Family-friendly vacation rentals in Holiday

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Holiday

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

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Guest favorite

Home in Seminole

4.87 out of 5 average rating, 259 reviews

⭐️Ultimate Vacation Home🌴Tropical Heated Pool Oasis

🌴 4min to the beach! Over 200 great reviews from guests! 🕶 Huge and gorgeous 4 bedroom home. Living, Dining, AND family room with pool table! Fully equipped kitchen. 🦋⛱PRIVATE tropical outdoor area with sparkling large private HEATED pool, lounging areas, outdoor grill, FIRE PIT! ⛹️‍♂️Basketball on the driveway! If your looking for vacation home here it is! 🏖Minutes away beaches! Beach chairs and beach towels provided. Experience the charm of Florida in a home you will want to call your own

Guest favorite

Home in St. Petersburg

4.95 out of 5 average rating, 236 reviews

Beach Pool Home+ Outdoor Theater ABFab Decor!

*WE WERE NOT AFFECTED BY STORM* This 4 BR/3Bath home sleeps 14. Prepare to walk in and your heart to skip a beat! Pictures don't capture how stunning this home is in person!!! Let's start with all the IG-worthy decor and the POP-ART inspired by famous women! Did you see the poolside cabana? Or the outdoor movie theater and dining area! SUPER location: beaches 4 mins. and 25 mins. to downtown. Optional heated pool for add'l cost. Check my Airbnb profile for all 17 of our nearby home options.

Superhost

Townhouse in Indian Rocks Beach

4.89 out of 5 average rating, 201 reviews

Beach Bungalow with Southern Charm, walk to beach

No flooding from Helene. Condo is elevated. Enjoy semi-private beach access, as well as 10+ restaurants, coffee and ice cream shops, boat rentals, parks, playgrounds, a water park, brewery, and nature preserves and trails all within walking distance. Make yourself at home in our quaint, cozy, and clean three-story townhouse. Spend your days relaxing at the beach, kayaking, exploring local parks and preserves, playing putt putt golf, and more. Our homes are child and infant-friendly!

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

4.81 out of 5 average rating, 175 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

Condo in Indian Shores

4.89 out of 5 average rating, 118 reviews

On the Beach "Little Peace of Heaven" Beach Condo

Spacious - Complete Renovation - Come see!! Our building is on an Island and on the beach! Our unit faces East or the Inter-coastal but the beach is just downstairs. Our 8 unit building is ‘On the beach. Downstairs we have a patio area which is a beautiful semi-private area with sea grape plants, equipped with 2 tables, 8 chairs , 16 beach chairs, outside shower, and firepit. Wonderful & quiet for families & couples............ No smoking in the unit... No pets.

Guest favorite

Rental unit in Dunedin

4.99 out of 5 average rating, 225 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

Superhost

Condo in Indian Rocks Beach

4.93 out of 5 average rating, 168 reviews

Waterview 2/2 condo-water park-walk to IRB BEACH!

4 FREE daily water park passes and parking for one car is included! Just a few minutes walk to the BEACH! This 2/2 condo is located at the 'Harborside@Marker 33' and 'Splash Harbour Water Park' complex. This 7th floor "end unit" has been newly renovated and has a balcony that overlooks the Intracoastal and anther one that overlooks the Water Park. A fully stocked kitchen which includes a washer/dryer makes for that perfect place to bring the whole family.

Guest favorite

Condo in Indian Shores

4.95 out of 5 average rating, 131 reviews

Good Times and Tan Lines @ #105intercoastal

** Heated Pool ** | Great vacation location | Check the reviews below: 2 Bedroom / 2 Bath Condo across the street from the award-winning beaches of St Pete. All the conveniences you would expect! Granite counter tops, kitchen appliances, dishwasher, washer/dryer, new towels and linens, beach towels, 4K Smart TV, Cable TV, WIFI and AC. Grounds with private pool, small pool side grill, sunbeds, tables & chairs and restroom.

Guest favorite

Condo in Indian Rocks Beach

4.84 out of 5 average rating, 214 reviews

6620 Harbourside, 2/2 Condo, Water Park!

4 FREE daily water park passes and parking for one car is included! 3/5 minute walk to the BEACH! This 2/2 condo is located at the 'Harborside@Marker 33' and 'Splash Harbour Water Park' complex. This 6th floor "end" unit has a balcony that overlooks the Intracoastal and another that overlooks the Water Park! Come stay in this rare unit. There is a fully stocked kitchen that even includes a stackable washer and dryer.

Guest favorite

Rental unit in Dunedin

4.98 out of 5 average rating, 225 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

Guest favorite

Home in Crystal Beach

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!