
House holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Osprey
House rentals with a pool

Gorgeous Home / Heated Pool and Spa

Luxury Oasis Home 3BR 2Bath with Heated Pool

Pool Courtyard, patio w/ fire pit, 2 mls downtown

3 Bed Penthouse w/ Waterview!

Spacious 3 Br Home w/ Heated pool -1 Mile to Beach

Sarasota Escape | Minutes to Beaches + Downtown

Intercostal Oasis

The Pineapple Escape
Weekly house rentals

Ashota - The Jellyfish

Good Beach Bungalow

14 acre home peaceful, private, 5 minutes to beach

Modern, Spacious Villa close to the Beach!FreeWiFi

Walking distance to Nokomis Beach!

Casa Playa Sleeps 6

The Mango House Beach Cottage

Modern Waterfront Bliss
Private house rentals

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Venice Gardens getaway

Magical Secluded Retreat

Morning Side

Coastal Retreat near Siesta Key Beach and Downtown

Tropical Oasis | Fully Remodeled | Private Pool

Luxury Pet friendly home, 2.7miles to Siesta Key!

Charming Home in Sarasota-8min from Siesta Key
Quick stats about house rentals in Osprey
Total rentals
40 properties
Nightly prices starting at
₹4,338 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 Holiday rentals
- Miami Holiday rentals
- Central Florida Holiday rentals
- Orlando Holiday rentals
- Saint Johns River Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Havana Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Kissimmee Holiday rentals
- Four Corners Holiday rentals
- Rentals with pools Osprey
- Rentals with a washing machine and dryer Osprey
- Rentals with a hot tub Osprey
- Pet-friendly rentals Osprey
- Fitness-friendly rentals Osprey
- Family-friendly rentals Osprey
- Rentals with a patio Osprey
- Rentals with outdoor seating Osprey
- Rentals with a firepit Osprey
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- Anna Maria Island
- Siesta Beach
- Captiva Island
- Crescent Beach
- John's Pass
- Turtle Beach
- Anna Maria Public Beach
- Caspersen Beach
- Bean Point Beach
- Lido Key Beach
- Coquina Beach
- Cortez Beach
- Gulfport Beach Recreation Area
- Fort De Soto Park
- Vinoy Park
- Manasota Key Beach
- Jannus Live
- North Beach
- Streamsong Resort
- Myakka River State Park
- North Beach At Fort DeSoto Park
- Alafia River State Park
- River Strand Golf and Country Club
- Mahaffey Theater