Holiday rentals with a pool in Progress Village

4.89 out of 5 average rating, 102 reviews

The kitchen features a central island with dark cabinetry and a white countertop, providing ample workspace. In the background, stacked washers and dryers are visible. Comfortable bar stools are positioned at the island, and a light fixture hangs overhead, illuminating the area.

Townhouse in Tampa

Cozy & Chic Townhome in the Heart of South Tampa

LOCATION, LOCATION, LOCATION! I have absolutely adored living in this hidden DIAMOND of a townhome. It’s time to share my favorite place with the world. Welcome to Diamond in The Bay! *5 mins to Bayshore Blvd *10-15 mins to all Downtown Tampa has to offer (Soho, Hyde Park Village, Amalie Arena, etc) *10 mins to Tampa International Airport *15 mins to Historic Ybor *20 mins to Raymond James Stadium *20-25 mins to Downtown St Petersburg *30-35 mins to St Pete Beach *45 mins to Clearwater Beach

Superhost

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

4.89 out of 5 average rating, 258 reviews

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).

A comfortable living space is shown, featuring a light-colored sofa near a large window. The window offers a view of lush greenery outside. A television sits on a wooden console, which holds various books and decorative items.

4.98 out of 5 average rating, 229 reviews

PondView/Pool/Pickleball/Dryer/Washer/Ground Floor

Pond View ground floor Condo located in within minutes of Tampa Bay's main attractions: Bush Gardens, Hard Rock Cafe and Casino, Tampa Aquarium, Top Golf, Ybor City, Convention Center, I FLY and shopping malls. Condo has a large Resort Style pool, Keyless entry, washer/dryer in the unit and owner on site for if needed. Pickleball, Tennis court, Volleyball, Disc Golf and 24/7 Gym also available. Relaxing community with several ponds and trails to be explored near the unit. FUN/SUN/Business

Bungalow in Riverside Heights

A contemporary saltwater pool is surrounded by lush tropical foliage and tall palm leaves, providing a serene setting. The pool area features lounge chairs and a view of the bungalow, blending indoor and outdoor spaces beautifully.

4.99 out of 5 average rating, 309 reviews

Saltwater Pool Oasis ⭐ 1925 Bungalow in ❤ of Tampa

1925 Bungalow, 3 bedrooms, saltwater pool, private backyard/large deck. In the perfect location to explore the best of Tampa, including: Tampa International Airport-4.7 miles Armature Works/Riverwalk-.9 of a mile University of Tampa-1.5 miles Downtown Tampa-2.1 miles Raymond James Stadium-2.4 miles Ybor City Historic District-2.3 miles Amalie Arena/Channelside-2.6 miles USF-9.2 miles Clearwater Beach-25 miles Disney World-1 hour The Bungalow is on a busy main road & the pool is not heated.

4.94 out of 5 average rating, 135 reviews

A serene outdoor area is highlighted by a private pool surrounded by spacious patio space. Two sun loungers face the water, with palm trees gently swaying in the breeze. A large outdoor dining table is situated nearby, providing ample seating for gatherings.

Home in Apollo Beach

Waterfront Pool Oasis •Kayak, Games & Sunset Views

Relax at your waterfront oasis in Apollo Beach with a private pool, kayaks, and sunset views. Spot dolphins and manatees from the backyard or unwind on loungers with outdoor dining and games. Inside: full kitchen, dining area, 2 bedrooms, 2 baths, plus an extra living room with sleeper sofa and closet that serves as a 3rd bedroom. Close to Tampa, beaches, dining, and family attractions — ideal for families, friends, or a romantic getaway in a spacious private home. LIC# DWE3913431

4.81 out of 5 average rating, 192 reviews

An open living area features a spacious gray sectional sofa facing a mounted flat-screen TV. The kitchen, visible in the background, showcases dark wood cabinetry and stainless steel appliances. Bright, recessed lighting highlights the modern design, creating a welcoming environment.

Home in Riverview

Spacious Modern Retreat for Family Fun Near Tampa!

Experience the ultimate Florida getaway in this spacious 3,000 sq ft modern home, perfect for families or groups. Enjoy a dedicated office, plus an 80-inch 3D TV for movie nights or sports games. Conveniently located near top attractions: 15 mins to downtown, 10 mins to dining and shopping, 50 mins to beaches, 10 mins to TopGolf, 15 mins to the casino, 20 mins to Busch Gardens, and just 1 hour from Disney. Embrace comfort, convenience, and excitement—book your stay today!

4.84 out of 5 average rating, 136 reviews

An outdoor space features a sparkling swimming pool surrounded by a screened enclosure. A hot tub is adjacent to the pool under warm string lights. Various games are available, including a ping pong table and a billiard table, providing entertainment options for guests.

Villa in Brandon

Tampa heat pool /hot tub lake view near airport

Welcome to home away from home! This beautiful 4 bedroom 2 bathroom house is new with modern decor and has everything you need for a comfortable and relaxing stay. The house features a sparkling swimming pool and a hot spa, perfect for unwinding after a long day. Located in brandon, you’ll be just 15 minutes away from downtown, where you can experience the city’s vibrant culture and attractions. Get ready to create some unforgettable memories in this charming abode.

4.99 out of 5 average rating, 150 reviews

An aerial view showcases the property nestled among lush greenery along the Alafia River. A spacious yard is bordered by trees, and a covered pool area is visible. The river reflects the surrounding landscape, contributing to the tranquil setting of the retreat.

Guest suite in Riverview

The Guest House at Riverbend Retreat Fla.

True Florida-style living under the oaks and palms on the Alafia River with beautiful views and comfortable beds. We include use of the pool, spa, fire pit, hammock, putting green, yard games, BBQ and dock area. There are additional bedrooms in the adjoining house for larger groups. Fisherman can cast into the river with expectations of catching Sheepshead, Red Snapper, Speckled Trout, Snook, Spotted Bass and Florida Gar off the dock. We also catch blue crabs.

4.92 out of 5 average rating, 130 reviews

A refreshing pool area is enclosed by a screen, featuring clear blue water and two colorful inflatable loungers. Sunlight filters through, and two lounge chairs are positioned nearby, offering an inviting space for relaxation.

Home in Brandon

Relaxing 3BR/2BA POOL Home w. Pond View & HOT TUB

Stay in this waterfront house and live like a true local in Tampa. We're within driving distance to parks, beaches, and casinos. Our rental comes with 3 bedrooms, and a hot tub, pool, and living room that you're free to use any time. Wi-Fi, self check-in, laptop-friendly workspace -- we've got everything you need. * Garage is not accessible to guests. * Pool is NOT heated! The spa is heated, though, please contact host for instructions on how to turn on spa.

Guest suite in Ridgewood Park

A spacious sleeping area features a dark quilted bedspread and a ceiling fan providing airflow. Natural light enters through the nearby windows, illuminating the decor. The kitchen area is visible in the background, with dark cabinetry contrasting against lighter walls.

4.96 out of 5 average rating, 363 reviews

The Pearl at Ridgewood Park

Enjoy this stylish and specail studio located in the most desired area of Tampa!! Walk or bike to Armature Works, The River Walk, Downtown Tampa, Ulele Restaurant and so many more cool and trendy places in the area. This studio is located less than 5 mins from our unique ans historic Ybor City! We are just 10 mins from Tampa International Airport so convenient for business trips. Pool area is available from 9 Am to 9 Pm No glass in pool area.

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, 296 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.

Popular amenities for Progress Village rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A covered patio area features a built-in seating arrangement with soft cushions, accompanied by a round coffee table. The space opens to a sparkling pool surrounded by wooden decking and lush greenery, offering a serene outdoor experience.

4.99 out of 5 average rating, 122 reviews

Hacienda Hideaway w/ heated pool

4.97 out of 5 average rating, 31 reviews

An inviting poolside area is seen with submerged lounge chairs and a clear blue pool, illuminated in soft pink tones. Surrounding seating includes a shaded umbrella and chairs, with scenic water views beyond. A tree provides gentle shade, enhancing the tranquil outdoor setting.

Home in Apollo Beach

Waterfront Retreat in Apollo Beach –Relax & Unwind

4.95 out of 5 average rating, 99 reviews

A serene outdoor space features a sparkling pool framed by lush tropical landscaping. A relaxing spa is integrated into the pool area, accompanied by comfortable lounge chairs. A shaded cabana and grilling station are visible in the background, enhancing the inviting ambiance.

Home in Palma Ceia

The Jungalow SOHO - Pool/Hot Tub

4.95 out of 5 average rating, 131 reviews

A sparkling outdoor pool is surrounded by a spacious patio, featuring light-colored paving stones. A thatched-roof cabana is visible in the background, providing shaded seating. The clear blue water of the pool reflects the sunlight under a bright sky, creating a serene outdoor retreat.

Home in Ballast Point

Private House with Pool and Cabana

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.

4.94 out of 5 average rating, 141 reviews

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

Superhost

A screened-in pool area features a turquoise pool surrounded by light-colored tile flooring. Two lounge chairs provide seating beside a small table with a red top. Sunlight casts soft shadows, creating a serene atmosphere for relaxation and enjoyment.

4.86 out of 5 average rating, 161 reviews

North Ybor escape with Private POOL and POOL TABLE

4.84 out of 5 average rating, 116 reviews

Fun, Trendy, Tropical 3/2 Pool Home in South Tampa

4.91 out of 5 average rating, 131 reviews

An aerial view showcases a spacious home surrounded by greenery, with a large screened-in swimming pool at the center. The pool area features a deck, while the backyard is lined with lush landscapes, providing a private outdoor experience.

Home in Brandon

Beautiful Waterfront Home -(Pool with Jacuzzi)

Apartment rentals with a pool

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, 191 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, 522 reviews

Tropical Waterfront Escape

4.92 out of 5 average rating, 154 reviews

The sleeping area features two queen beds with soft bedding and decorative pillows. Nightstands with lamps are placed on either side. A neutral color palette enhances the space, complemented by wall art and subtle lighting elements in the room.

Apartment in Ruskin

Beach Condo with water view!

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, 253 reviews

Rocky Point paradise

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.

Apartment in New Tampa

Beautiful and spacious condo centrally located

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, 336 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.

4.84 out of 5 average rating, 121 reviews

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

4.86 out of 5 average rating, 123 reviews

A well-lit room features two spacious beds dressed in blue linens. A small table and chairs are positioned nearby, along with a flat-screen television mounted on the wall. Sliding glass doors open to a balcony, inviting natural light and providing views of the surrounding area.

Apartment in Ruskin

Oasis at Little Harbor

Other holiday rentals with a pool

5 out of 5 average rating, 5 reviews

Relax & Explore in a Private Pool Oasis

Superhost

An aerial view shows a large swimming pool surrounded by landscaped gardens and palm trees. A red water slide and a hot tub are visible near the pool area. In the background, residential buildings are set amid expansive green lawns.

Flat in Tampa

4.8 out of 5 average rating, 44 reviews

Tampita Inn

Guest house in Crescent Lake

A serene outdoor space features a saltwater pool surrounded by lush greenery. Two lounge chairs are positioned under a striped umbrella, providing shade on the pool deck. The light-colored stone tiles enhance the calming atmosphere of this private retreat.

5 out of 5 average rating, 14 reviews

Luxury Pool House

4.89 out of 5 average rating, 63 reviews

A wooden bed frame with a decorative headboard is centered in the room, featuring a light-colored bedding set adorned with a subtle floral pattern. A wooden dresser and bedside lamp provide functional space, while a wall-mounted mirror reflects the natural light.

Guest house in Brandon

Beautiful and Cozy apartment

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.

4.89 out of 5 average rating, 63 reviews

your home close to everything

4.98 out of 5 average rating, 42 reviews

The living space features a large sectional sofa in a deep blue hue, a round coffee table, and a decorative fireplace with a blue stone facade. A dining area with a table for six is visible, alongside two window seats adorned with cushions.

Home in Brandon

Blue Serenity Retreat w/Free Heated Pool & Jacuzzi

4.86 out of 5 average rating, 98 reviews

Flat in Tampa Downtown

Stylish Studio | Downtown Views | Saltwater Pool!