
Vacation rentals with a pool in Holiday
Find and book unique homes with a pool on Airbnb
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

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.

Gulf Harbors Vacation Oasis
This lovely Gulf Harbors home with open floor plan & in-ground heated pool is the perfect getaway! Home on canal that leads directly to the Gulf in minutes-amazing view & quiet, safe neighborhood! Perfect home base for shopping, restaurants, kayaking, exploring, & especially Scalloping in Pasco county! This region includes all state waters south of the Hernando – Pasco county line & north of the Anclote Key Lighthouse in northern Pinellas County,& includes all waters of the Anclote River.

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

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!

Private Pool Home Near Clearwater & Tampa
Only 25 minutes from Clearwater Beach and Tampa, 33 minutes from Buch Gardens, 1.5 hrs from Disney, 18 minutes from Tampa International Airport. This house is completely renovated with a lot of space for you, family and/or friends. The entire house for you and your family. We have a beautiful pool with a Grill for your convinience and a garage for your car. 3 bedrooms for up to 7 persons. A 65" TV in the living room. Wi-Fi. The house has everything you need to have a relaxing time.

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…

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

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!

Tiki Hut Cottage
This unit private vacation rental is privately located on the property, plenty of space for 4 quest, 2 bedroom, upper bedroom has a half bath, toilet and sink, lower bedroom has a walk in shower with stack washer and dryer. Spacious living area with a kitchenette. The property is an acre of lush tropical plants Conveniently located to the downtown & beach.All our units are non-smoking and vaping.
Popular amenities for Holiday rentals with a pool
House rentals with a pool

Stunning *Newly Remodeled Riverfront Oasis - Kayak

Clearwater Getaway off the Gulf Coast

Cozy home! Pool.

Waterfront Oasis

New Port Richey.Private heated pool(solar panels).

Waterfront Pool Home with dock

New Waterfront house pool hot tub golf cart kayaks

Pirate’s Cove
Condo rentals with a pool

Oceanfront View, Spacious Townhouse, Heated Pool

Beach Haven in South Clearwater Beach

Blue Sea Renity-2-min walk to beach|Heated Pool

Lovely-2 bedroom condo with 2 pools, Madeira beach

Ocean Breeze • Easy - Heated Pool Access

Captain's Cove Waterside Condo 103 We are open!

Tiki Themed Waterfront Condo on Tampa Bay

Lovely Condo minutes from beach & King bed
Other vacation rentals with a pool

Beautiful sunsets, waterfront 2/2 pool home

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

Luxury Waterfront w/ Private Heated Pool

Cottage on the Cotee River

Quiet Cottage w/ pool, 10 minute walk to beach

Pool home in Port Richey dog friendly

Sunny Escape: Vibrant Pool Home

Preservation-Jacuzzi-Golf- Kayaks-Fishing-Pool !
When is the best time to visit Holiday?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 155 | € 171 | € 176 | € 171 | € 146 | € 155 | € 155 | € 145 | € 121 | € 129 | € 142 | € 159 |
| 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 |
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 € 26 per night before taxes and fees

Verified guest reviews
Over 1,420 verified reviews to help you choose

Family-friendly vacation rentals
30 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
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- Rentals with a fireplace Holiday
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- 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
- Weeki Wachee Springs
- Vinoy Park
- Amalie Arena
- Dunedin Beach
- Bean Point Beach
- Anna Maria Public Beach
- Jannus Live
- ZooTampa at Lowry Park
- Tampa Palms Golf & Country Club
- Hard Rock Casino
- River Strand Golf and Country Club
- Tampa Convention Center
- North Beach At Fort DeSoto Park
- Fort Island Beach
- Busch Gardens
- Splash Harbour Water Park
- Adventure Island
- The Don CeSar
- Gulfport Beach Recreation Area
- Tropicana Field




