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
Home in Sarasota
4.98 out of 5 average rating, 161 reviewsThe Palms-Private Heated Pool Hot Tub-5mi to beach
Home in Sarasota
4.97 out of 5 average rating, 113 reviewsGorgeous Home / Heated Pool and Spa
Guest suite in Sarasota
4.95 out of 5 average rating, 155 reviewsROYS PLACE Romantic, Private, Paradise!
Condo 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, 260 reviewsPalm Retreat Gold: Luxury Edition of #1 Rental
Apartment in Bradenton Beach
4.88 out of 5 average rating, 330 reviewsLas Palmas Beach Rentals unit 2
Condo in Siesta Key
4.92 out of 5 average rating, 140 reviewsSiesta Key Serenity At The Palm Bay Club
Home in Punta Gorda
4.9 out of 5 average rating, 125 reviewsTropical themed Island style home!
Family- and pet-friendly home rentals
Home in Sarasota
4.82 out of 5 average rating, 201 reviewsPrivate Siesta Beach House Oasis with Heated Pool.
Bungalow in Sarasota
4.87 out of 5 average rating, 103 reviews2BR, 2BA home in the heart of downtown Sarasota
Guest suite in Sarasota
4.85 out of 5 average rating, 273 reviewsSapphire Shores Arcadia 1Bed/1Bath - Walk to Bay!
Townhouse in Sarasota
4.95 out of 5 average rating, 337 reviewsPeacock🦚1/2 m Walk to Downtown #TheTropicalNut ☀️🥳👙
Guesthouse in Sarasota
4.99 out of 5 average rating, 102 reviewsSarasota Pool House
Home in Sarasota
4.95 out of 5 average rating, 187 reviews2bed/2bath with POOL house, close by SIESTA KEY!!!
Home in Sarasota
4.93 out of 5 average rating, 143 reviewsSarasota Sandpiper: 4 Bed/3 bath + Pool
Cottage in Bradenton
4.94 out of 5 average rating, 155 reviewsCozy Cottage L-Steps to Riverwalk/Close to Beaches
Family-friendly home rentals with a pool
Apartment in Sarasota
4.94 out of 5 average rating, 134 reviewsSuper Clean! 2/2 condo Walk to SKey!
Condo in Siesta Key
4.96 out of 5 average rating, 108 reviewsSiesta Key Condo. Checkout our great rates!
Home in Siesta Key
5.0 out of 5 average rating, 127 reviewsOne-of-a-kind*Beach, Village, Dock & Private Pool!
Home in Venice
4.93 out of 5 average rating, 103 reviewsGorgeous Private Pool! Fountains! Near Beach- os
Condo in Sarasota
4.91 out of 5 average rating, 218 reviewsNew Renovation! Walk to Beach, Pool, Restaurants!
Guest suite in Cape Coral
4.9 out of 5 average rating, 480 reviewsCosy pool side Cabana
Apartment in Sarasota
4.85 out of 5 average rating, 291 reviews· King bed . Pool. Daily rentals
Condo in Sarasota
4.83 out of 5 average rating, 149 reviewsBest Gulf Coast Condo in Siesta Key
Quick stats about vacation 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
$83 CAD before taxes and fees
Destinations to explore
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- Family-friendly rentals United States
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- Family-friendly rentals Sarasota County
- Rentals with a hot tub Osprey
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- Pet-friendly rentals Osprey
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- Monthly Rentals Osprey
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