Vacation Rentals & House Rentals in Gulfport

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2,157 house rentals

The Lovely Guesthouse

Gulfport house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$115

Flamingo Cottage: Romantic Tropical Retreat in Gulfport Waterfront District

Gulfport cottage

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$114

Palm Cottage:Vintage Tropical Hideaway in the Waterfront District

Gulfport house

2 bedrooms / 1 bathroom / sleeps 6

“Palm Cottage” Exceeded our expectations! Absolutely the perfect location. Palm Cottage was adorable, clean, well stocked with supplies, and sooo relaxing. Restaurants and beach an easy walk on brick streets. So much charm. Will definitely be back.

Price per night from

$159

NEW - Desirable Art District

Gulfport bungalow

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$109

Gulfport Waterfront Mid-Century Modern Masterpiece

Gulfport house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 42 minutes

Price per night from

$366

Charming Gulfport Guest Cottage

Gulfport house

2 bedrooms / 1 bathroom / sleeps 5

“Loved staying in this Gulfport Guest House!” What a wonderful experience not just for us but for our dogs too. We truly felt like we were in a resort. The furniture and artwork is just beautiful. Hosts Daniel and Michael are so friendly and welcoming. We were even lucky enough to experience Daniel as the DJ at manatees in Gulfport so much fun. I highly recommend this wonderful Gulfport property book now you'll never be disappointed!

Price per night from

$92

The Sand Dollar: Historic Charm Meets Beach Chic in the Waterfront District

Gulfport apartment

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$126

Dolphin House at Gulfport's Pier

Gulfport house

3 bedrooms / 2 bathrooms / sleeps 8

“Great time at Dolphin House” We went to Florida for my brother's wedding and needed to find a place to stay that would accommodate 7 people (2 kids included) and this was perfect. The bedrooms were a great size; very clean; the house is laid out nicely so that you are not all grouped together. There are two living rooms with TVs which helped our family so we weren't on top of each other the entire trip. We went over 4th of July weekend and the location ended up being perfect. We walked 2 mins down to the beach and watched an amazing fireworks display! It was also a close drive to St. Pete beach where my brother was staying. Overall, great experience.

Price per night from

$201

The Beach House - Gulfport Beach, Florida - Weekly & Monthly Discounts

Gulfport house

2 bedrooms / 1 bathroom / sleeps 7

Price per night from

$269

Strickland's Calypso Beach House - Gulfport (St. Petersburg) FLORIDA

Gulfport house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 57 minutes

Price per night from

$458

3 bedroom, 2 bath home with a pool and Florida room, near Gulfport Waterfront

Gulfport house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$245

Beach Cottage, Old-Florida Style!

Gulfport cottage

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$103

Fish Camp - Efficiency in Gulfport Waterfront District

Gulfport apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$119

Your Hidden Private Gem "La Playa Azul"

Gulfport condo

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$143

Peace and Quiet in Gated Community on Boca Ciega Bay

Gulfport apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$63

Tangerine Dream, Pet Friendly, Fenced Yard

Gulfport bungalow

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$115

Harbor Mist: Fresh & Friendly in Marina District + Private Outdoor Oasis

Gulfport house

2 bedrooms / 1 bathroom / sleeps 6

“Quiet and cozy” We wanted a vacation rental close to my Mother's home. The property was comfortable and located in a cute neighborhood. We walked to nearby restaurants, shopping and a quite beach. There was a nice playscape at the beach. There was also a boat dock very close and we went on a dolphin cruse that took us to a nearby island we could explore, I think it was Sand Key island, it was wonderful for us and the kids. There was also a bike trail nearby "Pineallas", you could ride for miles. Not far was St Pete's beach and shopping. The house was charming, nicely decorated and fully equipped with linen and dishes. They also had a grill on the deck and little pond in the backyard. There was also a video library to choose from, something for everyone.

Price per night from

$149

Price per night from

$195

SunKissed - (heated) POOL HOME

Gulfport house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 14 minutes

Price per night from

$358

Spacious Family Friendly 3 bd/ 1ba with Huge Heated Pool, Fire Pit and more!

Gulfport house

3 bedrooms / 1 bathroom / sleeps 8

Price per night from

$298

Private and Gracious Florida Cottage

Gulfport house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$115

"Lovers Den" Your Hidden Private Gem

Gulfport condo

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$91

3/2 in Gulfport yard, Wifi, pets welcome - Casa Sol

Gulfport house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$149

Luxe Mid Century Modern near beach and Downtown

Gulfport house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$274

Great rentals within 20 miles that match your search

Waterside at Coquina Key

St. Petersburg condo

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$143

Sunsets+fishing+2bikes+Beachhouse Getaway fun! N1

St. Pete Beach bungalow

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 31 minutes

Price per night from

$441

Family friendly condo on the beach - Ocean Sands

Madeira Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$133

Banana Breeze/Lazy Lemon Cottage-2 heated Pools, Clearwater Beach,Gulf of Mexico

Clearwater cottage

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 55 minutes

Price per night from

$131

Surfside Condos 204 Beachfront Condo

Clearwater apartment

3 bedrooms / 2 bathrooms / sleeps 10

“Surfsude Condo 204” The view was great....the condo was roomy enough for our family. Everything was good except needed more instruction on using TV in living room. Also needed more electrical outlets. We would stay here again. Had a great time.

Price per night from

$737

Bay Breeze House Waterfront home with pool

Clearwater house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$291

Island Key Condos 303 Large Balcony overlooking Bay

Clearwater apartment

3 bedrooms / 2 bathrooms / sleeps 6

“Amazing” We were first time renters and we're very anxious. We couldn't have been more impressed. There was so much space and the condo was spotless. The area was quiet and the apartment block was spotless. The pool was heated and spa was hot. The staff in the office were so nice and helpful made us feel really valued. Will definitely be returning and would highly recommend the rental company.

Price per night from

$151

Lovely one story home on the water

Palmetto house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 7 minutes

Price per night from

$458

Paradise Awaits on St. Pete Beach! **FULL Gulf Front** Panoramic Ocean Views!

St. Pete Beach condo

2 bedrooms / 2 bathrooms / sleeps 5

“It's the best beach in Florida!” If you want to stay at a plush yet reasonably priced condo on the water, Vistas on the Gulf is the place for you! Very clean facility with pool, hot tub, exercise room and oh what a view! The staff is great too. We've stayed one week and most recently last fall two weeks...I didn't want to go home...this was it!

Price per night from

$385

3BR/2BA Beautiful Beach Location

Indian Rocks Beach apartment

3 bedrooms / 2 bathrooms / sleeps 8

“Amazing location, just perfect!” The location of this condo is absolutely perfect. Access to the beach, lots of little shops, restaurants near. Nice pool to enjoy when you are not on the beach. It was clean and super nice to have a washing machine and dryer available. Went home with clean clothes! Would definitely recommend this to friends and family, and hope to go back sometime!

Price per night from

$229

Spectacular Beach House With GulfView Only Steps to a Pristine Beach

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$687

Desirable Resort Style Condo in Clearwater

Clearwater apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$86

Beautiful waterfront apartment with stunning views

Madeira Beach apartment

1 bedroom / 1 bathroom / sleeps 2

“Brilliant location and very friendly hosts.” This is a condo with a kitchen/diner and lounge area downstairs and a bedroom (and very comfy bed) and bathroom upstairs. There is a balcony outside the bedroom, which faces east so you have the beautiful sunrise. The condo is well equipped, and you have the use of the pretty patio/garden at the rear which is right on the intracoastal and which is shared with the hosts. There is the usual abundance of wildlife including dolphins, and a very pretty outlook. The beach is three or four minutes walk away, along with local shops and restaurants. We loved our stay there and would certainly go back. The hosts are very friendly and amenable.

Price per night from

$119

2-Unit Beach to Bay Cottage...NOT Grandma's place!...100 feet to beach!

Bradenton Beach cottage

3 bedrooms / 2 bathrooms / sleeps 8

“Perfect Beach House” We loved the quaint little duplex. The house was clean and ready for us when we arrived. Tim was a dream to work with. The A/C one of the units went out while we were there, and he had someone there first thing to take care of it. We will definitely be looking to rent from Tim again in the future.

Price per night from

$164

Viewing 38 of 2,157
rentals in Gulfport

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Top Destination reviews

The Lovely Guesthouse
Great place to relax

The Lovely Guesthouse was a great place to Relax. It had all the things we needed. 5 minute drive to the beach too. Also close to grocery stores and restaurants. Stephanie B was a very nice host. She checked on us when were having a thunderstorm and had lost power. We will definitely stay there again! Thanks Stephanie!see more
Flamingo Cottage: Romantic Tropical Retreat in Gulfport Waterfront District
Excelent place to scape

I had a wonderful time. The cottage has everything to make you feel like home. Gulfport is a very peacefull place. On the afternoon, when the sun is going down, you can walk near the beach and watch the sky beautiful colors and' if you are luky, the dolphins. … see more
The Sand Dollar: Historic Charm Meets Beach Chic in the Waterfront District
Just love this place!!!

This winter we will be returning to the Sand Dollar for our 4th time! We look forward to our winter break at the Dollar every year. It feels like a second home for us. Cute, Clean and quiet!!! Beautiful backyard, private fencing, Cozy and bright. So close to downtown Gulf Port - easy walking distance - and the markets, restaurants and shops. The water front is right at the end of the street. Clam Bayou is a nice walk from the house with it's marina and walking trails. We have stayed at many different rentals in the past - but have found that the Sand Dollar is our "Go To" place for our yearly breaks. Plus the owner is always friendly and makes sure that our stay is a terrific one. Best of the Best for us!!!see more
Dolphin House at Gulfport's Pier
Wonderful home walking distance to beach & yummy food

We stayed for three nights in July 2013 and had a wonderful time. The home has plenty of room and is very cozy! We enjoyed walking to the beach & restaurants! It was a fun family reunion! … see more
Palm Cottage:Vintage Tropical Hideaway in the Waterfront District
Wonderful Palm Cottage

We had a fantastic time in Gulfport this Thanksgiving! Palm cottage was a great home and a fantastic location. Very clean and nice! … see more
Charming Gulfport Guest Cottage
Joy & Angie’s 2020 Beach Vacation

Daniel & Mike were excellent hosts! The accommodations were GORGEOUS! The pictures do not do it justice! It was clean and had everything and more we could ask for! In good area, felt safe, even at night! Short walk to down town Gulfport and beach. Very quaint little town. Close to other towns and beaches! Will be staying there again, (probably every time from now on)!see more

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