Holiday rentals with a pool in Progress Village

4.93 out of 5 average rating, 15 reviews

A spacious living area is depicted, featuring two soft sofas adorned with cushions in soothing colors. A glass coffee table sits at the center, while a light neutral palette enhances the feeling of openness that leads to a kitchen area in the background.

Townhouse in Riverview

Modern Beach House! By Deinys SR Properties

Welcome to your home away from home! This 2 bed, 2.5 bath townhome has private baths & walkin closets in each room, inunit washer/dryer, and private driveway parking. Fur babies are welcome, and families with little ones too we offer a PacknPlay and baby utensils upon request. As a mom of twin toddlers, I’ve made it my mission to make your stay comfy and stress free. Just 15–20 mins from Downtown Tampa & Busch Gardens, and 45 mins from the beach! Our home is ready to welcome you with open arms.

4.89 out of 5 average rating, 285 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).

4.95 out of 5 average rating, 113 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

The Jungalow is the ultimate urban oasis. Enjoy the luxuries of the home or venture out to local attractions like the iconic Bayshore Boulevard, Historic Hyde Park, SOHO, Downtown and more. This home was designed with comfort and convenience in mind. Fully equipped with a smart tv, high-speed WIFI, pool and hot tub - this place is paradise. Central to the action - walk to unique rooftop bars, restaurants and shops or Uber to local attractions like Water Street, Amalie Arena, and the Riverwalk.

The exterior of the home is presented, featuring a well-maintained lawn with greenery. A welcoming entrance is highlighted by a centered door framed with large columns. The driveway is visible on the left side, and the surrounding neighborhood structures provide a sense of community.

4.92 out of 5 average rating, 25 reviews

Tampa Paradise For All Occasions

Planning a family trip? Couples trip? Girls/Guys trip? Business travel? Our home provides an amazing experience for all occasions. Our beautiful 4 bedroom, 2 bath home is the perfect get away. We have put special care in providing amenities for your stay from fully equipped kitchen with Keurig to plasticware and towels for the screened in HEATED pool. You will enjoy surround sound while accessing your wi-fi entertainment platforms. Come experience our home away from home.

The exterior of the house features a light gray façade with white trim. A neatly manicured lawn is adorned with colorful flower beds. A palm tree stands prominently in the foreground, while the garage door and front entry are visible, inviting a welcoming entrance.

4.98 out of 5 average rating, 161 reviews

The Sunset Getaway

Step into The Best Sunset Getaway to relax with friends and family. As you enter this beautiful home, you will immediately feel the coziness it provides, and you will feel right at home. You will have access to a fenced backyard overlooking a beautiful lake with the most amazing sunsets. There is 2 community pools, just 1 block away. Close to shops and restaurants and less than 50 minutes away from beautiful beaches. Just 30 minutes away from the airport and Busch Gardens.

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.

4.81 out of 5 average rating, 192 reviews

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, 255 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.

4.86 out of 5 average rating, 169 reviews

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.

Home in Tampa

North Ybor escape with Private POOL and POOL TABLE

Safe Ybor home with screened in pool featuring a pool table for your entertainment. Located across the street from Al Barns Park which offers a baseball field, tennis & basketball courts, and a playground. Less than 15 minutes from Raymond James Stadium, 10 minutes away from Amelie Arena, 10 minutes away from the convention center and downtown Tampa, and only 4 minutes away from the Histroric Ybor City Strip where you will find restaraunts, cigars, bars, clubs, etc.

4.99 out of 5 average rating, 158 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.

4.94 out of 5 average rating, 155 reviews

The backyard features a heated pool with a unique shape surrounded by palm trees and vibrant flowers. Comfortable loungers are arranged for relaxation, while a thatched-roof gazebo offers shade. A spacious patio provides room for gatherings, enhancing the outdoor living experience.

Home in Apollo Beach

*Apollo Escape* – Canalfront Home + Private Pool

Escape to this canalfront pool home—perfect for families or groups looking to unwind and reconnect. With 4 bedrooms, 2 kitchens, a game room, and a private dock, there’s space for everyone to relax. Swim in the pool, grill in the backyard, or enjoy movie night in one of two living rooms. Just 30 minutes from Tampa and minutes to beaches, marinas, and waterfront restaurants—This dog-friendly retreat offers the Florida summer your family deserves.

4.92 out of 5 average rating, 187 reviews

Bungalow in Bayside West

Boutique Bungalow with Private Saltwater Pool

Relax in a crisp Florida bungalow with a private saltwater pool set in a fully private backyard oasis. Whether you are coming to Tampa for an event, extending your cruise vibe, or coming to Tampa for work, this home has got you covered. You’ll be 15 minutes from the Tampa Convention Center and the Port Tampa Bay Cruise Terminal, close to South Tampa dining and nightlife, 10 minutes to TPA, and an easy drive to award-winning Gulf beaches.

5 out of 5 average rating, 154 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

Popular amenities for Progress Village rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The aerial view captures a spacious, single-story house surrounded by a well-maintained lawn. Nearby residences and green areas are visible, along with a serene lake reflecting the sky in the background. The property is located in a peaceful neighborhood.

4.96 out of 5 average rating, 100 reviews

Entire home, Heated Pool, Lake view, and Gazebo!

4.97 out of 5 average rating, 94 reviews

Heated Pool Near Tampa w/ games, firepit, kingbeds

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.

4.84 out of 5 average rating, 181 reviews

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

4.98 out of 5 average rating, 46 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

An inviting outdoor space features a fire pit surrounded by four comfortable chairs on a lush green lawn. The serene pond reflects the colorful sunset sky, with tall trees framing the tranquil landscape, providing a perfect setting for evening gatherings.

5 out of 5 average rating, 24 reviews

Serene 4BR Lakeside Retreat | Central Location

The exterior of a two-story house is shown, featuring a light blue facade with white trim. A well-maintained lawn with palm trees and shrubs frames the driveway, which leads to a garage. A clear sky complements the appearance of the home.

4.92 out of 5 average rating, 59 reviews

4bd/2.5ba Heated Pool Home w. Pond View

4.79 out of 5 average rating, 24 reviews

A row of modern townhouses is displayed, featuring light-colored exteriors and pitched roofs. Lush greenery from palm trees lines the front, while a cobblestone pathway leads to driveways. The inviting architecture is complemented by a clear blue sky with scattered clouds.

Home in Palmetto Beach

Stylish Urban Modern Home with Rooftop Patio

4.97 out of 5 average rating, 30 reviews

The exterior of a single-story house is visible, featuring a welcoming entrance with large windows and a landscaped front yard. Lush greenery, including palm trees and vibrant flowers, decorates the area. A two-car garage is seen on the left side, complemented by a concrete driveway.

Home in Providence Lakes

Spacious Home near Tampa- Pool/Hot Tub/Cold Plunge

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.

4.93 out of 5 average rating, 228 reviews

Waterfront Condo - Sunset View of Tampa Bay

4.9 out of 5 average rating, 164 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!

4.87 out of 5 average rating, 151 reviews

The marina features a variety of boats docked in calm waters, with a warehouse structure visible in the background. The scene includes several sailboats and a large yacht, complemented by industrial surroundings, reflecting a serene nautical atmosphere.

Condo in Maximo

"The Merry Yacht" excellent location

4.91 out of 5 average rating, 188 reviews

A sunset is captured over the intercoastal waterway, with warm hues reflecting on the water's surface. Silhouettes of palm trees line the foreground, while distant markers indicate the waterway's navigation. The scene conveys a tranquil ambiance, enhanced by the fading light.

Condo in St. Petersburg

Heron's Hideaway- Studio by the bay!

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, 268 reviews

Rocky Point paradise

4.95 out of 5 average rating, 116 reviews

Condo in St. Petersburg

Updated Condo-Heated Pool-Private Balcony

4.98 out of 5 average rating, 283 reviews

A serene balcony offers a view of the waterfront, with two green chairs and a glass table positioned to enjoy the scenery. Palm trees are visible in the foreground, and the calm water reflects the bright blue sky, creating a tranquil outdoor space.

Condo in St. Petersburg

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

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.

4.79 out of 5 average rating, 131 reviews

Beautiful and spacious condo centrally located

Other holiday rentals with a pool

4.93 out of 5 average rating, 41 reviews

A spacious gray sectional sofa with a decorative blue pillow is positioned in the living area. Natural light enters through large windows, illuminating the modern kitchen and dining space in the background. A light-colored area rug adds texture to the floor.

Home in Bloomingdale

Lake Oasis Heated Pool

4.94 out of 5 average rating, 89 reviews

The charming exterior features a blue wooden house with a welcoming front porch. Two bright yellow chairs sit invitingly on the porch. Lush greenery surrounds the home, and a white picket fence adds to the inviting atmosphere. A decorative plant is positioned beside the door.

Bungalow in Tampa

• Casa De Belen • Bungalow in Ybor City!

Apartment in Channel District

5 out of 5 average rating, 19 reviews

Lux 2BR/2BA Channelside Condo | Pool, Sauna, Gym

4.81 out of 5 average rating, 48 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

5 out of 5 average rating, 5 reviews

Home in Coquina Key

Bayfront Oasis | Pool, Hot Tub & Dock

Luxe

Home in Dana Shores

5 out of 5 average rating, 46 reviews

Tampa Luxe Waterfront Private Pool, Hot Tub & More

4.98 out of 5 average rating, 59 reviews

A spacious living area features high ceilings and natural light, with a comfortable seating arrangement that includes a gray sectional and armchairs. A modern coffee table sits at the center, complemented by a decorative lamp and plants. The area seamlessly connects to a dining space with a large table.

Home in Wesley Chapel

Designers Villa @ Saddlebrook

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.