
Vacation rentals with a pool in Gulfport
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Gulfport
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

"The Merry Yacht" excellent location
EXCELLENT Location…near Eckerd College, beach, grocery, interstate access, Marina, Gulfport, downtown Take a break and unwind at this peaceful nautical retreat. -across the street to Maximo Marina & The famous Tiki Docks Restaurant & bar. Location of marina is one block -Publix Grocery, McDonalds all in walking distance -shared pool -nice area to ride bikes and walk -enjoy Yacht like dining -table for 6 with china & crystal for a change. -Beach chairs and Umbrella provided -keyless entry

Inground Pool w/ Game Room - Fully Renovated House
Beautifully remodeled 3 bedroom 2 bath farmhouse with INGROUND POOL in the heart of Gulfport. Looking for the BEACH?(St Pete Beach, Treasure Island etc) We are 6 mins away! If you are looking for amazing restaurants and bars in the middle of St Petes we are only 10 minutes to DOWNTOWN! If your are here for some baseball we are 15 minutes away from Tropicana field and St Pete Pier! If you are looking to explore In clearwater or Downtown Tampa we are only 25 minutes away including TAMPA Airport!

Heated Pool! Huge Walk In Shower! 5 min to beach!
Welcome to Coastal Paradise! This modern villa is newly remodelled and professionally furnished with a beautiful coastal theme. It has a very spacious open layout with plenty of space for the whole family. A huge master walk in shower with two shower heads and four body jets! Out back is a private heated pool with lounge chairs, grill, a hammock, corn hole and a beautiful patio set to enjoy a meal outdoors. Madeira beach is only a 5 min drive away! We also provide all your beach necessities!!

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.

Tropical Disco|Luxury|Top 5%|Pool|Mins to Beach
There's even a disco ball! 🪩Perfect for Bachelorette & Bachelor get aways, 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 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.

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.

Heated Pool and hot tub luxury vacation house
Spend your vacation in luxury! The hot tub and heated swimming pool are perfect for a family vacation or a couples' retreat. In winter we keep the pool temperature at 85 degrees. Enjoy the stylish furniture, a huge luxurious master suite with a large walk-in closet and work desk, a fully equipped kitchen and all the extras you would expect at the resorts. The living room features a 75’ TV! Short drive to Madeira Beach and Treasure Island. Small parties are allowed. A lot of parking space.

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!

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.

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.

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
Popular amenities for Gulfport rentals with a pool
House rentals with a pool

The Jungalow SOHO - Pool/Hot Tub

Bungalow w/ heated pool-separate garage studio

Tropical Escape | Pool | Game Room | Near Beach

Coastal Pool Retreat *5 Min to Madeira Beach Sand

Amazing Home w/ Heated Pool! Sleeps 10! Book Now!

Waterfront /Pool /Golf Cart /Pet + Boat Friendly!

Pool Paradise | Gym, Sauna, Bar

The Blue Fin, 3 Bed/ Heated Pool/ XBOX
Condo rentals with a pool

Gulf Strand Beach Resort

850 Sqft - 1 Bedroom 1.5 Bath (GULF FACING!) Condo

Sea La Vie- Studio by the bay!

Beach Front at “The Shore”

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

Beach, dolphin/manatee sightings, fishing, sunsets

Stunning BEACH FRONT Condo, KING Size Bed, Balcony

Luxury Seashell Oceanfront Condo with Pool
Other vacation rentals with a pool

NEW Designer Pool Oasis •10m DT St Pete •15m Beach

Pet Friendly Pool Oasis St Pete/Gulfport

"Catching Rays " 2 BR 2 Bath Condo

Luxury Pool House

Your Island Escape! • Discounted Summer Rates

Heated Pool~2 Miles St Pete Beach~Hot Tub~Games!

Guesthouse close to St Pete Beach

Waterfront Home with Heated Pool 2 Mi from Beaches
When is the best time to visit Gulfport?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $284 CAD | $365 CAD | $365 CAD | $290 CAD | $245 CAD | $251 CAD | $255 CAD | $254 CAD | $244 CAD | $263 CAD | $282 CAD | $291 CAD |
| Avg. temp | 17 °C | 18 °C | 20 °C | 23 °C | 26 °C | 28 °C | 29 °C | 29 °C | 28 °C | 25 °C | 21 °C | 18 °C |
Quick stats about vacation rentals with a pool in Gulfport

Total vacation rentals
Explore 130 vacation rentals in Gulfport

Nightly prices starting at
Gulfport vacation rentals start at $14Â CAD per night before taxes and fees

Verified guest reviews
Over 4,290 verified reviews to help you choose

Family-friendly vacation rentals
90 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wifi availability
130 of Gulfport vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Gulfport rentals

4.9 Average rating
Gulfport stays are highly rated by guests—averaging 4.9 out of 5!
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