
Holiday rentals with a pool in Harbour Island
Find and book unique homes with a pool on Airbnb
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.
4.94 out of 5 average rating, 140 reviews
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.
4.89 out of 5 average rating, 439 reviews
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!
4.92 out of 5 average rating, 229 reviews
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.
4.95 out of 5 average rating, 127 reviews
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.
4.84 out of 5 average rating, 246 reviews
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.
4.98 out of 5 average rating, 267 reviews
Private House with Pool and Cabana
Beautifully updated house with pool and cabana. 3 Bedrooms with queen beds, upscale bedding, TV's in every room, full kitchen and dinning area, BBQ, ready to cook, outdoor pool with cabana with a TV, firepit, gardens, park like backyard. Great for families and business trips. Close to everything, all shopping, 15 minutes to downtown, airport, Hyde Park, International Plaza, Busch Gardens and more. Close to parks, beaches, fishing, Bayshore Blvd, Gandy Bridge.
4.94 out of 5 average rating, 139 reviews
•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.
4.94 out of 5 average rating, 142 reviews
Luxe Villa • Pool • Spa • Fire Pit • Games & More!
Welcome to your private luxury retreat! This brand-new villa was thoughtfully designed for unforgettable family vacations and group getaways. Enjoy a resort-style backyard featuring a heated pool, spa, playground, fire table, gazebo, and plenty of space to relax. Inside, you’ll find stylish décor, a fully equipped kitchen, spacious living areas, and a fun-filled game room, creating the perfect place to unwind, reconnect, and make lifelong memories.
4.9 out of 5 average rating, 143 reviews
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.
4.97 out of 5 average rating, 138 reviews
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.
4.93 out of 5 average rating, 340 reviews
Workers Paradise | Spacious | Saltwater Pool!
Welcome to our charming 1-bedroom apartment in North Downtown Tampa. Conveniently located within 10 minutes of Downtown, Channelside, Hyde Park, Ybor City, and Tampa Heights, our cozy space offers a comfortable bedroom, fully equipped kitchen, and modern amenities including a saltwater pool, gym, yoga studio, and clubroom. Explore Tampa Bay with ease during your stay with us.
4.88 out of 5 average rating, 136 reviewsPopular amenities for Harbour Island rentals with a pool
House rentals with a pool

Charming 4 bedroom home in the BEST location.
4.81 out of 5 average rating, 160 reviews
Disfruta cada momento
4.88 out of 5 average rating, 139 reviews
The T and C Club
4.98 out of 5 average rating, 211 reviews
Historic Pool Home (heated pool) in South Tampa.
4.97 out of 5 average rating, 117 reviews
Luxury Heated Pool/Spa Villa w/ Game Room & More!
4.97 out of 5 average rating, 129 reviews
Villa Paradise
4.8 out of 5 average rating, 139 reviews
Unique and Private Oasis w/ Heated Pool and More
4.95 out of 5 average rating, 122 reviews
Pool, putt putt, walkable, great for families
5.0 out of 5 average rating, 12 reviewsCondo rentals with a pool

Centrally Located/Pickleball/Pool/Washer/Dryer/Fun
4.96 out of 5 average rating, 271 reviews
Modern Waterfront Condo - Captivating Sunset Views
4.95 out of 5 average rating, 384 reviews
Top Floor | Mangrove Bayview + Pool at Tampa Bay
4.9 out of 5 average rating, 233 reviews
262*NEW! 3 beds x 2 bath. Amazing Waterfront Views
4.86 out of 5 average rating, 142 reviews
Waterfront Condo - Sunset View of Tampa Bay
4.93 out of 5 average rating, 251 reviews
Spacious 2/2 ResortStyle Condo near Downtown Tampa
4.9 out of 5 average rating, 127 reviews
Tropical Waterfront Escape
4.92 out of 5 average rating, 550 reviews
Rocky Point paradise
4.76 out of 5 average rating, 284 reviewsOther holiday rentals with a pool

Welcome to The Plaza Tampa
4.98 out of 5 average rating, 104 reviews
Chic Downtown Condo
4.98 out of 5 average rating, 85 reviews
Summer Getaway with Pool and Spa
4.98 out of 5 average rating, 60 reviews
Lux Top-Floor Bayfront 2BR | Pool, Hot Tub, Sauna
5.0 out of 5 average rating, 37 reviews
Our Own Danube (River) on Davis Islands
4.91 out of 5 average rating, 11 reviews
Luxe PentHouse Getaway in ChannelSide Tampa
5.0 out of 5 average rating, 60 reviews
Urban Fun: Lightning Fans, Concerts & Conventions!
5.0 out of 5 average rating, 18 reviews
Pool Oasis | Near RJ Stadium, Hyde Park & Downtown
4.97 out of 5 average rating, 34 reviewsDestinations to explore
- Miami Holiday rentals
- Four Corners Holiday rentals
- Miami Beach Holiday rentals
- Orlando Holiday rentals
- Fort Lauderdale Holiday rentals
- Panama City Beach Holiday rentals
- Tampa Holiday rentals
- Destin Holiday rentals
- Hollywood Holiday rentals
- Savannah Holiday rentals
- Jacksonville Holiday rentals
- Kissimmee Holiday rentals
- Anna Maria Island
- Siesta Beach
- Weeki Wachee Springs
- Anna Maria Island Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Coquina Beach
- Lido Key Beach
- Bean Point Beach
- Amalie Arena
- Turtle Beach
- Hard Rock Casino
- LEGOLAND Florida Resort
- University of South Florida
- Dunedin Beach
- Vinoy Park
- Epperson Lagoon
- John's Pass
- Crescent Beach
- Tropicana Field
- MidFlorida Credit Union Amphitheatre
- Weeki Wachee Springs State Park
- Sand Key Beach
- Fort De Soto Park





