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, 160 reviewsThe Palms-Private Heated Pool Hot Tub-5mi to beach
Home in Sarasota
4.97 out of 5 average rating, 109 reviewsGorgeous Home / Heated Pool and Spa
Condo in Longboat Key
4.82 out of 5 average rating, 159 reviewsUpdated Beachfront Condo at Prestigious Long Boat
Home in Bradenton
4.91 out of 5 average rating, 254 reviewsPalm Retreat Gold: Luxury Edition of #1 Rental
Condo in Siesta Key
4.92 out of 5 average rating, 137 reviewsSiesta Key Serenity At The Palm Bay Club
Apartment in Bradenton Beach
4.87 out of 5 average rating, 326 reviewsLas Palmas Beach Rentals unit 2
Home in Punta Gorda
4.93 out of 5 average rating, 123 reviewsTropical themed Island style home!
Home in Sarasota
5.0 out of 5 average rating, 12 reviews3681 White Pine Ct, Sarasota, FL
Family- and pet-friendly home rentals
Home in Venice
4.78 out of 5 average rating, 113 reviewsSouth Venice, FL. Ideal vacation home.
Guest suite in Sarasota
4.86 out of 5 average rating, 270 reviewsSapphire Shores Arcadia 1Bed/1Bath - Walk to Bay!
Condo in Nokomis
4.83 out of 5 average rating, 142 reviewsPrivate Beachside Kitchenette
Home in Englewood
4.96 out of 5 average rating, 104 reviewsWaterfront Cottage by Manasota Key
Home in Sarasota
4.95 out of 5 average rating, 181 reviews2bed/2bath with POOL house, close by SIESTA KEY!!!
Townhouse in Sarasota
4.93 out of 5 average rating, 242 reviewsFlamingo🦩1/2M Walk to Downtown #TheTropicalNut☀️🦩⛱🥳
Cottage in Bradenton
4.94 out of 5 average rating, 153 reviewsCozy Cottage L-Steps to Riverwalk/Close to Beaches
Guesthouse in Punta Gorda
4.9 out of 5 average rating, 230 reviewsCharming Cottage
Family-friendly home rentals with a pool
Apartment in Sarasota
4.94 out of 5 average rating, 133 reviewsSuper Clean! 2/2 condo Walk to SKey!
Condo in Siesta Key
4.94 out of 5 average rating, 138 reviewsSea Club 2-Relaxing Siesta Key Condo-Mermaids Rest
Home in Siesta Key
5.0 out of 5 average rating, 124 reviewsOne-of-a-kind*Beach, Village, Dock & Private Pool!
Cottage in Sarasota
4.84 out of 5 average rating, 154 reviewsHeated Pool! Beach! Drift Inn Unit B Siesta Key!
Bungalow in Sarasota
4.92 out of 5 average rating, 310 reviewsPool & fenced-in yard in downtown edge bungalow
Condo in Siesta Key
4.96 out of 5 average rating, 105 reviewsSiesta Key Condo. Checkout our great rates!
Condo in Sarasota
4.91 out of 5 average rating, 216 reviewsNew Renovation! Walk to Beach, Pool, Restaurants!
Home in Venice
4.93 out of 5 average rating, 100 reviewsGorgeous Private Pool! Fountains! Near Beach- os
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
$60 before taxes and fees
Destinations to explore
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