Guesthouse vacation rentals in Gulfport

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Top-rated guesthouse rentals in Gulfport

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

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Guest favorite

Guesthouse in Gulfport

4.92 out of 5 average rating, 729 reviews

graceful haven...

This boutique-sized, moon-drenched studio is more than just a place to lay your head. From the delicate metal birds swirling above your bed, to the tender light reflecting off the burnished aluminum countertop, your senses will be soothed and tickled by its quietly exuberant design & decor. Nestled in a lush tropical garden, the space is just a block away from Gulfport's Art Village with its sunset waterfront, delightful shops, and many fine restaurants. (or, see my “bohemian treat” listing)

Nov 26 – Dec 3

$99 per night

Superhost

Guesthouse in St. Petersburg

4.91 out of 5 average rating, 442 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.

Jul 15 – 22

$129 per night

Guest favorite

Guesthouse in St. Petersburg

5.0 out of 5 average rating, 154 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!

Aug 27 – Sep 3

$132 per night

Guest favorite

Guesthouse in Gulfport

4.95 out of 5 average rating, 191 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.

Aug 18 – 25

$95 per night

Guest favorite

Guesthouse in Saint Petersburg

4.85 out of 5 average rating, 716 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, cable, Netflix, 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. It's definitely a great place to relax and get a good night's sleep. Pets welcome.

Jan 17 – 24

$68 per night

Guest favorite

Guesthouse in St. Petersburg

4.96 out of 5 average rating, 156 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.

$105 per night

Guest favorite

Guesthouse in Seminole

4.95 out of 5 average rating, 144 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. 4 Miles to Madeira Beach/Treasure Island, 9 miles to Clearwater and St Pete Beach. 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 and access to washer/dryer for stays 4 nights or more. No pets, no children under 12.

Jun 26 – Jul 3

$75 per night

Guest favorite

Guesthouse in St. Petersburg

4.93 out of 5 average rating, 138 reviews

Sunny Guest Suite in the Heart of St. Pete!

Tucked away in the heart of sunny St. Petersburg, FL, this 1 bedroom, 1 bathroom guest suite is the perfect home base for couples, small groups & solo adventurers to rest, recharge & enjoy all that the Sunshine City has to offer. Ready to explore? Our central location is a 10 minute drive to the exciting nightlife of Downtown St. Pete (DTSP) and 15 minutes to St. Pete Beach! No need to bring your own beach gear, we'll provide the beach chairs, umbrella, cooler, sunscreen and towels!

May 6 – 13

$99 per night

Guest favorite

Guesthouse in St. Petersburg

4.95 out of 5 average rating, 212 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.

Aug 12 – 19

$140 per night

Guest favorite

Guesthouse in St. Petersburg

4.98 out of 5 average rating, 131 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 NEW 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. DEI honored here. Come & enjoy!

Aug 4 – 11

$108 per night

Superhost

Guesthouse in Gulfport

4.84 out of 5 average rating, 104 reviews

Bamboo Carriage House

Welcome to Bamboo Carriage House originally built in 1920, a cute and comfortable guest house in the quaint and quirky village of Gulfport, Florida. Located just a short drive from downtown St. Pete and St. Pete beaches. The Bamboo Carriage house offers comfortable quarters in an eclectic "Old Florida"-style small town. Just 1.2 miles from Gulfport's waterfront district full of independent shops, restaurants, galleries. Convenient to the Gulf beaches, Downtown St. Pete and Tampa.

May 4 – 11

$108 per night

Guest favorite

Guesthouse in St. Petersburg

4.87 out of 5 average rating, 158 reviews

Coconut Cottage near the Water and Downtown

Cozy, stylish studio on the first 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. Fully stocked kitchenette with all the basic cooking essentials and everything you need for a getaway. Parking right behind the unit. Dog friendly with a fenced in yard.

Aug 18 – 25

$73 per night