
House vacation rentals in Osprey
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Top-rated house rentals in Osprey
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Osprey house rentals
House rentals with a pool

Venice Gardens getaway

Spacious 2 Bedroom Home | Near Beach | Heated Pool

1 House 1400sq. ft. 12 min from Siesta Key!

Cozy 2BD/2BA with Heated Pool Near Siesta Key

Private Siesta Beach House Oasis with Heated Pool.

True Island Living House/beach/water views

Sarasota Escape | Minutes to Beaches + Downtown

Living The Dream: Heated Pool + Mini Golf +Swings
Weekly house rentals

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Perfect Getaway Home - 12/min from siesta w/HotTub

The Pool house retreat

Cute 2 bedroom home close to it all.

Florida Escape 7-minute Drive from the Beach

Beach Home Away From Home > 5 miles to Siesta Key

Siesta Key Fully-Renovated Unit 5 min to the beach

Summer sunset. 3 minutes away from beach!
Private house rentals

Luxury Oasis Home 3BR 2Bath with Heated Pool

Spacious Cozy Tropical Retreat!

14 acre home peaceful, private, 5 minutes to beach

6 Miles to Beaches | Cozy Home w/ Screened Lanai

Great price for the summer 3/2 Beach House

Cheerful 3-Bedroom home with parking

Peaceful Getaway just minutes from the beach

Lake View, 6 Miles From Beach
Quick stats about house rentals in Osprey
Total rentals
40 properties
Nightly prices starting at
R870 ZAR before taxes and fees
Total number of reviews
680 reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
20 properties have a pool
Destinations to explore
- Seminole Vacation rentals
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- Miami Vacation rentals
- Orlando Vacation rentals
- Saint Johns River Vacation rentals
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- Havana Vacation rentals
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- Four Corners Vacation rentals
- Family-friendly rentals Osprey
- Pet-friendly rentals Osprey
- Rentals with pools Osprey
- Rentals with a washer and dryer Osprey
- Rentals with a patio Osprey
- Rentals with outdoor seating Osprey
- Fitness-friendly rentals Osprey
- Rentals with a hot tub Osprey
- Rentals with a fire pit Osprey
- House rentals Sarasota County
- House rentals Florida
- House rentals United States
- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Captiva Island
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Coquina Beach
- Anna Maria Public Beach
- Lido Key Beach
- Cortez Beach
- Vinoy Park
- Gulfport Beach Recreation Area
- Streamsong Resort
- Jannus Live
- North Beach
- Manasota Key Beach
- River Strand Golf and Country Club
- North Beach At Fort DeSoto Park
- Englewood Beach
- Point Of Rocks
- Lakewood National Golf Club
- Fort De Soto Park