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

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).

The Jungalow SOHO - Pool/Hot Tub
The Jungalow is the ultimate urban oasis. Enjoy the luxuries of the home or venture out to local attractions like the iconic Bayshore Boulevard, Historic Hyde Park, SOHO, Downtown and more. This home was designed with comfort and convenience in mind. Fully equipped with a smart tv, high-speed WIFI, pool and hot tub - this place is paradise. Central to the action - walk to unique rooftop bars, restaurants and shops or Uber to local attractions like Water Street, Amalie Arena, and the Riverwalk.

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.

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!

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.

Single Family Pool Home, Close to Downtown Tampa!
Cypress House is conveniently located to explore the best of Tampa Bay, including Downtown, South Tampa, USF, University of Tampa, other Universities, Busch Gardens, the zoo, aquarium, restaurants, walking distance to University Of Tampa and River Walk, & much more! Situated in an upmarket family-friendly residential neighborhood, this 3 bed/4 full bath luxury single-story home boasts a large outdoor pool, outdoor gas grill, outdoor table, laundry, full kitchen gas stove and oven.

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.

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.

Downtown Views | Saltwater Pool | Free Parking!
Step into our serene studio in North Downtown Tampa, where tranquility meets convenience. Centrally located minutes away from Downtown, Channelside, Hyde Park, Ybor City, and Tampa Heights. Enjoy a peaceful retreat with cozy furnishings, a well-equipped kitchenette, and modern amenities including a serene saltwater pool, rejuvenating gym, blissful yoga studio, and comfortable clubroom. Experience the idyllic side of Tampa Bay.

Walk to Raymond James Stadium! Pool/ Hot Tub Home!
Enjoy this stylish and charming Tampa home with fun outdoor vibes and a pool to relax in. This home is centrally located and within minutes from Downtown Tampa, Hyde Park, Harbour Island, International Mall, Ybor City, etc. This is the perfect home to stay in for a Bucs game, as it is within walking distance to the stadium!

Cozy Channelside 1BR • Free Parking • Pool/Gym
Welcome to your modern, comfortable home base in Channelside/Downtown Tampa—perfect for a weekend getaway, a concert or hockey night, or a work-friendly stay. This stylish 1BR/1BA apartment blends a cozy vibe with upscale finishes and a bright, open layout that feels like a true retreat after exploring the city.
Popular amenities for Harbour Island rentals with a pool
House rentals with a pool

Walk to Stadium • Pool • Grill • Arcade •75"TV•FUN

Private House with Pool and Cabana

Boho Oasis • Pool •Fire Pit • Near Beach & Airport

Tampa Retreat with Heated In-Ground Pool & Spa

Lakeview Retreat with Private Pool Perfect Getaway

Elegant 5BR Historic Gem w/ pool, walk to Bayshore

North Ybor escape with Private POOL and POOL TABLE

Private Oasis w/ Heated Pool and Arcade!
Apartment rentals with a pool

Spacious 2/2 ResortStyle Condo near Downtown Tampa

Tampa Winter Stay w/Waterfront Bay & Sunset Views

Tiki Themed Waterfront Condo on Tampa Bay

Tropical Waterfront Escape

Tampa Bay Waterfront Views Rocky Point

Waterfront condo with sunset views of Tampa Bay.

Rocky Point paradise

Waterfront Condo with Heated Swimming Pool
Other holiday rentals with a pool

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

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- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Turtle Beach
- Weeki Wachee Springs
- Coquina Beach
- Vinoy Park
- Dunedin Beach
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- Amalie Arena
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- Jannus Live
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- River Strand Golf and Country Club
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