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.

4.97 out of 5 average rating, 268 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!

LocationValueAccess

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, 182 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!

LocationFamilySleep quality

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.

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.

LocationFamilyWalkability

4.99 out of 5 average rating, 119 reviews

4.95 out of 5 average rating, 245 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.

ValueFamilyBiking

The studio features a spacious layout with a comfortable futon couch adorned with decorative cushions. A fully equipped kitchen is visible in the background, complemented by a dining table with white chairs. Large windows provide natural light, enhancing the airy feel of the blue walls.

4.94 out of 5 average rating, 115 reviews

Private Guesthouse Near Beach & Downtown

Welcome to our charming studio in the heart of St. Petersburg, Florida! Our cozy dog-friendly space is the perfect retreat for solo travelers or couples looking to experience all this vibrant city offers. Located just 10 mins from Treasure Island and less than a half mile from a Sun Runner bus stop, the location offers easy access to all of the city’s great destinations. Enjoy your own private entrance and plenty of street parking in our quiet, shaded neighborhood. We can't wait to host you!

LocationValueCondition

The kitchenette features green cabinets and a wooden countertop, equipped with a microwave and coffee maker. A window provides natural light, while open shelves display glassware and decorative items. A mini-fridge and amenities create a functional and cozy cooking space.

4.96 out of 5 average rating, 122 reviews

The Perfect Studio

Enjoy an amazing experience at this centrally-located, newly renovated, private studio apartment! Adorable kitchenette, dreamy walk-in tiled shower, and close to everything!! •1.7 miles from Sunken Gardens •3.2 miles from The Dalí Museum •2.8 miles from Tropicana Field •2.5 miles from the best shopping, restaurants, and coffee shops in downtown St. Pete and our gorgeous pier! •10 miles from our World Famous Bay Beaches All while staying in a relaxing neighborhood. Come live like a local!

LocationValueGetting around

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, 184 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.

ValueLocationComfort

4.96 out of 5 average rating, 142 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!

LocationValueLayout

A modern living space is presented with light-colored tile flooring and large glass doors providing access to the pool area. Soft blue curtains frame the doors, while a grey sofa and sleek entertainment unit add to the contemporary design. A ceiling fan circulates air in the room.

4.99 out of 5 average rating, 156 reviews

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.

LocationFamilyWi-Fi

4.85 out of 5 average rating, 141 reviews

Private Guesthouse in St. Pete w/ Pool & Jacuzzi

Enjoy privacy & tranquility in this detached guesthouse, with POOL & HOT TUB ACCESS! Ten minutes from Downtown, 17 minutes from St. Pete Beach, this spacious guesthouse has AC, its own Wifi, TV w/ Firestick, with a private entrance & parking. Host lives in a separate house on the property & is available if needed! We welcome guests to bring their beloved pets, however they cannot exceed over 50lbs. Sorry, pets are not allowed in the pool.

ValueLocationPool

Guesthouse in Historic Kenwood

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.

ValueFamilyTV

4.97 out of 5 average rating, 379 reviews

4.96 out of 5 average rating, 117 reviews

Private Studio Near Downtown St. Pete & Beaches

Welcome to your home away from home in St. Petersburg's Central Oak Park neighborhood. This private upstairs studio offers a peaceful retreat just minutes from downtown, The Pier, award-winning Gulf beaches, restaurants, shopping, and local attractions. Enjoy a fully equipped kitchen, comfortable queen bed, walk-in shower, Smart TV, private patio, and everything you need for a relaxing getaway, business trip, or extended stay.

LocationFamilyCleanliness

Popular amenities for Gulfport guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

A cozy living area features a beige sofa adorned with bright orange pillows, inviting relaxation. A white coffee table sits in front, while a wall shelf displays decorative items. Natural light filters through two windows, brightening the space. A door leads to the outside.

4.88 out of 5 average rating, 604 reviews

Private Guest House sleeps 4 w/POOL & near beach!

ValueFamilyDecor

A light-filled living area features a comfortable beige sofa adorned with patterned throw pillows. In the background, two bikes are parked beside a well-equipped kitchenette with navy cabinetry and a wine fridge. Sunlight streams through an open door, illuminating the space.

4.9 out of 5 average rating, 347 reviews

Beautiful Guest House in Historic Old Northeast

ValueLocationWalkability

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.

4.94 out of 5 average rating, 276 reviews

C'est La Vie [RENOVATION COMPLETED JUNE 2020]

ValueFamilyDecor

4.94 out of 5 average rating, 174 reviews

Bright 1BR Cottage — 10 min to Downtown & Beach

FamilyValueDecor

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.

4.96 out of 5 average rating, 135 reviews

Crescent Heights Cottage

ValueLocationParking

A bright living space features a brown leather sofa and light-colored accent chairs. A medium-sized coffee table is arranged with magazines. Natural light filters through window treatments, highlighting the white walls and wood flooring. A mounted television is centered on the wall, enhancing the open atmosphere.

4.93 out of 5 average rating, 150 reviews

Private guesthouse in Historic Old Northeast

LocationValueBiking

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, 344 reviews

Private Guest Studio w/Courtyard

LocationValueAccuracy

4.97 out of 5 average rating, 255 reviews

Centrally Located Cozy 1-bed Private Cottage!

ValueLocationTV

Guesthouses with a patio

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, 424 reviews

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

LocationValueBackyard

4.92 out of 5 average rating, 143 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!

ValueLocationParking

A sunlit outdoor space features a screened-in pool area with a shimmering blue pool and a connected spa. Paved stone decking surrounds the pool, with lush greenery visible beyond the enclosure. A seating area is located nearby, enhancing the recreational opportunities in this serene environment.

4.97 out of 5 average rating, 108 reviews

Beautiful Tampa Bay Casita | Pool, kayaks

FamilyValueLong stay

4.9 out of 5 average rating, 183 reviews

Cozy Renovated Studio – Private Entry + Parking

FamilyLocationAccess

A studio-style room features a spacious bed with a textured headboard, complemented by light bedding. Nearby, a simple chair and pouf offer additional seating. Shelves display plants and kitchen essentials, with a microwave and mini-fridge visible in the background.

4.91 out of 5 average rating, 132 reviews

Adorable Historic Old NorthEast Bungalow

LocationValueBeach

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.

4.97 out of 5 average rating, 268 reviews

Central Cozy Cottage w/ Heated Pool & Hot Tub!

FamilyValueSleep quality

A bright studio apartment is showcased, featuring a queen bed with colorful decorative pillows. A small kitchen area is equipped with modern appliances, including a refrigerator and stovetop. A seating bench and vibrant area rug complement the space. Natural light flows through the windows.

4.98 out of 5 average rating, 123 reviews

The Salty Dunes… Adorable Studio near downtown

ValueLocationHeating

A spacious studio is highlighted by a queen murphy bed with green striped bedding. A wooden nightstand and lamp are positioned beside the bed. A small shelf displays decorative plants, and a window with natural light is adorned with bamboo blinds.

4.91 out of 5 average rating, 98 reviews

Quiet, small backyard studio w/ kitchenette

ValueLocationWi-Fi

Guest house rentals with a washing machine and dryer

4.99 out of 5 average rating, 374 reviews

The image captures a serene outdoor area featuring a charming entrance to the cottage. Surrounding tropical plants and tall trees create a lush environment. A decorative fountain stands to the left, and comfortable seating under an umbrella adds to the inviting atmosphere.

Guesthouse in Largo

Paradise Cottage Largo Beaches 1 mile High ground

LocationFamilyCheck-in

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, 271 reviews

Cozy Coastal Casita

LocationFamilyBarbecue

4.96 out of 5 average rating, 237 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.

LocationValueNearby

A modern kitchen features sleek gray cabinets and white quartz countertops, enhanced by open shelving adorned with decorative items. A stainless steel refrigerator and kitchen appliances, including a gas stove and coffee maker, are neatly positioned, ensuring a functional and inviting cooking space.

4.97 out of 5 average rating, 102 reviews

Updated Old NE Apt - Walking Distance to Downtown

FamilyValueOutdoor spaces

Guesthouse in Pass-a-Grille Beach

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

FamilyValueGetting around

4.93 out of 5 average rating, 247 reviews

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, 133 reviews

Private 2 BR Backyard Oasis, Walk to Downtown!

FamilyLocationAir conditioning

4.93 out of 5 average rating, 112 reviews

The living area is furnished with a light-colored sofa and an ottoman, offering comfortable seating. A smart TV is mounted on the wall, and a wooden dining table is visible nearby. A ceiling fan provides airflow, with natural light filtering through a nearby window.

Guesthouse in Clearwater

Adorable Vintage Style guest house | King size bed

LocationFamilyHospitality

Superhost

A serene beach scene features several chairs positioned on the sand, facing a calm sea at sunset. Gentle waves lap against the shore, with soft colors painting the horizon. A distant structure, possibly a pier, is visible, enhancing the tranquil atmosphere.