK
    Free cancellation · 24/7 support Book Now
  44. Sarasota
    Private Cozy Sarasota Home

    HOUSE

    Private Cozy Sarasota Home

    3 Bedrooms 2 Bathrooms 6 Guests

    Sarasota, FL, Private Cozy Sarasota Home vacation rental.

    Free cancellation · 24/7 support Book Now
  45. Sarasota
    Ringside on Ringling

    HOUSE

    Ringside on Ringling

    4 Bedrooms 3 Bathrooms 8 Guests

    Sarasota, FL, Ringside on Ringling vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  46. Siesta Key
    Salty Soldi

    CONDOMINIUM

    Salty Soldi

    2 Bedrooms 2 Bathrooms 4 Guests

    Siesta Key, FL, Salty Soldi vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  47. Sarasota
    Uptown Luxury on Audubon

    TOWNHOUSE

    Uptown Luxury on Audubon

    4 Bedrooms 3.5 Bathrooms 10 Guests

    Sarasota, FL, Uptown Luxury on Audubon vacation rental.

    Hot Tub Pets OK
    Free cancellation · 24/7 support Book Now
  48. Captiva
    Captivated by the Sea

    CONDOMINIUM

    Captivated by the Sea

    2 Bedrooms 2 Bathrooms 8 Guests

    Captiva, FL, Captivated by the Sea vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  49. Sarasota
    Fanta Sea

    HOUSE

    Fanta Sea

    3 Bedrooms 2 Bathrooms 6 Guests

    Sarasota, FL, Fanta Sea vacation rental.

    Pool Pets OK
    Free cancellation · 24/7 support Book Now
  50. Longboat Key
    Beach Haven at Beach Castle #21

    CONDOMINIUM

    Beach Haven at Beach Castle #21

    2 Bedrooms 2 Bathrooms 8 Guests

    Longboat Key, FL, Beach Haven at Beach Castle #21 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  51. Siesta Key
    My Happy Place

    CONDOMINIUM

    My Happy Place

    2 Bedrooms 2 Bathrooms 4 Guests

    Siesta Key, FL, My Happy Place vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  52. Sarasota
    Poolside Paradise

    HOUSE

    Poolside Paradise

    3 Bedrooms 3 Bathrooms 8 Guests

    Sarasota, FL, Poolside Paradise vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  53. Siesta Key
    Crystal Sands on Siesta

    CONDOMINIUM

    Crystal Sands on Siesta

    2 Bedrooms 2 Bathrooms 6 Guests

    Siesta Key, FL, Crystal Sands on Siesta vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  54. Siesta Key
    Imperial Sunsets on Siesta

    CONDOMINIUM

    Imperial Sunsets on Siesta

    2 Bedrooms 2 Bathrooms 4 Guests

    Siesta Key, FL, Imperial Sunsets on Siesta vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  55. Longboat Key
    It's a Shore Thing at Beach Castle #14

    CONDOMINIUM

    It's a Shore Thing at Beach Castle #14

    1 Bedroom 1 Bathroom 4 Guests

    Longboat Key, FL, It's a Shore Thing at Beach Castle #14 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  56. Sarasota
    Sarasota Seascape

    HOUSE

    Sarasota Seascape

    4 Bedrooms 2 Bathrooms 7 Guests

    Sarasota, FL, Sarasota Seascape vacation rental.

    Pool Pets OK
    Free cancellation · 24/7 support Book Now
  57. Sarasota
    Sarasota Serenity

    HOUSE

    Sarasota Serenity

    3 Bedrooms 2 Bathrooms 10 Guests

    Sarasota, FL, Sarasota Serenity vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  58. Siesta Key
    Siesta Bayside Bliss

    CONDOMINIUM

    Siesta Bayside Bliss

    1 Bedroom 2 Bathrooms 4 Guests

    Siesta Key, FL, Siesta Bayside Bliss vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  59. Sarasota
    Dream Island

    HOUSE

    Dream Island

    8 Bedrooms 8 Bathrooms 10 Guests

    Sarasota, FL, Dream Island vacation rental.

    Pool Hot Tub Pets OK
    Free cancellation · 24/7 support Book Now
  60. Longboat Key
    Bayside Hideaway at Beach Castle #27

    VILLA

    Bayside Hideaway at Beach Castle #27

    3 Bedrooms 3 Bathrooms 8 Guests

    Longboat Key, FL, Bayside Hideaway at Beach Castle #27 vacation rental.

    Pool Hot Tub
    Free cancellation · 24/7 support Book Now
  61. Siesta Key
    Siesta Treasure

    HOUSE

    Siesta Treasure

    4 Bedrooms 2 Bathrooms 8 Guests

    Siesta Key, FL, Siesta Treasure vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  62. Siesta Key
    Siesta Treasure #4

    VILLA

    Siesta Treasure #4

    2 Bedrooms 1 Bathroom 4 Guests

    Siesta Key, FL, Siesta Treasure #4 vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now
  63. Siesta Key
    Siesta Treasure #3

    VILLA

    Siesta Treasure #3

    2 Bedrooms 1 Bathroom 4 Guests

    Siesta Key, FL, Siesta Treasure #3 vacation rental.

    Pool
    Free cancellation · 24/7 support Book Now