Guesthouse holiday rentals in Gulfport

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.

4.98 out of 5 average rating, 246 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!

Guesthouse in Historic Kenwood

A warm living room is presented, featuring a light-colored sectional sofa and a dark blue armchair. A coffee table is centered on an area rug, adorned with decor. Two large windows allow natural light to fill the space, complemented by framed artwork on the wall.

4.99 out of 5 average rating, 101 reviews

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.

4.95 out of 5 average rating, 223 reviews

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

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.

The exterior of a cozy converted workshop features a gray wood-paneled facade with a vibrant yellow front door. Two chairs are positioned on the porch, beside a barrel and trash bins. A privacy fence can be seen in the background, surrounded by greenery.

4.84 out of 5 average rating, 881 reviews

Private & Cozy Tiny Home/Cottage

This is a cozy converted workshop with all the amenities of a traditional home! You'll have a comfy bed that sleeps 2 with an air mattress upon request, TV with streaming options, fun decorations, WiFi, air conditioning, W/D, closet space, cooking stuff, & bathroom. If you love tiny homes, you'll love this. Because of it being a converted workshop, it still has that feeling in some regard. It's a little rustic, but still charming. It's not a hotel, nor does it try to be. Pets are welcome.

Guesthouse in Central Oak Park

A private backyard features a heated pool surrounded by lush tropical plants and trees. The pool has a gentle curve and is accompanied by stone steps leading into the water. A small seating area is partially visible in the background, set amongst vibrant greenery.

4.98 out of 5 average rating, 231 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 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!

Guesthouse in Greater Woodlawn

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.

4.95 out of 5 average rating, 263 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.

4.98 out of 5 average rating, 208 reviews

Centrally Located Cozy 1-bed Private Cottage!

This adorable cottage is close to great views, art, culture, restaurants, dining, the beach, and family-friendly activities! You’ll love this private cottage because of the location, the ambiance, and the outdoor space. This cozy cottage is good for couples, solo adventurers, business travelers, and anyone needing a cozy place to stay! Parking is just steps away from the cottage with a private entrance. BBQ is available, new hot tub, and an outdoor gas fireplace for a relaxing evening!

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.

4.97 out of 5 average rating, 155 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.

4.97 out of 5 average rating, 125 reviews

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

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!

Guesthouse in Old Southeast

A bright studio space features a comfortable seating area with a loveseat, a small television on a teal stand, and a vibrant area rug with a leaf pattern. Natural light fills the room through large windows dressed in bamboo shades, highlighting a cozy bed in the corner.

4.8 out of 5 average rating, 265 reviews

Sunny Side Up near the Water and Downtown St. Pete

Cozy studio apartment on the second floor of our detached guest house in the Old Southeast Neighborhood of St. Petersburg. One block from the bay at beautiful Lassing Park, one mile south of downtown, and only a 15 minute drive to St. Pete Beach. Full sized refrigerator and full kitchenette fully stocked all the basic cooking essentials. Fenced in back yard with a turf area perfect for relaxing in Florida's amazing weather. Parking right behind the unit.

Guesthouse in Historic Kenwood

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.

4.98 out of 5 average rating, 346 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.

4.94 out of 5 average rating, 303 reviews

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

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

Popular amenities for Gulfport guesthouses

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

Guesthouse in Crescent Lake

A spacious sleeping area features a large bed with crisp white bedding, complemented by colorful curtains. Two light sources illuminate the room, including a bedside lamp and a floor lamp. A soft area rug adds texture to the floor, while a chair provides additional seating.

4.9 out of 5 average rating, 251 reviews

Crescent Heights/St. Petersburg Entire Guest House

A private pool area is enclosed by a mesh screen, featuring a sparkling blue pool. Two light blue chairs are positioned adjacent to the pool, with the guest house and windows visible in the background. Lush greenery provides a serene contrast to the home.

4.93 out of 5 average rating, 249 reviews

Cozy Coastal Casita

4.96 out of 5 average rating, 192 reviews

An outdoor tiki hut porch is illuminated by soft string lights. Comfortable seating creates a cozy gathering area, surrounded by lush greenery. A wooden dining table sits in the center, offering a relaxed space for meals or conversation.

Guesthouse in Dunedin

Tiki Hut Cottage

The entrance to the guest studio is framed by two windows and is highlighted by a grey door. A welcoming doormat is placed at the foot of the door, and the exterior is adorned with light blue siding and decorative outdoor lighting.

4.89 out of 5 average rating, 317 reviews

Private Guest Studio w/Courtyard

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.

4.98 out of 5 average rating, 261 reviews

Historic Old Northeast Get A Way

A charming yellow cottage is framed by lush palm trees and tropical plants, featuring a welcoming front door at the end of a paved walkway. Sunlight filters through the greenery, creating a bright and inviting atmosphere near the entrance.

4.91 out of 5 average rating, 149 reviews

St Pete Casita Studio with Salt Water Pool & Yard

Guesthouse in Old Southeast

4.77 out of 5 average rating, 363 reviews

The Lassing House

4.93 out of 5 average rating, 128 reviews

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

Beachy Bohemian Bungalow with all the perks!

Guesthouses with a patio

A hot tub is surrounded by lush greenery and vibrant red flowers, creating a serene atmosphere. A tall palm plant is visible beside the tub, complementing the tropical landscape. A large umbrella is positioned nearby, providing shade on bright sunny days.

4.95 out of 5 average rating, 127 reviews

Cozy Tropical 2BR Casita + Hot Tub • Near Downtown

Guesthouse in Bay Crest Park

A cozy bed is adorned with a vibrant yellow coverlet and accented by decorative pillows. A tray holding a bottle of wine and two glasses is placed on the bed. Soft ambient lighting is provided by a black lamp, with artwork displayed on the wall above.

4.98 out of 5 average rating, 257 reviews

Beautiful Studio near Tampa Airport (TPA)

A sleeping area features a spacious bed adorned with multiple pillows and a decorative bolster pillow. A collection of framed artwork is displayed on the wall above. A bedside lamp and a wooden nightstand are positioned nearby, adding functionality to the space.

4.79 out of 5 average rating, 131 reviews

Sonia's Little House

Guesthouse in Virginia Park

A clear blue sky overlooks a private pool surrounded by lush greenery and palm trees. The patio features brick paving and lounge chairs positioned near the water, offering a serene setting for relaxation. A cozy cabana is visible in the background, enhancing the tranquil atmosphere.

4.92 out of 5 average rating, 200 reviews

Cozy Palma Ceia Cabana close to Westshore & TIA.

A charming guest house exterior is showcased, featuring a sloped roof and large glass doors. The inviting solarium area displays comfortable seating arrangements. Lush green plants are positioned beside the entrance, and the space is surrounded by well-maintained artificial grass, enhancing the outdoor atmosphere.

4.95 out of 5 average rating, 342 reviews

Tiny House Oasis Blue Vatican . Near MacDill Base

4.83 out of 5 average rating, 130 reviews

An exterior view of a well-lit garage with a modern stone façade. The white garage doors are flanked by tall, symmetrical planters with neatly trimmed shrubs. Soft illumination from the overhead lights enhances the clean lines of the architecture, creating a welcoming entrance.

Guesthouse in Seminole

Luxury Guest House close to the beach

A pathway is lined with pavers and flanked by a wooden fence and white vinyl fence, leading to the entrance of a guesthouse. Lush palm trees are visible in the background, and a small outdoor seating area with a table and chairs is present.

4.98 out of 5 average rating, 120 reviews

Peaceful & Private Dreamy Lodge TPA, DWTN, Beaches

A view from the entryway opens to a private patio area, featuring turquoise chairs arranged around a table. A doormat with a wine glass design is positioned at the threshold, welcoming guests into the space. Natural light brightens the entrance.

4.9 out of 5 average rating, 104 reviews

Relax in the tampa bay area #1

Guest house rentals with a washing machine and dryer

4.86 out of 5 average rating, 152 reviews

Guesthouse in Uptown

Pool & Close to dtwn w/2 Bikes

A serene pool area is surrounded by lush palm trees and tropical plants. The tranquil water reflects the sunlight, inviting relaxation. Planters with vibrant foliage enhance the natural beauty of the space, contributing to a welcoming atmosphere for guests.

4.92 out of 5 average rating, 131 reviews

Private 2 BR Backyard Oasis, Walk to Downtown!

An exterior view of the two-story house features a white siding complemented by black shutters. Lush greenery surrounds the property, and a welcoming awning covers the entrance. Soft lighting from the windows suggests a cozy ambiance as evening approaches.

4.91 out of 5 average rating, 122 reviews

Adorable South Tampa Two-Story Guest House

An outdoor seating area features two chairs and a small table under a covered porch. Soft string lights are hung above, illuminating the space. The adjacent wall is painted in a warm yellow tone, enhancing the inviting outdoor atmosphere.

4.78 out of 5 average rating, 279 reviews

Family & Pet friendly 2 bedroom Guest House

4.89 out of 5 average rating, 233 reviews

A light green room features a queen-size bed with a white quilt and decorative pillows. A small dining area with a round table and two chairs is visible alongside a neutral-toned sofa. Large windows provide natural light, and indoor plants are seen through the glass doors.

Guesthouse in Clearwater

Cottage on Pinellas Bike Trail

Superhost

An outdoor patio area is enclosed by a wooden fence, featuring a fire pit surrounded by two white adirondack chairs. Lush greenery and small shrubs border the space, which is accentuated by a stone path and grassy patches under a clear blue sky.

Guesthouse in Bayshore Beautiful

4.84 out of 5 average rating, 261 reviews

La Casa Azul - Private Detached Guest House

Superhost

A cozy living area features a blue sofa paired with a black ottoman and a small blue side table. A potted plant sits on the table, and a colorful wall art piece is displayed nearby. Natural light filters through two windows with blinds.

Guesthouse in Uptown

4.85 out of 5 average rating, 507 reviews

Cute home in historic neighborhood