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Kenwood Retreat - 1BR carriage house

This newly constructed carriage house was built to embrace the character and charm of the main house, a 1928 craftsman bungalow. Your 2nd floor 1 BR apartment is well appointed with a full chef's kitchen, a living room with a pull-out sofa, and washer/ dryer. Enjoy a morning cup of coffee or a glass of wine in the evening on the large porch. 2 min walk to Grand Central restaurants, coffee shops, boutiques, or grab a bike or scooter for a 5 min ride to Downtown St. Pete or 15 to the beaches.

The Happy House

Welcome to The Happy House, This piece of paradise was the spotlight home for the 2025 Flamingo Tour of homes ! 🦩The stunning property has everything you need for an unforgettable getaway. Discover a breathtaking garden, 2 charming bedrooms, a modern kitchen with eat-in dining, a welcoming living room, a dining room, and a timeless bathroom. Outside, enjoy a backyard paradise, an outdoor shower, griddle, umbrellas, lounging areas, and a quaint beach spot. Your next favorite escape is waiting!

The Driftwood - Pet Friendly

Welcome to The Driftwood's nautical retreat. This cozy 2-bedroom home is a haven of maritime-inspired style, offering a unique and refreshing escape for your stay. Unwind in your private yard with a fire or dinner at the outdoor dining area. Have your pet staying with you? They are welcome here! This beautiful diverse neighborhood is one mile away from Gulfport's beach blvd. where you can shop, dine, or stroll the beach. 6 miles away will take you to the famous St Pete Beach or St Pete Pier.

Flamingo Corner

Flamingo corner is spacious, clean and decorated peacefully. There are two bedrooms with queen beds and a queen sleeper sofa. A portable crib can be arranged if needed. It’s 10 blocks away from eclectic downtown Gulfport/Beach. There are many restaurants, boutiques and shops to browse through. Flamingo corner is less than 3 miles to beautiful Upham and St. Pete beaches! Downtown St Pete and the Tampa Bay are just over 5 miles away. We are so close to everything, you will never be bored!

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!

The Peaceful Turtle Retreat

Take it easy at this unique and peaceful turtle retreat!! It is located only 5 minutes to downtown Gulfport, and 10 min to St Pete Beach! This cozy apartment is brand new construction and has many wonderful amenities such as; an updated full kitchen, new washer/dryer, and a big spacious shower. There is a king size bed, and a roku Tv for your entertainment. Outside is a deck with a patio table and chairs set, two bikes to enjoy the outdoors, and a grill. Book your vacation here today!!

Cozy Cottage for Lovers

Relax, reconnect and revitalize in this private, intimate cottage that has everything you need to leave the hustle and bustle behind. Surrounded by lush tropical vegetation in the shade of giant live oaks and located in the Gulfport Arts District, you're a short walk or bike ride from excellent urban parks, restaurants, live music, fashion and art boutiques, dancing at the Gulfport Casino, community theater, and a beautiful beach that looks out over sailboats moored in Boca Ciega Bay.

Wine Cellar Charm Gulfport

The Beach Wine Cellar is a two-bedroom one-bathroom luxury home designed to immerse the guest in a Tuscany style vacation on the beach. Conveniently located 1 block from main street and 4 blocks from Gulfport Beach. Boasting a bar for 2, a living room for 6 with a 55" TV, an indoor dinning-room. There is an enclosed backyard with a privacy fence. The patio has a barbecue and a gas fire-pit. Enclosed 450 SF patio has 4 fans, dinning table, a living room set, 55" TV, and games.

1920s Cottage, 2BR/2BA, Walk to Beach & Art Walks

Tucked on a quiet brick-lined street in the heart of Gulfport’s historic waterfront arts district, this enchanting 1920s cottage is the real Florida — sun-drenched, unhurried, and full of character. Walk six blocks to the beach, four blocks to waterfront dining, and step outside on Tuesday mornings for the beloved Fresh Market. On First Fridays, the neighborhood comes alive with Art Walks, live music, and local makers. This is the kind of place people come back to every year.

Gulf Guesthouse - king bed, 3 blocks to downtown.

Be our guest! Welcome to our family compound where you will enjoy the treetop views from our second story carriage house guest apartment. You'll be surrounded by the tropical serenity of lush palms and plants, both inside and out, while being just around the corner from the excitement of downtown Gulfport. Our updated one bedroom apartment is fully furnished and stocked with all of the things you'll need for an extra comfortable, enjoyable stay. We look forward to hosting you!

Avocado Casita 10 mins to Beaches

Newly built studio -- small space, smart design. An intimate studio space meant for a minimalist lifestyle complete with full amenities. Compact yet comfortable, it’s the perfect place for a restful sleep in between your daytime adventures. Pack light, live easy. 3 blocks from Stetson Law School 3-4 blocks from the Pinellas Trail ~1.5 miles to Gulfport’s Beach Blvd 3 miles to Award Winning St. Pete Beach 4 miles to Award Winning Treasure Island ~4.5 miles to Downtown St Pete

Villa Splash, 1 room pool suite

Tropical pool villa in central St Pete built in 2022, only 1 mile from Pinellas Trail, 2 miles from downtown restaurants and 5 miles from Treasure Island Beach. One room efficiency includes a comfortable queen size murphy bed, full bathroom (w/shower-no tub), large flat screen tv, with wet bar, microwave & coffee maker. No cooktop. Guests will have private access to pool. It is not shared. Smoking is NOT permitted on property and will be reported.