Holiday rentals with a pool in Progress Village

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.

Flat 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

4.9 out of 5 average rating, 255 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).

Guest house in Tampa Heights

A serene pool area features a shimmering blue pool surrounded by lush greenery, including tropical plants. Two lounge chairs are positioned nearby on a brick patio, providing a comfortable spot for relaxation. A detached structure is visible in the background, set amongst a canopy of trees.

4.88 out of 5 average rating, 395 reviews

Pool Side Getaway, Walk/Bike Tampa River Walk

Experience Tampa from our little slice of Heaven right in the heart of Tampa Heights. This is a detached private Pool House in our backyard. At 264 sqft, It has a full Bath, Kitchen, and studio space with a Queen memory foam mattress, and work space / breakfast table. Enjoy the Pool and its tropical surroundings or just relax in a lounge chair. We are walking distance to Lee’s Pizza, Armature Works, River Walk, and much more... Included is a smart TV, WIFI, and Two Bicycles to go explore.

4.94 out of 5 average rating, 135 reviews

A spacious outdoor area features a serene pool, surrounded by a deck for lounging. Tall palm trees provide shade, and a dining area with ample seating overlooks the waterway. The calm surface of the water enhances the tranquil setting of this private waterfront home.

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!

A comfortable living area is highlighted by a black sofa with decorative pillows and a brown leather armchair. A round mirror adorns the wall, and a coffee table is placed on a patterned area rug. The open kitchen is visible in the background, featuring bar seating.

4.96 out of 5 average rating, 247 reviews

Centrally Located/Pickleball/Pool/Washer/Dryer/Fun

Entire ground floor De Luxe condo with washer/dryer in the unit located within minutes of Tampa Bay's main attractions like Bush Gardens, Hard Rock Casino, Tampa Aquarium, Top Golf, Ybor City, I Fly, shopping and beaches. Enjoy this lovely ground floor Condo with a relaxing community pool and convenient Keyless entry (owner on site if needed). Only 10 min to Downtown Tampa, convention center. Newly Renovated pool, tennis, volleyball, Pickleball, Disc Golf and 24/7 Gym.

4.99 out of 5 average rating, 148 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.

Guest house in South Seminole Heights

4.87 out of 5 average rating, 955 reviews

Seminole Heights Riverside Paradise w/Pool

Whether you're traveling for business, seeking a FL adventure or a short getaway staycation, the stunning waterfront views, pool & incredible amenities with convenient proximity to downtown Tampa, airport & area attractions, the guesthouse at Isla de Dij is the perfect accommodation. You'll fall in love with the massive live oaks that line the brick paved streets, the glassy waters of the Hillsborough River and the brilliant sunsets that paint the evening sky.

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.

Guest house 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.

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, 359 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.

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.

4.9 out of 5 average rating, 147 reviews

A vibrant sunset paints the sky in warm hues, with the sun descending toward the horizon over calm waters. Silhouettes of birds are seen flying across the scene, and people can be observed enjoying the beachfront, with gentle waves lapping at the shore.

Guest suite in Ruskin

Home Paradise, Cozy guest suite in Ruskin! Pools!!

Relax with the whole family at this peaceful place to stay. Enjoy the three swimming pools available in our community. You can enjoy the proximity to Apollo Beach just 15 minutes away, Manatee Viewing Center, Apollo Beach Nature Preserve, we are also close to I 75 and a wide variety of restaurants in the area. You can enjoy the Beaches of St Petersburg, Anna Maria Island. The Lagoon - Located in Wimauma FL.

Popular amenities for Progress Village rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.84 out of 5 average rating, 178 reviews

A fire pit with a diamond-shaped design showcases flames surrounded by decorative glass stones. The structure is positioned on a paved patio with a clear view of a heated pool and lake at sunset, creating a relaxing outdoor gathering space.

Home in Riverview

Cheerful 4 Bd home w/ Heated Salt Water Pool & Spa

4.85 out of 5 average rating, 75 reviews

A spacious backyard features a shimmering pool surrounded by lounge chairs and a vibrant orange umbrella. A dining table with four chairs is positioned nearby on the patio, with well-maintained grass and decorative stones accentuating the inviting outdoor space.

Home in Clair Mel City

3 Bedroom w/ Pool-near Downtown/ Bush Gardens

4.93 out of 5 average rating, 190 reviews

A bright, open living area features modern furnishings, including a comfortable sofa and a sleek coffee table. Large windows provide ample natural light, enhancing the spacious ambiance. The dining area, with a long wooden table, is seen adjacent to a well-equipped kitchen showcasing granite countertops and stainless steel appliances.

Home in Seffner

Stunning Heated Pool House Close to Tampa & Casino

4.95 out of 5 average rating, 129 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

4.94 out of 5 average rating, 141 reviews

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.

Home in Tampa

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

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

5 out of 5 average rating, 28 reviews

A spacious outdoor area is visible, featuring a screened lanai that surrounds a saltwater pool. Comfortable lounge chairs and a grill are positioned on the pool deck. The pool's clear blue water reflects the sunlight, and the area connects to the house through sliding glass doors.

Home in Providence Lakes

Salt Pool, Huge Lanai Outdoor Kitchen & Game Room!

Home in South Seminole Heights

A screened lanai surrounds a clear salt-water pool, featuring a floating pink flamingo. Colorful lounge chairs are positioned nearby on a sunlit deck, with tropical greenery visible in the background, enhancing the private outdoor space.

4.99 out of 5 average rating, 291 reviews

Pool + Park + Private = Perfect Place

Apartment 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

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

4.92 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, 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, 180 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.

Apartment in New Tampa

Beautiful and spacious condo centrally located

Apartment in St. Petersburg

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.

4.86 out of 5 average rating, 491 reviews

Waterfront condo on top floor @ Boca Ciega Resort

Apartment in St. Petersburg

A cozy living area features a comfortable gray sofa and a blue accent chest. Large glass doors open to a balcony, showcasing water views. A ceiling fan provides a gentle breeze, while decorative elements like wall art and a rug add a touch of charm.

4.97 out of 5 average rating, 146 reviews

Waterfront condo w heated pool and hottub

Other holiday rentals with a pool

4.95 out of 5 average rating, 98 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

5 out of 5 average rating, 3 reviews

Home in Valrico

Snowbirds Welcome! Upgraded 2bd 2bth with lanai

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

4.65 out of 5 average rating, 20 reviews

A modern living area features a light-colored sofa positioned opposite a television. Large windows allow natural light to fill the space, with a glimpse of the outdoors visible. A sleek kitchen bar with tall stools enhances the open layout, complemented by simple pendant lighting.

Flat in Channel District

Channelside getaway

4.94 out of 5 average rating, 32 reviews

An open-plan living area is presented, featuring a dark sofa adorned with yellow and gray cushions. A modern kitchen with dark cabinetry is visible, alongside a dining table set for six. Natural light filters in, complementing the neutral color palette and tile flooring.

Townhouse in Riverview

Cozy townhome near downtown Tampa/Busch Gardens

Apartment in Tampa Downtown

The image captures the reflective skyline of downtown Tampa during twilight. Tall buildings with illuminated windows rise above the calm waters of the Hillsborough River, while the distant shoreline features a wooden structure along the water's edge.

4.88 out of 5 average rating, 51 reviews

Sunset Views from a Stylish 1BR High Rise in Tampa

4.89 out of 5 average rating, 76 reviews

A large heated saltwater pool is framed by tropical palm trees and multiple lounge chairs. The building in the background features beige walls and large windows, creating a welcoming atmosphere. Umbrella-covered tables are visible to one side, providing shaded seating options.

Flat in Tampa

Tampa Tropical-Saltwater Pool-10 Min to TPA