
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.

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.

Tiny House! Raymond James Stadium 12 min!
Cabana Haya is an adorable 200 sq foot TINY pool/guest house featuring a queen-sized memory foam mattress, mini split heat/ac unit, smart TV, large bathroom, kitchenette stocked with cups, dishes, a microwave, a Keurig, a single burner cook top and tiny deck for outdoor relaxation by the pool (not heated). Cabana Haya is located in Historic Seminole Heights just minutes to Raymond James Stadium, Amalie Arena, The Tampa Riverwalk, Busch Gardens, The MidFlorida Amp , and all thing Tampa

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.

Tampa Paradise! Firepit, Golf, Pool, & Games!
🌴☀️ Welcome to The Saint Airbnb — your private Tampa resort getaway! 🏡💫 This stylish and colorful 4BR, 2BA retreat brings together everything you love about Florida living — sunshine ☀️, palm trees 🌴, and poolside fun 🏖️ — all just minutes from Hyde Park 🍸, Amalie Arena 🎶, Raymond James Stadium 🏈, and St. Pete’s beaches 🌅! Whether you’re here for a game day 🎉, a weekend escape 🧳, or a family vacation, The Saint is where good vibes ✨ and great memories 💕 meet!

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.

Mint House St. Petersburg | Studio Suite
Spanning 430 square feet, our Studio Apartment features a Queen-size bed dressed with Bokser linens, high-end bathroom essentials, and plush towels to enhance the bathing experience. It boasts a fully equipped kitchen stocked with premium, locally sourced coffee. Amenities include a 55-inch Smart TV, free high-speed Wi-Fi, and a dining or workspace for two. Housekeeping services are available by request. The apartment accommodates up to 2 guests.

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

Tootsie’s Beachside Retreat-New Heated Pool

The Jungalow SOHO - Pool/Hot Tub

Insta Worthy Retreat -Arcade Room- Htd Pool- Golf

CANAL Oasis Heated Pool-Hot Tub-Waterfront- Kayaks

Private House with Pool and Cabana

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

Lakeview Retreat with Private Pool Perfect Getaway

Pool + Park + Private = Perfect Place
Condo rentals with a pool

Lux Condo w/ 2 balconies, Ocean & Marina views

Tiki Themed Waterfront Condo on Tampa Bay

Tropical Waterfront Escape

New Beachfront Resort Condo in Paradise

Heron's Hideaway- Studio by the bay!

SUNNY DELIGHT! HEATED POOL 2 miles to the beach🐶

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

Spectacular beach to bay views from this resort.
Other vacation rentals with a pool

Welcome to The Plaza Tampa

Relax & Explore in a Private Pool Oasis

Allison Palms Luxury Tampa Townhome + Pool

Casa Del Rio "A Riverside Oasis"

Channelside getaway

Sunny 2-Bed Oasis: Pool & Gym in Apollo Beach

Riverfront Hideaway Near Downtown

ST Urban Oasis heated pool
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- 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
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