Cottage vacation rentals in Gulfport

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Top-rated cottage rentals in Gulfport

Guests agree: these cottages are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Indian Rocks Beach

4.9 out of 5 average rating, 286 reviews

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 Cooky Coconut 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

Top guest favorite

Cottage in Pass-a-Grille Beach

4.97 out of 5 average rating, 144 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.

Guest favorite

Cottage in Madeira Beach

4.84 out of 5 average rating, 128 reviews

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!

Top guest favorite

Cottage in Dunedin

4.96 out of 5 average rating, 205 reviews

Adorable Dog-Friendly Cottage in Quaint Dunedin

Discover a charming 1920's cottage nestled in the heart of Dunedin, 3 blocks from the water and downtown. This delightful cottage is ideally located 2 blks from the Pinellas Trail, the Fenway Hotel, and the Blue Jay's stadium. Surrounded by lush greenery, the cottage boasts a private outdoor space perfect for you to enjoy your coffee. Inside, you'll find a sunny kitchen, a spacious living and dining area, and comfortable beds to ensure a wonderful stay. Come and enjoy a memorable stay here!

Guest favorite

Cottage in Dunedin

4.8 out of 5 average rating, 123 reviews

Serene French Country Cottage near everything

Unwind in this rustic French provençal, Extra Cosy Cottage w/ Unique Decor in Charming, Artsy Dunedin. Fenced in yard. Free Parking&Wifi. CENTRAL LOCATION Close to Clearwater Beach, Honeymoon Island. Short walk to Downtown Dunedin, Pinellas Trail, Blue Jay Stadium & Beautiful sunsets! Perfect location for Walkers, Runners and Bikers! A home away from home in a very convenient location for quality shopping, dining, nature explorations and beaches! A short walk or Uber away from everything!

Guest favorite

Cottage in Indian Rocks Beach

4.77 out of 5 average rating, 102 reviews

#5 Beach Front Cottage w view- Indian Rocks Beach

LOCATION, location! Closest beach cottage to the water at Indian Rocks beach, view of the water from your porch & easy access to grass for pets. Perfect couples getaway. Enjoy some of Florida’s best beaches. Minimalistic living. *Kitchen recently updated* Shared gazebo & picnic table next door. Shared Washer & dryer takes quarters. Walking distance to local restaurants and bars. Minutes away from Clearwater beach, tourist attractions and mini golf. Property located next 2 public access.

Guest favorite

Cottage in Indian Shores

4.96 out of 5 average rating, 146 reviews

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.

Guest favorite

Cottage in Bayshore Beautiful

4.76 out of 5 average rating, 156 reviews

Good Vibes Cozy Cottage on Million $ Row

Great location for this cottage one block from Infamous Bayshore Blvd. Smart Tv's and quiet back porch with fire pit makes this location perfect for vacationers. Short walk to Bayshore blvd with scenic views of downtown Tampa and beautiful Tampa Bay water ways. Come and enjoy biking, running, skating or just walking along this 4 miles continuous waterfront walkway. You will have views of Tampa Bay on one side and views of multi-million dollar homes on the other during your stroll.

Superhost

Cottage in Clearwater Beach

4.88 out of 5 average rating, 119 reviews

Mermaid Cottage

Located in a three unit 'Olde Florida Style Complex' and just 45 steps to Clearwater Beach! The Mermaid Cottage is located on the 1st floor at the back of the complex. This Florida style unit is adorned wood floors and charming island decor. Open to an outdoor patio with furniture. The cottage has two bedrooms, two full baths and an outdoor shower! Living room has a queen pull-out bed. The patio area is completely fenced for private use. Nice, park like charcoal grill.

Top guest favorite

Cottage in Tampa

4.97 out of 5 average rating, 195 reviews

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, 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. Pet fee $50.

Top guest favorite

Cottage in Dunedin

4.97 out of 5 average rating, 301 reviews

Walk Downtown and Waterfront Barefoot Parrot 3

Discover coastal modern luxury in this stylish, spacious upstairs 2-bedroom cottage. Steps from Main Street Dunedin, enjoy nearby restaurants, shops, and breweries, or take a short walk to stunning waterfront sunsets. A quick drive to Honeymoon Island and Clearwater Beach, this pet-friendly retreat boasts two king beds, a sleeper sectional, and serene treetop views. Your bright, unforgettable coastal escape awaits—book your Dunedin getaway today!

Top guest favorite

Cottage in Treasure Island

5 out of 5 average rating, 191 reviews

Island Time Stay: Happy Hour

Check out our large studio cottage located on Gulf Blvd in Treasure Island, Florida. It is located less than 300 steps from the beautiful sand of Treasure Island Beach and 5 blocks from the world famous boardwalk, shopping and restaurants of John’s Pass Village in Madeira Beach. We have a crosswalk conveniently located in front of the property. You can stop traffic with the push of a button to safely walk across the street toward the boardwalk.

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What guests are saying

2 Bedroom Turtle’s Nest Beach Cottage,

4.91 out of 5 average rating, 11 reviews21 months ago

Staying at Shane's place was wonderful! Our family stayed for 8 nights. It was just as described, and the pictures were extremely acurate. The place was very clean and it really was just a short walk (maybe 3 minutes) to the beach. We had everything we needed for our stay. Diane was extremely helpful and responsive and she answered all of our questions in a very timely manner. The neighborhood is beautiful, quiet and very safe. Another family was staying upstairs during our stay, and although you could hear them a little bit, we had no issues with the shared access areas because they were super nice and friendly, too. The beach is absolutely gorgeous and not crowded at all. We had access to beach equipment (chairs, unbrellas, etc, which was a bonus for us). It was a perfect beach vacation for our family of 4 and we can't wait to stay at Shane's place again!

Cottage in Redington Shores

What guests are saying

Clearwater Cottage Short Drive to Beach & Dunedin!

4.82 out of 5 average rating, 209 reviews2 months ago

We found Debra's place to be very quiet and peaceful. It was about 15 minutes to Clearwater Beach and minutes from Dunedin, which is such a great place to go. The Pinellas Trail is about 4 blocks away and is a wonderful walking or bike trail. Debra was quick to respond and accommondating. We contacted her a day or 2 before we were supposed to arrive to see if we could arrive a day early and thankfully we were able to. We were there for 34 days and would definitely stay again. Thanks Debra!!

Cottage in Clearwater

What guests are saying

Private beach access, Dog-friendly home

5 out of 5 average rating, 54 reviews7 months ago

I went with two girlfriends for a girls weekend and this was the perfect spot. Across the street from a quiet beach and lots of things to use like bikes, stand up paddle boards, and beach chairs. The place itself is super cute and comfortable, although I think three people would be the most I’d try to fit in there. Andi was very friendly and responsive and made sure that we had everything we needed. There’s a cool bar that is literally right outside of the place, but unfortunately it was closed during our stay. Maybe it’s for the best though, because it’s open until 2am!

Cottage in Indian Shores

What guests are saying

Water Front Super Chic 2BD/ 1 bath - Cottage Wi-Fi

4.79 out of 5 average rating, 107 reviews1 month ago

We had to get another rental after our first fell through and Petie was so helpful in getting us set up quickly. Her hosting was attentive the entire time. And the place was so clean, well located and apportioned. The back patio was a great place to have breakfast and watch the boats and birds. It was a good space but ultimately the attentive hosting and being good with a last minute booking were what really pushed this over the top.

Cottage in Madeira Beach

What guests are saying

Central Quiet Bright Cottage, near Skyway Bridge.

4.98 out of 5 average rating, 83 reviews2 months ago

This was our second year of spending a month at Aileen's place. Again, it was so perfect for my husband and I. We did have guests stay for a couple of nights and the air mattress is REALLY nice! Everything about the space is so wonderful. Clean, cute, everything you would need for a month. It is also close to so many beaches (Fort Desoto Park ( our favorite), St. Pete's beach, and Anna Maria Island beaches. It's close to all that Bradenton, St. Petersburg and Sarasota have to offer. We felt right at home the day we arrived and it was hard to say good-bye. We definitely hope to visit again!

Cottage in Palmetto

What guests are saying

Historic Florida Beach Cottage steps from the sand

4.91 out of 5 average rating, 98 reviews2 weeks ago

We spent 4 days here with our 3 kids (11, 9 & 3) and absolutely loved it! The cottage is perfect for a family with small kids or a couple of adults. I wouldn’t recommend more than that because of the bathroom. They have really maximized the space & we were pleasantly surprised to see that it was a little different from the photos- in a great way! There is a counter top that wraps around in the kitchen/living area. The beach chairs were a huge bonus as half of us flew in and didn’t have much room for packing. Between the 5 of us, the house had plenty of dishes, towels, trash bags, etc.. much more was provided than your average condo/rental home stay. The neighborhood is amazing and truly a gem, rare to find such peace and quiet on a busy coast. My kids were enamored with Charlie the bird and we really enjoyed having so many walkable options for food (The Grove was our morning routine!) If you are looking in the area, do not hesitate to book this home- you’re in for a treat!

Cottage in Indian Rocks Beach

What guests are saying

Luna Cottage, managed by owners- No Chores

4.98 out of 5 average rating, 105 reviews3 months ago

We LOVED Luna cottage. We came to relax, so the short walk to the beach and to many local restaurants was perfect. If you’re looking to explore outside of Indian Rocks Beach, the Suncoast Beach Trolley system in the area is easy and convenient to use. Having laundry and beach materials (towels, chairs, etc) on-site was also extremely helpful. Rob was very communicative, and it was evident that he wanted us to have the best stay possible. He came to get us from the airport, even after we had unexpected flight changes and arrived hours later than we anticipated.

Cottage in Indian Rocks Beach

What guests are saying

GROUND FLOOR DIRECT BEACHFRONT COTTAGE!!

4.88 out of 5 average rating, 186 reviews1 day ago

This place is a true gem. The lovely town has plenty to offer without being overrun with tourists like many of the surrounding areas. The beach itself its breathtaking with a spectacular sunset every night. And the actual beach cottage is phenomenal, intimate but perfectly sized for a couple or family looking for a beach oasis escape. We could not recommend it enough. Thank you!

Cottage in Indian Shores

What guests are saying

Endless Summer Cottage 2

5 out of 5 average rating, 70 reviews1 month ago

we really enjoyed our stay. The cottage felt very much like being at home We appreciated that the cottage was well supplied with necessities. The furniture was comfortable unlike some places we have stayed. The community and location were great and the Pinelass trail made most things available by bike, which was great, because the local traffic is horrible. We never did completely figure out the Samsung tv set up for local stations. All in all this was one of the best Air B&B stays we’ve ever had.

Cottage in Dunedin