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

Total vacation rentals
Explore 40 vacation rentals in Holiday

Nightly prices starting at
Holiday vacation rentals start at R491Â ZAR per night before taxes and fees

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

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Holiday vacation rentals include wi-fi 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.

Pool Paradise - Private Solar Heated Pool
Welcome to your private vacation gateway. Escape to Florida Sunshine Sanctuary in Tampa Bay Area. Our 2 Bedroom/ 2 Bathroom House is nested in a quiet suburb not far from the Tampa Airport. It is 25 miles from the famous Clearwater Beach and 30 miles from the Busch Gardens. Take the ultimate one day trip to DisneyWorld which is a 2 hour drive form the house. Also a 15 min drive to Greektown and Tarpon Springs Sponge Deck. House is nicely decorated with everything needed to create special memorie

Gulf Access, Heated Pool, Near Islands, Beaches
Vacation on the Gulf of Mexico 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

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. *Starting 5/1, there is a spa heater charge.

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.

Tropical heated pool Oasis 5 min to Beach
Welcome to Tarpon House Florida, located in the exclusive and historic Tarpon Springs. Our home is a tropical oasis. Perfect for families, couples, and anyone who needs the space to spend time together or enjoy some privacy for enjoyment and relaxation. 10% discount for Military, First Responders, and Teachers - book & message me a photo ID, I'll apply the discount, that's it! Completely renovated with all new furniture. Link to 3D Tour of the house is in my guidebook (under my profile)

Sunny Pool Home • Near Tarpon & Beaches 5 mi
🌴 Heated private pool oasis (Nov–Mar) 5 mi to Tarpon Springs—ideal to recharge. 🏡 Private patio for BBQ and outdoor time in a quiet area for great sleep. Perfect for families & friends: fast Wi-Fi + workspace, fully equipped kitchen, 🔑 24/7 self check-in, and 🚗 on-site parking. Easy access to Dunedin, Clearwater, Tampa, and beaches (times vary with traffic). ✨ Note: pool heat available Nov–Mar (weather permitting). ⏳ Last-minute promos active—book and lock in your dates!

J&M Homestead
Relax with the whole family at this peaceful place to stay. Close to I-75 and Suncoast Parkway in Pasco County. Located north of Land O Lakes, Florida, in Pasco Trails, a gated community of acreage and horses. Outlet mall, many eating establishments and sports complexes within half-hour drive. We have had to institute a policy of "no smoking. To be clear, we are retired couple who live in the main house. The apartment is attached but has its own entrance and is self contained.

Luxury Private Pool House ! Mackarosa ! Tampa Bay.
If you are used to traveling in comfort,then this is best choice for you.House after renovation.High ceilings and beautiful decor will give you a pleasant feeling of comfort.The king bed,will give you pleasant sleep after an active day or a long trip.The kitchen has everything.The pool has a solar panel heated.Airport(35 min)Beaches(19min) Smoking in the house and living with animals are prohibited.After each gust the house is disinfected.Enjoy your stay

*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.

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.
Popular amenities for Holiday rentals with a pool
House rentals with a pool

Spring Hill, Florida Quaint Paradise

Pool Home in New Port Richey

Newly remodeled 3 bedroom with heated pool

Relaxing Beach-Theme Pool Home!

Lakefront House with Heated Pool

Saltwater Pool • Kayaks • Pedal boat + more!

Dolphin-Watch Waterway – Pool/Spa Tarpon

Living your dream
Condo rentals with a pool

Tiki Themed Waterfront Condo on Tampa Bay

Modern and Cozy Condo 6 Minutes from the Beach !

Sea La Vie- Studio by the bay!

Beachfront in exclusive resort

Clearwater Retreat • Gated Community + Heated Pool

Beach Front Madeira Beach

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

Florida Breeze
Other vacation rentals with a pool

Stunning *Newly Remodeled Riverfront Oasis - Kayak

Waterfront Retreat with Heated Pool, Hot Tub&Dock

Pool-Sauna-Water Dolphin view house - sleeps 10

Lake House | Heated pool |10 PPL | Games | BBQ

The Sunrise house

Luxury Waterfront w/ Private Heated Pool

Beachy 3 Bedroom Hot Tub and Saltwater Pool

Pool home in Port Richey dog friendly
When is the best time to visit Holiday?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R2,945 ZAR | R3,256 ZAR | R3,338 ZAR | R3,240 ZAR | R2,765 ZAR | R2,945 ZAR | R2,945 ZAR | R2,749 ZAR | R2,291 ZAR | R2,454 ZAR | R2,700 ZAR | R3,011 ZAR |
| 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
- Seminole Vacation rentals
- Central Florida Vacation rentals
- Miami Vacation rentals
- St Johns River Vacation rentals
- Orlando Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Tampa Vacation rentals
- Four Corners Vacation rentals
- Kissimmee Vacation rentals
- Panama City Beach Vacation rentals
- Rentals with a washer and dryer Holiday
- Rentals with lake access Holiday
- Waterfront rentals Holiday
- Family-friendly rentals Holiday
- Rentals with a patio Holiday
- Rentals with a fireplace Holiday
- House rentals Holiday
- Rentals with a fire pit Holiday
- Rentals with outdoor seating Holiday
- Rentals with beach access Holiday
- Pet-friendly rentals Holiday
- Rentals with pools Pasco County
- Rentals with pools Florida
- Rentals with pools United States
- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Bean Point Beach
- Weeki Wachee Springs
- Anna Maria Island Beach
- Vinoy Park
- Amalie Arena
- Dunedin Beach
- Sand Key Beach
- Tampa Convention Center
- Jannus Live
- St Pete Beach
- Anna Maria Public Beach
- Hard Rock Casino
- ZooTampa at Lowry Park
- Tampa Palms Golf & Country Club
- River Strand Golf and Country Club
- North Beach At Fort DeSoto Park
- Splash Harbour Water Park
- Fort Island Beach
- Busch Gardens
- The Don CeSar




