Family-friendly vacation rentals in Gasparilla Island
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Gasparilla Island
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 Gasparilla Island family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Punta Gorda
4.93 out of 5 average rating, 123 reviewsTropical themed Island style home!
Sep 20 – 27
Apartment in Fort Myers Beach
4.9 out of 5 average rating, 193 reviewsMermaid Oasis
Sep 24 – Oct 1
Home in Fort Myers Beach
4.96 out of 5 average rating, 120 reviewsCoastal Oasis of Fort Myers Beach
Feb 26 – Mar 5
Home in Sarasota
4.97 out of 5 average rating, 109 reviewsGorgeous Home / Heated Pool and Spa
Sep 24 – Oct 1
Home in Sarasota
4.97 out of 5 average rating, 159 reviewsThe Palms-Private Heated Pool Hot Tub-5mi to beach
Jul 28 – Aug 4
Home in Fort Myers
4.94 out of 5 average rating, 107 reviewsPrivate Heated Pool and Spa
Nov 24 – Dec 1
Bungalow in Fort Myers
4.93 out of 5 average rating, 285 reviewsRowan's Retreat - Historic Downtown Fort Myers
Sep 22 – 29
Condo in Longboat Key
4.82 out of 5 average rating, 159 reviewsUpdated Beachfront Condo at Prestigious Long Boat
Aug 14 – 21
Family- and pet-friendly home rentals
Home in Port Charlotte
4.84 out of 5 average rating, 155 reviewsWaterfront Pool and Dock! Great Family Retreat
Dec 7 – 14
Vacation home in Venice
4.83 out of 5 average rating, 110 reviews🌟Venice Cute Pool Villa with bikes Kayaks 🌈🐬
Jul 11 – 18
Home in Venice
4.78 out of 5 average rating, 113 reviewsSouth Venice, FL. Ideal vacation home.
Nov 3 – 10
Home in Cape Coral
4.96 out of 5 average rating, 157 reviewsSurfside Elegance SW Cape Coral Luxe Vacation home
Aug 1 – 8
Guesthouse in Fort Myers
4.97 out of 5 average rating, 279 reviewsChameleon Guest Cabana
Jul 24 – 31
Bungalow in Sarasota
4.92 out of 5 average rating, 264 reviewsDowntown Bungalow...Beaches- Restaurants- Cafes!
Jul 2 – 9
Townhouse in Sarasota
4.93 out of 5 average rating, 242 reviewsFlamingo🦩1/2M Walk to Downtown #TheTropicalNut☀️🦩⛱🥳
Jun 22 – 29
Home in Sarasota
4.87 out of 5 average rating, 204 reviewsThe Pineapple Suite.Teal tropical home in Sarasota
Dec 11 – 18
Family-friendly home rentals with a pool
Hotel room in Venice
4.88 out of 5 average rating, 175 reviewsNear Downtown/Beach | Tropical Villas Venice Beach
Aug 7 – 14
Apartment in Fort Myers Beach
4.98 out of 5 average rating, 125 reviewsFt. Myers Beach Condo - Location-Location-Location
Nov 4 – 11
Home in Rotonda West
4.9 out of 5 average rating, 152 reviews❤ROTONDA RETREAT❤*Spacious*Fully Furnished*Pool*
Nov 29 – Dec 6
Apartment in Sarasota
4.85 out of 5 average rating, 292 reviewsSarasota Downtown close to Lido Beach
Jun 28 – Jul 5
Home in Fort Myers
4.9 out of 5 average rating, 280 reviewsCaptivating Pyramid home in S Ft Myers-7019
Aug 16 – 23
Home in Siesta Key
5.0 out of 5 average rating, 124 reviewsOne-of-a-kind*Beach, Village, Dock & Private Pool!
Dec 8 – 15
Apartment in Sarasota
4.96 out of 5 average rating, 206 reviewsPrivate 2 Bedroom Suite with Kitchenette
Jun 29 – Jul 6
Home in Cape Coral
4.99 out of 5 average rating, 211 reviewsGulf access waterfront heated pool
Nov 17 – 24
Destinations to explore
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