
Family-friendly holiday rentals in Holiday
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Holiday

Total holiday rentals
Explore 110 holiday rentals in Holiday

Nightly prices starting at
Holiday holiday rentals start at $26 SGD per night before taxes and fees

Verified guest reviews
Over 2,970 verified reviews to help you choose

Pet-friendly holiday rentals
Find 80 rentals that welcome pets

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
110 of Holiday holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Holiday rentals

4.6 Average rating
Holiday stays receive an average rating of 4.6 out of 5 from guests
Top-rated family-friendly rentals in Holiday
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Angelita's Lake Home 3br3ba w/heated pool
+Spacious family retreat on lake +Free heated pool +Huge last-minute discounts +Big deck, BBQ, dining & firepit +Private backyard lakefront +3 bedrooms, 1 king, 1 queen, 2 twin +3 full baths +Easy to cancel +Pet friendly +Fishing +Games +Quiet serene safe +5 minutes to Gulf sunsets +5 min to Sims Park +20 min to Tarpon Springs +39 min to Tampa airport +50 min to Busch Gardens +5 min to restaurants +Fully equipped kitchen +Free parking & garage +Washer-Dryer +Work area +Hi-speed WIFI +Smart TVs
Indoor spacesFamilyView

Dream Home in Holiday with POOL & SPA and More
Dream home in Holiday with POOL & SPA,This beautifully remodeled 3-bedroom, 2-full-bathroom residence offers modern and comfort. Key Features, Updates: Benefit from recent upgrades, including a new roof , kitchen, appliances, Bathrooms, Doors and fresh paint . Step into stylish luxury brand new luxury vinyl wood flooring. Outdoor Oasis: Relax in your fully Pcv fenced backyard with your pool and spa. The jacuzzi and the Pool is Not Heated, Pet Allow (Only ONE)with a fee $100 Please ask you host
FamilyGetting aroundParking

Coastal Escape: Heated Pool, Playground&Family fun
★ Family-friendly Palm Harbor retreat near beautiful beaches - Honeymoon Island: 6 miles away - Clearwater Beach: 15 miles away ★ Heated saltwater pool ★ Screened-in lanai ★ BBQ grill ★ Large fenced backyard with playground ★ Outdoor dining area ★ 3 bedrooms with new mattresses - California king size bed - Queen size bed - Kid-friendly room w/ 2 bunk beds ★ Renovated kitchen and bathrooms ★ Open living space for family gatherings and movie nights ★ Toys, games and kid-friendly extras
Indoor spacesKitchenBreakfast

Paradise!Renovated waterfront pool home.Sunsets!
Sunsets to die for! Remodeled in 2023 pool house on the Anclote River with access to the Gulf of America.Imagine fishing,kayaking in the backyard & and spotting dolphins!Watch birds, ducks, manatees. All new appliances and granite countertops. New quartz bathroom cabinets!New tiles throughout the house including Florida room. Cooler,chairs&umbrella, kids beach toys. Fishing rods.Bonfire pit.Grill.Heated pool for a fee. Portable crib,stroller, high chair. Come,relax&enjoy No hurricane damage!
Indoor spacesFamilyPool

Screened in Heated Pool/Coffee Bar/Fully Stocked
🏡 Private Pool House with Large Covered & Screened-In Porch Relax and unwind in this inviting private pool home, featuring a large covered and screened-in porch—perfect for enjoying the outdoors without the bugs. 🌊 Heated Pool Take a dip in the private pool, heated year-round with an electric heat pump (weather permitting), offering comfort no matter the season. Whether you're sipping coffee on the porch or enjoying a swim, this cozy retreat is ideal for a peaceful and private getaway.
Indoor spacesKitchenTV

Relaxing Beach-Theme Pool Home!
Whatever your reason for visiting New Port Richey you will find this Cul-de-sac home to be comfortable and inviting having a screened in, heated pool and large pool deck and lanai with outdoor gas grill. The pool area is lighted in the evening for an enjoyable atmosphere. There are three bedrooms and a game/TV room that works as a forth bedroom with a futon. The back is fully fenced in. Fast internet with three new smart TVs. Kitchen is well equipped and has three kinds of coffee makers..
FamilyIndoor spacesTV

Sunny Pool Home • Near Tarpon & Beaches
🌴Make yourself at home at Sun-Water House, a family-friendly and pet-friendly retreat made for sunny pool days and relaxed evenings. Enjoy the privacy of a fully fenced backyard, share a meal outdoors, or take the provided beach kit on your next adventure. With comfortable interiors and easy access to Tarpon Springs, nearby Gulf beaches, and many Florida Gulf Coast destinations to discover, it’s the perfect home base for your getaway. ✨ Book your stay and start planning your escape!
FamilyKitchenCheckout

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.
FamilyKitchenQuiet

Waterfront, Sunsets & Heated Pool & Pet Stay Free!
Close to the beach, family activities, public transport, and the Tampa Airport. You’ll love my place because of the ambiance, the outdoors space, the water view, & the sunsets, PRIVATE Heated pool and VERY comfy beds! I provide fishing poles, tackle box My place is great for everyone and furry friends (pets) too!. Third bedroom is Florida room with sliding glass door. Two twin beds and desk. dinning table. Let me know about your pets. Your pets stay free. Totally fenced yard.
FamilyIndoor spacesDecor

HolidaySpring|CozyPrivate Apt near beach|2 parking
Private & cozy apartment with independent entrance and free parking for two vehicles. Located in a quiet and safe area just minutes from the beach and Tarpon Springs (“Little Greece”) and just minutes from Fred Howard Park Beach.Enjoy a fully equipped kitchen, comfortable bedroom with work desk, Smart TV, fast WiFi, spacious bathroom, and outdoor terrace. Perfect for couples, small families, or remote workers Scan the QR in the last photo for a full video tour
FamilyIndoor spacesValue

*NEW* Riverside Retreat w/Pool
Take it easy at this unique and tranquil getaway. Welcome to our Riverside Retreat where you will enjoy incredibly relaxing peaceful days, and sunset views. Recently renovated 2 Bedroom, 2 Full Bathroom, pool home with dock and privacy fenced backyard on the Anclote River. This home is fully equipped and is ready for you to enjoy. Conveniently located and only a 9-minute drive to the World-famous Sponge Docks and minutes from our award winning beaches…
KitchenFamilyTV

Lakefront Paradise with Heated Saltwater Pool
Discover lakeside bliss at this 2-bedroom retreat with a private pool, dock, and outdoor fire pit. Enjoy stunning waterfront views, relax by the pool, or gather around the fire under the stars. The bedrooms offer a cozy haven, and the fully equipped kitchen ensures convenience. Just minutes from pristine beaches, this retreat provides the ideal balance of relaxation and recreation. Your perfect lakefront getaway awaits!
Indoor spacesFamilyTV
Popular amenities for Holiday family-friendly rentals
Family-friendly home rentals with a hot tub

Downtown Madison Steps Away!
KitchenIndoor spacesAmenities

Warmth In Holiday
Indoor spacesFamilyBack garden

Waterfront Studio Apartment w/access to Gulf
Indoor spacesFamilyHot tub

FREE Heated Pool & Spa l Book your Winter Vacation
KitchenFamilyGetting around

Modern Waterfront Home with Hot Tub, Dock, Kayaks
KitchenFamilyCleanliness

TreeHouse, Swings, HotTub, HeatedPool, ClearSpring
FamilyKitchenQuiet

salt living at its best
KitchenIndoor spacesAir conditioning

Ranch Pool Resort with Horses jacuzzi nearby park
Indoor spacesFamilyHot tub
Family- and pet-friendly home rentals

Charming Blue Bungalow With Amazing Yard
Indoor spacesKitchenCheckout

Private 3 Bedroom House w/ Heated SaltWater Pool
FamilyKitchenBeach

Modern 3 Bedroom 2 Bathroom House
FamilyIndoor spacesValue

Screened Lanai /Clear Kayak / Waterfront / Fire Pi
FamilyKitchenView

Cozy Home w/ Fire Pit & Outdoor Lounge
FamilyIndoor spacesAccuracy

Tarpon Family Retreat-Heated Pool, Fire Pit & Fun!
KitchenFamilyGetting around

Coastal Holiday Home w/Pool - Minutes to Beaches
Indoor spacesFamilyAir conditioning

Relax & Recharge Getaway minutes from Howard Park
Indoor spacesFamilyValue
Family-friendly home rentals with a pool

Tropical Pool Retreat in Tarpon Springs
Indoor spacesFamilyWalkability

Palm Haus • Heated Pool • Near Beach • Game Room
FamilyIndoor spacesAmenities

River Home Heated Pool, Sunset, Dolphin & Fishing
Indoor spacesFamilyPool

Cozy Home, Country Setting, Close to Gulf Beaches
FamilyIndoor spacesAccuracy

Northern Point of Treasure Island NPR
KitchenFamilyComfort

Beach Gulf Oasis-Pool, Elevator, Tiki Hut & Dock
KitchenIndoor spacesBack garden

Deluxe 3bd/2ba w/Heated Pool
KitchenIndoor spacesAir conditioning

Endless Summer
Indoor spacesFamilyPets
When is the best time to visit Holiday?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $170 SGD | $202 SGD | $228 SGD | $207 SGD | $170 SGD | $174 SGD | $180 SGD | $170 SGD | $159 SGD | $158 SGD | $167 SGD | $182 SGD |
| Avg. temp | 17°C | 18°C | 20°C | 23°C | 26°C | 28°C | 29°C | 29°C | 28°C | 25°C | 21°C | 18°C |
Destinations to explore
- Miami Holiday rentals
- Four Corners Holiday rentals
- Miami Beach Holiday rentals
- Orlando Holiday rentals
- Fort Lauderdale Holiday rentals
- Panama City Beach Holiday rentals
- Tampa Holiday rentals
- Destin Holiday rentals
- Hollywood Holiday rentals
- Savannah Holiday rentals
- Jacksonville Holiday rentals
- Kissimmee Holiday rentals
- Anna Maria Island
- Weeki Wachee Springs
- Anna Maria Island Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Bean Point Beach
- Amalie Arena
- Hard Rock Casino
- University of South Florida
- Vinoy Park
- Dunedin Beach
- Epperson Lagoon
- John's Pass
- Tropicana Field
- MidFlorida Credit Union Amphitheatre
- Sand Key Beach
- Weeki Wachee Springs State Park
- Anna Maria Public Beach
- River Strand Golf and Country Club
- Busch Gardens
- Fort De Soto Park
- Splash Harbour Water Park
- North Beach At Fort DeSoto Park
- Fort Island Beach





