
Holiday rentals with a pool in Holiday
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Holiday

Total holiday rentals
Explore 40 holiday rentals in Holiday

Nightly prices starting at
Holiday holiday rentals start at $39 SGD per night before taxes and fees

Verified guest reviews
Over 1,410 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Holiday holiday rentals include wifi access

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

4.7 Average rating
Holiday stays receive an average rating of 4.7 out of 5 from guests
Top-rated rentals with a pool in Holiday
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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

Coastal Family Escape w/Private Pool•Near Beaches
Slip into vacation mode in this bright, newly renovated home just minutes from Gulf Coast beaches and the Tarpon Springs Sponge Docks. Plenty of shopping and restaurants nearby. With 2 living rooms, there’s space for movie nights, games, and foosball. Step outside to your private oasis with a heated pool, outdoor dining, and a BBQ grill. Whether you're exploring the famous Sponge Docks, hitting the beach, or simply soaking up the sun at home, this retreat makes every moment feel like vacation.

Luxury Private Pool House ! Mackarosa ! Tampa Bay.
Experience comfort and style in this beautifully renovated home with high ceilings and elegant design. Bright, airy spaces create a relaxing atmosphere, and the king bed offers restful sleep after a day of travel or exploring. Fully equipped kitchen. Private pool with solar heating — perfect year-round. Airport – 35 min • Beaches – 19 min No smoking. No pets. Professionally cleaned and disinfected after each stay. Located in a quiet, safe neighborhood — ideal for families and peaceful stays.

Paradise!Renovated waterfront pool home.Sunsets!
No hurricane damage!Sunsets to die for! Completely remodeled in 2023 pool house on the Anclote River with access to the Gulf of America.Imagine fishing,kayaking in the backyard &sometimes you can spot 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 that you can take to the beach.Bonfire pit.Grill.Heated pool for a fee. Come,relax&enjoy

Heated & Screened in 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.

River Side Home. Three mins to Downtown.
Cozy apartment for family vacations completely renovated, The SIDE RIVER HOME is very close to downtown, restaurants, bars, boat ramp and walking park overlooking the river, beaches, a few miles from Tarpon Spring Sponge Docks , located 20 mins from Fred Howard Park, if you want to kayak and Canoe the perfect place is Weeki Wachee, just 35 minutes from the house , clearwater beaches are for 42 mins, ahh if the passion is the parks we have Busch Gardens only 52 mins away . PETS ARE WELCOME!

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.

*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…

"Wet Feet Retreat" pool home
Cozy beach themed 1,000sq ft pool home in Port Richey, FL. Relax by your private outdoor heated year round pool or take a drive over to the sponge docks in Tarpon Springs to sample authentic greek cuisine. Want to swim with the Manatees or go scalloping? Then check out the nearby city of Weeki Wachee. Close to multiple beaches, state parks, restaraunts, and local attractions. Fishing poles and equipment on site to take with you to the beach or pier.

Heated Pool, Hot Tub & Sand Volleyball
Your perfect getaway awaits in this pet-friendly 2BR/2BA retreat! Relax by the in-ground pool and hot tub, play a game of sand volleyball, unwind on the deck or have a BBQ. The fully fenced yard offers privacy, while the covered outdoor seating, pool-side hammock, fire pit, and a variety of games make it fun for all. With WiFi, AC, and a workspace, it’s perfect for both short and long stays. Just minutes from the beach, dining, and entertainment.

Private 3 Bedroom House w/ Heated SaltWater Pool
Spend your holidays in HOLIDAY, FL! We welcome you to our cozy, fully renovated house with a large, heated private in-ground, SALTWATER pool. The house has three bedrooms and enough room for 7 guests, along with two full bathrooms. The kitchen is stocked with all cookware essentials needed. The house has everything you need for vacations, so you may kick back and relax. It is centrally located to many attractions if you're up for a drive.

Bayside Retreat your tropical oasis
"Bayside Retreat" is a Charming Private 1~bedroom/1 bath with full living room suite, located right on the water of upper Tampa Bay. Spend a quiet day lounging in the grotto pool, kayaking the bay, or a lazy day reading in the hammock. Enjoy breath taking sunrise and sunsets from the dock. Your own Tropical Paradise away from the rest of the world....... Just 15min to Raymond James Stadium. Centrally located 15 miles from TPA Airport
Popular amenities for Holiday rentals with a pool
House rentals with a pool

Relaxing Poolside Oasis - 5 minutes to Sponge Dock

River Home with Pool, Sunset, Dolphin & Fishing

Coastal Paradise Waterfront with Dock, Gulf Access

Richey Suncoast Resort- Pool, Spa & Arcade Oasis

Coastal Holiday Home w/Pool - Minutes to Beaches

Gulf Harbors Getaway!

Endless Summer

Florida style home !
Apartment rentals with a pool

Ocean Breeze • Easy - Heated Pool Access

Tiki Themed Waterfront Condo on Tampa Bay

BEACHFRONT Condo - Belleair Beach Club - RENOVATED

Beachfront in exclusive resort

Top floor condo, magnificent water views

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

Five Star Beachfront Condo Newly Renovated

Florida Breeze
Other holiday rentals with a pool

Gulf Harbors Getaway Home with Pool

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

Pool • Ocean View • Walk to Beach & Restaurants

The Tarpon Sunset Retreat

Holiday Coast Hideaway

Relaxing Beach-Theme Pool Home!

Lakefront House with Heated Pool

Cottage on the Cotee River
When is the best time to visit Holiday?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $220 SGD | $259 SGD | $279 SGD | $256 SGD | $219 SGD | $233 SGD | $233 SGD | $217 SGD | $181 SGD | $194 SGD | $213 SGD | $238 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
- Family-friendly rentals Holiday
- Rentals with a washing machine and dryer Holiday
- Rentals with a fireplace Holiday
- Rentals with outdoor seating Holiday
- Rentals with a firepit Holiday
- Pet-friendly rentals Holiday
- Rentals with beach access Holiday
- Rentals with lake access Holiday
- Rentals with a patio Holiday
- Waterfront rentals Holiday
- House rentals Holiday
- Flat rentals Holiday
- Rentals with pools Pasco County
- Rentals with pools Florida
- Rentals with pools United States
- Anna Maria Island
- Weeki Wachee Springs
- Anna Maria Island Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Bean Point Beach
- Amalie Arena
- Dunedin Beach
- Tampa Convention Center
- Vinoy Park
- Hard Rock Casino
- University of South Florida
- John's Pass
- Fort De Soto Park
- Tropicana Field
- Sand Key Beach
- Epperson Lagoon
- Weeki Wachee Springs State Park
- Anna Maria Public Beach
- MidFlorida Credit Union Amphitheatre
- River Strand Golf and Country Club
- Busch Gardens
- North Beach At Fort DeSoto Park
- Jannus Live





