Holiday rentals with a pool in Progress Village

A resort-style pool is surrounded by vibrant greenery and palm trees. Lounging chairs are arranged beside the water, creating a relaxing outdoor space. The sky is bright with a few clouds, complementing the tranquil atmosphere of the community.

4.73 out of 5 average rating, 415 reviews

SUN/BIZ Getaway/King bed/resort Pool/pickleball

Great business getaway, less then 15min. from downtown! Peaceful quiet relaxing! Modern one bedroom condo for business, pleasure, or getaway. King size bed in private bedroom. Sofa bed, and Queen air mattress, can sleep up to 4 people. Close to all Tampa has to offer, as well as beaches, Busch Gardens Disney World all driving distance Enjoy the Florida sun relaxing in a hammock by the resort style pool! Additional fees $25 to check in 1hr. early $20 if ID not submitted in 2hrs on day of booking

Apartment in Tampa Downtown

The spacious studio features a comfortable bed adorned with an elegant blanket and modern throw pillows. A cozy sofa is positioned in front of a glass coffee table. Natural light filters through large windows, highlighting a stylish wall hanging and contemporary decor.

4.87 out of 5 average rating, 101 reviews

Warm, inviting studio | Location! | Free Parking!

Embrace the charm of our studio apartment in Downtown Tampa, where convenience and comfort blend seamlessly. Positioned centrally to Downtown, Channelside, Hyde Park, Ybor City, and Tampa Heights, our cozy space offers a sanctuary for urban adventurers. Revel in the simplicity of our studio layout, featuring a well-appointed living area, fully equipped kitchenette, and modern amenities such as a saltwater pool, gym, and yoga studio. Discover the vibrant pulse of Tampa Bay right at your doorstep.

4.9 out of 5 average rating, 261 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).

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, 232 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

Guesthouse in South Seminole Heights

4.86 out of 5 average rating, 966 reviews

Seminole Heights Riverside Paradise w/Pool

Our stunning waterfront views, pool, kayaks, paddle boards, and beach cruisers are a few of the many amenities that make our property perfect for your Florida vacation. Our convenient proximity to downtown Tampa, air & sea ports, beaches, and parks make the guesthouse at Isla de Dij 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.

4.94 out of 5 average rating, 136 reviews

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!

4.83 out of 5 average rating, 137 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.

4.85 out of 5 average rating, 155 reviews

Apartment in Ruskin

Sunset Del Mar (studio with a view)

***UPDATED***Living the Florida lifestyle right on beautiful Tampa Bay. The Inn at Little Harbor is a secluded resort style community offering waterfront accomodations with amenities that include 2 heated pools, jacuzzi, tennis courts, a beautiful sandy beach, 2 full service restaurants/bars with live music,kayak and boat rentals and fishing charters and some of the most beautiful sunsets you have ever seen. Amenities are within walking distance from your doorstep.

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, 197 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.

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, 370 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.

Popular amenities for Progress Village rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.87 out of 5 average rating, 148 reviews

A screened-in pool area features a spacious swimming pool accompanied by a spa. The surrounding paver deck offers ample space for lounging, with green landscaping visible through the screens. Natural light filters in, enhancing the serene environment.

Home in Seffner

Tampa Bay area OASIS

4.85 out of 5 average rating, 78 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

5 out of 5 average rating, 6 reviews

Allison Palms Luxury Tampa Townhome + Pool

4.92 out of 5 average rating, 131 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, 14 reviews

An aerial view captures the canalfront property, showcasing the large pool and spa surrounded by tropical landscaping. The private dock accommodates a boat, while a beach area is visible with lounge chairs and palm trees enhancing the waterfront setting.

Home in Apollo Beach

*New* Waterfront Retreat: Pool, Spa, Dock & Views

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

4.85 out of 5 average rating, 118 reviews

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

4.76 out of 5 average rating, 21 reviews

A spacious living room showcases a comfortable white leather sectional sofa positioned around a modern coffee table. An 82" screen TV is mounted on the wall opposite, while a ceiling fan enhances airflow. Natural light filters through large windows, creating an open and airy feel.

Home in Valrico

Serenity Suite Your Cozy Getaway

Condo rentals with a pool

An open-concept kitchen and living area is highlighted by a marble countertop with modern stools. Glassware hangs above, and a cozy seating area features a light-colored sofa and an accent chair with a playful pattern. Large windows provide a view of the water through sheer blue curtains.

4.88 out of 5 average rating, 141 reviews

Luxury Waterfront Balcony, Heated Pool and more

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.

4.93 out of 5 average rating, 216 reviews

Waterfront Condo - Sunset View of Tampa Bay

4.78 out of 5 average rating, 140 reviews

Condo in Ruskin

Little Harbor Resort #202 Tampa Bay FL Beach, Hot

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, 155 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.

Condo in Ruskin

Beach Condo with water view!

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, 182 reviews

Luxury Blue Haven - Stunning Tampa Bay Views!

4.82 out of 5 average rating, 126 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

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, 342 reviews

Modern Waterfront Condo - Captivating Sunset Views

Other holiday rentals with a pool

5 out of 5 average rating, 4 reviews

Home in Valrico

Snowbirds Welcome! Upgraded 2bd 2bth with lanai

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.

4.96 out of 5 average rating, 77 reviews

Cozy Family Retreat, Tampa: Private Pool Oasis

4.94 out of 5 average rating, 95 reviews

Guest suite in Tampa

West Tampa Villas 1 With Pool Oasis-Near Stadium

4.8 out of 5 average rating, 44 reviews

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.

Apartment in Tampa

Tampita Inn

4.94 out of 5 average rating, 33 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

A serene pool area is framed by lush greenery, with a clear blue pool inviting relaxation. Gentle steps lead into the water, and a wooden deck extends nearby, offering additional seating. The tranquil view of the lake canal enhances the peaceful atmosphere of the space.

4.97 out of 5 average rating, 99 reviews

Lakeview Retreat with Private Pool Perfect Getaway

4.9 out of 5 average rating, 79 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.

Apartment in Tampa

Tampa Tropical-Saltwater Pool-10 Min to TPA