Holiday rentals with a pool in Gulfport

"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!

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.

Heated Pool l BBQ | Karaoke | Outdoor Projector

✨ Welcome to Your Stylish Florida Escape — Heated Pool, Resort Vibes, and Endless Entertainment✨ Lovingly designed St. Pete retreat crafted for comfort and connection. Enjoy a private pool, cozy firepit, outdoor movie theater, pool table, and karaoke machine for endless fun. Sip tropical drinks from the margarita maker and unwind in luxurious rain showers. With stylish décor, a fully equipped kitchen, and a coffee/tea bar, every detail was thoughtfully created to make you feel right at home.

The Blue Fin, 3 Bed/ Heated Pool/ XBOX

Kick back and relax in this calm, stylish beach-vibin home. The 2 bedroom plus queen size sleeper sofa in sunroom is the perfect spot to get away and never have to leave. Enjoy your morning coffee or afternoon cocktail lounging by the fire pit. Light up the grill and cook your meal while you enjoy a pool heated to 86 degrees for free! Wifi and 3 streaming TV's. If you want to get out and explore, you are only 6 minutes from the award winning beaches and 25 minutes from downtown St Pete.

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.

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 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!

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!

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.

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!

Bungalow Heated Pool Home 10 minutes to Beaches

Welcome to the Starfruit House. A completely renovated three bedroom two bathroom beach cottage with a in-ground heated pool! This home features the feel of old Key West with all new modern updates. Within a few miles of the most popular beaches in the area, minutes to downtown St. Pete, and a quick bike ride to Gulfport. Enjoy the tropical feel of the outdoors, and then come inside to relax.

Sea La Vie- Studio by the bay!

*Newly Designed* Keep it simple at this peaceful and centrally-located condo! Sea La Vie is located on the top (4th) floor with amazing views of the intercoastal waterway. Step out onto the balcony in the morning to sip coffee and watch the dolphins play and go back out at night with wine to watch a stunning sunset! This cozy studio is packed with everything you need to enjoy paradise!