Gulfport vacation rentals

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Top-rated vacation rentals in Gulfport

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

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Guest favorite

Cottage in Gulfport

4.96 out of 5 average rating, 135 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

G$24,495 GYD per night

Superhost

Home in Gulfport

4.78 out of 5 average rating, 119 reviews

The Gecko House Unit 3

Romantic little apartment next to Downtown Gulfport. It is up one flight of stairs as shown in the pics. 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 10 blocks away. 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.

Sep 22 – 29

G$17,319 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 15 – 22

G$22,944 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!

Sep 21 – 28

G$25,768 GYD per night

Superhost

Home in Gulfport

4.78 out of 5 average rating, 241 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!

Sep 6 – 13

G$16,978 GYD per night

Guest favorite

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))

Sep 16 – 23

G$23,793 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.

Jul 11 – 18

G$25,116 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$28,891 GYD per night

Guest favorite

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 1 – 8

G$25,612 GYD per night

Guest favorite

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

Nov 1 – 8

G$28,825 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.

Jan 7 – 14

G$28,031 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!

Oct 12 – 19

G$27,653 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Gulfport vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

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 vacation rentals in Gulfport

Guest favorite

Bungalow in Gulfport

4.78 out of 5 average rating, 108 reviews

Tranquil bungalow near the bay! Bikes Available.

Jun 9 – 16

G$29,986 GYD per night

Superhost

Apartment in Gulfport

4.94 out of 5 average rating, 104 reviews

Bindy’s Bungalow

Sep 30 – Oct 7

G$18,319 GYD per night

Guest favorite

Home in Gulfport

4.94 out of 5 average rating, 209 reviews

Charming Gulfport Guest Cottage

Jul 13 – 20

G$23,863 GYD per night

Guest favorite

Home in Gulfport

4.89 out of 5 average rating, 117 reviews

The Brenda Ann/Pet Friendly/Walk to downtown!

Dec 28 – Jan 4

G$40,433 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!

Aug 25 – Sep 1

G$26,687 GYD per night

Guest favorite

Guest suite in Gulfport

4.97 out of 5 average rating, 336 reviews

WATERFRONT SUITE WITH POOL

Jan 26 – Feb 2

G$36,700 GYD per night

Guest favorite

Guest suite in St. Petersburg

4.96 out of 5 average rating, 112 reviews

Charming Side Garden Suite (no cleaning fee)

Jun 17 – 24

G$20,467 GYD per night

Guest favorite

Bungalow in Gulfport

4.89 out of 5 average rating, 196 reviews

Historic Bungalow in the Heart of the Art District

Apr 23 – 30

G$46,477 GYD per night

Show all

Other great vacation rentals in Gulfport

Guest favorite

Condo in Tierra Verde

4.96 out of 5 average rating, 237 reviews

Natural Beauty on Tierra Verde, Waterfront Condo

Dec 2 – 9

G$27,393 GYD per night

Guest favorite

Cottage in Gulfport

4.97 out of 5 average rating, 67 reviews

Cozy Cottage for Lovers

Dec 11 – 18

G$23,722 GYD per night

Guest favorite

Home in Gulfport

5.0 out of 5 average rating, 28 reviews

AdorableTiny House

Oct 20 – 27

G$20,606 GYD per night

Guest favorite

Guesthouse in Gulfport

5.0 out of 5 average rating, 66 reviews

Gulf Guesthouse - king bed, 3 blocks to downtown.

Jul 1 – 8

G$28,341 GYD per night

Guest favorite

Villa in Gulfport

5.0 out of 5 average rating, 18 reviews

Cozy funky duplex with KING bed

Jan 18 – 25

G$14,347 GYD per night

Guest favorite

Cottage in Gulfport

5.0 out of 5 average rating, 8 reviews

Gulfport Breezy Cottage KING - Outdoor living too!

May 6 – 13

G$33,130 GYD per night

Guest favorite

Home in Gulfport

5.0 out of 5 average rating, 98 reviews

Peaceful Getaway Close to Amazing Beaches!

Sep 23 – 30

G$22,488 GYD per night

Guest favorite

Apartment in Gulfport

5.0 out of 5 average rating, 64 reviews

Poe's Place: In The Heart of Gulfport Art District

Sep 28 – Oct 5

G$26,336 GYD per night

Show all

Quick stats about vacation 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
G$2,091 GYD before taxes and fees

Frequently Asked Questions

Where should I stay in Gulfport?
Make yourself at home in Gulfport by choosing from our most frequently booked neighborhoods. We have over 1,800 vacation rentals in Pasadena Golf-Yacht Club, over 2,380 vacation rentals in Bayview, and over 1,800 vacation rentals in Childs Park.
Are there vacation rentals with a dedicated workspace in Gulfport?
Yes! Work meets play with ease at over 270 vacation rentals in Gulfport featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Gulfport?
Four-legged friends are welcome in Gulfport. Choose from more than 220 vacation rentals for guests traveling with pets.
Are there Gulfport vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 110 vacation homes with pools in Gulfport, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in cottage rentals in Gulfport?
Experience the best of Gulfport with our cottage rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Gulfport have a gym?
Absolutely! We offer over 10 house rentals with a gym in Gulfport. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Gulfport have wifi?
Absolutely! We offer over 30 condo rentals with wifi in Gulfport. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Gulfport have a bbq area?
Absolutely! We offer over 10 cottage rentals with a bbq area in Gulfport. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Gulfport have self check-in?
Absolutely! We offer over 20 cottage rentals with self check-in in Gulfport. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly cottage rentals in Gulfport?
Gulfport has more than 10 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Gulfport vacation rentals

Top-rated vacation rentals in Gulfport

Vacation rentals for every style

Houses

Cottages

Apartments

Popular amenities for Gulfport vacation rentals

Stay near Gulfport's top sights

Other great vacation rentals in Gulfport

Bungalow in Gulfport

Apartment in Gulfport

Home in Gulfport

Home in Gulfport

Guesthouse in St. Petersburg

Guest suite in Gulfport

Guest suite in St. Petersburg

Bungalow in Gulfport

Other great vacation rentals in Gulfport

Condo in Tierra Verde

Cottage in Gulfport

Home in Gulfport

Guesthouse in Gulfport

Villa in Gulfport

Cottage in Gulfport

Home in Gulfport

Apartment in Gulfport

Quick stats about vacation rentals in Gulfport

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Where should I stay in Gulfport?

Are there vacation rentals with a dedicated workspace in Gulfport?

Are there pet-friendly vacation rentals in Gulfport?

Are there Gulfport vacation rentals on Airbnb with pools?

How much does it cost to stay in cottage rentals in Gulfport?

Do house rentals in Gulfport have a gym?

Do condo rentals in Gulfport have wifi?

Do cottage rentals in Gulfport have a bbq area?

Do cottage rentals in Gulfport have self check-in?

Are there family-friendly cottage rentals in Gulfport?

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