
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

Condo w/ Pool, Hot Tub and Restaurant! Book now !
Plan your unforgettable stay at this 1 bedroom condo at Beso ( not a studio) with 2 Balconies for your morning coffee or beautiful sunsets The location is perfect to walk to town where you’ll find many Quaint shops, restaurants and Breweries Free Wi-fi Free parking Only 10 min to honeymoon island and the ferry to Caladesi Island 15 minutes to Clearwater Beach 2 salt water Pools and a hot tub Marker 8 Tiki Bar and restaurant 28 mile trail across St. Bicycle rental through the office for a fee

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.

Tarpon Springs Oasis: Heated Pool, 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)

Oasis Getaway
Relax with the whole family at this peaceful place to stay. Perfect Getaway with amazing sunset views from the upstairs balcony and a floating dock on a canal perfect for kayaking and manatee sight seeing. This canal will also take you straight to the ocean. Very spacious home with a tennis table located on the first floor and a beautiful pool to enjoy! Close to many attractions like Weeki Wachee Springs, Outdoor trails, a Marina, Water Park, Hudson Beach and great seafood restaurants.

Heated Pool • Near Tarpon & Gulf 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, steps to gulf, fishing, bike trails
Escape to your private Palm Harbor oasis! This updated studio features a cozy queen bed, sofa bed, and kitchenette, plus a sparkling in-ground pool reserved just for guests. Walk to the Gulf for fishing, boating, or paddleboarding, or hop on the nearby Pinellas Trail for biking and exploring. Enjoy beaches just minutes away, along with amazing dining, breweries, and live music in historic downtown. Pet-friendly, with keyless entry and free cleaning for 14+ night stays.

Insta Worthy Retreat -Arcade Room- Htd Pool- Golf
☀️ Looking for a place the whole family/group can enjoy? This centrally located modern home is full of fun and style, with everything you need—from a fully stocked kitchen 🍽️ to beach supplies ⛱️ and more. Enjoy an Insta-worthy space with 5-hole mini golf, giant outdoor games, a heated pool, arcade & board games, and cozy spaces inside and out. 📍 Just 6 miles to the beach and Downtown St. Pete—perfect for your getaway!

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!

Beach House!
Great for Family Vacation! Close to restaurants ,water view, gulf access and more!If you looking for a breathtaking view to go along with your coffee or drink, look no further than waterfront bar overlooking the swimming pool in our backyard. Our bar offers a unique blend of style, functionality and ambiance, transforming backyard into a social hub. You would enjoy the sunrise and sunset!!!
Popular amenities for Holiday rentals with a pool
House rentals with a pool

Gulf Harbors Getaway Home with Pool

Tarpon Fun'n Sun-Pool, Beaches + Backyard Chickens

Florida style home !

Heated pool, hot tub, game room, 10 min to beach

3 BR/2B pool home WiFI and Brand new furnishings

Renovated Pool Home • Sleeps 7 • Downtown NPR

Private 3 Bedroom House w/ Heated SaltWater Pool

Luxury Airbnb on Wesley Chapel
Condo rentals with a pool

Relax in a Newly Renovated Beach Front Paradise

Resort living on the beach

Tiki Themed Waterfront Condo on Tampa Bay

Modern and Cozy Condo 6 Minutes from the Beach !

Little Harbor Resort #109 Tampa Bay FL Beach, Pool

Free Parking Pool & Water Front

SUNNY DELIGHT! HEATED POOL 2 miles to the beach🐶

Upgraded 3 Bed, 3 Bath Corner Water Front Condo!
Other vacation rentals with a pool

Clearwater Lake House

Anclote Oasis-Sunsets-Pool-Kayak-Fish-Gulf Access

Clearwater Mediterranean Retreat • Pool & Fire Pit

Coastal Cottage

Nautical Landings - The Mainsail

Sunny 2-Bed Oasis: Pool & Gym in Apollo Beach

Beautiful house with pool, fire pit, billiard room

Dolphin-Watch Waterway – Pool/Spa Tarpon
When is the best time to visit Holiday?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ661 | ﺩ.ﺇ731 | ﺩ.ﺇ749 | ﺩ.ﺇ727 | ﺩ.ﺇ621 | ﺩ.ﺇ661 | ﺩ.ﺇ661 | ﺩ.ﺇ617 | ﺩ.ﺇ514 | ﺩ.ﺇ551 | ﺩ.ﺇ606 | ﺩ.ﺇ676 |
| 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 ﺩ.ﺇ110 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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- House rentals 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
- Dunedin Beach
- Amalie Arena
- Bean Point Beach
- Anna Maria Public Beach
- Jannus Live
- Tampa Palms Golf & Country Club
- ZooTampa at Lowry Park
- River Strand Golf and Country Club
- Hard Rock Casino
- North Beach At Fort DeSoto Park
- Fort Island Beach
- Splash Harbour Water Park
- Adventure Island
- Busch Gardens
- Tampa Convention Center
- The Don CeSar
- Gulfport Beach Recreation Area
- Fred Howard Park




