Vacation rentals with outdoor seating in Gulfport

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Top-rated outdoor seating rentals in Gulfport

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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)

Sep 8 – 15

G$23,769 GYD 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

G$22,941 GYD per night

Guest favorite

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!

Jun 26 – Jul 3

G$25,765 GYD 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

G$25,815 GYD 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

G$26,186 GYD per night

Guest favorite

Tiny home in Gulfport

4.95 out of 5 average rating, 142 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.

Jul 14 – 21

G$28,921 GYD per night

Guest favorite

Apartment in Gulfport

4.99 out of 5 average rating, 166 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.

Apr 16 – 23

G$27,121 GYD per night

Guest favorite

Guest suite in St. Petersburg

4.96 out of 5 average rating, 111 reviews

Charming Side Garden Suite (no cleaning fee)

This private guest suite is centrally located between the beaches on Treasure Island and the nightlife, shopping, and dining of the Grand Central and Pier districts, along the Sun Runner public transportation route. The suite includes one bedroom, bathroom, and kitchenette, separated from the main house, with a private entrance through the side garden. Come enjoy your morning coffee in the garden, and all that St. Petersburg has to offer.

Jun 17 – 24

G$20,331 GYD per night

Guest favorite

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!

Aug 22 – 29

G$27,159 GYD per night

Guest favorite

Guest suite in Gulfport

4.97 out of 5 average rating, 336 reviews

WATERFRONT SUITE WITH POOL

PLEASE READ THE LISTING and some reviews before booking, and ask questions...we love questions! . 'Like a private retreat on the water'. This is a Private Suite plus use of shared areas, pool, etc, IN A SHARED HOME, close to downtown Gulfport and convenient to all of Tampa Bay. Room 1 has a queen bed. Room 2, a double. The comfy bath features a ceiling fan and massage jets. The suite is all yours...not shared with other guests.

Apr 18 – 25

G$36,695 GYD per night

Guest favorite

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

G$45,514 GYD per night

Guest favorite

Tiny home in Gulfport

4.94 out of 5 average rating, 108 reviews

Beautiful Gulfport Container Home

Bright, clean and fresh container home nestled in a great central neighborhood. < 2mi from downtown Gulfport (fantastic food and shops and beach) < 4mi from award winning St Pete Beach ~ 1mi from multiple grocery stores < 1mi from the new Sun Runner bus and Pinellas Trail < 6 mi from Downtown St Petersburg and the all new St Pier which is a must visit for all ages.

Dec 28 – Jan 4

G$20,243 GYD per night