Holiday rentals with a pool in Carrollwood

An open concept living space features a spacious kitchen with dark wood cabinetry and stainless steel appliances. Connection to a cozy seating area is provided by a light-colored sofa adorned with decorative pillows. A dining area with a red tablecloth and seating for six enhances the welcoming atmosphere.

4.83 out of 5 average rating, 138 reviews

5 star Tampa Pool Oasis 2

Fully renovated 3bed 2bath open concept home with beautiful pond view and brand new POOL! Luxurious Travertine floors and handscraped wood floors throughout the home and beautifully modern renovated bathrooms. Large county park just 75 steps from the front door featuring kids play areas, fitness trail, and basketball courts make this a great family friendly or long term place to stay. 15 minutes to Busch Gardens, 20 minutes to downtown Tampa, 40 minutes to Gulf beaches, 1hr 15 mins to Disney.

A vibrant outdoor oasis features a cozy plunge pool surrounded by sun loungers. A shaded seating area includes a table with four chairs. The space is enhanced by decorative elements, including a pergola with hanging egg chairs, all set against a lush green lawn.

4.97 out of 5 average rating, 102 reviews

Cozy Family Retreat, Tampa: Private Pool Oasis

Welcome to Sunshine on the Bay, a charming 2-bed/1-bath villa that blends comfort and style in a quiet area. Located just 3 mins from Citrus Park Mall and 13 mins from airport you'll have easy access to shopping, dining, and top Tampa attractions. Step outside into your own private backyard oasis, complete with a refreshing plunge pool & grill – the perfect spot to unwind after a long day. Enjoy all the essentials, fully equipped kitchen, as well as a 240V outlet for your EV charger. Book today!

4.86 out of 5 average rating, 108 reviews

Home in Forest Hills

Golf • Hot Tub • Pool • Fire Pit • Putting Green

➤ Spacious Tampa Pool Retreat in a peaceful community, overlooking Babe Zaharias Golf Course! • 10 min to Restaurants, Raymond Stadium & USF • 15 min to Busch Gardens, TPA ➤ Hot Tub Jacuzzi, Putting Green, Fire Pit, Pool ★ Loaded Game Room – Pool Table, Darts, Karaoke & More ★ Sunrise views from the Balcony ★ Courtyard for Yoga & Coffee • Sleeps 14 comfortably with Smart TVs in every room • Wi-Fi & Workspaces ➤ Perfect for family vacations, group trips, snowbirds, remote work, celebrations.

4.96 out of 5 average rating, 113 reviews

Townhouse in Tampa

Colorful, Comfy Townhome - Community Swimming Pool

Townhome in the heart of Carrollwood/Northdale with all the comforts of home. 1,136 sq ft. Updated everything, including black matte GE Appliances & fully stocked kitchen. Close to countless restaurants, shopping & easy commute to interstates & expressways. Large, community swimming pool. Come As You Are, I try to provide anything you may need for your stay! 9.5 miles-Ray Jay 10 miles-USF 14 miles-Tampa International Airport 15 miles-Downtown Tampa 16 miles-Ybor 36 miles-Clearwater Beach

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.

4.81 out of 5 average rating, 121 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. outside a beautiful backyard with your own private pool! Pool heated at a fee.

A comfortable gray sectional couch is adorned with decorative pillows in various colors and patterns. A vibrant piece of artwork is displayed on the wall, along with a lush green plant nearby. A dining area with round table and bright orange bar stools is visible in the background.

4.85 out of 5 average rating, 147 reviews

Zen Holistic Retreat by Carrollwood/Westchase

Holistic sustainable wellness centered spaces that are comfortable, memorable and inspiring. Welcome to Serenity...Enjoy your time in Tampa in premium accommodations! King Casper luxury memory foam mattress's. Spa quality toiletries, amenities and linens. Located less than 20 minutes from ALL the following locations...Busch Gardens, Adventure Island, Lowry Park Zoo, Tampa International Airport (TPA), International Plaza, Raymond James Stadium, Amalie Arena and the Tampa Convention Center.

Bungalow in Riverside Heights

4.98 out of 5 average rating, 110 reviews

Luxury Stay • Hot Tub & Heated Pool • Fenced Yard!

Explore the charm of this three-bedroom, two-bathroom bungalow – a luxurious haven where style meets relaxation. Enjoy moments of tranquility by the spa and screened pool, complete with inviting swim-up barstools, or unwind in the indulgent hot tub accommodating up to eight guests. Step into the serene outdoor oasis, adorned with elegant furnishings against the picturesque backdrop of a fenced backyard. Your getaway awaits, conveniently situated near the city's premier attractions.

A bright living area features a plush, mustard-colored sofa adorned with colorful cushions. In the background, a modern kitchen is visible, equipped with stainless steel appliances and white cabinetry. Pendant lights hang above the kitchen island, enhancing the open-concept layout.

4.95 out of 5 average rating, 152 reviews

3/2, 3 miles to Busch Gar *Pool, Game,CoffeeBar*

Welcome to A Little Havana in Tampa Florida! Located just 6 mins from Busch Gardens, 7 mins from the Hard Rock Casino, Florida Fairgrounds and less than 10 miles to downtown Tampa. Easily accesible to the James A Hanley VA Hosp, Moffit Cancer Ctr and USF. Enjoy your unique stay in this one of a kind home. It features a vibrant design, a fully equiped game room with projector, a screened inground pool, a firepit with BBQ grill, outdoor seating and a yoga space for your enjoyment.

A comfortable living area is highlighted by a plush sofa and a modern coffee table, with a 75-inch Smart TV mounted on the wall. Natural light floods the room through sliding glass doors that provide a view of the outdoor pool area.

4.84 out of 5 average rating, 108 reviews

Family Friendly Oasis Heated POOL - Ace Location

NEW NEW! SPACIOUS ! HEATED POOL. Perfect for longer Stay! Stunningly 2022 renovation. Pool Table, Corn holes, King Bed. Nestled in the quaint Lake Magdalene Carrollwood neighborhood! Located 15 Min to Busch Garden, Downtown Tampa. 45 min to FL best beaches. Enjoy best of both worlds! Grocery and Restaurants within 3 min from the home. Large deep pool and nice backyard space perfect for entertaining! Optional Pool Heater available Oct - March $25 per night

A vibrant red flower stands in the foreground, drawing attention to the tranquil blue pool beyond. The pool area, enclosed by white fencing, is set against a backdrop of green foliage, complementing the peaceful outdoor setting.

4.81 out of 5 average rating, 116 reviews

Getaway & Golf- Heated Pool Home

HEATED POOL HI OUSE. Enjoy the total renovated heated pool, deck and patio in the entire cozy house NOT shared, 4 bedr, 2 Pack N Play, 2 bathr, 2 kitch, 2 living rooms and laundry. Private 4-6 cars parking. Large covered porch excellent for board games w/nice view of the pool area, lake & nature reserve. Total privacy & fenced patio w/lounge chairs & hammock for total enjoyment.Comfortable sofabeds to enjoy SMART TV FREE WiFi & HIGHEST Internet.Bikes available.

4.95 out of 5 average rating, 145 reviews

A spacious outdoor area showcases a heated saltwater pool surrounded by lounge chairs and shaded seating under a bright parasol. The tranquil space is framed by lush greenery and features large sliding glass doors leading into the home.

Home in Beach Park Isles

Private Oasis w/ Heated Pool and Arcade!

-9FT DEEP *HEATED* SALTWATER POOL ($25 / day) AT 85 DEGREES UPON REQUEST -COMMERCIAL ARCADE WITH >4500 GAMES 4 PLAYERS! -NBA JAM, GOLDEN TEE, THE SIMPSONS, NFL BLITZ, MUCH MORE! -MASTER KING BEDROOM -FULLY FENCED BACKYARD -OUTDOOR FIRE PIT -Propane Grill Stay comfortably in this quiet, 4/3 pool home, with a commercial family arcade! Enjoy a staycation at this tastefully updated home or take a quick ride to one of the many local Tampa area attractions!

4.9 out of 5 average rating, 109 reviews

Relaxing yard & pool at Downton Blue

Welcome to Downton Blue, a beautifully maintained two bedroom, two bath home, where timeless charm meets modern comfort. Nestled in a quiet neighborhood, your stay here will leave you feeling rejuvenated and relaxed. It offers a private pool- perfect for morning coffee or an afternoon dip. Just minutes from top rated dining, shopping, and local attractions. Whether you are exploring the area or working, you will appreciate the unbeatable convenience.

Popular amenities for Carrollwood rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.94 out of 5 average rating, 111 reviews

The exterior of a two-story mansion is showcased, featuring elegant arched windows and a red-tiled roof. A stairway leads to the entrance, while a decorative fountain is positioned in front. Lush landscaping surrounds the home, enhancing its inviting appearance.

Home in Riverbend

** Tampa Riverfront Mansion ** Pool / Hot Tub / ..

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.

4.82 out of 5 average rating, 130 reviews

Villa Paradise

5 out of 5 average rating, 7 reviews

Large Home • Hot Pool • Entertainment • 12 Guests

4.79 out of 5 average rating, 28 reviews

Tampa Luxe Oasis Pool, Spa & Games 14 Guests

5 out of 5 average rating, 9 reviews

Villa Bellissima near Golf Course & Busch Gardens!

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.

4.99 out of 5 average rating, 203 reviews

Tropical Getaway, Perfect Home & Great Location

Home in Logan Gate Village

4.83 out of 5 average rating, 53 reviews

Family Oasis with Pool and Spa

The modern kitchen features sleek white cabinetry and stainless steel appliances, including a large oven and refrigerator. A spacious island with seating is centered in the room, complemented by a dining area visible in the background. Natural light filters through a window, enhancing the inviting atmosphere.

4.82 out of 5 average rating, 91 reviews

Cozy Hideout w/ pool ~ Close to everything

Condo rentals with a pool

4.89 out of 5 average rating, 219 reviews

Lovely Waterview Condo/ heated pool

The living area showcases a stylish futon, designed to convert into a bed, complemented by a circular coffee table atop a textured rug. A modern kitchen area features a granite countertop, wooden cabinetry and two bar stools, while large windows allow natural light to fill the space.

4.94 out of 5 average rating, 433 reviews

Stunning Waterfront Suite with Bay & Sunset Views

A vibrant, themed living area features colorful hanging lamps and intricate wall decorations. Lush greenery is present, alongside a mixture of patterned seating arrangements. Large glass doors open to a balcony, allowing natural light to fill the space and offering a view of the outdoors.

4.97 out of 5 average rating, 215 reviews

Tiki Themed Waterfront Condo on Tampa Bay

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, 537 reviews

Tropical Waterfront Escape

A vibrant sunset is captured over the water, displaying hues of orange and yellow in the sky. The sun descends toward the horizon, with silhouettes of distant trees visible along the shoreline.

4.95 out of 5 average rating, 122 reviews

Tampa Bay Waterfront Views Rocky Point

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.

4.76 out of 5 average rating, 272 reviews

Rocky Point paradise

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, 364 reviews

Modern Waterfront Condo - Captivating Sunset Views

Lounge chairs are arranged on the sandy beach, accompanied by thatched umbrellas providing shade. The calm waters of the bay are visible in the background, and a multi-story building is situated beyond the beach area.

4.85 out of 5 average rating, 136 reviews

262*NEW! 3 beds x 2 bath. Amazing Waterfront Views

Other holiday rentals with a pool

5 out of 5 average rating, 20 reviews

Apartment in Tampa

Lux Top-Floor Bayfront 2BR | Pool, Hot Tub, Sauna

4.95 out of 5 average rating, 81 reviews

An outdoor patio area features a shaded table surrounded by four adirondack chairs. A tropical palm tree adds greenery, and a grilling station is positioned nearby. The space is enclosed by a white fence and showcases a well-maintained lawn.

Home in Oldsmar

Sunny Oasis: Villa Retreat

Bungalow in Riverside Heights

A spacious backyard is shown, featuring a vibrant green lawn and shaded areas created by large umbrellas. Comfortable lounge chairs are positioned under the shade, while potted plants add a touch of greenery. A covered seating area can be seen in the background.

4.99 out of 5 average rating, 90 reviews

Welcome to The Plaza Tampa

A single-family home with a dark exterior is framed by lush greenery and palm trees. A spacious driveway leads to a two-car garage, while a vibrant lawn adds a touch of color. Large windows create a welcoming facade, showcasing the inviting entrance.

4.86 out of 5 average rating, 58 reviews

CasaBella

4.83 out of 5 average rating, 71 reviews

Spacious 5BR Oasis with Pool & Hot Tub

The backyard features a spacious pool surrounded by a stone patio, offering an area for relaxation. A mini golf green is visible, accompanied by a basketball hoop. The two-story house's exterior is complemented by a gray shed and lush greenery, all under a clear blue sky.

4.85 out of 5 average rating, 81 reviews

“Sunny Retreat”Pool & Mini Golf

A screened-in pool area features a clear blue pool under a bright sky filled with clouds. Sunlight reflects off the water's surface, and a seating area with two chairs is positioned nearby, offering a spacious environment for relaxation.

4.8 out of 5 average rating, 41 reviews

Tranquil Tides Pool House, 3-BR, 2 miles from Zoo

A peaceful lakeside view features gentle ripples created by ducks gliding across the water. Reflections of nearby apartment buildings are visible on the serene surface, surrounded by lush greenery and a clear sky.