Family-friendly vacation rentals in Hillsborough County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Hillsborough County

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Dunedin

4.96 out of 5 average rating, 222 reviews

FLOH - delightful days in Dunedin!

Cute quaint house with 2 bedrooms, 1 bath, located in downtown Dunedin Florida. All furniture in the house is new. Bathroom is newly remodeled, and includes a shower with a jet tub. Cozy family room with 60" flat screen smart TV, and sleeper sofa. We have a desk, and elliptical machine, along with a comfy chair for reading/relaxing in the extra room on the back. The kitchen is fully functional, with most conveniences of home. Come and enjoy delightful Dunedin, and have the time of your life!

Home in Gulfport

4.78 out of 5 average rating, 169 reviews

16 Sandals

According to City of Gulfport ordinances, this property can be rented short term less than 30 days only 3 times per 12 month calendar year, minimum night stay for those short term rentals is 3 nights. All other rentals are 30 days. Home has a private non heated pool. Disclaimer: pool is cleaned by private service every Wednesday. Owner has no control over inclement weather and will not refund any portion of rental due to any issues directly related to weather as related to pool usage.

Guest favorite

Home in Tarpon Springs

4.96 out of 5 average rating, 350 reviews

Tarpon Fun'n Sun-Pool, Beaches + Backyard Chickens

This home is ideally located near Florida's beautiful Sunset Beach and Howard Park Beach - only 17 miles from Clearwater Beach. Take a short ride to world famous attractions like Disney, or Busch Gardens. Don't settle for a hotel when you and your guests can enjoy a home with a gas grill, multiple patios, large kitchen/family room, a large 4K TV and a private jacuzzi/pool with gas heater *option. It's a perfect place for creating family memories or getting together with old friends.

Guest favorite

Home in St. Petersburg

4.96 out of 5 average rating, 247 reviews

Beach Pool Home+ Outdoor Theater ABFab Decor!

Host's FAVORITE home! Prepare to walk in and your heart to skip a beat because pictures do not capture how stunning this home is in person! EVERYTHING is IG-worthy and the effort put in to make this fantastic will not be lost! Did you see the poolside cabana? Or the outdoor dining and movie theater! Home sleeps 14 with 4BR+3baths. Just 4 minutes to beaches and 25 mins. to downtown. Optional heated pool for add'l cost. Check my Airbnb profile for all 17 of our nearby home options.

Guest favorite

Home in Largo

4.86 out of 5 average rating, 119 reviews

#RespectCreation

This is a beautiful 3/2 full baths, with heated pool. Extremely well cared for and offers many great amenities. Sits on a 1/2 acre with an awesome yard, variety of different fruit trees and plants. Has a heated pool, 2 firepits, 2 day beds, hammock, lots of seating. Only 5-10minutes to the sugar sand beaches, walking distance to a big park, as well as the Pinellas Trail, (biking, workout trail 35 miles long) Grocery stores, gas stations, banks, restaurants, etc all within 10 min.

Guest favorite

Home in Clearwater

4.86 out of 5 average rating, 203 reviews

Spacious FamilyFriendly home, Large Saltwater Pool

Best Family vacation! Renovated Nov 2021 Central to CW Beach, Tampa & St Pete. Lg open split floor plan, 4 Bedroom 2 bath & add’l office, Smart TVs. Lg Master Bedroom, dressers, closets. Lg new saltwater pool, indoor pool table, laundry rm. Enclosed pool area. Walk 2 Eagle Lake Park- walking, fishing, bike trails & Lake. Just 6 miles to CW Beach. 5 min to all shops & food stores. Busch Gardens 30 min. Real home not just rental. Pool Heated for added cost based on outside temps.

Guest favorite

Home in Riverview

4.82 out of 5 average rating, 182 reviews

Spacious Modern Retreat for Family Fun Near Tampa!

Experience the ultimate Florida getaway in this spacious 3,000 sq ft modern home, perfect for families or groups. Enjoy a dedicated office, plus an 80-inch 3D TV for movie nights or sports games. Conveniently located near top attractions: 15 mins to downtown, 10 mins to dining and shopping, 50 mins to beaches, 10 mins to TopGolf, 15 mins to the casino, 20 mins to Busch Gardens, and just 1 hour from Disney. Embrace comfort, convenience, and excitement—book your stay today!

Guest favorite

Apartment in Dunedin

4.99 out of 5 average rating, 233 reviews

Tropical Paradise

Please visit our website Grovekeeper collective for a video of the property Private vacation rental I know if you are coming to Delightful Dunedin you know how amazing this waterfront community is, from award winning restaurants , micro breweries, one of the #1 beaches in America, 40 miles of bike trails, waterfront parks. Just bring food and clothes, we have the rest covered! This rental is for a maximum of 5 guest all our units are non-smoking and vaping

Guest favorite

Guesthouse in Saint Petersburg

4.97 out of 5 average rating, 301 reviews

Charming apartment in Historic Kenwood

Cute, spacious apartment located in Historic Kenwood, which was named 2020 “Neighborhood of the year” by NUSA. Our apartment is above our large garage. Lots of charm and just enough space to spread out a little for some privacy. Located close to downtown, walking distance to lots of restaurants, breweries and bars but still a short drive to our beautiful beaches. You access the apartment through our side gate and up an exterior stairway.

Guest favorite

Apartment in Dunedin

4.98 out of 5 average rating, 233 reviews

My Favorite Place 🍊downtown & city approved

LEGAL, CITY APPROVED 1 bedroom apartment w full kitchen, living , dining & separate bedroom located on the red brick streets of downtown Dunedin. Private entrance. BIKES Super clean Private driveway free parking Two great bikes Great for couples Tastefully decorated. Comfortable Queen bed. Luxurious bedding. Super clean. Shampoo, conditioner, body wash, coffee, tea, drinking water provided. SUPER CLEAN No pets

Superhost

Condo in Clearwater

4.86 out of 5 average rating, 142 reviews

☼ CHARMING CONDO MINUTES FROM GORGEOUS BEACHES

Hurricane Milton Update (10/10/2024): We have not been impacted by hurricane Milton. Our rental is fully functional awaiting your reservation. ***Please message us about the latest discounts and offers*** 2 BEDROOM / 2 BATH CONDO APARTMENT MINUTES AWAY FROM PRISTINE CLEARWATER BEACHES, WATER SPORTS, AND LOTS OF FAMILY ATTRACTIONS!!! HEATED SWIMMING POOL, GYM, FAST WIFI INTERNET, CABLE TV, NETFLIX!

Guest favorite

Home in Palm Harbor

4.95 out of 5 average rating, 163 reviews

*Family Paradise with Pool in Crystal Beach*

Escape to Crystal Beach Paradise, a spacious 6-bedroom retreat on Florida's Gulf Coast. This stylish getaway features a private saltwater pool, outdoor bar, and two well-equipped kitchens. Just minutes from pristine beaches, it's perfect for family relaxation and adventure. Book now for a memorable coastal retreat!