
Family-friendly vacation rentals in Osprey
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Osprey
Guests agree: these family-friendly homes 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 family-friendly rentals
Family-friendly home rentals with a hot tub

Quiet Retreat-5mi to Beach-Hot Tub, Outdoor Shower

The Oasis-Private Heated Pool Hot Tub-5mi to beach

La Villa des Pins

Peaceful Getaway just minutes from the beach

Coastal Home in Sarasota-8min from Siesta Key

Private house with loft

Spectacular Sunsets! 15 min Siesta Key!

Sandy Feet Retreat- Cozy Bungalow & Outdoor living
Family- and pet-friendly home rentals

Spacious 2 Bedroom Home | Near Beach | Heated Pool

Chic & Cozy Getaway • Near Siesta Key Beach

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

Sarasota Tropical Place in the Heart of the Gulf!

Perfect Florida location: Craftsman Carriage House

Pink Flamingo: 4 Beds/3 Baths Screened Pool Oasis

TROPICAL OASIS, MINUTES FROM THE BEACH!!

Duplex - just mins to Siesta Beach - Pet Friendly
Family-friendly home rentals with a pool

Venice Getaway 3 bedrooms, private heated pool

"Sea Turtle" Saltwater Pool, Shore Beach House

Spacious Cozy Tropical Retreat!

Vacation Villa/Resort Pool 4 miles to Siesta Key

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Paradise with a pool, pier and private beach area

Lake View, 6 Miles From Beach

Cozy & Beautiful Pool Villa in Sarasota County, FL
Quick stats about vacation rentals that are family-friendly in Osprey
Total rentals
60 properties
Nightly prices starting at
€ 34 before taxes and fees
Total number of reviews
710 reviews
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
30 properties have a pool
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Destinations to explore
- Seminole Vacation rentals
- Central Florida Vacation rentals
- Miami Vacation rentals
- Orlando Vacation rentals
- Saint Johns River Vacation rentals
- Gold Coast Vacation rentals
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- Pet-friendly rentals Osprey
- Rentals with a patio Osprey
- House rentals Osprey
- Rentals with pools Osprey
- Rentals with a washer and dryer Osprey
- Rentals with a hot tub Osprey
- Rentals with outdoor seating Osprey
- Rentals with a fire pit Osprey
- Fitness-friendly rentals Osprey
- Family-friendly rentals Sarasota County
- Family-friendly rentals Florida
- Family-friendly 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