
Holiday houses in Osprey
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Top-rated holiday rentals in Osprey
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Osprey holiday rentals
Other great holiday rentals in Osprey
Top Guest favourite

Home in Nokomis
4.92 out of 5 average rating, 64 reviewsCheerful, sparkling 2 bedroom cottage, 1.8 miles from beach
Guest favourite

Apartment in Sarasota
4.92 out of 5 average rating, 26 reviewsThe Cozy Bungalow: Sleeps 4, private patio & grill
Top Guest favourite

Apartment in Nokomis
5 out of 5 average rating, 6 reviewsBrand New Apartment by the Beach
Guest favourite

Home in Sarasota
4.9 out of 5 average rating, 31 reviewsCute 2 bedroom home close to it all.
Superhost

Guesthouse in Sarasota
4.9 out of 5 average rating, 97 reviewsCabana/Guest house w/spa/pool 5min to Siesta key.
Top Guest favourite

Home in Osprey
5 out of 5 average rating, 14 reviews5 mins to the beach! Come relax!
Top Guest favourite

Guest suite in Sarasota
5 out of 5 average rating, 62 reviewsOcean Breeze Retreat 6min to Siesta BEACH!
Guest favourite

Villa in Sarasota
4.96 out of 5 average rating, 52 reviews7891 Timberwood, Sarasota, Florida
Quick stats about holiday rentals in Osprey
Total rentals
90 properties
Nightly prices starting at
$60 AUD before taxes and fees
Total number of reviews
1.7K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
50 properties have a pool
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami 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
- Pet-friendly rentals Osprey
- Rentals with a patio Osprey
- House rentals Osprey
- Rentals with pools Osprey
- Rentals with a washing machine and dryer Osprey
- Rentals with a hot tub Osprey
- Family-friendly rentals Osprey
- Rentals with outdoor seating Osprey
- Rentals with a fire pit Osprey
- Fitness-friendly rentals Osprey
- 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