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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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A serene view of the Anclote River at sunrise, with a coffee cup placed on the dock's edge. The sun is seen rising above the water, reflecting golden hues on the surface. Lush trees frame the scene, creating a peaceful atmosphere.

Home in Holiday

4.88 out of 5 average rating, 16 reviews

Anclote Oasis - Waterfront Sunsets, Private Pool

Come choose your pleasure; take a swim in the saltwater pool, fish from the dock, kayak or take a boat ride to the islands. Or you might just relax and watch sports on the 50”TV overlooking the Anclote River. This home brings room for the family, all the necessities and a quick drive or bike ride to Tarpon Springs. Watch Birds, Dolphin & Manatee from the dock. Beautiful sunrises and sunsets from the backyard. Easy Access - 15 min to Sponge Docks 20 min to beaches, 35 min to Clearwater airport.

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, 107 reviews

Coastal Escape: heated saltwater pool & beaches

★ 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

Top guest favorite

A private screened pool area features an oval-shaped swimming pool surrounded by a brick patio. Lounge chairs are positioned along the edge, with two bright blue chairs situated nearby. The area is illuminated by natural light filtering through the mesh enclosure.

Guesthouse in Palm Harbor

4.97 out of 5 average rating, 317 reviews

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.

Top guest favorite

A welcoming exterior view of the house, featuring a landscaped front yard with palm trees and decorative rocks. A large driveway leads to a garage, while outdoor seating is visible on a covered porch, framed by large windows and soft natural light.

Home in Palm Harbor

4.99 out of 5 average rating, 136 reviews

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

Home in Holiday

4.97 out of 5 average rating, 74 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

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, 102 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.

A serene view from the screened lanai highlights a private heated pool, reflecting the soft colors of a sunset. The tranquil waters of the Anclote River can be seen beyond the pool, framed by lush greenery and trees along the riverbank.

Home in Holiday

4.97 out of 5 average rating, 39 reviews

River Home with Pool, Sunset, Dolphin & Fishing

Welcome to the waterfront oasis situated along the serene banks of Anclote River connecting to the Gulf. Enjoy privacy as no backyard neighbors, just a nature. Step outside to your own private paradise, where a screened lanai awaits with a private heated pool. Spend your days lounging poolside, soaking up the Florida sunshine, or marveling at dolphins and manatees. Close driving distance to the world famous beaches (Clearwater, Honeymoon Island), Tarpon Spring, Weeki Wachee & Tampa Bay

Top guest favorite

A spacious living area is furnished with a large sectional sofa and additional seating, centered around a rustic coffee table. Large windows provide natural light, while a ceiling fan adds comfort. An open layout connects to a dining area and kitchen in the background.

Home in Tarpon Springs

4.96 out of 5 average rating, 363 reviews

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

This home is ideally located near Florida's beautiful Sunset Beach and Howard Park Beach - only 17 miles from Clearwater Beach. Take a short ride to world famous attractions like Disney, or Busch Gardens. Don't settle for a hotel when you and your guests can enjoy a home with a gas grill, multiple patios, large kitchen/family room, a large 4K TV and a private jacuzzi/pool with gas heater *option. It's a perfect place for creating family memories or getting together with old friends.

A screened-in lanai offers a comfortable seating area with a wicker couch and coffee table overlooking a swimming pool. The space is adorned with potted plants and hanging light fixtures. A dog sits by the couch. The backdrop features a private yard, enhancing the outdoor atmosphere.

Home in Holiday

4.91 out of 5 average rating, 11 reviews

Holiday Escape w/ Pool & Sand Volleyball

Your perfect getaway awaits in this pet-friendly 2BR/2BA retreat! Relax by the in-ground pool, play a game of sand volleyball, unwind on the deck or have a BBQ. The fully fenced yard offers privacy, while the covered outdoor seating, pool-side hammock, fire pit, and a variety of games make it fun for all. With WiFi, AC, and a workspace, it’s perfect for both short and long stays. Just minutes from the beach, dining, and entertainment. *no heat or jets in pool/jacuzzi until October

Top guest favorite

A fenced solar-heated swimming pool features smooth, blue water. Lounge chairs and a small table are positioned on the surrounding patio, while a floating pool toy and a colorful ball are visible in the water. A laundry drying rack stands beside the pool area.

Home in New Port Richey

4.93 out of 5 average rating, 140 reviews

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

Top 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 Holiday

4.98 out of 5 average rating, 57 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…

Top guest favorite

A spacious outdoor area reveals a crystal-clear heated pool, surrounded by a screened patio. Comfortable lounge chairs and a dining table with an umbrella enhance the idyllic setting, inviting relaxation. Large glass doors along the back wall provide a view into the home, blending indoor and outdoor experiences.

Home in Tarpon Springs

4.99 out of 5 average rating, 106 reviews

Tropical Pool Retreat in Tarpon Springs

Welcome to your sun-kissed Florida escape! - 3 spacious bedrooms with king size beds and TVs - Relaxing atmosphere perfect for families and groups - Private heated saltwater pool and tropical backyard - Fully-equipped kitchen and tastefully decorated living area - Game Room with table tennis, dartboard, and foosball - Complimentary bikes for exploring the area - Close to Tarpon Springs Sponge Docks and Fred Howard Park

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Popular amenities for Holiday rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Top guest favorite

A private pool area features a spacious swimming pool with a gentle fountain. Two red lounge chairs are positioned on the patio, alongside a light blue inflatable ball and a colorful floating mattress. Lush greenery surrounds the enclosure, enhancing the tranquil atmosphere.

Home in New Port Richey

5 out of 5 average rating, 61 reviews

Luxurious Pool Private Oasis, Nearby Beaches

A spacious living area features a large grey sectional sofa adorned with orange and blue accent pillows. A marble coffee table sits in front, while a ceiling fan is visible above. Light enters through large windows, illuminating the open layout connecting to a dining area.

Home in Palm Harbor

4.96 out of 5 average rating, 28 reviews

The Coastal Calm - Entire Unit

Top guest favorite

The entrance features a covered porch supported by white columns. A vibrant blue front door is the focal point, framed by decorative planters. The landscape includes diverse plants, with a mixture of foliage and decorative stone, creating an inviting and well-maintained exterior.

Home in Holiday

5 out of 5 average rating, 28 reviews

Waterfront, Beach, Pool,Kayaks near Islands, Parks

Top guest favorite

A spacious screened-in pool area features a heated swimming pool, surrounded by a white deck. Sun loungers are positioned beside the water, with a shaded seating area nearby. The fenced backyard is visible in the background, offering privacy and open space.

Home in New Port Richey

5 out of 5 average rating, 74 reviews

Relaxing Beach-Theme Pool Home!

Top guest favorite

An outdoor area features a private pool surrounded by a concrete deck. Lounge chairs and a dining table are visible beneath a covered patio, while tropical landscaping adds greenery. A path of stepping stones leads toward the pool, inviting relaxation and leisure.

Home in Palm Harbor

4.94 out of 5 average rating, 68 reviews

Private pool, Golf Cart, Completely Renovated!

Top guest favorite

A private heated pool is surrounded by a spacious patio area, featuring two lounge chairs. The pool offers a clear view of the canal, while palm trees line the shoreline, contributing to the serene outdoor ambiance.

Home in Palm Harbor

4.98 out of 5 average rating, 54 reviews

Luxury Waterfront w/ Private Heated Pool

A spacious living area features high ceilings and natural light, with a comfortable seating arrangement that includes a gray sectional and armchairs. A modern coffee table sits at the center, complemented by a decorative lamp and plants. The area seamlessly connects to a dining space with a large table.

Home in Wesley Chapel

4.98 out of 5 average rating, 42 reviews

Designers Villa @ Saddlebrook

Top guest favorite

The exterior of a single-story home is presented, featuring a large palm tree in the center of the yard. Lush green grass surrounds the home, with various potted plants enhancing the entrance. A welcoming pathway leads to the front door, complemented by a clear blue sky.

Home in Port Richey

5 out of 5 average rating, 14 reviews

Pool home in Port Richey dog friendly

Condo rentals with a pool

A private balcony offers a cozy seating area with blue cushions and a small table. Palm trees and beach views are visible beyond the railing, where the sand meets the water, enhancing the relaxing beach atmosphere.

Condo in Indian Rocks Beach

4.89 out of 5 average rating, 101 reviews

Oceanfront View, Spacious Townhouse, Heated Pool

Top guest favorite

A spacious heated pool is surrounded by lush palm trees and well-maintained landscaping. Comfortable lounge chairs are positioned along the poolside, providing ample relaxation spots. The pool area is framed by the community buildings, creating a welcoming atmosphere for guests.

Condo in Clearwater

4.99 out of 5 average rating, 107 reviews

Seasalt Breeze private unit No hidden fees

A clear blue swimming pool is surrounded by lounge chairs and palm trees, providing a sunny space for relaxation. Umbrellas are positioned nearby for shade. The pool area offers views of the surrounding greenery and the apartment complex in the background.

4.82 out of 5 average rating, 203 reviews

Lakeside 2- Bed Apartment Near Clearwater Beaches

Top guest favorite

The living area features a comfortable sofa and two accent chairs surrounding a glass coffee table. Natural light filters in through large windows adorned with soft drapes. Decorative art pieces are displayed on the walls, complementing the cozy and inviting interior.

Condo in Clearwater Beach

4.99 out of 5 average rating, 111 reviews

Dock of the Bay, Coastal Elegance | Walk to Beach!

A clear view of the pool area features a well-maintained heated pool surrounded by paved walkways. Lounge chairs are positioned nearby, with lush greenery and well-kept bushes framing the scene, enhancing the tranquil outdoor environment.

Condo in Clearwater Beach

4.93 out of 5 average rating, 145 reviews

Beachfront Condo with Centerline Sunsets

Top guest favorite

A serene balcony offers a view of the waterfront, with two green chairs and a glass table positioned to enjoy the scenery. Palm trees are visible in the foreground, and the calm water reflects the bright blue sky, creating a tranquil outdoor space.

Condo in St. Petersburg

4.98 out of 5 average rating, 271 reviews

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

Top guest favorite

A panoramic view captures the tranquil beachfront and the wide, calm waters of the Gulf. The shoreline is lined with soft, white sand. In the foreground, several low-rise buildings are visible, contributing to the serene coastal atmosphere, with a backdrop of partly cloudy skies.

Condo in Indian Shores

4.99 out of 5 average rating, 101 reviews

Five Star Beachfront Condo Newly Renovated

Top guest favorite

An outdoor seating area features a colorful table surrounded by white and pastel chairs. A fire pit is present nearby, with patio heaters positioned for comfort. The view overlooks a heated pool and blue umbrellas, with lounge chairs arranged around the poolside.

4.95 out of 5 average rating, 306 reviews

Modern Waterfront Condo - Captivating Sunset Views

Quick stats about vacation rentals with a pool in Holiday

Total rentals
30 properties
Nightly prices starting at
€ 34 before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

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