Vacation rentals in Gulfport

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Top-rated vacation rentals in Gulfport

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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...!

Aug. 12 – 19

$211 CAD per night

Guest favourite

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.

Oct. 10 – 17

$182 CAD per night

Guest favourite

Guest suite in Gulfport

4.92 out of 5 average rating, 452 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!

Jul. 31 – Aug. 7

$199 CAD per night

Guest favourite

Home in Gulfport

4.88 out of 5 average rating, 145 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.

Oct. 30 – Nov. 6

$225 CAD per night

Guest favourite

Apartment in Gulfport

4.92 out of 5 average rating, 396 reviews

Bohemian Treat

This boutique-sized, two-room haven will tickle your senses with its quietly exhuberant art & design. It has low east/west light & a tiny private seating space just out the door. ...wander my tropical garden, have your coffee in the gazebo, or take a moment's walk to Gulfport's Art Village with its many restaurants, charming boulevard & cozy little bay beach. (or, if you prefer a high-ceilinged studio, look up my other listing "Graceful Haven". It's also on my property))

Aug. 8 – 15

$183 CAD per night

Guest favourite

Tiny homes in Gulfport

4.95 out of 5 average rating, 141 reviews

Pelican's Nest - Pet Friendly

The Pelican's Nest is a cozy tiny home that has been remodeled with you in mind. Enjoy the beachy vibes inside the home or relax outside where you can connect to nature with your private yard. Enjoy a fire or dinner on your outdoor dining table. Have your pet staying with you? No worries! They are welcome here. Located a mile from Gulfport's beach blvd. Where you can shop, dine, or stroll the beach. 6 miles away will take you to the famous St Pete Beach or the St Pete pier.

Aug. 1 – 8

$215 CAD per night

Guest favourite

Bungalow in Gulfport

4.96 out of 5 average rating, 154 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

Aug. 24 – 31

$173 CAD per night

Guest favourite

Home in Gulfport

4.9 out of 5 average rating, 101 reviews

Romantic Tropical Retreat in Waterfront District

Welcome to Flamingo Cottage, located in the heart of Gulfport's Art and Beach district. This charming cottage is perfect for a romantic getaway or a leisurely vacation. This a 1 bedroom, 1 bath retreat is just one block from Gulfport Beach. Walk to everything in Gulfport – shops, restaurants, bars, Gulfport Beach and the Tuesday market and other festivities. Access the shared laundry through a door from the kitchen, small fenced courtyard out the front. King bed

Sep. 4 – 11

$232 CAD per night

Guest favourite

Apartment in Gulfport

4.99 out of 5 average rating, 165 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.

Nov. 13 – 20

$201 CAD per night

Guest favourite

Apartment in Gulfport

4.8 out of 5 average rating, 214 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!

Jul. 22 – 29

$216 CAD per night

Superhost

Bungalow in Gulfport

4.9 out of 5 average rating, 124 reviews

Jackie O Suite/1 block to shops/Restaurants

The Jackie O is an elegantly decorated apartment with-in walking distance to the beach and downtown amenities of Gulfport FL. Enjoy local jazz music in town and Tuesday markets for finding unique items. The locals will make you feel like one of them and the beach will soothe your soul. We try to provide everything you will need for your comfort and will respond immediately with any issues or concerns.

Aug. 21 – 28

$199 CAD per night

Guest favourite

Home in Gulfport

4.99 out of 5 average rating, 107 reviews

The Boho - 2BR Gulfport Waterfront District House

Boho inspired cottage in the heart of the Gulfport Waterfront District. Steps away from Gulfport beach, restaurants, and nightlife. Enjoy strolling along Beach Boulevard where you'll find local coffee shops, ice cream parlors, Gulfport brewery, and eclectic shops. Relax in the comfort of your backyard oasis or enjoy some fun in the sun with the best Gulfport has to offer right outside your back door.

Dec. 22 – 29

$346 CAD per night