Guesthouse vacation rentals in Gulfport

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Top-rated guesthouses in Gulfport

Guests agree: these guesthouses are highly rated for location, cleanliness, and more.

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Guest favourite
A vibrant sunset paints the sky in warm hues of orange and yellow, as the sun sinks below the horizon over a tranquil ocean. The image conveys a serene coastal atmosphere, resonating with the proximity to nearby beaches.
Guesthouse in Clearwater
4.9 out of 5 average rating, 422 reviews

Minutes to Beaches w/King Bed Private Updated

This private home away from home near pristine beaches sits behind the main house in a quiet neighborhood conveniently located near downtown Clearwater, Clearwater Beach, Tampa, St Petersburg, Dunedin, Tarpon Springs, and other great towns. Restaurants, shopping, & entertainment venues. • Clearwater Beach= 4 miles / 8 minutes • Downtown Dunedin= 3 miles • Honeymoon Island= 9 miles • Tarpon Springs Sponge docks= 14 miles • Tampa Airport (TPA)= 14 miles • St Pete/Clearwater Airport (PIE)= 9 miles

Top guest favourite
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.
Guesthouse in Crescent Heights
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!

Top guest favourite
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
4.98 out of 5 average rating, 241 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!

Guest favourite
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.
Guesthouse in St. Petersburg
4.9 out of 5 average rating, 142 reviews

St Pete Casita Studio with Salt Water Pool & Yard

Keep it simple at this peaceful and centrally-located place. La Casita is located minutes from bustling downtown and beautiful bay waterfront restaurants and bars. Tampa International Airport is only 20 minutes away. The property itself is great for relaxing. La Casita is surrounded by lush palm trees and has its own access to the pool a few feet from your front door. Come relax, go to the pool, beach, enjoy the outdoor shower and finish off the day at One of the many nearby restaurants!

Top guest favourite
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
4.96 out of 5 average rating, 214 reviews

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.

Top guest favourite
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, 222 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 favourite
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.
Guesthouse in Historic Kenwood
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.

Top guest favourite
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, 210 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 favourite
Guesthouse in St. Petersburg
4.97 out of 5 average rating, 194 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!

Top guest favourite
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, 148 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.

Top guest favourite
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
4.97 out of 5 average rating, 119 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 favourite
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, 337 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.

Popular amenities for Gulfport guesthouses

When is the best time to visit Gulfport?

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Avg. price$141 CAD$162 CAD$157 CAD$141 CAD$141 CAD$141 CAD$141 CAD$113 CAD$106 CAD$125 CAD$140 CAD$140 CAD
Avg. temp17 °C18 °C20 °C23 °C26 °C28 °C29 °C29 °C28 °C25 °C21 °C18 °C

Quick stats about guesthouse rentals in Gulfport

  • Total vacation rentals

    Explore 20 vacation rentals in Gulfport

  • Nightly prices starting at

    Gulfport vacation rentals start at $71 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,510 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Gulfport vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Gulfport rentals

  • 4.8 Average rating

    Gulfport stays are highly rated by guests—averaging 4.8 out of 5!

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