Holiday Rentals in Osprey
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5 km
55 rentals in Osprey.
Paradise with a pool, pier and private beach area
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Pool, Hot tub, Close to Beaches, Shopping, More!
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The Shoreland Hideaway 4BR/ 2BA with pool, 15 mins from Siesta Key
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3 Bedroom Penthouse with Stunning Sunset Views of Blackburn Bay!
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2 bedroom condo in osprey
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Private guest house with king bed & loft. Deck with hot tub and putting green
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Stunning 2 Bedroom Condo---- 5 Minutes from the Beach!
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Just South of Sarasota Gorgeous Waterfront Condo 2 Bedrooms, 2 Baths.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Enjoy your own 2bd/2ba Condo, Pool, Pickleball, Tennis, amazing sunsets!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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2BR Florida Home Near the Shore!
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Pet Friendly Paradise Close To Sarasota-Venice
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Lovely 2 bed 2 bath condo with spectacular sunsets from the pier
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Luxury Condo on the water with Intercostal view
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Renovated Waterfront Home
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Creekside Paradise, 3BR, 2BA, private heated pool, North Creek boat dock
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New Custom Smart Home Sarasota Family Getaway
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Casey Key Paradise
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Tropical pool home close to beaches
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Sarasota Vacation paradise!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxury 2 BR Condo on the water located between Sarasota and Venice, Florida.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Pine Run Dog Friendly Condo! Close to beaches!
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Waterfront Property with dock. Private and stunning backyard, bring your boat!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming cozy coastal house�minutes away from Venice beach
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Fall is the best time! To vacation here, Avail ALL Autumn till NYE 2025!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Windsor Lodge Unit 7, studio, close to the beaches, pool access
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Osprey Home | King & Queen Beds | Sleeps 6
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Single-story duplex near beach with renovated interior, AC-Dogs ok
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Condo Windsor Lodge Unit 5 1BR/1BA
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Southbay Yacht and Racquet Club Retreat close to Casey Key and Nokomis Beach
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Renovated duplex near beach with central AC & private W/D-Dogs ok
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Cozy Cottage in south Sarasota Florida, Close to Beaches!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Windsor Lodge Unit 3, studio, close to the beaches, pool access
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Windsor Lodge Unit 15, studio, close to the beaches, pool access
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Bright & Comfortable Florida Cottage, Within 15 Min to Siesta and Nokomis Beach
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Phoenix Retreat - Relaxing 3 bedroom home away from home
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ground Floor, walking distance to fishing pier, restaurants & shopping.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Royal Luxury Edenville House by Casey Key
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Windsor Lodge Unit 19, studio, 1BR/1BA, close to the Beaches, pool access
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Oaks Preserve Condominium
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Milton Has electric and water! . Furnished! Near Nokomis, Venice and Siesta.
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A Tropical 2 Bedroom/2 Bath House w/ Pool and Dock
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Cozy 1-bedroom condo in amazing Osprey, near the beach, WiFi, AC, Pool, Tennis
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Full duplex near beach with renovated interior, screened porches-Dogs ok
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful 3 Bedroom Penthouse --- 5 Minutes to the beach!
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Family Guesthouse with Pool Views minutes from Nokomis Beach
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RELAX. ENJOY.
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5 minutes to the BEACH! Beautiful neighborhood on intercoastal. Family friendly
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Windsor Lodge Unit 10, Studio, close to the beaches, pool access
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Welcome to Lime on Green! I also have a rental CAR listed/available on ********
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Beach-House, wonderful elec. heated Pool with a Natural Waterfall, Jacuzzi, Wifi
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Showing results 1-50 of 55
Frequently Asked Questions about Osprey
- Yes, here are some popular holiday rentals in Osprey that have a pool:
- Paradise with a pool, pier and private beach area
- Pool, Hot tub, Close to Beaches, Shopping, More!
- The Shoreland Hideaway 4BR/ 2BA with pool, 15 mins from Siesta Key
- Yes, here are some popular holiday rentals in Osprey that have internet access:
- Paradise with a pool, pier and private beach area
- Pool, Hot tub, Close to Beaches, Shopping, More!
- The Shoreland Hideaway 4BR/ 2BA with pool, 15 mins from Siesta Key
- Some of the most popular kid friendly rentals in Osprey are:
- Paradise with a pool, pier and private beach area
- Pool, Hot tub, Close to Beaches, Shopping, More!
- The Shoreland Hideaway 4BR/ 2BA with pool, 15 mins from Siesta Key
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