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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Guest favorite
Home in Clearwater Beach
4.95 out of 5 average rating, 112 reviews

Waterfront Coastal Bliss at Brightwater w/ Heated

PLEASE ASK ABOUT OUR OTHER 2 WATERFRONT PROPERTIES ON CLEARWATER BEACH IF YOUR DATES ARE NOT AVIALABLE!! Welcome to Brightwater Blue, our newer vacation Town Home in Clearwater Beach! 3 floors of fun, elegance & relaxation await you. Custom interior decorated with Restoration Hardware & other high end furnishings. Located on Clearwater Bay & within easy walking distance to Clearwater Beach, Beach Walk, restaurants, shopping & everything Clearwater Beach has to offer! Why book 3 hotel rooms when

Superhost
A private solar-heated pool is surrounded by lush greenery, creating a serene outdoor space. Two lounge chairs are positioned poolside, with a small table nearby, inviting relaxation in a peaceful atmosphere.
Home in New Port Richey
4.79 out of 5 average rating, 121 reviews

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

Guest favorite
A tranquil poolside view captures the serene waters of the Anclote River at sunset. Soft purple lighting reflects from the pool's surface. Spacious seating areas invite relaxation, with silhouettes of boats visible in the background against the vibrant sky.
Home in Forest Hills
4.96 out of 5 average rating, 95 reviews

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

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, 269 reviews

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.

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, 118 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.

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, 131 reviews

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!

Guest favorite
A heated saltwater pool is framed by a spacious patio, featuring several lounge chairs. A pink flamingo float adds a playful touch to the water. The view includes surrounding palm trees and a serene waterway, enhancing the outdoor relaxation space.
Home in New Port Richey
4.89 out of 5 average rating, 19 reviews

Waterfront Oasis

Ideal for boating (rentable boat lift) , fishing, and kayaking/paddle boarding or exploring nearby islands. Bring your own boat. . Breathtaking sunrises and sunsets from patio. Heated saltwater pool (upon request and $50 fee daily) Grill in the outdoor kitchen. The master bathroom offers a private commercial grade steam room. Enjoy a dedicated pool table room with a fireplace, a retro gaming station and many family board/card games. Pets are welcome with a $450 non refundable fee.

Guest favorite
Home in Port Richey
4.92 out of 5 average rating, 38 reviews

Cozy Oasis Screened Pool Picturesque Canal Views!

5⭐⭐⭐⭐⭐ Service & Accommodations! Welcome to our serene waterfront retreat, a 3-bedroom, 2-bathroom home that comfortably sleeps 10 guests. Nestled along a picturesque canal, our property offers the perfect blend of tranquility and convenience for your next vacation. Unbeatable spot to have a relaxing and rejuvenating vacation experience ❤️❤️❤️❤️❤️ Inquire with us today for last minute specials, availability and other info! Professionally Managed by ❤️ Emperor Rentals 👑

Guest favorite
A serene outdoor space features a heated saltwater pool surrounded by a screened enclosure. Lounge chairs are positioned poolside, and a children's swing set is visible in the background. The vibrant sunset creates a warm ambiance over the tranquil setting.
Home in Seminole
4.95 out of 5 average rating, 133 reviews

Sleeps 8 Near Beach | Pool + Game Retreat

Discover your tropical retreat at Paradise Palms in Seminole! This newly renovated, pet-friendly home features a game room, outdoor dining, and a sparkling, saltwater swimming pool - with heating provided at no extra cost. mid Oct- April. Just minutes from Madeira Beach, we've equipped you with all the beach essentials for your convenience. Professionally hosted by Tropical Oasis, FL, we've meticulously prepared all the essentials to ensure a memorable stay.

Top guest favorite
Home in New Port Richey
4.93 out of 5 average rating, 148 reviews

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

Guest favorite
Home in Palm Harbor
4.95 out of 5 average rating, 190 reviews

Heated Pool 4 bed 6.9 miles to Honeymoon Island.

This stylish place is perfect for family vacation or work trip.. all brand new furnishing and appliances.. heated pool and three TVs for your enjoyment. The home is also conveniently located near many beaches, honeymoon island 6.9 miles Fred Howard park 11 miles ,Clearwater beach 14 miles ,Tampa and St. Pete . Please check house rules for more info. When you book, please put the exact number of guests that are going to be staying at the property.

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, 106 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?

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Avg. price€ 156€ 172€ 176€ 171€ 146€ 156€ 156€ 145€ 121€ 130€ 143€ 159
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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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  4. Pasco County
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