Family-friendly holiday houses 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
4.97 out of 5 average rating, 109 reviewsGorgeous Home / Heated Pool and Spa
17 – 24 Aug
Home in Sarasota
4.98 out of 5 average rating, 160 reviewsThe Palms-Private Heated Pool Hot Tub-5mi to beach
11 – 18 Aug
Condo in Longboat Key
4.82 out of 5 average rating, 159 reviewsUpdated Beachfront Condo at Prestigious Long Boat
7 – 14 Apr
Condo in Holmes Beach
4.96 out of 5 average rating, 116 reviewsBeautiful beachfront condo for perfect vacation
20 – 27 July
Home in Punta Gorda
4.93 out of 5 average rating, 123 reviewsTropical themed Island style home!
24 – 31 Aug
Home in Bradenton
4.91 out of 5 average rating, 254 reviewsPalm Retreat Gold: Luxury Edition of #1 Rental
27 Apr – 4 May
Condo in Siesta Key
4.92 out of 5 average rating, 137 reviewsSiesta Key Serenity At The Palm Bay Club
17 – 24 Nov
Apartment in Bradenton Beach
4.92 out of 5 average rating, 262 reviewsLas Palmas Beach Rentals unit 3
29 Aug – 5 Sept
Family- and pet-friendly home rentals
Home in Venice
4.78 out of 5 average rating, 113 reviewsSouth Venice, FL. Ideal vacation home.
8 – 15 Nov
Condo in Nokomis
4.83 out of 5 average rating, 140 reviewsPrivate Beachside Kitchenette
3 – 10 June
Bungalow in Sarasota
4.92 out of 5 average rating, 265 reviewsDowntown Bungalow...Beaches- Restaurants- Cafes!
9 – 16 May
Home in Sarasota
4.95 out of 5 average rating, 181 reviews2bed/2bath with POOL house, close by SIESTA KEY!!!
19 – 26 Sept
Home in Englewood
4.96 out of 5 average rating, 104 reviewsWaterfront Cottage by Manasota Key
12 – 19 Sept
Bungalow in Sarasota
4.8 out of 5 average rating, 212 reviewsCharming Mid-Century Retreat by Arlington Park
20 – 27 June
Townhouse in Sarasota
4.93 out of 5 average rating, 242 reviewsFlamingo🦩1/2M Walk to Downtown #TheTropicalNut☀️🦩⛱🥳
9 – 16 June
Cottage in Bradenton
4.94 out of 5 average rating, 153 reviewsCozy Cottage L-Steps to Riverwalk/Close to Beaches
22 – 29 July
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!
28 May – 4 June
Home in Siesta Key
5.0 out of 5 average rating, 124 reviewsOne-of-a-kind*Beach, Village, Dock & Private Pool!
12 – 19 Dec
Home in Venice
4.93 out of 5 average rating, 99 reviewsGorgeous Private Pool! Fountains! Near Beach- os
16 – 23 Aug
Condo in Siesta Key
4.96 out of 5 average rating, 105 reviewsSiesta Key Condo. Checkout our great rates!
26 Aug – 2 Sept
Condo in Siesta Key
4.92 out of 5 average rating, 130 reviews*A Stones Throw from #1 Voted Siesta Key Beach*
26 May – 2 June
Condo in Sarasota
4.91 out of 5 average rating, 215 reviewsNew Renovation! Walk to Beach, Pool, Restaurants!
24 – 31 Mar
Home in Sarasota
4.81 out of 5 average rating, 126 reviewsVacation Paradise Close to Beach!
20 – 27 Aug
Home in Sarasota
4.88 out of 5 average rating, 120 reviewsLAKE SARASOTA VACATION HOME Cable! Sport channels!
5 – 12 Apr
Quick stats about accommodation & 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
$93 AUD before taxes and fees
Destinations to explore
- Sarasota 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 Naples
- Family-friendly rentals Sarasota County
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