
Holiday rentals with a pool in Hillsborough County
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Top-rated rentals with a pool in Hillsborough County
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

5 star Tampa Pool Oasis 2
Fully renovated 3bed 2bath open concept home with beautiful pond view and brand new POOL! Luxurious Travertine floors and handscraped wood floors throughout the home and beautifully modern renovated bathrooms. Large county park just 75 steps from the front door featuring kids play areas, fitness trail, and basketball courts make this a great family friendly or long term place to stay. 15 minutes to Busch Gardens, 20 minutes to downtown Tampa, 40 minutes to Gulf beaches, 1hr 15 mins to Disney.

The T and C Club
Welcome to The T and C Club! A featured home for the Make-A-Wish Foundation. Located 6 miles from the Tampa Airport, 7 miles from Raymond James Stadium and only 15 miles from award winning Clearwater Beach, this home is convenient as it gets. Completely refurbished, there is plenty of space to sleep 10 individuals comfortably, dining table for 10, a large resort-like backyard, saltwater pool, propane grill and all the fun you can imagine. This will truly be a case of you won’t want to leave!

Luxury Oasis • Heated Salt Pool • Near Beaches
Welcome to Paradise Palms 🌴☀️- your tropical, family-friendly getaway w/ a private heated saltwater pool! Newly renovated & cleaner than a hotel, the home is filled w/ luxury amenities to create a truly unforgettable family vacation. With 7 comfy beds, there's plenty of room for everyone. Just 14 min to the famous Clearwater Beach & other beautiful white sand beaches! It's finally time to relax & soak up some Florida sun! Come experience all that Paradise Palms & Clearwater have to offer.

Cozy Casita in NE St. Petersburg
Our Cozy Casita is located adjacent to the main house in a quiet residential neighborhood with a separate entry and fenced in parking space for our Guests. Enjoy our tropical garden and beautiful pool area. The pool is not heated. Small kitchen with Whirlpool electric stove, microwave and mini-fridge. 40” Samsung Smart HDTV and WIFI. Located within minutes of great restaurants, craft breweries, and local museums. Lots of great outdoor activities along St. Pete’s beautiful waterfront.

Private Pool Home Near Clearwater & Tampa
Only 25 minutes from Clearwater Beach and Tampa, 33 minutes from Buch Gardens, 1.5 hrs from Disney, 18 minutes from Tampa International Airport. This house is completely renovated with a lot of space for you, family and/or friends. The entire house for you and your family. We have a beautiful pool with a Grill for your convinience and a garage for your car. 3 bedrooms for up to 7 persons. A 65" TV in the living room. Wi-Fi. The house has everything you need to have a relaxing time.

Private Oasis w/ Heated Pool and Arcade!
-9FT DEEP *HEATED* SALTWATER POOL ($25 / day) AT 85 DEGREES UPON REQUEST -COMMERCIAL ARCADE WITH >4500 GAMES 4 PLAYERS! -NBA JAM, GOLDEN TEE, THE SIMPSONS, NFL BLITZ, MUCH MORE! -MASTER KING BEDROOM -FULLY FENCED BACKYARD -OUTDOOR FIRE PIT -WEBER GRILL (Kamado Joe Smoker broke) Stay comfortably in this quiet, 4/3 pool home, with a commercial family arcade! Enjoy a staycation at this tastefully updated home or take a quick ride to one of the many local Tampa area attractions!

Watch the Sunrise at Sunrise! @ Clearwater home.
Welcome to your perfect vacation getaway! Our beautiful home offers a heated pool, perfect for relaxing any time of year—whether you’re enjoying a sunny afternoon swim or a peaceful evening under the stars. The property features plenty of space for everyone to feel comfortable, both indoors and outdoors. With open living areas, comfortable furnishings, and a spacious layout, it’s ideal for families, friends, or groups looking to unwind and create unforgettable memories.

Bright, Spacious 2BD in heart of Tampa | Free Prkg
Discover our cozy 2-bedroom apartment in North Downtown Tampa, where ease and comfort meet. Perfectly located near Downtown, Channelside, Hyde Park, Ybor City, and Tampa Heights, our inviting space offers a warm welcome. This home away from home includes two bedrooms, a fully-equipped kitchen, and contemporary facilities such as a saltwater pool, fitness center, yoga studio, and clubroom. Explore the finest attractions of Tampa Bay just moments from your front door.

UPDATEDVacation condo! HEATEDpool3 miles to beach
Wow!! Super value !! 2 bed 1 bath condo 1st floor - Welcome to Beachway Condos a GATED SAFE private full amenity community featuring a gym, tennis courts, HEATED POOL, grills, located 3 miles to the beautiful gulf beaches. You are close to everything - the Pinellas trail biking/walking is 1/4 mile away, Indian shores beach is the closest beach at 3 miles away. Clearwater/st Pete beaches are 7 miles away. Across the street are grocery stores malls, restaurants

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.

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.

Tampa Retreat with Heated In-Ground Pool & Spa
🏠 Experience comfort and style in this excellent and super cute home, perfectly located near MacDill Air Force Base. This beautifully designed property features a heated in-ground saltwater pool, ideal for relaxing and enjoying the Florida sunshine. Inside, you’ll find everything you need for a memorable stay. Whether you’re visiting for business or leisure, this home offers the perfect blend of fun, function, and relaxation. 🌴✨
Popular amenities for Hillsborough County rentals with a pool
House rentals with a pool

*Apollo Escape* – Canalfront Home + Private Pool

The House of Relaxation

Coastal Pool Retreat *5 Min to Madeira Beach Sand

Tarpon Fun'n Sun-Pool, Beaches + Backyard Chickens

Heated Salt Pool & Spa | Near Airport & Downtown

Walk to Raymond James Stadium! Pool/ Hot Tub Home!

Heated Pool, Golf, FUN! Clearwater Game Villa

Elegant 5BR Historic Gem w/ pool, walk to Bayshore
Apartment rentals with a pool

Resort Complex is Directly on St. Pete Beach

Little Harbor Resort #202 Tampa Bay FL Beach, Hot

Captain's Cove Waterside Condo 103 We are open!

Tiki Themed Waterfront Condo on Tampa Bay

Modern and Cozy Condo 6 Minutes from the Beach !

Updated Condo-Heated Pool-Private Balcony

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

Upgraded 3 Bed, 3 Bath Corner Water Front Condo!
Other holiday rentals with a pool

Waterfront Retreat in Apollo Beach– Relax & Unwind

Welcome to The Plaza Tampa

•La Casa De Belen• Bungalow in Ybor City!

2BR Retreat|Pool|BBQ|Near Bay & Downtown

Casa Brisa - Htd. Pool-Unique Bungalows-Hot Tub

Land's End Beachfront Elegance: Top Floor Corner

Boho Pool House Near Downtown, Raymond James

Luxurious New Heated Pool & Spa! 4 mins to beach!
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- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Weeki Wachee Springs
- Coquina Beach
- Vinoy Park
- Lido Key Beach
- Dunedin Beach
- Amalie Arena
- Cortez Beach
- Bean Point Beach
- Island H2O Live!
- Anna Maria Public Beach
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- Jannus Live
- Reunion Resort Golf Courses - Palmer & Watson
- Tampa Palms Golf & Country Club
- ZooTampa at Lowry Park
- River Strand Golf and Country Club
- Hard Rock Casino
- North Beach At Fort DeSoto Park
- Bok Tower Gardens
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