Guest house holiday rentals in Gulfport

4.97 out of 5 average rating, 236 reviews

Centrally Located Cozy 1-bed Private Cottage!

This charming private cottage is ideally located near beautiful views, beaches, art, culture, restaurants, and a variety of family-friendly activities. Guests love the space for its peaceful ambiance, great location, and inviting outdoor areas. It’s a perfect stay for couples, solo travelers, business guests, or anyone looking for a cozy getaway. Enjoy private parking just steps from the entrance, along with a BBQ grill, a brand-new hot tub, and an outdoor gas fireplace—perfect for relaxing!!!

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, 264 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 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, 589 reviews

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

This adorable pool house is light and airy with plenty of room for 4. There’s a king size bed, queen pullout sofa, dining area, efficiency kitchen perfect for light cooking, oversized closet and a newly remodeled bathroom. Guests have private entrance with small yard and patio of their own, and are encouraged to use the pool and backyard anytime, which we enjoy along with our sweet dogs, Frog and Bella. 3 miles from beach and downtown, lots of restaurants and shopping centers within 1.5 miles.

4.94 out of 5 average rating, 171 reviews

Bright 1BR Cottage — 10 min to Downtown & Beach

Tucked away in sunny St. Pete FL, this private 1-bedroom, 1-bath guest suite offers a relaxed and comfortable home base for couples, solo travelers, or a small group looking to enjoy the Sunshine City. You’re just 10 minutes from Downtown St. Pete’s (DTSP) waterfront, restaurants and nightlife and 15 minutes from our renowned Gulf beaches, including St. Pete Beach. We provide beach chairs, an umbrella, cooler, sunscreen, and towels, so you can head straight to the sand and start your vacation.

Guest house 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, 112 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, 241 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.

Guest house 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 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, 110 reviews

Quiet & Cozy Studio 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!

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.

4.95 out of 5 average rating, 111 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!

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.

4.85 out of 5 average rating, 405 reviews

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

Welcome to Casita Citron, a beautiful new tropical paradise in the heart of St. Pete! Tranquil & centrally-located: close to nature trails, shopping, downtown St. Petersburg, & Tampa. Minutes to St. Pete Beach, ranked #1 in USA! Washer & dryer on site. Private fully fenced in backyard with fire pit. Luxurious hot tub spa with speakers, water shooters, & LED lights. Heated outdoor shower. Memory foam mattress. SmartTV. Second queen size bed available upon request (AeroBed with foam topper).

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, 182 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.

4.96 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.

Guest house 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!

Guest house in Historic Kenwood

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

Walkable to the beating heart of the artsy Grand Central and Edge district of St. Pete. Newly built (2022) garage apartment with two bedrooms, one-bathroom, full-sized kitchen with brand new appliances. The bedrooms have all the comforts of a hotel with a personality that matches the vibrancy of the Grand Central community. This space is perfect for travelers looking for a local vibe. Stay in the sunshine inspired apartment and soak up all St. Pete has to offer.

Popular amenities for guest house rentals in Gulfport

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

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, 133 reviews

Crescent Heights Cottage

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, 260 reviews

Cozy Coastal Casita

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.

4.89 out of 5 average rating, 165 reviews

Cozy Renovated Studio – Private Entry + Parking

Guest house in Davis Islands

A charming cottage exterior is framed by lush tropical plants and colorful flowers. Double French doors are highlighted with decorative glass, leading to a welcoming entrance. Brick flooring extends to the doorstep, adding to the cozy, inviting feel of the outdoor space.

4.86 out of 5 average rating, 1,090 reviews

Charming private guest house.

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, 335 reviews

Private Guest Studio w/Courtyard

Guest house in Clearwater

A guest house with bright yellow siding is set against a backdrop of lush trees. The entrance features a dark door and a small patio area with seating. Surrounding greenery adds a touch of nature, complemented by a white fence providing privacy.

4.98 out of 5 average rating, 161 reviews

Cozy 2 Bedroom - 12 Minutes from Clearwater Beach

Superhost

The living area features a comfortable sofa paired with a round coffee table, complemented by wooden flooring. A dining table with black chairs is visible, along with a small work desk and shelves showcasing artwork. Natural light filters through the nearby window.

4.85 out of 5 average rating, 221 reviews

Casa Magnolia- Cute and spacious remodeled unit

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, 127 reviews

Adorable Historic Old NorthEast Bungalow

Guest house rentals 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, 145 reviews

Cozy Tropical 2BR Casita + Hot Tub • Near Downtown

A welcoming entrance to a bungalow is presented with a light blue door and decorative wall art. Surrounding greenery is visible, complemented by a pebbled pathway leading up to the stairs. White fencing provides privacy, enhancing the tranquil setting.

4.98 out of 5 average rating, 144 reviews

Beautiful Private Bungalow near Hyde Park & SOHO

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, 369 reviews

Tiny House Oasis Blue Vatican . Near MacDill Base

4.87 out of 5 average rating, 166 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.

Guest house in Seminole

Luxury Guest House close to the beach

Guest house in Clearwater

A tiki-style patio features a wooden bar with a blue-tiled backsplash, illuminated by soft lighting. Decorative curtains in teal frame the area, enhancing its cozy ambiance. A small fountain adds a soothing element, surrounded by tasteful tropical decor.

4.96 out of 5 average rating, 188 reviews

Newly reopened Airbnb! Freshly remodeled !

4.97 out of 5 average rating, 376 reviews

9 Mins to Downtown, Full Kitchen, KingBed, Balcony

4.95 out of 5 average rating, 114 reviews

A serene beach scene captures the gentle waves lapping at the shore under a colorful sunset. The sandy beach is lined with sparse vegetation, while the horizon showcases soft hues of orange, pink, and blue reflecting off the water.

Guest house in Seminole

Ollie's Beach House

Guest house in Town 'n' Country

4.91 out of 5 average rating, 130 reviews

Cosy Retreat close to everything

Guest house rentals with a washing machine and dryer

A modern, two-story house is depicted with a clean white facade. A metal staircase leads to a second-floor entrance, flanked by large planters containing lush greenery. A shaded patio area is visible below, featuring outdoor seating.

4.95 out of 5 average rating, 188 reviews

Dee's 5-star Tampa Location Unit 2

Guest house 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, 122 reviews

Luxe Apartment - Partial Water View - XL Balcony

4.86 out of 5 average rating, 157 reviews

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, 133 reviews

Private 2 BR Backyard Oasis, Walk to Downtown!

Guest house in Clearwater

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.

4.88 out of 5 average rating, 246 reviews

Cottage on Pinellas Bike Trail

Guest house in Pass-a-Grille Beach

4.93 out of 5 average rating, 232 reviews

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

Guest house in Historic Hyde Park

A cozy living area features a neutral sofa and an orange ottoman, complemented by a light wooden table and a television. Natural light filters through the white blinds, illuminating the soft, carpeted floor. Two framed artworks are displayed on the pastel green wall.

4.92 out of 5 average rating, 166 reviews

HYDE PARK! Walk to Bayshore, Riverwalk, &. UT!