
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 €26 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.

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.

Coastal Paradise Waterfront with Dock, Gulf Access
Vacation on the Gulf of America near Islands Places to visit * Key Vista Nature Preserve: .05 miles * Anclote Gulf Park: 1.4 miles * Anclote River Park: 2.6 miles * Tarpon Springs Docks: 5.7 miles * Fred Howard Park Beach: 8.5 miles * Downtown Palm Harbor: 11 miles * Dunedin Causeway Beach: 16 miles * Honeymoon Island State Park: 17 miles * Clearwater Beach: 23 miles *Downtown Tampa: 34 miles Theme Parks * Busch Gardens: 31 miles * Adventure Island: 31 miles * Florida Aquarium Tampa: 35 miles

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!

River Home with Pool, Sunset, Dolphin & Fishing
Welcome to the waterfront oasis situated along the serene banks of Anclote River connecting to the Gulf. Enjoy privacy as no backyard neighbors, just a nature. Step outside to your own private paradise, where a screened lanai awaits with a private heated pool. Spend your days lounging poolside, soaking up the Florida sunshine, or marveling at dolphins and manatees. Close driving distance to the world famous beaches (Clearwater, Honeymoon Island), Tarpon Spring, Weeki Wachee & Tampa Bay

*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.

Private pool home near Tarpon Springs 5 mi
🌴 Private pool home near Tarpon Springs, Gulf beaches, restaurants, and local attractions—perfect for a relaxing Florida getaway. Enjoy a fenced patio, BBQ area, fast WiFi, workspace, fully equipped kitchen, 24/7 self check-in, and on-site parking. Easy access to Dunedin, Clearwater, Tampa, and nearby beaches. ✨ Note: pool heat is available Nov–Mar, weather permitting. ⏳ Last-minute promos active—book and lock in your dates!
Popular amenities for Holiday rentals with a pool
House rentals with a pool

Gulf Harbors Getaway Home with Pool

Pool Home in New Port Richey

Waterfront Retreat with Heated Pool, Hot Tub&Dock

Newly remodeled 3 bedroom with heated pool

Richey Suncoast Resort- Pool, Spa & Arcade Oasis

Relaxing Beach-Theme Pool Home!

Endless Summer

Deluxe 3bd/2ba w/Heated Pool
Apartment rentals with a pool

Ocean Breeze • Easy - Heated Pool Access

BEACHFRONT Condo - Belleair Beach Club - RENOVATED

Updated Condo-Heated Pool-Private Balcony

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

Spectacular beach to bay views from this resort.

Amazing views on beachfront

Five Star Beachfront Condo Newly Renovated

Florida Breeze
Other holiday rentals with a pool

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

Lazy Day Oasis

Pool, Oceanview, Walk to Beach/Restaurants, Canal

Heated Pool & Spa Oasis Near Clearwater Beach

Waterfront Pool Dock Golf Boat Rent Beach 2K/2T/2b

On the Water! *Pool & Golf Cart

Cottage on the Cotee River

Studio near Anclote River Park
When is the best time to visit Holiday?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €149 | €176 | €190 | €174 | €148 | €158 | €158 | €148 | €123 | €132 | €145 | €162 |
| 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
- Orlando Holiday rentals
- Kissimmee Holiday rentals
- Miami Beach Holiday rentals
- Panama City Beach Holiday rentals
- Tampa Holiday rentals
- Fort Lauderdale Holiday rentals
- Destin Holiday rentals
- Savannah Holiday rentals
- Hollywood Holiday rentals
- Jacksonville Holiday rentals
- House rentals Holiday
- Flat rentals Holiday
- Family-friendly rentals Holiday
- Rentals with a washing machine and dryer Holiday
- Rentals with a fireplace Holiday
- Rentals with a firepit Holiday
- Rentals with outdoor seating Holiday
- Pet-friendly rentals Holiday
- Rentals with beach access Holiday
- Rentals with lake access Holiday
- Rentals with a patio Holiday
- Waterfront rentals Holiday
- Rentals with pools Pasco County
- Rentals with pools Florida
- Rentals with pools United States
- Anna Maria Island
- Raymond James Stadium
- Weeki Wachee Springs
- Anna Maria Island Beach
- Busch Gardens Tampa Bay
- Bean Point Beach
- Amalie Arena
- Dunedin Beach
- Vinoy Park
- Tampa Convention Center
- University of South Florida
- Hard Rock Casino
- John's Pass
- Tropicana Field
- Fort De Soto Park
- Sand Key Beach
- Anna Maria Public Beach
- Weeki Wachee Springs State Park
- Epperson Lagoon
- River Strand Golf and Country Club
- MidFlorida Credit Union Amphitheatre
- Jannus Live
- ZooTampa at Lowry Park
- Busch Gardens





