
Vacation rentals with a pool in Hillsborough County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Hillsborough County
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

"Twilight Sands Stud" Prvt Ent,Pool,Pk,Keyless Ent
Welcome to our cozy guest suite—where comfort is personal over perfect, and full of charm you won’t find at a hotel. Guests love the thoughtful touches, eclectic decor, cloud-like bed, and the irreplaceable feeling of being at home when you’re far from home. Our home uses one central AC unit. Because Florida is warm and humid year-round, we keep the thermostat at 70°F by day and 67°F at night for proper cooling and comfort. If you prefer more warmth, two space heaters are in the suite closet.

Cozy & Chic Townhome in the Heart of South Tampa
LOCATION, LOCATION, LOCATION! I have absolutely adored living in this hidden DIAMOND of a townhome. It’s time to share my favorite place with the world. Welcome to Diamond in The Bay! *5 mins to Bayshore Blvd *10-15 mins to all Downtown Tampa has to offer (Soho, Hyde Park Village, Amalie Arena, etc) *10 mins to Tampa International Airport *15 mins to Historic Ybor *20 mins to Raymond James Stadium *20-25 mins to Downtown St Petersburg *30-35 mins to St Pete Beach *45 mins to Clearwater Beach

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).

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.

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

Central Cozy Cottage w/ Heated Pool & Hot Tub!
Welcome to cute & cozy Turtle Cottage located right in the center of St. Pete, close to both Downtown AND several gorgeous Florida beaches. NO CLEANING FEE with competitive, seasonal pricing = a FANTASTIC DEAL for this space! A BEAUTIFUL NEW HEATED POOL & HOT TUB await in the private, fenced-in tropical backyard. Sorry, no pets/animals or babies/children/teens. Adults 21+ only and limited to 2 verified guests. 100% smoke-free property, inside & out. EVERYONE is welcome here. Come & enjoy!

Saltwater Pool Oasis ⭐ 1925 Bungalow in ❤ of Tampa
1925 Bungalow, 3 bedrooms, saltwater pool, private backyard/large deck. In the perfect location to explore the best of Tampa, including: Tampa International Airport-4.7 miles Armature Works/Riverwalk-.9 of a mile University of Tampa-1.5 miles Downtown Tampa-2.1 miles Raymond James Stadium-2.4 miles Ybor City Historic District-2.3 miles Amalie Arena/Channelside-2.6 miles USF-9.2 miles Clearwater Beach-25 miles Disney World-1 hour The Bungalow is on a busy main road & the pool is not heated.

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

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.

Luxury Blue Haven - Stunning Tampa Bay Views!
Experience breathtaking waterfront views from your private balcony at Sailport Waterfront Suites, Tampa. This stunning 1BR/1BA condo is beautifully renovated and offers direct water views, providing the perfect balance of relaxation and adventure for you and your group. Enjoy easy access to exciting local attractions while indulging in the peace and tranquility of this desirable location. With an array of amenities, your stay is sure to be comfortable and memorable.

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.

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 Hillsborough County rentals with a pool
House rentals with a pool

Hacienda Hideaway w/ heated pool

Insta Worthy Retreat -Arcade Room- Htd Pool- Golf

CANAL Oasis Heated Pool-Hot Tub-Waterfront- Kayaks

Beach or Golf Getaway • Heated Pool/Spa • Pets OK

Private House with Pool and Cabana

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

Pool + Park + Private = Perfect Place

NEW Heated Salt Pool & Spa on Waterfront Canal
Condo rentals with a pool

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach

COASTAL CHIC! Luxury Apartment with Oceanviews

Tampa Events & Suite w/WtrFrt Bay & Sunset Views

Tiki Themed Waterfront Condo on Tampa Bay

Tropical Waterfront Escape

Heron's Hideaway- Studio by the bay!

Amazing views on beachfront

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209
Other vacation rentals with a pool

Stunning Bay Views | Walkable Retreat

Welcome to The Plaza Tampa

• Casa De Belen • Bungalow in Ybor City!

Allison Palms Luxury Tampa Townhome + Pool

Tampa Luxe Waterfront Private Pool, Hot Tub & More

Sunset Views from a Stylish 1BR High Rise in Tampa

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

Poolside Tiny Guesthouse – Palm Oasis
Destinations to explore
- Farmstay rentals Hillsborough County
- Townhouse rentals Hillsborough County
- Guesthouse rentals Hillsborough County
- Rentals with a home theater Hillsborough County
- Rentals with an EV charger Hillsborough County
- Rentals with a washer and dryer Hillsborough County
- Rentals with a fire pit Hillsborough County
- Family-friendly rentals Hillsborough County
- Rentals with outdoor seating Hillsborough County
- Rentals with a patio Hillsborough County
- Bed and breakfasts Hillsborough County
- Rentals with beach access Hillsborough County
- Hotel rooms Hillsborough County
- Rentals with a hot tub Hillsborough County
- Rentals with an accessible height bed Hillsborough County
- Boutique hotels Hillsborough County
- Resort rentals Hillsborough County
- Cottage rentals Hillsborough County
- Fitness-friendly rentals Hillsborough County
- Rentals with lake access Hillsborough County
- RV rentals Hillsborough County
- Beachfront rentals Hillsborough County
- Villa rentals Hillsborough County
- Condo rentals Hillsborough County
- Tiny house rentals Hillsborough County
- Rentals with a sauna Hillsborough County
- Luxury rentals Hillsborough County
- Apartment rentals Hillsborough County
- Loft rentals Hillsborough County
- Rentals with breakfast Hillsborough County
- Rentals with an accessible height toilet Hillsborough County
- Bungalow rentals Hillsborough County
- Smoking-friendly rentals Hillsborough County
- Private suite rentals Hillsborough County
- Pet-friendly rentals Hillsborough County
- House rentals Hillsborough County
- Waterfront rentals Hillsborough County
- Rentals with a kayak Hillsborough County
- Aparthotel rentals Hillsborough County
- Rentals with a fireplace Hillsborough County
- Rentals with pools Florida
- Rentals with pools United States
- Anna Maria Island
- John's Pass
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Dunedin Beach
- Weeki Wachee Springs
- Reunion Resort Golf Courses - Palmer & Watson
- Coquina Beach
- Lido Key Beach
- Vinoy Park
- Cortez Beach
- Anna Maria Public Beach
- Amalie Arena
- Island H2O Water Park
- Bean Point Beach
- Jannus Live
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- ZooTampa at Lowry Park
- Gulfport Beach Recreation Area
- North Beach
- River Strand Golf and Country Club
- Tampa Palms Golf & Country Club
- Bok Tower Gardens
- Things to do Hillsborough County
- Sightseeing Hillsborough County
- Sports activities Hillsborough County
- Art and culture Hillsborough County
- Nature and outdoors Hillsborough County
- Tours Hillsborough County
- Things to do Florida
- Wellness Florida
- Art and culture Florida
- Tours Florida
- Sightseeing Florida
- Entertainment Florida
- Nature and outdoors Florida
- Food and drink Florida
- Sports activities Florida
- Things to do United States
- Food and drink United States
- Sightseeing United States
- Wellness United States
- Entertainment United States
- Tours United States
- Sports activities United States
- Art and culture United States
- Nature and outdoors United States
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes




