Family-friendly holiday 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.
Holiday 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
Home in Sarasota
4.98 out of 5 average rating, 160 reviewsThe Palms-Private Heated Pool Hot Tub-5mi to beach
Home in Sarasota
4.97 out of 5 average rating, 110 reviewsGorgeous Home / Heated Pool and Spa
Apartment in Longboat Key
4.82 out of 5 average rating, 159 reviewsUpdated Beachfront Condo at Prestigious Long Boat
Home in Bradenton
4.9 out of 5 average rating, 256 reviewsPalm Retreat Gold: Luxury Edition of #1 Rental
Flat in Bradenton Beach
4.87 out of 5 average rating, 327 reviewsLas Palmas Beach Rentals unit 2
Home in Punta Gorda
4.93 out of 5 average rating, 123 reviewsTropical themed Island style home!
Apartment in Siesta Key
4.92 out of 5 average rating, 137 reviewsSiesta Key Serenity At The Palm Bay Club
Home in Sarasota
4.86 out of 5 average rating, 29 reviews3650 White Pine
Family- and pet-friendly home rentals
Apartment in Nokomis
4.83 out of 5 average rating, 144 reviewsPrivate Beachside Kitchenette
Bungalow in Sarasota
4.92 out of 5 average rating, 265 reviewsDowntown Bungalow...Beaches- Restaurants- Cafes!
Home in Sarasota
4.87 out of 5 average rating, 205 reviewsThe Pineapple Suite.Teal tropical home in Sarasota
Townhouse in Sarasota
4.95 out of 5 average rating, 329 reviewsPeacock🦚1/2 m Walk to Downtown #TheTropicalNut ☀️🥳👙
Home in Sarasota
4.95 out of 5 average rating, 182 reviews2bed/2bath with POOL house, close by SIESTA KEY!!!
Cottage in Bradenton
4.94 out of 5 average rating, 153 reviewsCozy Cottage L-Steps to Riverwalk/Close to Beaches
Guest house in Punta Gorda
4.9 out of 5 average rating, 232 reviewsCharming Cottage
Home in Sarasota
4.82 out of 5 average rating, 196 reviewsPrivate Siesta Beach House Oasis with Heated Pool.
Family-friendly home rentals with a pool
Flat in Sarasota
4.94 out of 5 average rating, 133 reviewsSuper Clean! 2/2 condo Walk to SKey!
Bungalow in Sarasota
4.92 out of 5 average rating, 310 reviewsPool & fenced-in yard in downtown edge bungalow
Apartment in Siesta Key
4.96 out of 5 average rating, 105 reviewsSiesta Key Condo. Checkout our great rates!
Home in Venice
4.93 out of 5 average rating, 100 reviewsGorgeous Private Pool! Fountains! Near Beach- os
Home in Siesta Key
5.0 out of 5 average rating, 125 reviewsOne-of-a-kind*Beach, Village, Dock & Private Pool!
Apartment in Sarasota
4.91 out of 5 average rating, 216 reviewsNew Renovation! Walk to Beach, Pool, Restaurants!
Home in Sarasota
4.81 out of 5 average rating, 126 reviewsVacation Paradise Close to Beach!
Apartment in Siesta Key
4.92 out of 5 average rating, 131 reviews*A Stones Throw from #1 Voted Siesta Key Beach*
Quick stats about holiday rentals that are family-friendly in Osprey
Total rentals
60 properties
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
20 properties allow pets
Total number of reviews
500 reviews
Nightly prices starting at
£48 before taxes and fees
Destinations to explore
- Sarasota Holiday rentals
- Anna Maria Island Holiday rentals
- Tampa Holiday rentals
- Naples Holiday rentals
- Kissimmee Holiday rentals
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- Family-friendly rentals United States
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- Family-friendly rentals Florida
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- Family-friendly rentals Sarasota County
- Rentals with pools Osprey
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