Cottage vacation rentals in Gulfport

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Top-rated cottage rentals in Gulfport

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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$24,492 GYD per night

Guest favorite

Cottage in Treasure Island

4.97 out of 5 average rating, 150 reviews

Peacock Beach Cabana beach in 100 steps

Escape to a cozy retreat! The Peacock Beach Cabana at The Mermaid Beach Cottages, in Treasure Island is a bright 1938 Florida style boutique cottage. Professionally remodeled and decorated. This cabana offers accommodations for two guests. It is located 100 steps from the beach and walking distance to restaurants, beach bars and live music. No detail has been overlooked and we hope you enjoy our little piece of We are also 1.5 hour drive from Walt Disney World and 45 minutes from Busch Gardens.

Mar 29 – Apr 5

G$41,632 GYD per night

Guest favorite

Cottage in St Pete Beach

4.95 out of 5 average rating, 109 reviews

Pass-a-Grille Historic Cottage Unit 2

PASS-A-GRILLE HISTORIC COTTAGE UNIT 2 A fully renovated historic beach cottage located in beautiful Pass a Grille, Florida. Steps from the Gulf of Mexico and Boca Ciega Bay. This is a duplex; Unit 2 - 2 bedroom/1 bath. Household linens, towels, cookware & dishes provided. Appliances include; dishwasher, washer/dryer, flat screen TVs and wi-fi. Vintage-style tiled bathroom and shower. High end window shades on all windows. Front and back patio area w/ BBQ grill. Private parking for 2 vehicles.

Jul 27 – Aug 3

G$75,918 GYD per night

Guest favorite

Cottage in Madeira Beach

4.91 out of 5 average rating, 113 reviews

Flipper's @ Mad Beach Cottage

Flipper's at Mad beach is a few steps away from the sugary sands of Madeira Beach, and close by the famous John's Pass Village & Boardwark where shopping and entertainment is always great. Completely renovated with light porcelain tile, nice furniture, queen bed with memory Thempur-Pedic mattress, exquisite modern shower, tall kitchen cabinets with plenty of storage. Huge private paved fenced backyard with gazebo, great for entertainment and outdoor grilling. You will love the beach decor.

Aug 12 – 19

G$25,193 GYD per night

Guest favorite

Cottage in Gulfport

4.95 out of 5 average rating, 235 reviews

Gulfport Cottage 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 23 – 30

G$38,818 GYD per night

Guest favorite

Cottage in Indian Shores

4.95 out of 5 average rating, 110 reviews

OPEN! Beautiful Beachfront Cottage on the Water

Renovated, romantic 1937 beach front cottage. Last of its kind in the quiet family setting of Indian Shores Florida, halfway between Clearwater Beach and Treasure Island/John's Pass. Truly an "Old Florida" experience with original pine floors, Florida room and covered porches, as well as updated kitchen and bathroom. This house, uniquely built near ground level, allows it to be waterfront on the beach while shaded by huge pine trees. You won't find a more tranquil setting on the beach.

Oct 30 – Nov 6

G$92,453 GYD per night

Guest favorite

Cottage in Indian Rocks Beach

4.93 out of 5 average rating, 178 reviews

Kooky Coconut Cottage, Indian Rocks Beach

Coconut Cottage only steps away from the beautiful beaches of Indian Rocks Beach. 2 bedroom,1 bath. The entire cottage has been renovated. Next door to the local famous Kooky Coconut Cafe. Perfect for couple, friends or small families. ONLY 3 GUESTS ALLOWED. NO sleeping on the sofa ALLOWED. If you bring more then 3 guests you will be charged $100.00 surcharge per night per extra guest. Due to cleaning restriction we DO NOT allow cooking with CURRY or FISH OIL in the cottage.

Apr 21 – 28

G$37,194 GYD per night

Guest favorite

Cottage in Madeira Beach

4.8 out of 5 average rating, 163 reviews

20% OFF Quaint Madeira Beach Cottage w Heated Pool

Enjoy a Gulf vacation in a private beach cottage located directly across the street from the beach. In less than a one minute walk from your doorstep you will be enjoying the sun on the white powdery sands of Madeira Beach. Our quaint resort grounds are meticulously taken care of and beautifully landscaped. You can swim in the large heated pool with plenty of seating and lounge chairs. A quiet shaded area with barbecue grills and tables are available to prepare and enjoy a nice meal.

Dec 13 – 20

G$29,014 GYD per night

Guest favorite

Cottage in St. Petersburg

4.87 out of 5 average rating, 142 reviews

Beachy St. Pete Cottage Retreat!

Fully immerse in a private oasis at this beachy cottage. Centrally located to Downtown St. Pete, all Gulf beaches, and surrounded by excellent shops, local restaurants, bars, and craft breweries, you can enjoy all this amazing city has to offer or bring some of that culture back to enjoy at home! Eclectic accents include unique artwork scattered throughout the home, and an emphasis on furniture with a modern/beachy esthetic. We can’t wait to welcome you to our stylish beach cottage!

May 10 – 17

G$25,239 GYD per night

Guest favorite

Cottage in Largo

4.94 out of 5 average rating, 124 reviews

Fall special 3rd night free! “The Sweet”

Cozy, romantic, 1 king bed, super cute and super sweet! Just a short walk to beautiful Indian Rocks Beach, nature parks with trails, shopping, orange grove, and many restaurants and fun beach bars! Guests have private entrance, full bath, laundry facilities, large back yard with fire pit, bbq grill, beach chairs and cooler. With each stay guests receive a mini super rummy Island Rum Cake and a gift certificate PJ's Oyster Bar! **Fall Special stay 2 nights get 1 free**

Mar 13 – 20

G$28,270 GYD per night

Guest favorite

Cottage in Gulfport

4.99 out of 5 average rating, 257 reviews

Gulfport Art District - One Block From Beach!

Welcome to Uncle Finley's! Situated in the heart of Gulfport's Art and Waterfront District, This cottage listing is for unit A of the duplex. 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.

Oct 1 – 8

G$34,870 GYD per night

Guest favorite

Cottage in Treasure Island

4.91 out of 5 average rating, 114 reviews

Historic Holly House on Treasure Island

This charming Beach Cottage in the Coney Island area of Treasure Island is nestled among a rare set of Key West Style beach cottages only STEPS to the beach! This awesome beach cottage, known as The Historic Holly House, has some unique history. In 1961 the New York Yankees rented out all the cottages in this Coney Island area for spring training. This cottage was the one the Home Run King Roger Maris stayed in before he went on to hit 61 home runs that season.

Sep 25 – Oct 2

G$42,932 GYD per night