
Cottage holiday rentals in Gulfport
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Top-rated cottage rentals in Gulfport
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Walk to beach shops food drinks “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, private full bath, kitchenette, sofa sleeper, large back yard with fire pit, bbq grill, beach chairs, wagon and cooler. Zoning permits 2 people per bed only and one on futon. All guests must be listed on the reservation. No Pets allowed. Florida State License # DWE6215889

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...!

Pass-a-Grille Historic Cottage Unit 1
PASS-A-GRILLE HISTORIC COTTAGE UNIT 1 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 1 - 1 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 patio area w/ BBQ grill. Private parking for 1vehicle on premises.

Family Friendly Beach Cottage in Madeira Beach, FL
Mad Beach Cottage is a single family home in the Surf Song Resort on Madeira Beach 60 flip-flop steps to SAND! No streets, boardwalks or stairs! You'll enjoy a heated pool, 3 Weber grills, shuffleboard and sundeck with lounge chairs for gazing at spectacular sunsets every night. It's located across from famous John's Pass Fishing Village Boardwalk for shopping, dining, ice cream, coffee, live music, brew pubs, dolphin/fishing/sunset/pirate boat cruises, wave runner/kayak rentals. 5* LOCATION!

Wonderful 2-Br, 2 Bath Cottage near the river.
Welcome to my little cottage in the city. The house was built in 1926 but has been fully remodeled with modern style, while keeping the charm of an older home. Even though it's close to everything Tampa has to offer, it still has the feeling of that little, quiet neighborhood near the river. This is my get away home. I love the front porch to sit on with a cold beverage and watch neighbors stroll by walking their dogs. The river park is very close by which is a nice walk from the cottage.

Artsy guest house; near downtown w/ private patio
This uniquely decorated guest house is a private oasis with a lovely, private patio. The house is decorated with Latin American art from the owner's collection & travels. Only 11 blocks to downtown and very close to grocery stores, art galleries and all the night light life St. Pete offers. The home has a full kitchen and a very comfortable bedroom for one or two people. A perfect location for those that want to experience a comfortable and relaxing place. Only 12 block walk to Tropicana.

BEACH! Sunny Escape! Steps 2 Famous Beach w/2 Bike
Welcome to your island beach escape! This charming coastal abode boasts all the island vibes you need for a relaxing getaway. Enjoy the quaint historic village (5 houses wide) while being just steps away from the most beautiful beach in Florida! Take a stroll through the picturesque streets of Pass A Grille and soak up the old beach charm. The rental home has hardwood floors, a screened-in porch, and a sun patio, 2 bikes to cruise around the area! open-concept kitchen + bar and smart TVs.

Luxury Beach Bungalow | Walk to Dining & Sunset
Escape to paradise at Sunshine Escapes! Welcome to #MangoIRB, nestled in the heart of Indian Rocks Beach. IRB is a hidden gem radiating a whimsical, small-town charm that evokes nostalgic memories of carefree childhood summers by the shore. Just ✌🏽 blocks away, the Gulf of Mexico beckons, offering pristine fluffy sand and unforgettable sunsets. As the sister cottage of Coco, #MangoIRB invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect beach getaway awaits!

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.

Bay Lake Cottage
You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake.Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dogs okay, sorry no cats, pet fee $50.

Adorable Cottage, Pet friendly, near beach & DT
The Cottage is a beautiful, comfy, clean, peaceful home where you will feel just at home, in the hearth of St Pete. It is in a great location, safe & quiet neighborhood, easy-to-access, just a short drive or bike ride away (5-10 minutes) to many good restaurants, grocery stores, museums, library, coffee place, breweries, hospitals, bars and night clubs in downtown & sandy white beaches. Jumped in the sun runner or public transport to downtown or beaches. Perfect for long stay.

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.
Popular amenities for cottage rentals in Gulfport
Cottage rentals with a hot tub

Harbor Oasis | Hot Tub | Private | Lush Backyard

Tiki Cottage Sleeps 6, Pets OK, Steps to Beach

Pink Gulfside Cottage, Steps to Beach, Pets OK

Steps to Beach, Sleeps 6, Pets OK

Lemon Cottage Steps from Beach

Beachy Keen Cottage A only steps to the Beach

Sleep 7 Steps to Beach Pets OK Real Beach Cottage

Corner Cottage Sleeps 5, Steps to Beach, Pets OK.
Pet-friendly cottage rentals

Cool Breeze Cottage by the Bay in South Tampa

Perfect Location Cottage in Delightful Dunedin

Vintage Florida Beach Cottage B

Cozy up in a French Country nest NEAR EVERYTHING

Beachy Paradise

The Cottage at Wishing Well, Gulfport

Walk Downtown and Waterfront, Mins to Beaches

ALL NEW! Coral Sands II ~Coastal Modern 2/2 IRB
Private cottage rentals

Coquina Cove Studio #3 Heated Pool & Steps to Sand

"Sweet Harbor Cottage" Walk to Downtown

Beach Cottage October and November Openings!

Coveted Sunset Beach Rental: Beautiful 2 Bdrm

Safety Harbor Cottage

🏡Cottage near Clearwater & Belleair Beaches🏖🌴☀️

Endless Summer Cottage 2

Cheerful Coastal Cottage Close to Beach
Quick stats about cottage rentals in Gulfport

Total holiday rentals
Explore 10 holiday rentals in Gulfport

Nightly prices starting at
Gulfport holiday rentals start at $91 SGD per night before taxes and fees

Verified guest reviews
Over 1,230 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Wifi availability
10 of Gulfport holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Gulfport rentals

4.9 Average rating
Gulfport stays are highly rated by guests – averaging 4.9 out of 5!
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- Anna Maria Island
- Siesta Beach
- Crescent Beach
- John's Pass
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Dunedin Beach
- Turtle Beach
- Coquina Beach
- Cortez Beach
- Lido Key Beach
- Anna Maria Public Beach
- Vinoy Park
- Amalie Arena
- Bean Point Beach
- Jannus Live
- Gulfport Beach Recreation Area
- ZooTampa at Lowry Park
- North Beach
- River Strand Golf and Country Club
- Adventure Island
- Tampa Palms Golf & Country Club
- Splash Harbour Water Park
- Honeymoon Island Beach




