Vacation Rentals

Page 7: Vacation Rentals in Osprey, FL

(91 - 105 of 723)
  1. Downtown Sarasota Gem. Perfect for a weekend retreat or an extended stay. Completely remodeled in June 2020, this turnkey apartment has been completely revamped for comfortability & relaxation. Kitchen boasts brand new quartz countertops with stai...
    Posted on ListedBuy
  2. This fully furnished 2 bedroom vacation rental is located in the Meadows Golf & Country Club. It is home to a 360-acre campus filled with all the excellent sport, dining and social activities that you would want to enjoy all year round. The outsta...
    Posted on ListedBuy
  3. Welcome to Sunflower! Newly listed, this modern one-story 2-bedroom, 1-bath condo is located just a few blocks away from Downtown Sarasota! Upon arrival, you will find a newly installed wooden gate that opens up to your backyard retreat! Through t...
    Posted on ListedBuy
  4. VACATION RENTAL! Call for availability! 'Old Florida' style vacation rental cottage - 2 bedroom, 1 bath just one block from Lido Beach! Nestled in the back of Pelican Gardens, this tropical Villa is a short stroll to Ted Sperling Park and St. Arma...
    Posted on ListedBuy
  5. Welcome to a Coastal living vibe in the heart of Sarasota. A great family vacation home, a short drive & minutes from all the beaches: Siesta Key, Lido Key, Bradenton Beach, and Ana Maria Beach. Sorry already rented Feb-Mar 2023 and Feb-Apr 2024. ...
    Posted on ListedBuy
  6. SIESTA KEY DREAM VACATION RENTAL! Just across the street from Siesta Key beach, with a private deeded boat dock and water views! This lovely first floor, end unit condo has everything you need and checks all the boxes. Two bedrooms, two baths, ope...
    Posted on ListedBuy
  7. The Meadows Golf and Country Club Vacation Rental ---NOT AVAILABLE JAN-MAR 2024 (ALREADY LEASED)--- Completely Renovated and Gorgeous Furnished in a colorful yet calm and contemporary style that invites you to relax. Tile flooring, upgraded ceilin...
    Posted on ListedBuy
  8. Available for the 2024 season! Welcome to your dream destination on beautiful Venice Island! Nestled in a serene corner of Venice Island, this short term rental offers an ideal escape for those seeking quiet, tranquility, and peace. Tucked away fr...
    Posted on ListedBuy
  9. This gorgeous 1 bedroom 1 bathroom fully furnished unit in the exclusive Terrace building on Siesta Key beach steps away from Siesta Key Village. Enjoy a swim from the elevated pool and catch a sunset with a drink steps away from the unit. This un...
    Posted on HERO PM
  10. New monthly vacation rental alert! An Ascendia Group Property! Escape those cold winters and gloomy rainy seasons and stay at this charming first floor two-bedroom two-bathroom condo in the popular Siesta Key beach community, Beachway! Located in ...
    Posted on ListedBuy
  11. Seasonal. Amazing location, luxurious community with amazing views and amenities! You'll absolutely love the state of art gym, Gulf front pool and concierge services. Orchid Beach Club is a rare vacation rental. Private elevator, magnificent views...
    Posted on ListedBuy
  12. RDL68582296 - Under contract-accepting backup offers. Quarter Acre Residential Lot North Port 34288. Welcome to Florida's Gulf Coast. If you've been searching for a great deal on a centrally located yet private site to build your dream home, this ...
    Posted on ListedBuy
  13. LOCATION, LOCATION, LOCATION! Stunning turnkey recently furnished two bedroom, two bathroom condo available in the sought after community of St. Armand's Tower North. Totally updated with top of the line appliances. Beautifully decorated, Crestron...
    Posted on ListedBuy
  14. Three beds +office, 2 bath vacation rental home in Tahiti Park. Tastefully decorated, flat screen TV's and Wi Fi throughout. This wonderful home has all you need for the perfect vacation retreat. The master bedroom features a king-sized bed, walk ...
    Posted on ListedBuy
  15. Enjoy this beautifully 3-bedroom and 3-bathroom remodeled pool home on Siesta key, named the #1 Beach in the country! Brand new heated salt water pool has been completed! We are LESS THAN 1 minute to the powdered sugar sands and turquoise waters. ...
    Posted on HERO PM
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