Holiday rentals with a pool in Harbour Island

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.

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

New for 2026– Luxury Redesign in South Tampa! This 5 bedroom, 3.5 bath, 1923 home blends historic charm with a brand new upscale interior. Perfectly located just 2 blocks from Bayshore Blvd and Hyde Park, and minutes from Downtown, Riverwalk, and UT. Enjoy memory foam beds, organic cotton linens, 2 King suites, 2 California King bedrooms, 2 twins, custom sofas, designer finishes, and thoughtful touches throughout. A refined, comfortable base in Tampa’s most walkable, sought-after area.

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.

Luxury Stay • Hot Tub & Heated Pool • Fenced Yard!

Explore the charm of this three-bedroom, two-bathroom bungalow – a luxurious haven where style meets relaxation. Enjoy moments of tranquility by the spa and screened pool, complete with inviting swim-up barstools, or unwind in the indulgent hot tub accommodating up to eight guests. Step into the serene outdoor oasis, adorned with elegant furnishings against the picturesque backdrop of a fenced backyard. Your getaway awaits, conveniently situated near the city's premier attractions.

The Guest House at Riverbend Retreat Fla.

True Florida-style living under the oaks and palms on the Alafia River with beautiful views and comfortable beds. We include use of the pool, spa, fire pit, hammock, putting green, yard games, BBQ and dock area. There are additional bedrooms in the adjoining house for larger groups. Fisherman can cast into the river with expectations of catching Sheepshead, Red Snapper, Speckled Trout, Snook, Spotted Bass and Florida Gar off the dock. We also catch blue crabs.

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! IMPORTANT TO NOTE: This home has a detached 1/1 guest house located on the property, which may also be occupied by guests during your stay.

Private Oasis w/ Heated Pool and Arcade!

-9FT DEEP *HEATED* SALTWATER POOL ($25 / day) AT 85 DEGREES UPON REQUEST -COMMERCIAL ARCADE WITH >4500 GAMES 4 PLAYERS! -NBA JAM, GOLDEN TEE, THE SIMPSONS, NFL BLITZ, MUCH MORE! -MASTER KING BEDROOM -FULLY FENCED BACKYARD -OUTDOOR FIRE PIT -Propane Grill Stay comfortably in this quiet, 4/3 pool home, with a commercial family arcade! Enjoy a staycation at this tastefully updated home or take a quick ride to one of the many local Tampa area 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.