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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.

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Top guest favorite
A screened-in lanai features a heated saltwater pool surrounded by colorful outdoor furniture. Children’s toys and pool floats are placed nearby, alongside a small bike. The serene space is perfect for relaxation and play, with trees visible beyond the enclosure.
Home in Palm Harbor
5 out of 5 average rating, 132 reviews

Coastal Escape: heated saltwater pool & playground

★ Close to beaches - Honeymoon Island: just 6 miles away. - Clearwater Beach: 15 miles away - crowned the nation's #1 beach Trip Advisor in 2018 ★ Heated saltwater pool ★ Screened-in lanai ★ BBQ grill ★ Large backyard w/ playground ★ Outdoor dining area ★ 3 bedrooms New Mattresses - California king size bed - Queen size bed - Kid-friendly room w/ two bunk beds ★ Renovated kitchen and bathrooms ★ Open living space - great for family gatherings, movie nights ★ Children toys and games

Guest favorite
A bright studio space features a cozy seating area with a soft blue love seat and a spacious bed adorned with white linens. Natural light filters through sheer curtains, illuminating the wood furnishings and decorative accents throughout the room.
Guest suite in Largo
4.91 out of 5 average rating, 324 reviews

"Twilight Sands Stud" Prvt Ent,Pool,Pk,Keyless Ent

Welcome to our cozy guest suite—where comfort is personal over perfect, and full of charm you won’t find at a hotel. Guests love the thoughtful touches, eclectic decor, cloud-like bed, and the irreplaceable feeling of being at home when you’re far from home. Our home uses one central AC unit. Because Florida is warm and humid year-round, we keep the thermostat at 70°F by day and 67°F at night for proper cooling and comfort. If you prefer more warmth, two space heaters are in the suite closet.

Superhost
A modern bathroom is shown featuring a sleek vanity with a rectangular sink and black fixtures. A round mirror is illuminated by three overhead lights. Storage is provided by wooden drawers beneath the sink, and towels are neatly arranged on shelves.
Guesthouse in Palm Harbor
4.87 out of 5 average rating, 165 reviews

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.

Top guest favorite
A spacious covered screened porch features a heated pool visible nearby. Lounge chairs with cushions are arranged beside the pool. A dining table with chairs is positioned on the porch, alongside a propane gas grill, all set against a backdrop of surrounding greenery.
Home in Port Richey
4.99 out of 5 average rating, 261 reviews

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.

Top guest favorite
Two black rocking chairs with Buccaneers branding are positioned on a light-colored deck. Lush green grass and palm trees frame the view, with a path leading to a screened-in patio visible in the background under a bright blue sky.
Home in Port Richey
4.94 out of 5 average rating, 115 reviews

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.

Top guest favorite
A heated saltwater pool is surrounded by lush tropical landscaping, with clear blue water reflecting the sky above. A colorful float rests on the water's surface. The screened enclosure provides a barrier while allowing for views of the serene outdoor space.
Guest suite in Tarpon Springs
4.96 out of 5 average rating, 136 reviews

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!

Guest favorite
A resort-style pool area is softly illuminated by blue lighting, highlighting the inviting water. Surrounding trees and a fence create a sense of privacy. Lounge chairs are positioned nearby, providing a space for relaxation under the evening sky.
Apartment in Spring Hill
4.89 out of 5 average rating, 159 reviews

“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!

Guest favorite
A light-filled living area features a spacious sectional sofa and a wooden table with a decorative chair. Natural light streams in through large windows with shades, illuminating the neutral color palette and coastal-inspired decor, creating a relaxed environment.
Home in Forest Hills
4.96 out of 5 average rating, 67 reviews

*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…

Guest favorite
A sparkling saltwater pool is featured in the backyard, with a gently curving shape and a clear blue surface. The area is fenced for privacy, with a well-maintained lawn and a sunny sky visible above.
Home in Holiday
4.97 out of 5 average rating, 97 reviews

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.

Top guest favorite
The grotto-style pool area features natural rock formations with cascading waterfalls and lush tropical plants. A hot tub is integrated into the design, providing a relaxing space. The serene water reflects the clear blue sky, while views of the bay are visible in the background.
Home in Oldsmar
5 out of 5 average rating, 147 reviews

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

Top guest favorite
A private swimming pool is surrounded by a screened patio, with colorful floatation devices resting on the clear water. Lounge chairs are positioned nearby against a bright yellow wall. Natural light floods the area through glass doors, creating a refreshing atmosphere.
Home in Forest Hills
4.91 out of 5 average rating, 123 reviews

Heated Pool • Tarpon & Beaches

Oasis with a private pool heated Nov–Mar and a patio, 5 miles from Tarpon Springs, near Dunedin and a short drive to Clearwater/Tampa. Perfect for family or friends: fast Wi-Fi, workspace, fully equipped kitchen, and BBQ. 24/7 self check-in and on-site parking. Quiet for restful nights; beaches and parks minutes away. Note: pool heating available November–March (weather-dependent). Last-minute promos active. Book today!

Guest favorite
An aerial view captures a cozy lakeside home surrounded by lush greenery and palm trees. The screened-in private pool is visible, along with a nearby dock extending into the water. A fire pit area is seen, providing a space for gatherings. Scenic views enhance the outdoor experience.
Home in Holiday
4.92 out of 5 average rating, 101 reviews

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!

Popular amenities for Holiday rentals with a pool

When is the best time to visit Holiday?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price€ 153€ 169€ 174€ 169€ 144€ 153€ 153€ 143€ 119€ 140€ 140€ 145
Avg. temp17°C18°C20°C23°C26°C28°C29°C29°C28°C25°C21°C18°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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  2. United States
  3. Florida
  4. Pasco County
  5. Holiday
  6. Rentals with pools