Holiday rentals with a pool in Gulfport

4.91 out of 5 average rating, 157 reviews

An outdoor seating area is shown with a glass-top table surrounded by four blue chairs. Two charcoal grills are positioned nearby under palm trees, with a view of the water in the background. The screened cabana features a thatched roof, providing a relaxing atmosphere.

Condo in Treasure Island

Waterside Studio in the heart of TI, walk to beach

Location!!! This charming 2nd floor studio is located in the heart of legendary Treasure Island on the Intracoastal waterway of Boca Ciega Bay, only 3-7 min walk from the beautiful Gulf beaches, restaurants, shopping, and many great beach bars. Relax in the heated pool, have a cookout with the grills and screened waterfront cabana, complete with TV and minifridge, and watch the sunset or fish on one of two docks as dolphins frolic in the warm Gulf waters around you! Your perfect vacation awaits!

Superhost

Apartment in St. Pete Beach

4.89 out of 5 average rating, 221 reviews

Prime St Pete Beach Spot • No Cleaning/Service Fee

$0 Cleaning Fee, $0 Airbnb Guest Service Fee – we cover this fee. What you see is what you pay! Recently remodeled and beautifully refreshed, this coastal retreat sits just across from the sand—less than a one-minute walk. Enjoy modern design, bright coastal décor, and an inviting open living space that feels fresh and relaxing. Ideally located in vibrant St. Pete Beach, you’ll be steps from restaurants, beach bars and shops. Wi-Fi, parking, and beach essentials included - an unbeatable value!

4.99 out of 5 average rating, 201 reviews

An aerial view captures a multi-story condominium overlooking a beach. Lush palm trees surround a heated pool area, with docks lining the waterfront. The expansive coastline is visible in the background, highlighting the scenic proximity of beach and bay.

Condo in Treasure Island

Spectacular beach to bay views from this resort.

Our condo has spectacular water views from the Bay to the Beach. We have a large one of a kind kitchen that is unique to our resort, with granite counter tops, hardwood cabinets, and all stainless steel appliances. Everything you need to prepare a meal is provided along with basic spices and condiments, Coffee, creamer, and sugar. The master bedroom has a new king size bed and walk in closet with all beach gear also available for your use. We have 2 - 50" flat screen TV's with cable as well.

4.95 out of 5 average rating, 222 reviews

A charming pool area is surrounded by lush tropical foliage. The turquoise saltwater pool is framed with light stone paving. A small cottage with a red door is visible in the background, while lounge chairs and a colorful beach ball provide inviting accents to the outdoor space.

Guesthouse in Gulfport

A slice of paradise!

The guest cottage (approx. 300 sq ft) is separate from the main house, where we reside, with a beautiful saltwater pool to cool off in after your day's adventures! The property is 5 blocks from downtown Gulfport, with waterfront restaurants, bars, arts district, unique shopping, and beach. Close access to new tennis courts, bayside beach and minutes away from modern downtown St. Petersburg, and world-famous beaches. We are not set up to host pets or children and no unaccounted for guests.

Guesthouse in Central Oak Park

A private backyard features a heated pool surrounded by lush tropical plants and trees. The pool has a gentle curve and is accompanied by stone steps leading into the water. A small seating area is partially visible in the background, set amongst vibrant greenery.

4.98 out of 5 average rating, 219 reviews

Central Cozy Cottage w/ Heated Pool & Hot Tub!

Welcome to cute & cozy Turtle Cottage located right in the center of St. Pete, close to both Downtown AND several gorgeous Florida beaches. NO CLEANING FEE with competitive, seasonal pricing = a FANTASTIC DEAL for this space! A BEAUTIFUL NEW HEATED POOL & HOT TUB await in the private, fenced-in tropical backyard. Sorry, no pets/animals or babies/children/teens. Adults 21+ only and limited to 2 verified guests. 100% smoke-free property, inside & out. EVERYONE is welcome here. Come & enjoy!

A lively living room corner features a red sofa paired with soft cushions. A disco ball reflects light, while an aloe plant adds a touch of greenery. A magazine lies open on a wooden table, with warm light coming from nearby lamps and large windows.

4.93 out of 5 average rating, 137 reviews

Groove Under Palms Where Disco Vibes meet Paradise

There's even a disco ball! Perfect for Bachelorette, Bachelor, Reunions, Retreats, and Family Vacations! Gather in the spacious living room to watch movies on the 65-inch smart TV or prepare a feast in the well-equipped kitchen, complete with brand-new appliances. After a day of fun in the sun at St. Pete Beach, relax in your private bedroom with comfortable beds, soft linens, and modern decor. Wake up to beautiful natural light and enjoy a cup of coffee on the patio overlooking the pool.

A screened-in pool area features a shimmering blue pool surrounded by a tiled deck. Comfortable seating with tropical-patterned cushions is available near the pool. Lush greenery lines the space, providing a sense of privacy and tranquility.

4.85 out of 5 average rating, 344 reviews

Pool home with beach a few minutes away

This recently updated European style home comes with 3 bedrooms 2 bathrooms, screened-in pool and pool deck. Located in an upscale neighborhood, this beautiful home offers patio areas and large living room for relaxing. Equipped with a full size washer, dryer and full kitchen for a home away from home experience. 5min drive to beaches, parks, lakes, trails, shopping & restaurants. 10min to downtown, St. Pete. Boat Trailer parking available. Large driveway can accommodate up to 3 vehicles.

4.96 out of 5 average rating, 127 reviews

A heated stock tank pool is surrounded by a lush tropical landscape featuring a variety of green plants. An oversized umbrella provides shade, and a colorful bungalow is visible in the background, creating a serene outdoor retreat.

Tiny home in Gulfport

Shipwreck Bungalow

Shipwreck Bungalow, your own private paradise! Nestled in a quaint Gulfport neighborhood. Just 10 minutes from St. Pete beach, 10 minutes from lively downtown St. Pete and a few short minutes from funky downtown Gulfport. The Bungalow is surrounded by palms, tropical plants and flowers, beautiful outdoor shower, Tiki bar, heated stock tank pool, fire pit, outdoor games, grill and spacious outdoor seating area. Enjoy lounging by the pool or exploring all this sunny area has to offer!

Guest suite in St. Petersburg

A spacious patio area surrounds a clear swimming pool, framed by lush tropical plants. Two lounge chairs are positioned under a shaded umbrella, with a bike resting in the background. A barbecue grill is visible near the covered seating area, creating an inviting outdoor space.

4.98 out of 5 average rating, 367 reviews

Cozy Casita in NE St. Petersburg

Our Cozy Casita is located adjacent to the main house in a quiet residential neighborhood with a separate entry and fenced in parking space for our Guests. Enjoy our tropical garden and beautiful pool area. The pool is not heated. Small kitchen with Whirlpool electric stove, microwave and mini-fridge. 40” Samsung Smart HDTV and WIFI. Located within minutes of great restaurants, craft breweries, and local museums. Lots of great outdoor activities along St. Pete’s beautiful waterfront.

A welcoming living area features light-colored seating with orange and gray accents. A wooden coffee table is centered on a decorative rug. Natural light filters through the vertical blinds, illuminating the room's neutral tones, complemented by a potted plant and wall-mounted lighting.

4.88 out of 5 average rating, 139 reviews

Hibernate in our Bear Creek Home

This 3 bedroom 2 bath home is located in beautiful Bear Creek. Don't worry, no bears! Great place to relax and enjoy the pool, in a quiet, safe neighborhood. Next to Pinellas Trail, a 40 mile paved trail. Great for walking, running and biking. You can bike downtown 6 mi or 4.6 miles to beaches. We have bikes and for those more adventuresome we have kayaks you may use. House features stable, high speed internet. Close to great restaurants, drugstores, supermarkets and coffee shops.

A screened-in saltwater pool area is highlighted, featuring colorful pool floats and two blue lounge chairs. Natural light enters through large windows, and a door provides access to the adjacent living space. The bright walls reflect the sun, enhancing the cheerful atmosphere.

4.93 out of 5 average rating, 138 reviews

Creamsicle Dreamsicle- Saltwater Pool- Near Beach!

Find us on the 'gram! @creamsicledreamsicle ***This is NOT a party home*** Thanks for viewing our beloved Creamsicle Dreamsicle! Our home features 3 bedrooms, 1 bath, central AC, off street parking, and an in-ground, heated (for a fee) saltwater pool. We are 3 miles to St. Pete Beach and 4.5 miles to downtown St. Pete! Our home is located in a quiet, safe, small community with very little traffic. Welcome to Saint Petersburg!