
Cottage vacation 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...!

Vintage Florida Beach Cottage B
Just a short walk to the beach makes this a great beach getaway for couples or families. On your way you can stop at the Kooky Koconut for lunch, an awesome milkshake or a variety of snacks. With a totally new renovation in 2019, this unit is in updated, very clean and worry free condition. This cottage is located in a quiet residential neighborhood and a great place to relax. Common laundry on shared screened porch. Dogs allowed (extra $45 cleaning). Easy refund policy. Level 2 EV charger

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.

Clearwater Cottage Short Drive to Beach & Dunedin!
Perfectly nestled between the quaint town of Dunedin & Clearwater. Just a short drive across the bridge & you’ll be Sinking your toes into the beautiful white sandy beaches of Honeymoon Island State Park or Clearwater Beach. Enjoy Honeymoon Island natural beauty or exciting tourist attractions of Clearwater beach! Take a cruise on the dinner boats to watch the beautiful sunset. Walk or rent a bike & explore the Pinellas trail. Kayak or jet ski the Gulf. Max 5 Adult guests with government ID.

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.

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.

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.

Walk Downtown and Waterfront, Mins to Beaches
Experience modern coastal luxury in this stylish, spacious upstairs 2-bedroom cottage with beautiful decor. Steps from Main Street Dunedin. Walk to restaurants, shops, & breweries or take a short stroll to gorgeous sunsets at Dunedin's waterfront. Make the quick drive to award winning beaches, Honeymoon Island & Clearwater Beach. Pet-friendly w/ 2 king beds, a sleeper sectional, & serene treetop views. Treat yourself & book your getaway at the Barefoot Parrot by Lucky Guest.

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.

Gulfport Getaway-Close to Everything!
Take a step off the beaten path with a stay at this tropical 2-bedroom, 1-bath Gulfport Beach vacation rental! The 'Sirens Cove' is ideally situated between St Pete Beach, downtown St. Petersburg, and the quirky, vibrant Gulfport Arts District. Take a ride on our beach cruisers and enjoy the Gulfport vibe! You'll have plenty of opportunities to recharge your soul, relax, and soak up the beautiful Florida sun! 30+ Day Rentals Available!
Popular amenities for Gulfport cottage rentals
Cottage rentals with a hot tub

Pink Gulfside Cottage, Steps to Beach, Pets OK

Lemon Cottage Steps from Beach

Steps to Beach, Sleeps 6, Pets OK

Beachy Keen Cottage A only steps to the Beach

New Listing Hidden Gem 3 Bedroom Home

Heart of Safety Harbor | Hot Tub | Luxe Comfort

Sunset Beach cozy boutique cottage

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

Cottage by the Coast 2 bd - Pet Friendly

Luxury Beach Bungalow | Walk to Dining & Sunset

Perfect Location Cottage in Delightful Dunedin

Coveted Sunset Beach Rental: Beautiful 2 Bdrm

Cozy up in a French Country nest NEAR EVERYTHING

Beachy Paradise

The Cottage at Wishing Well, Gulfport

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

Yachtsman Gulf front on sand, Sleeps 6 Heated Pool

Beach Bliss Suite - New Steps to Beach and Sand

Cozy Cottage Downtown + near Waterfront

Adorable Villa 1 min to Downtown Dunedin

Beach Cottage October and November Openings!

NEW! 2BR/2BA Finest Vacation Home Steps to Beach

Cottage with Rooftop Patio & Private Beach Access

Flipper's @ Mad Beach Cottage
Quick stats about cottage rentals in Gulfport

Total vacation rentals
Explore 10 vacation rentals in Gulfport

Nightly prices starting at
Gulfport vacation rentals start at G$14,645 GYD per night before taxes and fees

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

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Wi-Fi availability
10 of Gulfport vacation rentals include wi-fi 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
- Raymond James Stadium
- Dunedin Beach
- Busch Gardens Tampa Bay
- Turtle Beach
- Coquina Beach
- Cortez Beach
- Anna Maria Public Beach
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- Gulfport Beach Recreation Area
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