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Holiday houses in Gulfport

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Top-rated holiday rentals in Gulfport

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

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Guest favourite

Guesthouse in Gulfport

4.92 out of 5 average rating, 727 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)

28 Sept – 5 Oct

$1,437 AUD total

Guest favourite

Cottage in Gulfport

4.96 out of 5 average rating, 134 reviews

The Pelicans Roost / Gulfport

The Pelicans Roost is a remodeled home, with a new fully stocked kitchen with all your cooking and entertaining needs. All new furnishings, a screened in back porch and a patio with an outside table and grill. The yard is completely fenced and lined with tropical plants and trees for your privacy. This spacious and comfortable home is clean and in a quiet neighborhood just 5 blocks from all that downtown Gulfport has to offer- the Marina,Beach,Restaurants, Shops, Fishing, Galleries and more...!

30 Oct – 6 Nov

$1,954 AUD total

Guest favourite

Home in Gulfport

5.0 out of 5 average rating, 26 reviews

AdorableTiny House

Relax and enjoy a tranquil getaway in this cozy tiny home that is minutes from beautiful beaches and an eclectic downtown. The house is one open space consisting of a dining & living room, and a sleeping area (queen bed) that is separated by a 4ft "half" wall. There is brand new separate bathroom with a large shower. The backyard has a stunning tree and large deck where you can enjoy your morning coffee, listen to the birds, or do yoga. Enjoy a fire pit on those chilly Florida winter nights.

28 Sept – 5 Oct

$1,293 AUD total

Guest favourite

Guesthouse in Gulfport

4.95 out of 5 average rating, 189 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.

25 Sept – 2 Oct

$1,441 AUD total

Guest favourite

Guest suite in Gulfport

4.92 out of 5 average rating, 449 reviews

Gulfport Studio STEPS to Beach & Restaurants

Calling all beach lovers! Fall in love with this unique Gulfport Beach Cottage! Colorful, light & bright. Located on a corner lot STEPS from popular Beach Blvd & Gulfport beach, fishing pier, eclectic Gulfport shops, cafes and everything FUN! Gulfport has artsy and quirky shops, fabulous waterfront restaurants and a thriving art scene. Gulfport is a funky community all its own. Gulfport has an Art Walk on the First Friday and Third Saturday and a Tuesday market every week. Don’t miss it!

12 – 19 June

$1,578 AUD total

Home in Gulfport

4.78 out of 5 average rating, 240 reviews

The Flamingo Flat

This is a charming freshly painted mid-century modern "Old Florida Coastal" home! Great location with off-street parking. Fully furnished covered porch with ceiling fans in very private partially fenced yard. Just a 1 mile walk or ride to Gulfport Beach and Arts District, and 3 miles to Sunset Beach on the pristine Gulf of Mexico. Two bedrooms (1 queen and 1 twin). People of ALL sizes, colors, beliefs, cultures, religions, sexes and backgrounds are welcome here as long they DO NOT SMOKE!

25 May – 1 June

$1,113 AUD total

Guest favourite

Home in Gulfport

4.88 out of 5 average rating, 144 reviews

Gecko House Unit #1

Romantic little apartment which is the lower left half of the house next to Downtown Gulfport. Here you will find many shops, restaurants, and even a dancing hall a short walk away. Enjoy live bands during the day and Karaoke at night at some of the greatest bars in Florida. Not to mention, one of the best beaches is right next door. It even contains beach volleyball nets for daily use. Take a stroll down to the pier and enjoy the sites of the marina, or enjoy a beautiful sunset at night.

20 – 27 Dec

$1,789 AUD total

Guest favourite

Cottage in Gulfport

4.97 out of 5 average rating, 64 reviews

Cozy Cottage for Lovers

Relax, reconnect and revitalize in this private, intimate cottage that has everything you need to leave the hustle and bustle behind. Surrounded by lush tropical vegetation in the shade of giant live oaks and located in the Gulfport Arts District, you're a short walk or bike ride from excellent urban parks, restaurants, live music, fashion and art boutiques, dancing at the Gulfport Casino, community theater, and a beautiful beach that looks out over sailboats moored in Boca Ciega Bay.

3 – 10 Dec

$1,552 AUD total

Guest favourite

Bungalow in Gulfport

4.96 out of 5 average rating, 150 reviews

Gulfport - St. Pete bungalow centrally located

Cozy and private apartment perfectly situated between St Pete Beaches, downtown St. Petersburg, and the quirky vibrant downtown Gulfport Arts District. This is a private apartment with 2 rooms, 1 bath, kitchenette, and patio. We live on the property in the other side of the Duplex, but your suite is completely private with your own entrance. Nature Park & bike trails: down the street! Downtown gulfport: 1mi / 3min St. Pete beach 4.6mi / 10min Downtown St Pete : 5mi / 10min

8 – 15 May

$1,427 AUD total

Guest favourite

Apartment in Gulfport

4.99 out of 5 average rating, 163 reviews

Studio- Gulfport Art District - 1 Block from Beach

Situated in the heart of Gulfport's Art and Waterfront District, this studio space is ideal for experiencing all Tampa Bay has to offer. Step outside and walk to Gulfport Beach only one short block away, experience the highly-rated restaurants and shops, or browse local arts and crafts during the weekly Tuesday Morning Market during your stay. Want to experience more of Tampa Bay? Downtown St. Pete, St. Pete Beach, and I-275 access are only ten minutes away.

28 Nov – 5 Dec

$1,602 AUD total

Guest favourite

Home in Gulfport

4.89 out of 5 average rating, 116 reviews

The Brenda Ann/Pet Friendly/Walk to downtown!

The Brenda Ann Suite is a pet friendly Private 1 Bedroom bungalow located in the heart of Gulfport, FL. You will enjoy the waterfront views as well as being just steps away from the beach, pier, Veterans Memorial Park and all of the attractions that Gulfport has to offer. You'll enjoy parking your car and not needing it again because you'll stroll our red brick streets to dinner and drinks. A perfect way to end a sun filled day at the beach!

28 Sept – 5 Oct

$1,648 AUD total

Guest favourite

Apartment in Gulfport

4.8 out of 5 average rating, 213 reviews

⭐STEPS to the Beach!! "The Nautical Escape"⭐

The "Nautical Escape" is located right in the heart of Gulfport's Waterfront District, just steps from the action on Shore Blvd and Beach Blvd! Spend the day soaking up the sun on the stunning white sand beach, meander through the funky local shops, check out the thriving art scene, or indulge in one of the many dining options Gulfport has to offer. Imagine...all these wonderful options of things to do, all right outside your front door!

17 – 24 Aug

$1,704 AUD total

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Gulfport holiday rentals

Free parking on premises

Air conditioning

Stay near Gulfport's top sights

O'Maddy's Bar & Grille147 locals recommend

Gulfport Beach64 locals recommend

Pia's Trattoria131 locals recommend

City of Gulfport Municipal Marina4 locals recommend

Stella's77 locals recommend

Habana Café32 locals recommend

Other great holiday rentals in Gulfport

Guest favourite

Guesthouse in Gulfport

5.0 out of 5 average rating, 64 reviews

Gulf Guesthouse - king bed, 3 blocks to downtown.

3 – 10 July

$1,814 AUD total

Guest favourite

Home in Gulfport

5.0 out of 5 average rating, 13 reviews

Seas the Day - Beautiful Gulfport Home

14 – 21 July

$1,648 AUD total

Guest favourite

Tiny home in Gulfport

5.0 out of 5 average rating, 11 reviews

Big Adventure in a Tiny House!!!

29 May – 5 June

$1,657 AUD total

Guest favourite

Apartment in Gulfport

4.89 out of 5 average rating, 89 reviews

Latitude 27 Marina Studio Apartment

23 – 30 June

$1,168 AUD total

Guest favourite

Home in Gulfport

5.0 out of 5 average rating, 97 reviews

Peaceful Getaway Close to Amazing Beaches!

24 Nov – 1 Dec

$1,423 AUD total

Guest favourite

Guesthouse in Gulfport

4.92 out of 5 average rating, 37 reviews

Avocado Oasis 10 mins to Beaches

11 – 18 June

$1,620 AUD total

Guest favourite

Cottage in Gulfport

5.0 out of 5 average rating, 6 reviews

Gulfport Breezy Cottage - Outdoor living too!

3 – 10 May

$1,918 AUD total

Guest favourite

Home in Gulfport

4.88 out of 5 average rating, 43 reviews

The Gulfport Sand Dollar, Walk to the waterfront

6 – 13 June

$1,461 AUD total

Quick stats about holiday rentals in Gulfport

Total rentals	460 properties
Rentals with a pool	110 properties have a pool
Pet-friendly rentals	220 properties allow pets
Family-friendly rentals	280 properties are a good fit for families
Total number of reviews	20K reviews
Nightly prices starting at	$16 AUD before taxes and fees

Destinations to explore