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
4.97 out of 5 average rating, 109 reviewsGorgeous Home / Heated Pool and Spa
Sep 24 – Oct 1
Condo in Holmes Beach
4.96 out of 5 average rating, 116 reviewsBeautiful beachfront condo for perfect vacation
Jul 20 – 27
Condo in Longboat Key
4.82 out of 5 average rating, 159 reviewsUpdated Beachfront Condo at Prestigious Long Boat
Dec 7 – 14
Home in Bradenton
4.91 out of 5 average rating, 254 reviewsPalm Retreat Gold: Luxury Edition of #1 Rental
Sep 12 – 19
Home in Punta Gorda
4.93 out of 5 average rating, 123 reviewsTropical themed Island style home!
Sep 20 – 27
Condo in Siesta Key
4.92 out of 5 average rating, 137 reviewsSiesta Key Serenity At The Palm Bay Club
Nov 17 – 24
Apartment in Bradenton Beach
4.92 out of 5 average rating, 262 reviewsLas Palmas Beach Rentals unit 3
Aug 29 – Sep 5
Home in Sarasota
5.0 out of 5 average rating, 12 reviews3681 White Pine Ct, Sarasota, FL
Sep 26 – Oct 3
Family- and pet-friendly home rentals
Home in Venice
4.78 out of 5 average rating, 113 reviewsSouth Venice, FL. Ideal vacation home.
Nov 3 – 10
Bungalow in Sarasota
4.92 out of 5 average rating, 264 reviewsDowntown Bungalow...Beaches- Restaurants- Cafes!
Jul 2 – 9
Condo in Nokomis
4.83 out of 5 average rating, 140 reviewsPrivate Beachside Kitchenette
Jul 7 – 14
Home in Sarasota
4.95 out of 5 average rating, 181 reviews2bed/2bath with POOL house, close by SIESTA KEY!!!
Aug 29 – Sep 5
Home in Englewood
4.96 out of 5 average rating, 104 reviewsWaterfront Cottage by Manasota Key
Sep 12 – 19
Townhouse in Sarasota
4.93 out of 5 average rating, 242 reviewsFlamingo🦩1/2M Walk to Downtown #TheTropicalNut☀️🦩⛱🥳
Jun 22 – 29
Cottage in Bradenton
4.94 out of 5 average rating, 153 reviewsCozy Cottage L-Steps to Riverwalk/Close to Beaches
Jul 22 – 29
Guesthouse in Punta Gorda
4.9 out of 5 average rating, 230 reviewsCharming Cottage
Mar 12 – 19
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!
Jun 5 – 12
Home in Siesta Key
5.0 out of 5 average rating, 124 reviewsOne-of-a-kind*Beach, Village, Dock & Private Pool!
Dec 12 – 19
Condo in Siesta Key
4.96 out of 5 average rating, 105 reviewsSiesta Key Condo. Checkout our great rates!
Aug 29 – Sep 5
Condo in Sarasota
4.91 out of 5 average rating, 215 reviewsNew Renovation! Walk to Beach, Pool, Restaurants!
Jan 24 – 31
Condo in Siesta Key
4.92 out of 5 average rating, 130 reviews*A Stones Throw from #1 Voted Siesta Key Beach*
May 24 – 31
Home in Sarasota
4.82 out of 5 average rating, 125 reviewsVacation Paradise Close to Beach!
Oct 24 – 31
Home in Venice
4.93 out of 5 average rating, 99 reviewsGorgeous Private Pool! Fountains! Near Beach- os
Mar 9 – 16
Home in Bradenton
4.87 out of 5 average rating, 205 reviewsSunny Oasis Near Beaches With Pool
May 6 – 13
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
R1,129 ZAR before taxes and fees
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- Family-friendly rentals United States
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