Holiday 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.

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Guest favourite

Apartment in Madeira Beach

4.94 out of 5 average rating, 410 reviews

Mad Bch Paradise Studio*APR-28-MAY-3*NOW*$99 PN !

*MB Paradise Studio is equipped with everything needed for a great beach getaway. There is a comfy QUEEN bed, table w/2 stools, dresser, sitting area for 2, full fridge/freezer, microwave, elec fry pan, all utensils, dishes, glassware. All paper products, hand sanitizer, dishsoap,, garb bags, body wash, shampoo, conditioner. Smart flatscreen TV. All Beach Gear ! We also co-host MB OASIS & SUNSET STUDIOS and MB TROPICAL CONDO (2BR,SLEEPS 6) & TROPICAL CONDO II (1 BR,SLEEPS 4) all same location...

16–23 Apr

$156 SGD per night

Superhost

Guest house in St. Petersburg

4.91 out of 5 average rating, 443 reviews

Private Guest House sleeps 4 w/POOL & near beach!

This adorable pool house is light and airy with plenty of room for 4. There’s a king size bed, queen pullout sofa, dining area, efficiency kitchen perfect for light cooking, oversized closet and a newly remodeled bathroom. Guests have private entrance with small yard and patio of their own, and are encouraged to use the pool and backyard anytime, which we enjoy along with our sweet dogs, Frog and Bella. 3 miles from beach and downtown, lots of restaurants and shopping centers within 1.5 miles.

16–23 Jul

$213 SGD per night

Guest favourite

Guest suite in Saint Petersburg

4.98 out of 5 average rating, 283 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 Guest. Enjoy our tropical garden and beautiful pool area. The pool/jacuzzi are 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.

21–28 Jun

$146 SGD per night

Guest favourite

Guest house in Gulfport

4.95 out of 5 average rating, 191 reviews

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.

18–25 Aug

$149 SGD per night

Guest favourite

Apartment in Redington Beach

4.97 out of 5 average rating, 458 reviews

AmazingBeachCondo/NoCleaningFee/AwesomeAmenities

Welcome to our condo. We have provided you with just about everything you need to come and vacation at this amazing beach area. The condo is right by the heated pool and a 2-minute walk to the beach. The complex has high-speed internet throughout and a laundry facility. Shopping/Grocery/Pharmacy are all close by. Restaurants/bars very close by. This is an amazing area of Florida, with so many things to see and do. You will love it here. We have also provided bikes for your use to get around.

4–11 Nov

$147 SGD per night

Guest favourite

Guest suite in Largo

4.95 out of 5 average rating, 234 reviews

"Twilight Sands Stud" Prvt Ent,Pool,Pk,Keyless Ent

Welcome to your private Studio located 10 minutes from Indian Rocks Beach FL. Come stay with us and dip your toes in the warm white sugar sands of the Gulf of Mexico. Our beautiful cozy studio has private parking, entrance and keyless entry, cozy cal king bed, on suite bath/shower w/bidet, sweet retro kitchenette including mini fridge/freezer, microwave and Keurig coffee/tea express. Beat the crowd, book your stay, relax at the best beaches in the country or explore Tampa Bay or St.Pete!

16–23 Feb

$129 SGD per night

Guest favourite

Flat in Treasure Island

4.84 out of 5 average rating, 357 reviews

Treasure Island Beach Unit

Privately owned Efficiency Unit on the 5th floor at the Island Inn Beach Resort right on Treasure Island Beach. Balcony of unit faces a view of part of the building, the street and Boca Ciego Bay. Beach directly to the left as step off of the elevators. NOTICE May 15, 2023 to Feb 26 GUESTS Building Renovations Scheduled on the exterior structure on these dates. There will be noise disturbances during the hours of 8am and 5pm weekdays, as well as the pool, pool deck, tiki bar closed

18–25 Dec

$181 SGD per night

Guest favourite

Apartment in Tierra Verde

4.96 out of 5 average rating, 237 reviews

Natural Beauty on Tierra Verde, Waterfront Condo

Feels like the Florida Keys! Fully renovated & well appointed second floor, 1 bed, 1 bath condo in Holiday Island condo resort. The condo features a beautiful waterfront & pool view, tennis, bicycles, hot tub, dock with grills, gym, and more. Remodeled in 2015 the condo features a fully equipped kitchen, Keurig coffee maker, beautiful views from the living room, dining room, kitchen, balcony. Walking distance to many local restaurants & minutes away from St. Pete Beach & Fort DeSoto.

14–21 Dec

$178 SGD per night

Guest favourite

Guest suite in Saint Petersburg

4.94 out of 5 average rating, 115 reviews

St. Pete OASIS ~ reduced price for November

LGBTQ+ / 420 friendly! We live on the property; the suite is detached from the main house. Back yard/Pool area is a shared space. Pvt. fenced back yard and pool! Room features full bath, small kitchenette with microwave, hotplate, coffee maker and minifridge. Beach chairs available to use. 8 min from downtown 10 min to the beach! "Grand Central" district with great shops, galleries, bars and restaurants! Free shuttle that runs all day just a block away, to downtown and to the beach.

30 Jun – 7 Jul

$136 SGD per night

Guest favourite

Guest house in St. Petersburg

4.98 out of 5 average rating, 131 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. DEI honored here. Come & enjoy!

4–11 Aug

$168 SGD per night

Guest favourite

Apartment in Redington Beach

4.94 out of 5 average rating, 356 reviews

Beach Condo, Heated Pool, 2 Minute Walk to Ocean

🏌️‍♂️ Golf courses only 15 minutes away! 🏝 Beach 2 minute walk! 💻 Free WIFI, cable TV, Netflix! 🍤 5 minute walk from dine-in restaurant 🏊🏻‍♂️ Private heated saltwater pool literally right outside your room 🏠 Kitchenette and full refrigerator, on-site washer/dryer, beautiful gated courtyard with grill, sun chairs and umbrellas 🏖 Beach chairs, umbrella, and cooler included 🚲 Rent bicycles and jet skis nearby ✈️ 25 minutes from PIE airport ✈️ 35 minutes from TPA airport

2–9 Aug

$129 SGD per night

Guest favourite

Apartment in St. Pete Beach

4.91 out of 5 average rating, 209 reviews

Sunset Beach Condo in Treasure Island

Enjoy a beach getaway in this newly renovated 1 bedroom/1 bath (one queen, twin pull out sofa and single bed foldout) condo with partial water views. This top floor condo (2nd floor) is equipped with new stainless steel appliances, new dishwasher and beach front pool. The perfect relaxation! Great view from the balcony. Across the street from the beach. Harbor House in Sunset Beach, is located on the southern tip of Treasure Island.

14–21 Sep

$162 SGD per night