
Vacation 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.

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.

Welcome to The Plaza Tampa
Minutes to the Riverwalk and Gasparilla & Hockey Stadium Series!! Charming private home near Downtown Tampa! 3BR/2BA with a full kitchen, full-sized washer-dryer, and a dedicated workspace. Relax in the beautiful backyard featuring a stock tank pool—ideal for both entertaining and unwinding. Perfect for anything from girls' trips to business meetings or family vacations, this retreat is close to Raymond James Stadium, Tampa Riverwalk, and Armature Works. Your ultimate Tampa getaway awaits!

Luxurious "Riverfront Oasis" - Waterfront w/pool
Luxurious, riverfront home with a coastal-farmhouse design, creating the ultimate Florida getaway or staycation! Spend your vacation relaxing in our private heated, waterfall pool, around the fire pit, or dining on the lit up boat dock. Beautifully furnished and professionally designed with lots of additional amenities, including bathrobes, aromatherapy diffusers, TWO fully stocked kitchens, bluetooth speaker, fishing poles and more! Plus, spectacular views of the Downtown Tampa Skyline!

Mint House by Kasa | Studio in Tampa Downtown
Step into the energy of Tampa’s thriving Channel District (Channelside), close to the Sparkman Wharf, Benchmark International Arena, and the Florida Aquarium. Perfect for work trips and longer stays, you’ll find comfort in our selection of apartment-style suites with full kitchens and in-unit laundry, plus an outdoor plunge pool, grill area, and fitness center. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text, and Virtual Front Desk via mobile device.

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.

Elegant 5BR Historic Gem w/ pool, walk to Bayshore
Luxury design in South Tampa! This 5 bedroom, 3.5 bath, 1923 home blends historic charm with an upscale interior. It’s perfectly located just 2 blocks from Bayshore Blvd, near Hyde Park, and minutes from Downtown, Riverwalk, and UT. Enjoy memory foam beds, organic cotton linens, 2 King suites, 2 California King rooms, 2 twins (with the option to convert to a King) custom sofas, and thoughtful designer finishes. A refined, comfortable base in Tampa’s most walkable, sought-after area.

Tampa Tropical-Saltwater Pool-10 Min to TPA
Take a break and unwind at this luxury apartment in the heart of Westshore. Killer location! -7 mins to TPA airport -5 mins to Raymond James -Walk to International Plaza Mall -10 mins to downtown Tampa Enjoy: -Saltwater pool w/ cabanas -2 level gym -Community game room w/ billiards & shuffleboard -Fully stocked chef's kitchen -Peaceful courtyard views -Gas grills -2 Flat screen Smart TVs -W/D in-unit -Complimentary coffee & tea -Dedicated parking upon request

•La Casa De Belen• Bungalow in Ybor City!
Welcome to La Casa de Belén — a home crafted with love in every corner. Every detail you’ll find here was thoughtfully designed by my husband and I. It’s a blend of us and my Latin roots Casa de Belén meaning house of bread. Serves a special purpose: a portion of every stay is donated to support two meaningful causes close to our hearts. Jan -Sept : Donations to “bridging freedom” to combat sex trafficking Oct- Dec : Christmas Gifts for kids in Colombia.

Lakeview Retreat with Private Pool Perfect Getaway
Welcome to our charming Tampa retreat! This newly renovated house has been carefully designed with an open layout, it features 2 bedrooms and 2 full bathrooms. The highlight of this home is undoubtedly the patio area, beautiful outdoor furniture, and an amazing pool with a stunning and unique view of the lake canal. The location is perfect, everything is nearby with quick access to major highways such as I-4, I-75, and I-275.

Hacienda Hideaway w/ heated pool
Welcome to the Hacienda Hideaway: a stunning Mediterranean-style retreat in historic West Tampa, Florida! Immerse yourself in the charm of this fully renovated and expertly designed home, boasting high-end finishes and luxurious touches throughout. Perfectly situated for convenience, the house is centrally located within ten minutes from the airport, stadium, downtown, shopping, restaurants, and the famous Riverwalk.

The Gem at Ridgewood Park
This adorable one bedroom apartment is located in the center of Tampa. It is close to everything, making it easy to plan your visit. 10 minutes from Airport. You can walk to Tampa's Riverwalk and iconic restaurants such as Armature Works and Ulele. Located less than three miles from Raymond James, Amalie Arena and Ybor city. The pool area is available from 9 AM to 9 PM no glass allowed in pool area.
Popular amenities for Harbour Island rentals with a pool
House rentals with a pool

Private House with Pool and Cabana

Charming 4 bedroom home in the BEST location.

Historic Pool Home (heated pool) in South Tampa.

Pool + Park + Private = Perfect Place

Bayshore - Pool - Outdoor Kitchen - Yard

Villa Paradise

Disfruta cada momento

5BR Serenity Tampa: Pool/Hot tub
Condo rentals with a pool

Centrally Located/Pickleball/Pool/Washer/Dryer/Fun

Waterfront Condo - Sunset View of Tampa Bay

Modern Waterfront Condo - Captivating Sunset Views

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

Spacious 2/2 ResortStyle Condo near Downtown Tampa

Tampa Bay Waterfront Views Rocky Point

Top Floor | Mangrove Bayview + Pool at Tampa Bay

Tropical Waterfront Escape
Other vacation rentals with a pool

Saltwater Pool Oasis ⭐ 1925 Bungalow in ❤ of Tampa

Chic Downtown Condo

Lux Top-Floor Bayfront 2BR | Pool, Hot Tub, Sauna

Summer Getaway with Pool and Spa

The Tampa Bay Suite | Private Channelside Gem

Our Own Danube (River) on Davis Islands

Channelside Retreat Near Amalie Cruise Terminal

Sun & Shade | Bayshore Beautiful
Destinations to explore
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