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.

%{current} / %{total}1 / 1
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

Top guest favorite
The exterior of the home features a welcoming entrance and landscaped yard, showcasing vibrant tropical plants and a decorative pathway. An inviting pool area includes seating along the deck, with loungers arranged for comfort. Scenic water views are visible from a nearby deck, with kayaks ready for use.
Home in Holiday
5 out of 5 average rating, 32 reviews

Gulf Access, Heated Pool, Near Islands, Beaches

Vacation on the Gulf of Mexico near Islands Places to visit * Key Vista Nature Preserve: .05 miles * Anclote Gulf Park: 1.4 miles * Anclote River Park: 2.6 miles * Tarpon Springs Docks: 5.7 miles * Fred Howard Park Beach: 8.5 miles * Downtown Palm Harbor: 11 miles * Dunedin Causeway Beach: 16 miles * Honeymoon Island State Park: 17 miles * Clearwater Beach: 23 miles *Downtown Tampa: 34 miles Theme Parks * Busch Gardens: 31 miles * Adventure Island: 31 miles * Florida Aquarium Tampa: 35 miles

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, 271 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
An outdoor screened area features a private heated pool surrounded by a spacious deck. Two lounge chairs are positioned nearby, with a barbecue grill present for outdoor cooking. A dining set with multiple chairs is also visible under a covered patio, providing shade and comfort.
Home in Spring Hill
4.95 out of 5 average rating, 143 reviews

Weeki Wachee Springs heated pool home retreat

Relax with the whole family at this Weekie Wachee/Springhill Heated pool home. 5 minutes from the crystal clear springs of Weekie Wachee state park and Buccaneer Bay that has spring fed beach with water slides , tiki bars and mermaid shows. It’s also located 10-15 minutes from Rodgers Park located on the river where you can swim, kayak with manatees and enjoy fun family time! Also 15 minutes away is Pine Island Beach Park and SunWest Beach Park for skiing, wake boarding and obstacle course.

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
The screened outdoor lanai features a heated pool with steps leading into the water. Comfortable seating options are present around the pool area, complemented by a shaded dining space nearby. Lush greenery surrounds the outdoor space, enhancing the relaxing environment.
Home in Tarpon Springs
4.96 out of 5 average rating, 146 reviews

Tropical heated pool Oasis 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)

Top guest favorite
A covered patio features two wooden loungers adorned with cushions, surrounded by lush tropical plants. A hammock hangs nearby, providing a relaxing spot. Accent lighting creates a warm ambiance, while a stone path leads through the gravel yard, complementing the serene outdoor setting.
Home in Tarpon Springs
4.9 out of 5 average rating, 29 reviews

Margaritaville house and Bunk House/bar

Location, location, location; in less than 1.8 miles there are two beaches, boat launch, downtown, and the sponge docks. And 3 bikes to get there! Best is “Margaritaville Bunk House” & bar. A kids PARADISE! Sleeps 3, w/mini fridge, vanity, 55 inch TV, Xbox series S (with Xbox live & 2 controllers). Soft serve/snow cone, cotton candy machine, microwave/air fryer combo. Outside a pond, fire pit beach, mini golf, hot tub, TWO outdoor theaters. Outdoor HEATED shower! Tons of seating areas.

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, 133 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!

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
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
4.96 out of 5 average rating, 103 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.

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?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price€ 156€ 172€ 176€ 171€ 146€ 156€ 156€ 145€ 121€ 130€ 143€ 159
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 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

  1. Airbnb
  2. United States
  3. Florida
  4. Pasco County
  5. Holiday
  6. Rentals with pools