Vacation rentals with a pool in Holiday

4.99 out of 5 average rating, 101 reviews

A heated salt-water pool is enclosed by a screened patio, providing a spacious area for relaxation. Comfortable lounge chairs are positioned nearby, with bright outdoor decor enhancing the inviting setting. Large glass doors open to the interior, allowing natural light to fill the space.

Home in Port Richey

Angelita's Lake Home 3br3ba w/heated pool

+Spacious family retreat on lake +Free heated pool +Huge last-minute discounts +Big deck, BBQ, dining & firepit +Private backyard lakefront +3 bedrooms, 1 king, 1 queen, 2 twin +3 full baths +Easy to cancel +Pet friendly +Fishing +Games +Quiet serene safe +5 minutes to Gulf sunsets +5 min to Sims Park +20 min to Tarpon Springs +39 min to Tampa airport +50 min to Busch Gardens +5 min to restaurants +Fully equipped kitchen +Free parking & garage +Washer-Dryer +Work area +Hi-speed WIFI +Smart TVs

4.94 out of 5 average rating, 161 reviews

Luxury Private Pool House ! Mackarosa ! Tampa Bay!

Experience comfort and style in this beautifully renovated home featuring high ceilings, elegant finishes, and bright open spaces. Three king beds and TVs in every bedroom ensure a relaxing stay after a day of travel or exploring. Fully equipped kitchen. Private solar-heated screened pool for year-round enjoyment. Airport – 35 min • Beaches – 19 min No smoking. Professionally cleaned and sanitized after every stay. Located in a quiet, safe neighborhood—perfect for families and peaceful getaways.

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.

4.96 out of 5 average rating, 110 reviews

Paradise!Renovated waterfront pool home.Sunsets!

Sunsets to die for! Remodeled in 2023 pool house on the Anclote River with access to the Gulf of America.Imagine fishing,kayaking in the backyard & and spotting 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. Fishing rods.Bonfire pit.Grill.Heated pool for a fee. Portable crib,stroller, high chair. Come,relax&enjoy No hurricane damage!

4.99 out of 5 average rating, 294 reviews

Home in Port Richey

Screened in Heated 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.

5.0 out of 5 average rating, 8 reviews

Lake House w/ Kayaks, Fishing & Heated Comm Pool

Relax at this peaceful 3BR/2BA lake house! Minutes from Tarpon Springs Sponge Docks & beaches, the home has a fully remodeled modern interior, and a fully equipped kitchen with wine fridge & a coffee station. Enjoy the back patio & 2 decks for outdoor lounging. Kayaks & fishing poles are available to explore the lake & wildlife. Down the street, guests have access to a community pool & lounge area with a lanai, BBQ, games & relaxing spaces. Bikes are available to ride to the pool and parks!

A screened-in heated pool area is highlighted, featuring a clear blue pool surrounded by a spacious deck. Comfortable seating is arranged nearby, and floating toys add a playful touch. The enclosure provides a bright and airy feel with natural light streaming in.

5.0 out of 5 average rating, 100 reviews

Relaxing Beach-Theme Pool Home!

Whatever your reason for visiting New Port Richey you will find this Cul-de-sac home to be comfortable and inviting having a screened in, heated pool and large pool deck and lanai with outdoor gas grill. The pool area is lighted in the evening for an enjoyable atmosphere. There are three bedrooms and a game/TV room that works as a forth bedroom with a futon. The back is fully fenced in. Fast internet with three new smart TVs. Kitchen is well equipped and has three kinds of coffee makers..

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.

4.98 out of 5 average rating, 65 reviews

River Home Heated 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

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.

4.95 out of 5 average rating, 387 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 view of Lake Conley is depicted, showcasing calm waters under a clear blue sky. Lush trees line the shore, with a walkway and dock visible on the left, offering access to the water. The scene reflects a tranquil outdoor environment.

4.87 out of 5 average rating, 135 reviews

Waterfront, Sunsets & Heated Pool & Pet Stay Free!

Close to the beach, family activities, public transport, and the Tampa Airport. You’ll love my place because of the ambiance, the outdoors space, the water view, & the sunsets, PRIVATE Heated pool and VERY comfy beds! I provide fishing poles, tackle box My place is great for everyone and furry friends (pets) too!. Third bedroom is Florida room with sliding glass door. Two twin beds and desk. dinning table. Let me know about your pets. Your pets stay free. Totally fenced yard.

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.

4.95 out of 5 average rating, 85 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…

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.

4.97 out of 5 average rating, 117 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.

An aerial view of the tropical backyard reveals a spacious layout with colorful lounge chairs and umbrellas scattered across a gravel surface. Several dining areas, outlined by lush greenery, create inviting spots for relaxation and gatherings, surrounded by the tranquility of the natural setting.

4.99 out of 5 average rating, 145 reviews

Tropical Pool Retreat in Tarpon Springs

Welcome to our Tropical Oasis, a stylish yet warm and inviting vacation retreat tucked into the idyllic neighborhood of Tarpon Springs, Florida. - Spacious 3-bedroom home for up to 8 guests - Thoughtfully decorated living area with smart TVs - Heated saltwater pool and screened lanai - Fully-equipped game room with table tennis and foosball - Complimentary bikes for exploring - Close to Tarpon Springs Sponge Docks and Fred Howard Park

Popular amenities for Holiday rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.93 out of 5 average rating, 14 reviews

Coastal Holiday Home w/Pool - Minutes to Beaches

5.0 out of 5 average rating, 22 reviews

Dream Home in Holiday with POOL & SPA and More

4.92 out of 5 average rating, 26 reviews

Tarpon Family Retreat-Heated Pool, Fire Pit & Fun!

Superhost

4.92 out of 5 average rating, 13 reviews

Coastal Family Escape w/Heated Pool•Near Beaches

4.97 out of 5 average rating, 62 reviews

Northern Point of Treasure Island NPR

A screened pool area showcases a clear blue pool featuring a dolphin design at the bottom. The surrounding patio is designed with light-colored tiles, and lush greenery is visible beyond the enclosure, contributing to a private outdoor atmosphere.

4.95 out of 5 average rating, 93 reviews

Cozy Home, Country Setting, Close to Gulf Beaches

The exterior of the home is showcased with a well-maintained lawn, bordered by a circular driveway. The facade features neutral stone and brick materials, with a welcoming entrance illuminated by soft outdoor lighting. A flagpole stands proudly at the front, adding a classic touch.

5.0 out of 5 average rating, 33 reviews

Deluxe 3bd/2ba w/Heated Pool

A spacious outdoor area features a heated saltwater pool and hot tub, surrounded by light-colored tiles. Palm trees provide shade, and seating is arranged along the poolside. The dock extends into the water, showcasing a tiki hut and boats in the distance under a clear sky.

5.0 out of 5 average rating, 25 reviews

Beach Gulf Oasis-Pool, Elevator, Tiki Hut & Dock

Condo rentals with a pool

A set of two white wicker chairs and a small table are positioned on a balcony, providing views of the Gulf of Mexico. The ocean and sandy beach stretch into the distance, with clear blue skies overhead.

4.9 out of 5 average rating, 482 reviews

Amazing views on beachfront

A scenic view of a fishing pier extends into the water, framed by gentle waves and a sandy beach. The sky is filled with colorful clouds, reflecting hues of orange and blue as the sun sets on the horizon.

4.98 out of 5 average rating, 181 reviews

Upgraded 3 Bed, 3 Bath Corner Water Front Condo!

A panoramic view captures the beach at sunset, showcasing soft white sand and tranquil turquoise waters. The sun sets gently on the horizon, casting warm colors across the sky and illuminating the landscape.

4.94 out of 5 average rating, 172 reviews

Beachfront Condo with Centerline Sunsets

4.92 out of 5 average rating, 113 reviews

A spacious living area features a dark sectional sofa and a large flat-screen television. Brightly colored artwork adorns the walls, and a glass coffee table adds a modern touch. Natural light enters through a sliding glass door, with views of the outdoor patio.

Condo in Hudson

Florida Breeze

4.98 out of 5 average rating, 183 reviews

Condo in Clearwater

Steps to Heated Pool • Near Beaches • Gated Condo

4.97 out of 5 average rating, 155 reviews

Condo in Clearwater

Spacious Key West Retreat, Fun 2 BR, Resort Pool

A balcony view features two cushioned chairs adorned with pink pillows, overlooking a quiet street leading to the beach. Palm trees and lush greenery frame the scene, while the ocean is visible in the distance. Bright blue skies enhance the coastal atmosphere.

4.98 out of 5 average rating, 195 reviews

Newly Reno Luxury Condo 30 Steps to Paradise

Gentle waves lapping against a sandy shore create a serene coastal scene. The sky is filled with wispy clouds and varying shades of blue, reflecting the tranquil atmosphere of the beach. The shoreline reveals patterns in the wet sand as the water recedes.

4.95 out of 5 average rating, 343 reviews

Steps 2 beach! Beachy and Luxurious! Easy Living!

Other vacation rentals with a pool

4.97 out of 5 average rating, 39 reviews

Waterfront Retreat H/Pool Private Dock Gulf Access

A serene waterfront view features a private dock with seating and mooring options. Behind, a home with a screened-in pool area is visible, surrounded by lush greenery. Palm trees sway gently in the breeze, adding a tropical element to the scene.

4.86 out of 5 average rating, 28 reviews

Dockside Nook | Waterfront Dock, Fishing, Pool

The collage showcases the cowboy pool surrounded by pebbled landscaping, a cozy bedroom with a spacious bed, a stylish living area with ample seating, and a fully equipped kitchen. Vibrant beach chairs and outdoor games are also visible, highlighting a welcoming atmosphere for relaxation and entertainment.

4.92 out of 5 average rating, 92 reviews

Lazy Day Oasis

5.0 out of 5 average rating, 94 reviews

Lakefront villa, with pool & hot tub near beaches

4.81 out of 5 average rating, 42 reviews

The Tarpon Sunset Retreat

A private pool area features sparkling blue water, surrounded by a well-maintained deck. A wooden pergola offers shaded seating nearby, while tropical plants provide a natural backdrop. The sky is mostly clear, creating a bright and inviting atmosphere.

5.0 out of 5 average rating, 60 reviews

Florida style home !

5.0 out of 5 average rating, 20 reviews

Newly remodeled 3 bedroom with heated pool