Guesthouse vacation rentals in Gulfport

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Top-rated guesthouse rentals in Gulfport

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Guest favorite

A private patio area is surrounded by wooden fencing adorned with greenery. Two blue chairs are positioned at a round table, creating a serene space for relaxation. Natural light filters through the nearby trees, enhancing the inviting atmosphere of the outdoor setting.

Guesthouse in St. Petersburg

4.97 out of 5 average rating, 231 reviews

Cozy Guesthouse Near Downtown (Non-Toxic)

Come relax in this calm, newly renovated guest suite. Clean, natural, & chemical free - diffusers and oils available on site. Amenities like central a/c, laundry, private patio, full kitchen, Netflix & Hulu. A short 5 minute drive from downtown - near tons of local restaurants, entertainment, and beaches. St. Pete loves the local vibe, be sure to check out our visitors guide for suggestions on spots to see while you’re here. It doesn’t get any better than St Pete! Book your stay with us today!

Top guest favorite

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

4.95 out of 5 average rating, 221 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.

Top guest favorite

A living area is presented with a blue sofa adorned with colorful pillows and a light gray armchair positioned nearby. A coffee table with a geometric design is placed atop a textured area rug. Natural light floods in through a large window, offering a view of palm trees outside.

Guesthouse in St. Petersburg

4.96 out of 5 average rating, 197 reviews

Casita Blue

Stay in Palmetto Park next to the Grand Central District and the Warehouse Arts district. This walkable neighborhood in St. Pete offers a wide variety of restaurants, bars and breweries. Downtown St. Pete entertainment is less than two miles away, and you can drive/rideshare to some of the best beaches in the world in 15 minutes. Tamp Int'l Airport is 30 minutes, Disney is 90 min, and Tropicana Field is 3/4 mile. This guesthouse offers an outdoor parking spot and w/d located in the garage.

Top guest favorite

A private outdoor deck is shown with a mix of seating areas. A cozy sectional sofa is paired with square coffee tables, surrounded by decorative chairs. A large umbrella provides shade, while a tree adds a natural element to the space, creating an inviting area for relaxation.

Guesthouse in Seminole

4.93 out of 5 average rating, 123 reviews

Beachy Bohemian Bungalow with all the perks!

This cozy spot sits in a quiet neighborhood that boasts access to the Pinellas Trail Bike rental close Full kitchen w/ extras Queen bed w/ built in drawers Shelves & clothing rack Smart TV Full bath w/ walk-in shower Ample outlets/ USB Private deck for sun & shade Beach chairs, towels etc for beach Convenient to a dozen parks, beaches, shopping & restaurants. 2 miles to Madeira Beach 3 m - Johns Pass 1.2 m - Seminole City Center 7.6 m - St. Pete/ Clearwater Airport NO SMOKING NO PETS

Guest favorite

A spacious living and dining area showcases a large wooden dining table with four chairs. Comfortable seating consists of a brown couch and a decorative area rug. A fireplace adds charm, with natural light filtering through multiple windows.

Guesthouse in St. Petersburg

4.96 out of 5 average rating, 254 reviews

C'est La Vie [RENOVATION COMPLETED JUNE 2020]

[Remodel completed June 2020] Stay in the beautiful Woodlawn Neighborhood of St. Petersburg in this gorgeous bungalow home. This fun and completely renovated two bedroom house can accommodate up to six guests comfortable and has plenty of open space to plan your excursions or relax and rejuvenate. You're only 6 minutes to downtown, 2 minutes to interstate, 11 miles to the main gulf beaches, 90 minutes to Disney World , 25 minutes to Busch Gardens, & 20 minutes to Tampa Int'l Airport.

Top guest favorite

A cozy living area features an inviting beige armchair and a small round table set with placemats. Light streams in through a nearby door adorned with a wreath, illuminating the space with a natural glow. A patterned rug adds texture to the wooden floor.

Guesthouse in Historic Old Northeast

4.98 out of 5 average rating, 253 reviews

Historic Old Northeast Get A Way

Carriage house converted to cozy updated 1 bedroom plus separate den/office above garage apartment in historic Old Northeast. The den/office has a new queen Murphy bed which will allow a second private sleeping space. Two blocks walking distance to Vinoy Waterfront Park and downtown St Pete. Twenty minute car ride to the beautiful Gulf Beaches or downtown Tampa. Great weekend get-a-way or longer term rental. Parking is available on the street with a parking permit which we provide.

Top guest favorite

The bright living area features a green sofa with a decorative pillow, a white coffee table, and a dining table with four chairs. Vibrant wall art enhances the space, complemented by large windows allowing natural light. A doorway leads to the private side yard.

Guesthouse in St. Petersburg

4.98 out of 5 average rating, 137 reviews

Relaxing & Charming Hideaway

Welcome to this centrally located St Petersburg guest suite. Our renovated guest house is located less than 10 minutes from Downtown and less than 10 minutes from Treasure Island Beach. You will be an 8-minute walk to the St Pete SunRunner - connecting St Pete Beach with downtown. The apartment has been carefully designed to include everything you will need to make your stay as comfortable as possible including private parking, a private side entrance, and an enclosed private yard.

Guest favorite

An inviting view into the living area is framed by a decorative arch. A vibrant green plant adds a touch of nature, while a cozy brown couch and accent chairs are arranged around a circular coffee table. Colorful artwork decorates the walls.

Guesthouse in Gulfport

4.96 out of 5 average rating, 114 reviews

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!

Top guest favorite

A cozy bedroom features a spacious bed adorned with decorative pillows and a bright, textured quilt. Wall decor includes framed artwork and decorative plates that add charm. A bedside lamp rests on a nightstand, providing soft illumination, while natural light filters through sheer curtains.

Guesthouse in Historic Kenwood

4.98 out of 5 average rating, 324 reviews

Charming apartment in Historic Kenwood

Cute, spacious apartment located in Historic Kenwood, which was named 2020 “Neighborhood of the year” by NUSA. Our apartment is above our large garage. Lots of charm and just enough space to spread out a little for some privacy. Located close to downtown, walking distance to lots of restaurants, breweries and bars but still a short drive to our beautiful beaches. You access the apartment through our side gate and up an exterior stairway.

Top guest favorite

Guesthouse in Town 'n' Country

4.98 out of 5 average rating, 245 reviews

Entire Guest House near Tampa airport

Welcome to our charming guest house! Located just 12 minutes away from Tampa Airport, 20 minutes from Raymond James Stadium, and a quick 35-minute drive from Clearwater, our entire guest house offers you convenience and comfort. With a private entrance, you'll have all the privacy you need. Whether you're here for a game, a beach getaway, or to explore the city, our cozy space is your perfect home base. Book now for an unforgettable stay!

Top guest favorite

A light-filled living area features a comfortable couch adorned with decorative pillows. A coffee table with shell motifs sits in front, complemented by two stylish lamps. Artwork depicting coastal scenes hangs on the walls, and a curtain in soft hues allows natural light to filter in.

Guesthouse in Gulfport

4.94 out of 5 average rating, 301 reviews

Lovely Guesthouse

We are ideally situated close to Tampa, Sarasota,Clearwater and St. Petersburg. Our neighborhood is wonderful, eclectic, alive. We have incredible restaurants a walk away. Our beach is walking distance. If you prefer you never have to leave Gulfport from the day you arrive. Everything you want is right here. There is free access for charging your electric vehicle on the beach in town which is walking distance from our guesthouse

Superhost

A staircase leads down to an enclosed Florida room, where a small round table with two decorative chairs is situated. Lush greenery and bamboo create a tranquil backdrop, enhancing the space's connection to nature.

Guesthouse in Gulfport

4.82 out of 5 average rating, 126 reviews

Bamboo Carriage House

Welcome to Bamboo Carriage House originally built in 1920, a cute and comfortable guest house in the quaint and quirky village of Gulfport, Florida. Located just a short drive from downtown St. Pete and St. Pete beaches. Just 1.2 miles from Gulfport's waterfront district full of independent shops, restaurants, and galleries. Convenient to the Gulf beaches, Downtown St. Pete and Tampa.