Vacation rentals with a pool in Hillsborough County

Bayshore - Pool - Outdoor Kitchen - Yard

Get away in elegance and soak up the South Tampa sun in this gorgeous 4 bedroom, 2 bath pool home. Visit with family and friends in the covered patio and pool area, cook in the outdoor kitchen or relax with a drink by the pool (not heated). Enjoy great restaurants or visit one of the many attractions nearby - The Aquarium, Armature Works, Sparkman's Wharf, just to name a few. Visit Bayshore Park Fitness Trail, just minutes away and explore the 4.5 miles of waterfront views. Enjoy all of Tampa!

Cozy Family Retreat, Tampa: Private Pool Oasis

Welcome to Sunshine on the Bay, a charming 2-bed/1-bath villa that blends comfort and style in a quiet area. Located just 3 mins from Citrus Park Mall and 13 mins from airport you'll have easy access to shopping, dining, and top Tampa attractions. Step outside into your own private backyard oasis, complete with a refreshing plunge pool & grill – the perfect spot to unwind after a long day. Enjoy all the essentials, fully equipped kitchen, as well as a 240V outlet for your EV charger. Book today!

Backyard Paradise! Pool, Golf, Fire Pit

Welcome to The Saint Airbnb — your private Tampa resort getaway! 🌴☀️ Perfect space for Bachelorette/Bachelor party get aways! Ask about our customized services for that special Bride/Groom! 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 Tampa Bay attractions! Whether you’re here for a game day, a weekend escape, or a family vacation, The Saint is where good vibes and great mem

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.

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.

Beautiful Tampa Bay Pool Home Near Gulf Beaches

A beautiful Gulf Coast residence with many amenities to offer. Bright and open furnished spaces, for relaxing and entertaining up to 10 guests. A quiet, upscale neighborhood , your just 6 minutes from Madeira Beach and many other Gulf of Mexico beaches. Or, fun & sun in the private pool outback. 20 minutes from Downtown St Pete, which offers restaurants, museums, the new Pier, and excellent night life. Very close to countless restaurants, shopping, coffee shops, and grocery stores.

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.

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.

5 STAR! Hot Tub-freeHeated Pool 4BD/2Ba 2 King bed

PARADISE best describes this GORGEOUS newly renovated VACATION HOME!! 4 bed room 2 bath HEATED POOL and GIGANTIC HOT TUB! 7 miles to the many local sugar sand gulf beaches and 3/4 mile away from grocery stores , Local ER, MANY restaurants, banks and gas stations/ convenience stores, GOLF COURSE, hair and nail salons, Walmart . Swimming POOL IS HEATED FOR FREE 80-85 degrees from oct 15 - april 15 seasonally SUPER FAST WIFI 571 mbps

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.

Insta Worthy Retreat -Arcade Room- Htd Pool- Golf

☀️ Looking for a place the whole family/group can enjoy? This centrally located modern home is full of fun and style, with everything you need—from a fully stocked kitchen 🍽️ to beach supplies ⛱️ and more. Enjoy an Insta-worthy space with 5-hole mini golf, giant outdoor games, a heated pool, arcade & board games, and cozy spaces inside and out. 📍 Just 6 miles to the beach and Downtown St. Pete—perfect for your getaway!

NEW Heated Salt Pool & Spa on Waterfront Canal

🏠 Welcome to this incredible, stunning & fully updated heated pool & spa home located on a serene waterfront canal of Tampa Bay! Enjoy the dock for fishing & relaxing. Fast WIFI, Samsung Smart TVs, a game room with an air hockey table, ping pong & pool table, and even a Pac-Man machine will make your stay memorable & fun! Most importantly, dive into this amazing heated pool & spa right in front of the canal!