
Holiday 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.

St Pete Casita Studio with Salt Water Pool & Yard
Keep it simple at this peaceful and centrally-located place. La Casita is located minutes from bustling downtown and beautiful bay waterfront restaurants and bars. Tampa International Airport is only 20 minutes away. The property itself is great for relaxing. La Casita is surrounded by lush palm trees and has its own access to the pool a few feet from your front door. Come relax, go to the pool, beach, enjoy the outdoor shower and finish off the day at One of the many nearby restaurants!

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

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

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.

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.

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.

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.

Tranquil poolside guesthouse on the river
The apartment is on the Hillsborough River surrounded by nature but only 3 minutes away from the great restaurants, bars and breweries of Seminole Heights. It is walking distance to Lowry Park Zoo and park. Spot the beautiful Florida wildlife up close from the river dock. Soak in the outdoor pool surrounded by mature live oaks or take a canoe out on the river. Top beaches are 35 minutes by car. Great for a couple or a small family.
Popular amenities for Hillsborough County rentals with a pool
House rentals with a pool

The Great Escape

Hacienda Hideaway w/ heated pool

CANAL Oasis Heated Pool-Hot Tub-Waterfront- Kayaks

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

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

Pool + Park + Private = Perfect Place

NEW Heated Salt Pool & Spa on Waterfront Canal

Coastal Escape: heated saltwater pool & beaches
Condo rentals with a pool

Seasalt Breeze, by the pool, NO PETS

Lux Condo w/ 2 balconies, Ocean & Marina views

New Beachfront Resort Condo in Paradise

Luxury Blue Haven - Stunning Tampa Bay Views!

Spectacular beach to bay views from this resort.

Stunning BEACH FRONT Condo, KING Size Bed, Balcony

~Shore Thing~ Coastal Exquisite Waterfront Condo

Literally: 15 steps to the Pool, GroundFloor Condo
Other holiday rentals with a pool

Lux 4BR Tampa Home | Pool, Jacuzzi, BBQ, Big Yard

Wonderful Condo at Avalon - Fully Renovated

High-Rise Apartment with Panoramic Skyline Views

The Urban Oasis – Serene Views!

your home close to everything

Tampa Luxe Waterfront Private Pool, Hot Tub & More

Sunset Views from a Stylish 1BR High Rise in Tampa

Riverfront Hideaway Near Downtown
Destinations to explore
- Rentals with a fire pit Hillsborough County
- Boutique hotels Hillsborough County
- Resort rentals Hillsborough County
- Rentals with a fireplace Hillsborough County
- Villa rentals Hillsborough County
- Beachfront rentals Hillsborough County
- Rentals with a washing machine and dryer Hillsborough County
- Rentals with an accessible height bed Hillsborough County
- Cottage rentals Hillsborough County
- Fitness-friendly rentals Hillsborough County
- Family-friendly rentals Hillsborough County
- Loft rentals Hillsborough County
- Apartment rentals Hillsborough County
- Bungalow rentals Hillsborough County
- Private suite rentals Hillsborough County
- Rentals with a hot tub Hillsborough County
- Pet-friendly rentals Hillsborough County
- Rentals with lake access Hillsborough County
- RV rentals Hillsborough County
- Farmstay rentals Hillsborough County
- Townhouse rentals Hillsborough County
- Condo rentals Hillsborough County
- Tiny house rentals Hillsborough County
- Luxury rentals Hillsborough County
- House rentals Hillsborough County
- Waterfront rentals Hillsborough County
- Aparthotel rentals Hillsborough County
- Rentals with a kayak Hillsborough County
- Rentals with beach access Hillsborough County
- Hotel rooms Hillsborough County
- Bed and breakfasts Hillsborough County
- Rentals with a sauna Hillsborough County
- Smoking-friendly rentals Hillsborough County
- Guesthouse rentals Hillsborough County
- Rentals with a home theatre Hillsborough County
- Rentals with an accessible height toilet Hillsborough County
- Rentals with breakfast Hillsborough County
- Rentals with an EV charger Hillsborough County
- Rentals with outdoor seating Hillsborough County
- Rentals with a patio 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
- Cortez Beach
- Lido Key Beach
- Vinoy Park
- Anna Maria Public Beach
- Amalie Arena
- Island H2O Water Park
- Bean Point Beach
- Jannus Live
- Southern Dunes Golf and Country Club
- Gulfport Beach Recreation Area
- ZooTampa at Lowry Park
- ChampionsGate Golf Club
- North Beach
- River Strand Golf and Country Club
- Tampa Palms Golf & Country Club
- Adventure Island
- Things to do Hillsborough County
- Sightseeing Hillsborough County
- Art and culture Hillsborough County
- Nature and outdoors Hillsborough County
- Tours Hillsborough County
- Sports activities Hillsborough County
- Things to do Florida
- Wellness Florida
- Entertainment Florida
- Tours Florida
- Art and culture Florida
- Sightseeing Florida
- Food and drink Florida
- Nature and outdoors Florida
- Sports activities Florida
- Things to do United States
- Entertainment United States
- Sports activities United States
- Food and drink United States
- Wellness United States
- Sightseeing United States
- Tours United States
- Nature and outdoors United States
- Art and culture United States




