
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.

2 BR/2 BA Key West Retreat, A+Pool, 3m to Beach
🌴 😎 Stunning Key West Style Retreat featuring: - Memory foam Queen bed - Covered porch for unwinding - Hotel linens, towels and many creature comforts Enjoy the beach 🏄♂️ vibes decor & accents in this spacious two bed two bath property. Located less than three miles from the white, sugar sand of Clearwater Beach 😎 (rated #1 beach in the US by Trip Advisor). Relax by the oversized resort style pool and clubhouse. Convenient walking distance to nearby restaurants and grocery stores.

Private Suite, 1 bedroom, 1 bathroom, pool, patio
Private suite attached to Large house located in Palm Harbor with king-size bed, Split unit A/C Amenities include: Large Bathroom with Jacuzzi, Walk-in Shower. Access to shared pool and patio, backyard and Sundeck. Room includes refrigerator/freezer, Microwave, Coffee maker, Iron and kitchenette. Bistro set in room. Private entrances to room and patio/backyard. No shared space. Cable TV, Streaming and Wi-Fi . Centrally located to Restaurants and shopping. 10 mins. to the beach/Pinellas Trail.

Home away from home
Private unit has designated parking, pool access, its own water heater, water softener, filtration system, 2 ceiling fans, heater, air purifier & a/c. Featuring a queen bed, dresser, 42” tv & fire stick w/ streaming accounts, wifi, full length mirror, recliner, eating table & chairs. The bathroom has a walk-in shower, large vanity mirror, & all the needed bathroom accessories. Full kitchenette w/ microwave, dual burner, air fryer, tea kettle, coffee maker, & more. Owner lives on property.

Heated Pool, 5 minutes 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, Teachers, friends and family - book & message me, 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)

Tropical Oasis Retreat w/ Heated Pool
Welcome to a Private oasis located in your very own backyard. Spend the day lounging by the heated pool, grill pit cooking your own food together with privacy fence. Master bed has ensuite bath. When you venture out, this Palm Harbor house is ideally located by Crystal Beach and bike ride to Honeymoon Island for some sparkling Gulf Coast beaches. With multiple golf spots like Innisbrook right next door and Clearwater beach just down the road, you can stay busy year-round. We are pet friendly

Heated & Screened in Pool-All Essentials Provided
🏡 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.

Private pool suite in heart of Tarpon Springs!
Charming private suite in a safe, serene neighborhood—just minutes from beaches, Downtown Tarpon, Sponge Docks & Sunset Beach! Your cozy retreat features a private entrance, queen bed, fast WiFi, cable television, a full kitchen & heated in-ground pool. Explore Tarpon Springs and the Pinellas Trail on provided bikes, then unwind at Sunset Beach with provided beach towels, chairs, umbrellas, toys, cooler & sunscreen. This space is a perfect blend of comfort, convenience & coastal charm!

“Couples Retreat” jacuzzi horses pool Apt 2
Take it easy at this unique and tranquil getaway. This is a one of a kind barndominium with all the luxuries of a paradise getaway. Indulge in the beautiful resort style pool area this is truly a stunning property gated on 6 acres private and secluded. Bike trail access is also included, so bring your bikes for a nice outing. We also have a private fire pit and outdoor dining exclusive to you! 4 horses are also on the property as well as a goat and 2 mini horses connect with nature!

Mackarosa Tampa Bay Luxury Pool House
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

By the POOL, Ground floor, King bed, NO PETS
The Avalon at Clearwater is a gated community with a nice size heated pool and community gym. Parking space is not assigned and it’s free of charge. Walk-in distance to Publix grocery store and nearby restaurants. Location is central with short distance to nearby beaches, attractions and other nearby towns. Great access from Tampa Airport 20 minutes and 1.5/hours drive from Orlando airport and Disney World This location is loved by “snowbirds”

Saltwater Pool • Kayaks • Pedal boat + more!
Discover the perfect spot for a fun-filled vacation with family and friends at Seaside Retreat! Nestled along the beautiful waterways of Hernando Beach, this waterfront getaway offers everything you need for relaxation and adventure. Whether you’re looking to unwind by the pool, paddle through the serene waters, or enjoy lively local entertainment, Seaside Retreat has it all. Book your stay today and make unforgettable memories by the water!!
Popular amenities for Holiday rentals with a pool
House rentals with a pool

Gulf Harbors Getaway Home with Pool

Waterfront Oasis-Tarpon Sunsets-Pool-Kayak-Fishing

The Palm Haus • Heated Pool • Near Beach • Games

marinita Sweet Home, Beach

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

Angie's Family-Fav Lake Home: Heated Pool 3br/3ba

Home with a View and heated pool/ solar panels

Coastal Escape: heated saltwater pool & beaches
Condo rentals with a pool

Waterfront Condo - Sunset View of Tampa Bay

Very cozy quality condo close to Clearwater Beach

Bright and Spacious 1Bed/1Bath condo.

The Avalon - 1/1 LUXE CORNER CONDO/King size bed/

☼ STUNNING CONDO MINUTES FROM GORGEOUS BEACHES

Modern Waterfront Condo - Captivating Sunset Views

Waterfront condo on top floor @ Boca Ciega Resort

Literally: 15 steps to the Pool, GroundFloor Condo
Other vacation rentals with a pool

The Coastal Calm - Entire Unit

Waterfront Oasis

Private pool, Golf Cart, Completely Renovated!

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

Cottage on the Cotee River

Peaceful Garden Oasis

The Pelican Cove - guest house

Cozy Waterview Condo on the Lake
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 | € 175 | € 170 | € 145 | € 155 | € 138 | € 131 | € 138 | € 144 | € 142 | € 146 |
| 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 30 vacation rentals in Holiday

Nightly prices starting at
Holiday vacation rentals start at € 26 per night before taxes and fees

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

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

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 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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