Holiday rentals with a pool in Keystone

4.97 out of 5 average rating, 133 reviews

Condo in Clearwater

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach

🌴 😎 Stunning Key West Style Retreat featuring: - Memory foam Queen bed - Covered porch for unwinding - Hotel linens, towels and many creature comforts Enjoy the beach 🏄‍♂️ vibes decor & accents in this spacious two bed two bath property. Located less than three miles from the white, sugar sand of Clearwater Beach 😎 (rated #1 beach in the US by Trip Advisor). Relax by the oversized resort style pool and clubhouse. Convenient walking distance to nearby restaurants and grocery stores.

Guesthouse in Palm Harbor

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.

4.86 out of 5 average rating, 162 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.

4.9 out of 5 average rating, 253 reviews

A modern kitchen area is seen with sleek cabinetry and a stylish gray sofa. The space features a silver dining table, a television mounted on the wall, and a large window revealing a private pool just outside. Fresh flowers add a touch of color.

Home in Tampa Heights

Downtown Tampa Pool House! Walk to Armature Works!

Location! Location! Enjoy Tampa at this modern brand new remodeled POOL HOUSE with the BEST LOCATION & with POOL access! SAFE & EASY location in downtown. Come Experience events, food, festivals & nightlife only 1 block from #1 destination, Armature Works- a famous destination for food, fine dining, events, & fun! Enjoy a quiet downtown getaway to enjoy the pool, biking, paddle board or walk the beautiful Riverwalk.Full kitchen! (* We had NO Damage from Hurricane and home is Not in Flood Zone).

4.88 out of 5 average rating, 180 reviews

The sleeping area features a cozy bed adorned with neutral-toned linens and decorative pillows. Three framed botanical prints are displayed on the wall above the bed. A bedside table with a lamp and a small potted plant is positioned next to the bed.

Apartment in Tampa

Private 1 Bed Apt with Pool and water front.

Enjoy the use of the onsite pool and Private 1-bedroom apartment in a peaceful waterfront community! Equipped with your own kitchenette and separate living area. Enjoy the serenity of swimming in your own pool on your vacation or relaxing work stay. Lounge chairs will make your stay even more relaxing. Close to the Veterans expressway and easy access to local restaurants, beaches, 10 minutes from the airport, 20 minutes from the river walk, and entertainment. This apartment is 300 square feet

A seating area features a woven bench adorned with tropical-patterned cushions, positioned against a green wall with a neon sign. The inviting pool glimmers in the background, surrounded by a screened enclosure that enhances the outdoor experience.

4.98 out of 5 average rating, 181 reviews

Tropical Getaway, Perfect Home & Great Location

Whether you're on vacation with family, or traveling for work, this is your perfect home away from home! A short drive to Walmart, the mall and numerous restaurants and shops. Just 10 minutes away from Tampa International Airport. Also, 15 minutes away from Bush Gardens, Adventure Island, Downtown Tampa, Raymond James Stadium, Amalie Arena, Channelside, and Cruise Ports. 30-45 minutes drive to Clearwater Beach, St. Pete Beach or Epperson Lagoon. One hour drive to Disney, Universal & lego land

A screened-in pool area features a private pool surrounded by a tiled deck, with ample space for seating and relaxation. The structure provides sun protection and is situated next to the house, blending outdoor and indoor elements.

4.82 out of 5 average rating, 111 reviews

Entire house in Tampa w/ Heated POOL!

Our home is a 3/2. You walk into a open space with the dining room, living room & bright kitchen. The 1st bedroom is the Master Bedroom, equipped with a full bathroom, spacious closet, King Size bed & full body mirror. The 2nd bedroom has a queen bed, closet space, decorated with touches of care & is right next to the bathroom. The 3rd bedroom has 2 twin beds, FL touch vibes & is steps away from the bathroom. Last but not least our beautiful backyard with your own private pool! Pool heated

4.83 out of 5 average rating, 151 reviews

A modern living area features a light-colored sofa and dark accent chairs arranged around a central ottoman. A wall clock complements the artwork displayed above the couch, while the kitchen area is visible in the background, showcasing sleek cabinetry and appliances.

Condo in Paradise Lakes

Millers, BeOne Naturally Clothing Optional Premium

Relax in your birthday suit in a fun clothing-optional Paradise lakes Resort. Modern furniture sleeps up to 4 People with a King Size Bed and a leather sleeper sofa in living room with Memory Foam mattress. Full kitchen with refrigerator, oven range and microwave for cooking, coffee maker, washer and dryer for laundry, 2 TVs, and a bath tub for relaxing. The clubhouse 2 Swimming Pools, Hot Tub, events like Karaoke, Live Bands and more (fees vary by days of week). Thank you and enjoy!

A serene balcony view captures a sunset over calm waters, with silhouetted palm trees in the distance. A small round table with a lantern sits next to a comfortable chair, creating an inviting space for relaxation.

4.95 out of 5 average rating, 333 reviews

Modern Waterfront Condo - Captivating Sunset Views

This waterfront one bedroom condo will be your perfect place to relax and make new beautiful memories whether is for holiday or business. It has a fully equipped kitchen. Laundry and dryers are coin operated located at third floor. Guests are allowed to use resort’s common areas like heated pool, fire pit bar/ restaurant. Located near Tampa airport (TPA). Within walking distance of public beach restaurants, and Courtney Campbell trail. Resort doesn't have access to the beach.

4.92 out of 5 average rating, 189 reviews

A well-equipped kitchen features sleek white cabinetry and countertops. Stainless steel appliances, including a microwave and a gas stove, are present. Decorative elements, such as red kitchenware and glassware, are arranged on open shelves, creating an organized and inviting space.

Guesthouse in Tampa

Red Comfort Trip Private Jacuzzi, near Busch Gard

Welcome to Red Comfort Trip – Private Jacuzzi & Pool near Busch Gardens. This cozy and fully private guest suite offers your own entrance, a comfortable bedroom, living area, full bathroom, and a private patio where you can relax after a busy day in Tampa. You’ll also enjoy a private jacuzzi and access to a large shared pool, all in a quiet residential area just a few minutes’ drive from Busch Gardens, the Hard Rock Casino, and other main attractions.

5 out of 5 average rating, 147 reviews

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

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

4.95 out of 5 average rating, 294 reviews

A dining area features a wooden table paired with two chairs, positioned near expansive glass windows that overlook a pool area. Sunlight filters through the glass, illuminating the space and providing a view of lounge chairs beside the water and surrounding trees.

Guest suite in Tampa

Tranquil poolside guesthouse on the river

The apartment is on the Hillsborough River surrounded by nature but only 3 minutes away from the great restaurants, bars and breweries of Seminole Heights. It is walking distance to Lowry Park Zoo and park. Spot the beautiful Florida wildlife up close from the river dock. Soak in the outdoor pool surrounded by mature live oaks or take a canoe out on the river. Top beaches are 35 minutes by car. Great for a couple or a small family.

4.84 out of 5 average rating, 176 reviews

A private entrance is visible, featuring a clean white gate that leads into the apartment area. A paved walkway of gray stones is bordered by white gravel and greenery, creating an inviting access point. Nearby structures can be seen, emphasizing the neighborhood's quiet environment.

Apartment in Tampa

Private apartment perfectly located in Citrus park

A comfortable, quiet, and private apartment located in the Citrus Park area. A private entrance to a fully furnished apartment; includes a small kitchen, washer and wifi. The veterans expressway is 1.5 miles away, that can get you anywhere in Tampa within 15 minutes! Citrus Park mall 1.7 miles away. Several eateries, shops, and Tampa trail within a 1 mile radius. Tampa internal airport 12 miles away.

Popular amenities for Keystone rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A tranquil outdoor pool area is highlighted, surrounded by lush greenery and palm trees. The pool's clear blue water reflects the sky, which features vibrant hues of pink and purple at sunset. Comfortable lounge chairs are positioned poolside for relaxation.

4.89 out of 5 average rating, 74 reviews

Tropical Haven: Private Pool, Hot Tub, and Bliss

A serene outdoor space features a rectangular swimming pool, surrounded by a spacious paved area. Two chairs are positioned near the pool. A white fence provides privacy, while trees line the background, enhancing the tranquil setting.

4.8 out of 5 average rating, 115 reviews

Villa Paradise

4.98 out of 5 average rating, 104 reviews

A serene waterfront view captures a canal lined with homes and docks. The still water reflects the soft hues of the sunset, while palm trees and boats add to the tranquil atmosphere.

Home in Bay Crest Park

CANAL Oasis Heated Pool-Hot Tub-Waterfront- Kayaks

4.9 out of 5 average rating, 113 reviews

A view of a heated saltwater pool is framed by two lounge chairs, positioned on a grassy area. Red umbrellas provide shade for seating areas, and a spacious patio can be seen in the background, featuring modern outdoor furniture and a neutral-colored house.

Home in Clearwater

Beach or Golf Getaway • Heated Pool/Spa • Pets OK

A dining area is featured with a dark wooden table surrounded by four light-colored chairs. A large artwork depicting a beach scene is mounted on the wall, complemented by ambient lighting. Doorways leading to other rooms are visible, enhancing the space's openness.

4.88 out of 5 average rating, 60 reviews

your home close to everything

A heated pool is enclosed by a screened lanai, featuring a unique shape with a brick border. Lounge seating is present around the pool, while a hammock is visible in the background. The tranquil area is surrounded by high wooden fencing for privacy.

4.92 out of 5 average rating, 225 reviews

Rooms with a Pool

4.86 out of 5 average rating, 110 reviews

A serene view of the waterfront home, featuring a clear blue pool and well-maintained lawn. Two bright green jet skis are docked at the wooden pier, which extends into the calm canal. The house's backyard is framed by palm trees, creating a relaxed outdoor environment.

Home in Dana Shores

Boaters Paradise- Waterfront Heated Pool King Beds

4.96 out of 5 average rating, 147 reviews

A heated saltwater pool and spa are presented, set against a serene waterfront view. Lush palm trees and well-maintained landscaping frame the area, while the tranquil canal reflects the clear blue sky. Comfortable seating is positioned nearby for relaxation.

Home in Tampa Shores

NEW Heated Salt Pool & Spa on Waterfront Canal

Condo rentals with a pool

A comfortable living area features a neutral-colored sofa, a round dining table, and a ceiling fan. Large sliding glass doors provide access to a balcony, allowing natural light to fill the space and offering views of palm trees outside.

4.92 out of 5 average rating, 210 reviews

Waterfront Condo - Sunset View of Tampa Bay

4.99 out of 5 average rating, 142 reviews

A modern kitchen features white cabinetry and sleek stainless steel appliances. A central island with two wooden stools invites gatherings. Natural light spills through a nearby doorway, illuminating decorative greenery and tasteful textures along the walls.

Condo in Clearwater

Seasalt Breeze, by the pool, NO PETS

A modern living area features a sleek futon couch with red cushions, positioned across from a wall-mounted television. Natural light floods in from sliding glass doors, which open to a private balcony with views of the waterway. Potted plants and decorative lighting add subtle accents.

4.92 out of 5 average rating, 521 reviews

Tropical Waterfront Escape

4.86 out of 5 average rating, 352 reviews

An inviting courtyard area is showcased, featuring a sparkling heated pool surrounded by lounge chairs. Lush greenery and well-maintained gardens add a natural touch, while the two-story yellow building encloses the area, creating a serene and communal atmosphere for relaxation.

Condo in Redington Beach

Royal Orleans at Redington Beach ( Studio )

A wooden pier extends over smooth waters, bordered by rocky outcrops. The sky is painted in vibrant hues of orange and purple as the sun sets on the horizon, casting a tranquil glow across the scene.

4.75 out of 5 average rating, 252 reviews

Rocky Point paradise

A modern living area features a gray sofa adorned with colorful pillows. A white coffee table is placed on a soft area rug. Large sliding glass doors provide direct views of the waterfront, while palm trees can be seen just outside, enhancing the tropical ambiance.

4.89 out of 5 average rating, 179 reviews

Luxury Blue Haven - Stunning Tampa Bay Views!

4.82 out of 5 average rating, 125 reviews

A living room features a comfortable sectional sofa positioned beside a glass coffee table. Natural light enters through large windows, illuminating a cozy reading area with a rocking chair. The walls display a colorful piece of artwork, and a ceiling fan enhances the airy atmosphere.

Condo in New Tampa

Beautiful and spacious condo centrally located

4.86 out of 5 average rating, 491 reviews

A spacious balcony offers water views featuring palm trees and lounge furniture. The exterior of the building showcases a light-colored facade. A living area is furnished with a soft couch and a dining set, bathed in natural light from large windows. A pool area is visible with lounge chairs and palm trees lining the water's edge.

Condo in St. Petersburg

Waterfront condo on top floor @ Boca Ciega Resort

Other holiday rentals with a pool

Home in Logan Gate Village

An open living area is showcased with a spacious sectional sofa, a rectangular coffee table, and a soft area rug. A dining table for six sits in the background, with natural light filtering through a large window adorned with sheer curtains.

4.95 out of 5 average rating, 22 reviews

The Gallery - Modern Home

The exterior view of a three-story condo building is shown, surrounded by lush greenery. Several parked cars are visible in the foreground, with designated spaces and a well-maintained landscape enhancing the inviting atmosphere of the property.

4.96 out of 5 average rating, 23 reviews

MJ’s Condo Minutes from TPA and Busch Gardens

A spacious living area features a contemporary sectional sofa, adorned with assorted cushions, positioned beside a glass coffee table. A mounted television is visible on the wall, while large sliding glass doors provide access to the balcony and overlook the community grounds.

4.83 out of 5 average rating, 6 reviews

The Urban Oasis – Serene Views!

4.88 out of 5 average rating, 17 reviews

The exterior of a two-story condo is showcased, featuring a well-maintained entrance with a concrete pathway bordered by lush green grass. The building has multiple windows and a combination of beige and brown siding, along with a row of palm trees enhancing the tropical setting.

Apartment in Oldsmar

Cozy Private 2BR FL condo

5 out of 5 average rating, 36 reviews

A charming exterior of a townhome is presented, featuring a bright red front door. Lush greenery and colorful plants frame the pathway leading to the entrance, with a well-maintained lawn inviting guests to explore. The surrounding area is dotted with additional townhomes.

Villa in Fox Chase

Coastal Cottage

4.87 out of 5 average rating, 15 reviews

Modern house w/pool 3BR luxury

4.93 out of 5 average rating, 60 reviews

A spacious sleeping area features a tufted bed topped with soft pillows and neatly arranged towels. A large mirror reflects the light from the window, while a potted plant adds a touch of greenery. Soft lighting is provided by ceiling fixtures and bedside lamps.

Home in Seffner

Dariana kuan