Vacation Rentals & House Rentals in Gulfport

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1,977 house rentals

The Lovely Guesthouse

Gulfport house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$115

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

Gulfport Waterfront Mid-Century Modern Masterpiece

Gulfport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$367

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

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

Gulfport house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$458

Price per night from

$229

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

$92

Your Hidden Private Gem "La Playa Azul"

Gulfport condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$144

Peace and Quiet in Gated Community on Boca Ciega Bay

Gulfport apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$69

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

Price per night from

$149

Responds fast! avg. 41 minutes

Price per night from

$187

Price per night from

$315

Price per night from

$298

"Lovers Den" Your Hidden Private Gem

Gulfport condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$91

Great rentals within 20 miles that match your search

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

$54

Brightwater Point 105 Grand Water Views

Clearwater apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Perfect in every way!” Perfect location; beautiful condo; everything we needed. If I could have a negative comment it would be that the couch was a little uncomfortable. I can't say enough about how perfect; we have made arrangements to return!

Price per night from

$233

Bay Breeze House Waterfront home with pool

Clearwater house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$541

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

$280

Villas of Clearwater Beach 2B Renovated condo that is just Steps to the beach an

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$210

Lovely one story home on the water

Palmetto house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$458

Panoramic Ocean Views 2

St. Petersburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Great place to stay” I stayed in this condo last February. It is calm, bright and perfectly clean. The balcony and the view on the water are outstanding! In addition to that, Sabina is perfectly organized, answered all the question I had and made sure I was feeling perfect. I definitely recommand it!

Price per night from

$212

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

$457

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

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

3 bedroom, 2 bath home, just steps to the beach

Treasure Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“What a great week we had” We recently had a family reunion at this beach house. There were eight of us and there was plenty of room. The house was a wonderful place and we really enjoyed morning coffee around the island in the kitchen and s'mores in the evening on the back deck around the fire pit. Several times we grabbed a glass of wine and walked to the beach to watch the sunset and even saw a few dolphins. The area seemed to have a lot of events happening nearby, sand sculptures on the beach, shopping at a restored fishing village with several unique shops, bands on the sands and fireworks. The oversized wrap around deck added extra room to what already felt like a spacious house. The house is beautiful and we look forward to vacationing there again.

Price per night from

$458

Tampa TreeHouse

Tampa house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

“Perfect Vacation Home!” This is the perfect vacation rental!! Clean, comfortable and well furnished. Close to beaches, entertainment and dining. The owner has all the bases covered and goes the extra mile to help with anything you need. I highly recommend this property for your vaction and am already planning our 2015 stay! Thanks again Javier!

Price per night from

$423

Serendipity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,260

Luxury Water Front Condo - Intercoastal Waterway

Treasure Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Exceptional” We just returned from a 4 week stay at another/similar condo in this same building, same owner. The unit was clean, comfortable, spacious and located in close proximity to everything we needed (i.e. Beach, supermarket, restaurants, shops). John (owner) was more than accomodating with helping us get online (wifi) and being flexible with our schedule. The Gulf view was great and the building was relatively quiet considering it was Spring Break month. Will definitely be returning.

Price per night from

$240

Ultimate St Pete Beach Front Rental Condo #101

St. Pete Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Comfort and Convenience” We only stayed for 2 nights, but would not hesitate to rent here again. The location on St. Pete Beach was perfect. Even though there was temporary beach dredging going on in front of the condo this did not ruin our stay. The access to the beach was very convenient and there were less people and more room at this end, away from the larger hotels. The accomodations were just as pictured. Beautifully updated - everything clean as could be. All the conveniences were there and in working order. We look forward to the next time we can book a visit.

Price per night from

$401

A Pearl of a Beach Home - now with luxury Saltwater heated pool and hot tub

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“out standing place to stay” I would/will stay here again when we come back down. Everything is top notch and the home has everything you need. We enjoyed the pool and hot tube, used it every night. Mike and Lesley are very easy to work with and do anything to make things go smoothly.

Price per night from

$476

*** BEAUTIFUL SPACIOUS CONDO IN SUNNY FLORIDA ***

Indian Shores apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Lovely vacation on the Gulf Coast” Jill and Peter were very friendly, accommodating hosts. They made sure we had everything we needed and gave us all the information to make us feel like locals to the Indian Shore. The apartment is impeccably clean and spacious. I would recommend this accommodation to anyone looking for a relaxing, sunny vacation on the Gulf Coast!

Responds fast! avg. 3 hours 20 minutes

Price per night from

$95

Luxury Penthouse Condo Overlooking Beach/Gulf

Treasure Island apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Review” The place was amazing! Perfect weather and a great week! Thank you so much for the opportunity! We had the best week!

Price per night from

$286

Panoramic ocean views 1

St. Petersburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Excellent Holiday Getaway!” My husband and I stayed at this beautiful condo for a week in October 2013 and it was absolutely beautiful. It was exactly what we were looking for. Beautiful birds to see right at your door step. This luxury condo is very close to downtown which was good for night life and great food. I would recommend this condo to anyone. Also the owner Sabina was very welcoming which made us feel as if we were right at home!

Price per night from

$212

"Something Fishy" Beach Front Condo & Sunset Views

Indian Rocks Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$166

Viewing 38 of 1,977
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
Harbor Mist: Fresh & Friendly in Marina District + Private Outdoor Oasis
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.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

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