Vacation rentals with a pool in Greater Carrollwood

An outdoor space features a heated pool enclosed by a screen. Lounge chairs are positioned nearby, surrounded by a fenced backyard with landscaping elements, including palm trees and a hammock. Sunlight reflects off the clear water, enhancing the inviting setting.

4.93 out of 5 average rating, 99 reviews

Cozy Tampa Home with Large Heated Pool

“No Cleaning Fee, No Chores” Your family will be close to everything when you stay at this centrally-located home. This home is located 5-10 mins from shopping centers, restaurants, gyms, pet and child daycares, community sport courts, local parks and hospitals. 20-30 mins from Bush Gardens, Downtown, ZooTampa, Tampa Airport, Cruise Port, Ben T Davis Beach, Raymond James Stadium, Hard Rock Casino, Hillsborough State Park and more. Only 1hr 30min from Disney, Universal, Sea World, Lego Park

Guesthouse in Palm Harbor

A private screened pool area features an oval-shaped swimming pool surrounded by a brick patio. Lounge chairs are positioned along the edge, with two bright blue chairs situated nearby. The area is illuminated by natural light filtering through the mesh enclosure.

4.97 out of 5 average rating, 308 reviews

Private Suite, 1 bedroom, 1 bathroom, pool, patio

Private suite attached to Large house located in Palm Harbor with king-size bed, Split unit A/C Amenities include: Large Bathroom with Jacuzzi, Walk-in Shower. Access to shared pool and patio, backyard and Sundeck. Room includes refrigerator/freezer, Microwave, Coffee maker, Iron and kitchenette. Bistro set in room. Private entrances to room and patio/backyard. No shared space. Cable TV, Streaming and Wi-Fi . Centrally located to Restaurants and shopping. 10 mins. to the beach/Pinellas Trail.

4.93 out of 5 average rating, 213 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).

4.9 out of 5 average rating, 166 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.

Apartment 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

A playground structure is shown with a slide and a small platform, set on green grass. Beyond the playground, a screened-in pool area is visible, with water reflecting the surrounding trees and sky. The tranquil backyard environment offers space for relaxation.

4.98 out of 5 average rating, 156 reviews

Tropical Getaway, Perfect Home & Great Location

Whether you're on vacation with family, or traveling for work, this is your perfect home away from home! A short drive to Walmart, the mall and numerous restaurants and shops. Just 10 minutes away from Tampa International Airport. Also, 15 minutes away from Bush Gardens, Adventure Island, Downtown Tampa, Raymond James Stadium, Amalie Arena, Channelside, and Cruise Ports. 30-45 minutes drive to Clearwater Beach, St. Pete Beach or Epperson Lagoon. One hour drive to Disney, Universal & lego land

4.89 out of 5 average rating, 129 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.

4.94 out of 5 average rating, 134 reviews

A screened-in patio showcases a private in-ground pool surrounded by paver stones. Lush greenery lines the spring-fed pond in the background, reflecting the blue sky and trees. Patio chairs and an umbrella provide space for relaxation by the water.

Guest suite in Lutz

Lakefront Retreat w/Pool-Views-Elegant Furnishings

Private UPSTAIRS GUEST SUITE comfortably accommodates 3 guests. Features an elegant bedroom, a combo bedroom/entertainment room with kitchenette; plus a full bath & work station. Enjoy a beverage overlooking the nature preserve; relax and swim in the pool. Located just north of Tampa, midway between Orlando & the Gulf Beaches. Just minutes by car to I-75, I-275, outlet mall, ice hockey complex & restaurants. 7 miles to USF/Moffitt/Busch Gardens; 20 to Airport; 30 to Beaches; 60 to Disney.

An enclosed pool area features a clear blue pool surrounded by vibrant plants and flower pots. Comfortable seating is provided on a patterned rug, creating an inviting space for relaxation. Lush grass is visible outside the pool enclosure, enhancing the serene outdoor atmosphere.

4.9 out of 5 average rating, 104 reviews

Global Inspired pool Retreat Oasis

Take in all the charm of this world travelers inspired home. Designed to be spacious, comforting, and quaint. Settle into the many areas perfect for reading or enjoying the company of your favorite friends and family. In the mood for outdoors, Enjoy the blue waters of the private backyard pool or large yard for family events. Fully equiped kitchen or Grill on back patio, or indulge in any of the local restaurants located minutes from home. Door bell cam and back yard flood cam on site

A private pool area is surrounded by a spacious patio featuring elegant stone tiles. A gazebo with seating is visible to the left, while a well-maintained fence ensures privacy. Lush greenery provides a tropical backdrop to this inviting outdoor space.

5 out of 5 average rating, 23 reviews

Fun Oasis! Private Pool, Hammock, Golf & Grill!

Welcome to your Tampa Oasis escape! This beautifully upgraded home features a resort-style backyard with a large pool, shaded gazebo, hammock, grill, putting green, and plenty of lounge space for relaxing in the sun. Inside, unwind in the cozy living room with a large sectional, electric fireplace, and foosball table for added fun. Ideally located just minutes from downtown Tampa, top restaurants, shopping, and attractions—this is the perfect spot for a stylish and memorable getaway.

An outdoor seating area features a colorful table surrounded by white and pastel chairs. A fire pit is present nearby, with patio heaters positioned for comfort. The view overlooks a heated pool and blue umbrellas, with lounge chairs arranged around the poolside.

4.95 out of 5 average rating, 300 reviews

Modern Waterfront Condo - Captivating Sunset Views

This waterfront one bedroom condo will be your perfect place to relax and make new beautiful memories whether is for holiday or business. It has a fully equipped kitchen. Laundry and dryers are coin operated located at third floor. Guests are allowed to use resort’s common areas like heated pool, fire pit bar/ restaurant. Located near Tampa airport (TPA). Within walking distance of public beach restaurants, and Courtney Campbell trail. Resort doesn't have access to the beach.

A private pool is bordered by a safety fence, designed to enhance security. The pool area, nestled among outdoor pavers, features a wooden bench positioned nearby. Sunlight filters through the enclosure, creating a serene environment, while a grassy area is visible in the background.

4.89 out of 5 average rating, 224 reviews

Your Home away from Home

This home is located in a charming neighborhood. This 3-bedroom, 2-bathroom, new vacation rental home is equipped with new furniture and a private pool. The house is perfect for responsible guests on a budget traveling by themselves or with their family. Where you would have plenty of entertainment. When you aren't on the beach, head to visit the Tarpon Aquarium or take a day trip to Tampa for Busch Gardens and ZooTampa! This space will surely be your home away from home!

A heated pool is located in a spacious backyard surrounded by a wooden fence, providing privacy. The pool features a relaxing curved shape and is complemented by a screened-in sitting area, visible in the background with outdoor furniture arranged for comfortable gatherings.

4.81 out of 5 average rating, 146 reviews

*1Der Stays* #1 Cozy 3 bedrooms home with pool.

Relax with the whole family at this peaceful place to stay. Enjoy sunny afternoon in the pool (heated) with plenty of space or a cozy night by the fireplace in our living area. In the heart of the city with shopping mall and restaurants close by. Only 20 minutes away from downtown and about 30 minutes away from the beach. Come enjoy the cool breeze of the bay. Equipped with tankless water heater and a water purification system for the entire home.

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Popular amenities for Greater Carrollwood rentals with a pool

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House rentals with a pool

A private heated pool is enclosed by a screen and features a spacious deck. Outdoor seating is available under an umbrella, while a stone outdoor kitchen is visible nearby. Lush greenery surrounds the area, promoting a serene environment for relaxation.

4.9 out of 5 average rating, 49 reviews

Lush Vacation Home with Pool

AbbyRating, 5 stars1 day ago

Our family of 4 enjoyed our stay. The house is updated with an open floor plan. TVs in each room, including the outside pool/kitchen area, beautiful kitchen. Highlights our family loved: private pool, nice lounge area, quiet community that was perfect for walking, close to amenities while being tucked away. Lissette was very responsive when we needed anything. And I loved the washer/dryer, which came in handy to keep up with pool towels.

4.99 out of 5 average rating, 234 reviews

A spacious covered screened porch features a heated pool visible nearby. Lounge chairs with cushions are arranged beside the pool. A dining table with chairs is positioned on the porch, alongside a propane gas grill, all set against a backdrop of surrounding greenery.

Home in Port Richey

Heated & Screened in Pool-All Essentials Provided

HeatherRating, 5 stars4 days ago

Beautiful home! Super close to my family exactly what we needed. Felt like home and will definitely book there again hopefully my bday weekend is open

An inviting outdoor space features a private pool surrounded by lush greenery and colorful flowering plants. A circular table with several chairs sits invitingly near the water, accompanied by a shading umbrella, creating a comfortable area for relaxation and outdoor dining.

4.8 out of 5 average rating, 5 reviews

Sunny Tampa Oasis: Pool, Patio & Gazebo

LeslieRating, 5 stars1 month ago

It was an absolutely lovely place to stay. It was very spacious and comfortable. Lots of room to lounge around in and relax. Just being in the home was a nice vacation by itself. The location was very convenient. We would absolutely book again on a future trip.

An aerial view showcases a covered inground pool surrounded by a landscaped yard featuring neatly trimmed hedges and pathways. The main house is visible in the background, set amid lush trees, with ample parking spaces provided on the property.

4.91 out of 5 average rating, 11 reviews

Huge Retreat near Busch Gardens and Moffit Center!

TorianoRating, 5 stars6 days ago

Excellent surroundings, quiet location, and everything that you'll need for vacation.

A private pool is surrounded by a spacious concrete deck, featuring several lounge chairs and tropical landscaping. The clear blue water is set against a backdrop of a blue sky and a white fence, creating an inviting outdoor retreat.

4.84 out of 5 average rating, 103 reviews

Luxurious House with private Pool.

KeithRating, 5 stars2 months ago

everything was as advertised and then some, perfect location for our stay, pool was nice a and refreshing, beautiful back yard.

5 out of 5 average rating, 102 reviews

A screened-in lanai features a heated saltwater pool surrounded by colorful outdoor furniture. Children’s toys and pool floats are placed nearby, alongside a small bike. The serene space is perfect for relaxation and play, with trees visible beyond the enclosure.

Home in Palm Harbor

Coastal Escape: heated saltwater pool & beaches

JessicaRating, 5 stars1 week ago

We absolutely LOVED the house! Cozy, inviting, CLEAN! Everything you can ask for! From the moment you walk in, it feels like home. The house is fully stocked with everything you could possibly need. The backyard is a dream! Our kiddo loved it and so did we! I would recommend this place to anyone! It is definitely worth it! We hope to return next year!

A spacious swimming pool area is enclosed by large glass panels, allowing ample natural light. Two comfortable chairs are positioned beside a small table, offering a relaxing view of the clear water. The pool deck features patterned stone tiles, enhancing the area’s openness.

4.96 out of 5 average rating, 127 reviews

Welcome to villa marcelo

KameronRating, 5 stars1 week ago

Absolutely great place to stay with a large group! My friends and I, a group of 13, stayed at Franddy’s place for my bachelor trip over Memorial Day weekend. Couldn’t have asked for a better bachelor pad! Very spacious with 6 king bedrooms! The pool area is AWESOME and we used it a lot - Even cooked the fish we caught on our fishing charter in the outside kitchen area. We are already looking into booking it again next year!

4.98 out of 5 average rating, 158 reviews

A serene outdoor space features a large swimming pool surrounded by lounge chairs. A covered area can be seen in the background, offering seating and a barbecue setup. The pool area is illuminated with soft lighting, creating an inviting atmosphere.

Home in Bay Crest Park

The T and C Club

JustinaRating, 5 stars1 week ago

Loved our stay at The T and C club! It was a great location and the pool was perfect for all of our children! The home was clean and beautiful!

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Condo rentals with a pool

A view from the balcony reveals a refreshing pool surrounded by palm trees and umbrellas. The water glimmers under bright sunlight, with the bay visible in the background. The area features manicured landscaping and a paved parking space.

4.97 out of 5 average rating, 156 reviews

Tiki Themed Waterfront Condo on Tampa Bay

AprilRating, 5 stars6 days ago

What a wonderful experience!! This condo is even nicer than the pictures! We absolutely loved the view, loved the onsite restaurant, and loved the live music. We hung out on the balcony and enjoyed a spectacular sunset paired with fun live music from the restaurant down below. Parking was a breeze. The security guard was super nice. Pro tip : don’t park in the front of the resort - you have a long walk to the condo with your luggage if you do. Also - there are elevators in the middle of the resort. Something else we didn’t know about bc we parked in front and never noticed them. The resort is quiet, and so lively at the same time. It was so relaxing and a very much needed reset! We will absolutely be back for our next Tampa staycation.

4.82 out of 5 average rating, 195 reviews

A clear blue swimming pool is surrounded by lounge chairs and palm trees, providing a sunny space for relaxation. Umbrellas are positioned nearby for shade. The pool area offers views of the surrounding greenery and the apartment complex in the background.

Condo in Palm Harbor

Lakeside 2- Bed Apartment Near Clearwater Beaches

CarynRating, 5 stars2 weeks ago

Had a great stay! Everything went smoothly. Would book again in the future.

A tranquil view of a swimming pool is showcased against a vibrant sunset over the water. Poolside loungers are arranged along the edge, providing ample space for relaxation. The surrounding area is landscaped, with a fence framing the picturesque scene.

4.75 out of 5 average rating, 239 reviews

Rocky Point paradise

ChristalRating, 5 stars3 weeks ago

View from balcony was exactly as pictured. Gate security were very helpful and friendly. Parking was easy. Area had a very private and peaceful vibe, and not too busy with other people. There were no bugs at all. Kitchen and bathroom were thoughtfully stocked with soaps, linens, coffee, etc.

4.81 out of 5 average rating, 151 reviews

The heated swimming pool is surrounded by palm trees and lounge chairs, offering a relaxing atmosphere. The pool area features a spacious deck with light-colored paving, while nearby buildings provide a serene backdrop, enhancing the inviting outdoor setting.

Condo in Clearwater

☼ STUNNING CONDO MINUTES FROM GORGEOUS BEACHES

SaraRating, 5 stars1 week ago

Great location, communication with host was good, pictures look accurate the condo in person, the condo was in a quiet area. The condo was clean and decor was simple.

A poolside bar and restaurant is visible adjacent to a heated pool, surrounded by lounge chairs. The building features a modern design, with balconies overlooking the pool area. Palm trees provide shade in the background, enhancing the tropical ambiance.

4.85 out of 5 average rating, 108 reviews

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

MollyRating, 5 stars1 month ago

Great area. Great view. Awesome pool/ bar area!

4.86 out of 5 average rating, 291 reviews

The inviting pool area is surrounded by palm trees, with lounge chairs on the pool deck. The view overlooks the intercoastal waterway, reflecting the evening sky. Soft lighting enhances the atmosphere as twilight sets in, creating a serene outdoor space.

Condo in St. Petersburg

Breathtaking Waterview & Pool View Condo

Bob And ShellyRating, 5 stars2 months ago

Awesome view and wonderful host. Easy to find and easy access check in. Will return again.

The pool area is illuminated under the night sky, reflecting soft light from surrounding palm trees and buildings. Features include a clear blue water surface and poolside seating. Soft lighting enhances the relaxing ambiance of the resort-style community.

4.98 out of 5 average rating, 217 reviews

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

OhadRating, 5 stars1 week ago

Amazing apartment! I found there every thing Ineeded. Henrique is amazing host and very friendly and responsive. The location was just perfect for my needs - private place which near to restaurants, shoping and main highways of FL