Vacation Rentals & House Rentals in Gulfport

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1,989 house rentals

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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

$160

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

Price per night from

$229

Beach Cottage, Old-Florida Style!

Gulfport cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$104

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

$212

Peace and Quiet in Gated Community on Boca Ciega Bay

Gulfport apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$77

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. 47 minutes

Price per night from

$240

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

$149

Great rentals within 20 miles that match your search

COZY RETREAT modern condo near Gulf of Mexico beaches

Clearwater condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Fabulous!” Owner was great! Condo is everything you need or want. Every detail is perfect. Pool was just steps away.

Price per night from

$161

Fine Waterfront Living . Steps to Beach

St. Pete Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$488

Seminole Vacation House Spacious Vacation House

Seminole house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 50 minutes

Price per night from

$107

Tranquil by Belleair Beach/Largo

Largo house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$167

Beautiful Sunkst Cottage Bradenton Beach - AMI-Tropical Setting - Heated Pool

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$516

Private Waterfront Home, Resort & Marina Sleeps 18

Madeira Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 18

Price per night from

$153

1BR Pool View Condo in Clearwater Florida

Clearwater condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Outstanding as usual.” Second year staying at the Avalon. Great location! About 5 miles to the beach one way, and about 6.5 the other way. Everything needed is within walking distance. Pool is great if the beach isn't your thing. Excellent workout room.

Price per night from

$104

SPECIAL! $650 8/24 - 8/31. PRIME LOCATION AMI DIRECTLY ON BEACH HEATED POOL

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$287

Charming 1 Bedroom Condo on Gulf of Mexico Beach

Indian Shores condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$287

Pirates Pointe Resort 1 Bedroom

Ruskin cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 12 minutes

Price per night from

$183

BEACH FRONT CONDO *** MADEIRA BEACH

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$368

4 Minutes From Beach, Beds for 6!

St. Petersburg apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$105

Beautiful Island on Boca Ciega Bay & The Beach

St. Petersburg condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$115

Amazing Sunset over Clearwater Beach

Clearwater condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$230

Luxury waterfront Condo Rooftop Terrace

Clearwater house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$568

3 Bed/2 Bath Handicap Madeira Beach Gulf side Condo w/ Heated pool and Spa

Madeira Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$344

Affordable Luxury Mediterranean Style Resort in Clearwater

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$96

440 West Condos 508-S Gulf Front Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

Price per night from

$368

Intercoastal 209 Water View from this Charming Condo

Indian Shores apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 50 minutes

Price per night from

$5,195

Surfside Condos 303 Beachfront Condo

Clearwater apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 50 minutes

Price per night from

$1,228

Bayside Condos 18 Just Updated Waterfront

Clearwater apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 50 minutes

Price per night from

$126

Viewing 38 of 1,989
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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