Guesthouse holiday rentals in Gulfport

Guesthouse in Crescent Heights

A light-colored cottage is highlighted, featuring a welcoming red door. A paved outdoor area with a round glass table and four chairs is situated under a pergola with string lights, providing an inviting space for relaxation.

4.95 out of 5 average rating, 115 reviews

Crescent Heights Cottage

Welcome to our cottage! This one bed, one bath apartment is an easy walk, bike, or a short drive to everything awesome in St. Pete. The cottage features a small dining area and kitchenette with a refrigerator, hot plate, microwave, toaster oven, & washer/dryer. The bedroom and bathroom are located up a short set of stairs. Guests have strong wifi access along with a shared outdoor patio & yard on a quiet street. We love hosting long term renters. Please reach out to ask about monthly rates!

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, 242 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!

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, 100 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.

4.96 out of 5 average rating, 215 reviews

A modern kitchen space features a marble countertop with two bar stools. Colorful wall art adorns the light-colored walls. Pendant lights hang above, casting a warm glow over the dining setup with turquoise dishes and a fruit bowl in view.

Guesthouse in Seminole

Quiet & Cozy Guesthouse minutes to the beach.

Newly remodeled, quiet and cozy guest house on a cul de sac. Great location close to shopping/restaurants, 4 miles to Gulf Blvd where you will find many beautiful beaches, Clearwater, St Pete etc. 1 Bedroom, queen bed, and sofa bed in living room which pulls out to a queen bed. Full kitchen with all the extras. Cable TV, WiFi, 1 private parking spot (can accommodate 2 or recreational vehicle just need a heads up). Access to washer/dryer for stays 4 nights or more. No pets, no children under 8.

4.95 out of 5 average rating, 222 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.

A light-filled living area features a comfortable sofa adorned with decorative cushions. A colorful area rug with leaf patterns covers the floor, adding vibrancy. A low coffee table sits centrally, complemented by a mirrored wall and access to the kitchen in the background.

4.98 out of 5 average rating, 130 reviews

Historic Kenwood KING walkable to Central Ave

Welcome to our newly renovated beachy 2nd floor guesthouse in Historic Kenwood. This spacious 1 bedroom (King bed), 1 bath is an easy walk, bike, or short drive to St Pete restaurants, bars, breweries, antique shops, museums, live entertainment and so much more. Grand Central District is just a 5 min walk, Edge District is 1 mile, Downtown is 2 miles, and St Pete beach is 15 minutes away. Guests have a private deck with seating for 2, Wi-Fi, and laundry accessible via shared fenced backyard.

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.

4.96 out of 5 average rating, 212 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.

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, 260 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.

4.97 out of 5 average rating, 196 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!

4.97 out of 5 average rating, 119 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!

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, 339 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, 302 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

5 out of 5 average rating, 24 reviews

An outdoor space features a small patio area with two metal chairs and a side table. A grill is positioned nearby. Green grass is laid down on the ground, and flowering plants frame the space, creating a relaxing retreat. A wooden fence borders the area.

Guesthouse in Largo

Restful Palms

An inviting dining area features a light wooden table surrounded by four brown chairs. A modern kitchen showcases white cabinetry and stainless-steel appliances. A cozy bedroom includes a Queen bed with white bedding. An in-unit washer and dryer are neatly organized in a corner.

5 out of 5 average rating, 18 reviews

Modern Downtown St.Pete Guesthouse + RV/ Boat Lot

4.79 out of 5 average rating, 124 reviews

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.

Guesthouse in Tampa

Sonia's Little House

Guesthouse in Town 'n' Country

4.99 out of 5 average rating, 268 reviews

Entire Guest House near Tampa airport

4.95 out of 5 average rating, 329 reviews

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.

Guesthouse in Tampa

Tiny House Oasis Blue Vatican . Near MacDill Base

4.91 out of 5 average rating, 56 reviews

An interior view of a camper trailer showcases a cozy sleeping area with a spacious bed dressed in light linens. Natural light enters through the windows, illuminating the minimalist dining area with two stools and a wooden surface. A small flat-screen TV is mounted on the wall.

Guesthouse in Uptown

Historic Uptown Hideaway Camper Trailer

5 out of 5 average rating, 19 reviews

A well-lit bedroom features a comfortable bed adorned with crisp white linens and a green throw. A ceiling fan circulates air in the space, complemented by soft lighting from a floor lamp. A nature-themed artwork adds a serene touch to the room's ambiance.

Guesthouse in Tampa

Traveler’s Nest – Close to the Airport

Superhost

A cozy studio interior is presented with a full-sized day-bed adorned with colorful throw pillows and a light blanket. A round wooden table with two stools is positioned nearby. Decorative wall panels feature floral artwork, complemented by a round mirror and a ceiling fan.

4.87 out of 5 average rating, 47 reviews

Adorable Private Studio

Guesthouses with a patio

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, 225 reviews

Central Cozy Cottage w/ Heated Pool & Hot Tub!

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, 244 reviews

Beautiful Studio near Tampa Airport (TPA)

Superhost

A well-designed fire pit area is surrounded by vibrant landscaping, featuring five blue adirondack chairs positioned around a stone circle. Lush palm trees provide a tropical ambiance, and a gravel path leads to the space, inviting relaxation in the private backyard.

4.84 out of 5 average rating, 367 reviews

NEW Luxury Casita w/Hot Tub, Fire Pit, Backyard🏝☀️🏖

A cozy bedroom features a spacious bed with light linens and decorative pillows. Green accent walls complement framed artwork. Soft lighting is provided by two wall-mounted lamps, and a mirror reflects the inviting atmosphere. A small nightstand holds an alarm clock.

4.88 out of 5 average rating, 135 reviews

Cozy Renovated Studio – Private Entry + Parking

4.87 out of 5 average rating, 120 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 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.

4.9 out of 5 average rating, 143 reviews

St Pete Casita Studio with Salt Water Pool & Yard

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.

4.98 out of 5 average rating, 149 reviews

Relaxing & Charming Hideaway

4.93 out of 5 average rating, 125 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!

Guest house rentals with a washing machine and dryer

Guesthouse in Safety Harbor

A modern living space features a comfortable blue sofa adorned with decorative cushions. A sleek coffee table with a candle sits in front. The open kitchen showcases contemporary cabinetry and a kitchen island with bar seating. Light fixtures illuminate the area, enhancing the inviting ambiance.

4.98 out of 5 average rating, 108 reviews

Luxe Apartment | Water Views | Covered Balcony

Guesthouse in Historic Old Northeast

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, 245 reviews

Cozy Coastal Casita

4.85 out of 5 average rating, 151 reviews

Guesthouse in Uptown

Pool & Close to dtwn w/2 Bikes

Guesthouse in Historic Old Northeast

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

The exterior of a newly built garage apartment is presented, featuring a modern design with light green siding. A single-car garage is visible, flanked by two small windows above. Natural light illuminates the gravel driveway and surrounding landscaping.

4.98 out of 5 average rating, 122 reviews

2 bedroom guesthouse in hip Grand Central District

Guesthouse in Pass-a-Grille Beach

A sandy path leads through coastal grasses towards the beach, with palm trees and picturesque homes visible in the background. The clear blue sky enhances the inviting beach atmosphere.

4.93 out of 5 average rating, 219 reviews

A Hidden Gem Steps to Pass-a-Grille Beach Dogs Ok!

4.96 out of 5 average rating, 315 reviews

A light blue bedroom features a queen size bed with coordinated bedding and decorative pillows. A cozy armchair with textured fabric is located in the corner. Natural light filters through two windows, highlighting the space's clean lines and calming atmosphere.

Guesthouse in Uptown

The Dollhouse in Downtown St Pete

A bright living space features hardwood floors and a comfortable seating area with a small coffee table. Natural light filters through the large windows, showcasing a cozy atmosphere. Outdoor views highlight the charming architecture of the surrounding neighborhood, inviting relaxation with a morning drink.