
Cottage holiday 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.
Holiday rentals for every style
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Popular amenities for cottage rentals in Gulfport
Cottage rentals with a hot tub

Harbor Oasis with Hot Tub
We enjoyed our stay, it was a very pleasant, clean, and a practical location. We give thanks to the host!

Sunny - Key West Vibe Cottage - Pool - Walkable
This place felt like a private retreat. The rooms were spacious with a sink, small refrigerator, microwave, comfortable bed, small table and chairs for dining, recliner for watching t.v., and full bathroom including a bathtub. The lounge area was also lovely for sitting to read or enjoy a cup of coffee or tea or do a bit of computer work. Everything was functional and well laid out. We even enjoyed the front porch with chairs for sitting in the morning with our coffee. We were able to walk about 10 minutes to get to many, many restaurants, shops, and the marina in downtown Dunedin. It was just delightful.

Beachy Keen Cottage A only steps to the Beach
Beautiful home, nice & spacious kitchen, and all beach amenities provided. Our family really enjoy our stay, perfect location with really short walk to the beach. Paula was a great host and quick to response. Thank you for our wonderful stay and we will be back.

Hot tub, 2 floors riverfront, Bush Gardens, kajaks
Cozy, comfortable, yet two stories with plenty space to stretch out, scenic view with a hot tub, nice balcony view for coffee in the morning. Can’t go wrong.

Downtown Luxe Comfort Cottage + Hot Tub!
We had a wonderful time staying here! The location is phenomenal and it was always quiet outside the home, day and night. You can walk to restaurants, bars, shops, and more in less than 2 minutes. Beach access is 15 or so minutes away as well. The home was clean and well appointed for 2 people and the host was always responsive and nice. We were also able to bring our dogs, which we appreciated. We love Safety Harbor and will definitely stay here again!

Corner Cottage Sleeps 5, Steps to Beach, Pets OK.
Awesome place! Captain Al and housekeeping were great and very hospitable. Great location. Will definitely go back.

Happy Camper Cottage | Cozy Oasis with Hot Tub
Anna was extremely helpful and accommodating for our last-minute trip with the kids. Her place was super cute and very clean and well kept and we would be happy to recommend it to friends and family or return ourselves. Thank you so much, Anna!

Family FUN~Pool, GameRoom+Bikes, Near Beach/Trail
We had an amazing experience at Laura’s cottage. The property was exactly as described—clean, comfortable, and fully equipped with everything we needed. The location was perfect, close to beaches, shops, and restaurants, yet in a quiet and peaceful neighborhood. The host was incredibly responsive and made sure we felt welcome. Check-in and check-out were seamless, and we really appreciated the photo shoot areas around the house. We would definitely stay here again and highly recommend it to anyone visiting the area!
Pet-friendly cottage rentals

Good Vibes Cozy Cottage on Million $ Row
I had a pleasant stay at Dallas’ little cottage. I was traveling alone with my medical foster and felt incredibly safe, even after arriving pretty late. There were guests in the house up front, but were quiet and respectful. The size is perfect for solo or a couple. The decor was tasteful, house was clean (no pet smell) and having a fence was convenient. Loved how walkable the neighborhood was too! It is an older house with typical character-filled imperfections, but I love that vibe and the warmth it gives. As a heads up to anyone unsteady on their feet, the floor does slope in some areas. The only star I knocked for description was for the additional pet rules posted in the house that weren’t in the online listing at the time of booking/stay. Biggest one to note is that pets are not permitted to be on the furniture (understandable, but a surprise). With a velcro dog, that put me in a predicament. If your needs match with the rules, it is a solid choice!

Little Manatee River Cottage
Had a great stay ! Fishing was fun and right across the street Would stay again for sure !

Modern Cottage
We stayed at Lisa’s place for a little over 2 months. We are from the area, however our home was unavailable. We liked walking the neighborhoods and to the lake each day. Downtown St Pete is about 1.5 miles away, so very nice walk or quick drive. Lots of great nightlife and restaurants there. A 4-5 block walk puts you on 4th with coffee shops, restaurants and breweries nearby. The cottage is also well equipped for making meals at home or relaxing in front of the TV. The patio area was beautiful and well maintained. It’s nice for coffee in the morning, or a glass of wine in the evening. King size bed! Big shower, laundry on premises. Everything we needed and at a great price!

Adorable Dog-Friendly Cottage in Quaint Dunedin
Barbara was a great host. She responded so quickly to my questions. Her cottage was immaculate, organized and had everything you would need to feel like you were at home. Location was walking distance to downtown and the Pinellas County Trail was across the street. It was great to be able to have our dog with us. Fenced in area to let him out. Barbara even had dog treats!!

Vintage Florida Beach Cottage B
We brought two toddlers to the little pink house, and they just loved it. The kitchen was set up Perfect. The Murphy bed in the living room was a bonus and let us all spread out when it was time to sleep. Eric was nearby in a nearby apartment, and so helpful with everything. The best is he provided just the right amount of beach toys, and two wagons to get toddlers to the beach, which is just a block away. If we would’ve stayed longer, we would’ve Used the laundry, which was lovely We discovered night frogs at the fountain around the corner, and the nature park and playground also just a walk away . Great spot

Beachy Paradise
Beautiful little house, only a 1 block walk to the beach. Many restaurants, bars, shopping areas all within walking distance. The sound of the pickle ball players and laughter in the park while sitting on the back patio was a very nice touch! Overall fantastic experience, we will be back!!

The Cottage at Wishing Well, Gulfport
Second time staying at the beautiful place! Will again!

ALL NEW! Coral Sands II ~Coastal Modern 2/2 IRB
A Hidden Gem by the Beach – Perfect for Families! I wanted to surprise my family visiting from Texas with a beach getaway, and discovering Mrs. Nicole’s home was truly the highlight of our trip. It couldn’t have been in a more perfect location—just steps from the beach and close to everything we needed. The home itself was charming, spacious, and beautifully maintained. Nicole thought of everything—from an abundance of fresh towels to a fully stocked kitchen that made me feel right at home. One of the best perks? A beach buggy ready to load up with all your supplies—no more lugging chairs and bags in the sun! My mom, who has difficulty walking long distances, especially appreciated how easy and quick the walk to the beach was. She had no complaints at all—which says a lot! If you’re looking for a relaxing, convenient, and family-friendly place by the ocean, I highly recommend Nicole’s home. It’s absolutely worth every penny. We’ll definitely be back!
Private cottage rentals

Cottage by the Coast 2 bd - Pet Friendly
3 of us were down there on a golf trip. I found the whole experience seamless, from booking to access to leaving. Jen was extremely responsive (within 30 min most times). The place was spotless and uncluttered. Had the right amount of kitchen ware for what we were looking for and the beds and chairs were comfortable. We would definitely stay there again.

"Sweet Harbor Cottage" Walk to Downtown
The most coziest, CLEAN, beautiful place to stay. It’s a small space, but the amazing skylights on the ceiling and the windows that give natural lighting make the space feel so much bigger. The neighborhood is quiet & peaceful. Really enjoyed how everything was walking distance. Loved going out & coming back feeling like I was right at home. Would definitely love to come back & stay here again.

Key Lime Cottage-Beach1 block
Location was perfect the beach was a block away, John’s Pass was just 5 minutes away aswell as the opposite way multiple shops about 10 minutes away. Lynne had nearly everything provided what you’d need for a beach getaway. Ice chest, sunscreen, chairs, snacks, umbrella, paddle ball game and more. There was even some cooking condiments in the fridge already aswell as chips. Only one thing we were suprised with is sharing the backyard area along with the host. Other than that it was a phenomenal stay and our host was very attentive.

Beach Cottage- Pass a Grille- Steps to beach
Very responsive, went above and beyond!

Safety Harbor Cottage
Lisa’s place was perfect for four of us attending graduation in Tampa. The house was clean, very comfortable, and the backyard was beautiful. The extra welcome gifts were a nice touch. Would definitely recommend!

Shady Nook Beachfront Cottage
Such a lovely cottage with an unbeatable oceanfront location. The beach is the backyard! We loved the Old Florida feel of the cottage, but it was also very clean and well-appointed. We also loved that there was plenty of beach gear, toys, and games available for the Scruggs Harbor guests to borrow. Morgan is a wonderful host — quick to respond and around if you need her. We most certainly would love to stay here again!

Mango Cottage, pet friendly, steps to gulf
Very nice and quiet neighborhood. Crystal Beach sunset was beautiful. Well’s Spring park was a nice park for walking the dog. Everyone was friendly that we met while walking. Would book again.

🏡Cottage near Clearwater & Belleair Beaches🏖🌴☀️
I absolutely adored this home! I live in Charleston and work remotely, but my corporate office is in Largo. I travel there quite often for work, and have always stayed in hotels. This time, I wanted to try something new and I will never be able to go back! I truly hope that I can stay in Chanel and Justin's place for ALL my future work trips and have already shared it with co-workers, as well. The photos are accurate and I would even say they don't do the place justice. It was spotless when I arrived, and I appreciated a soak in the tub after a long work day. I slept in the front bedroom and it was SO COZY! I really enjoyed the Florida room and ended up doing quite a bit of work out there on my laptop. Neighborhood was peaceful, quiet, and I felt safe. The beach was a quick 10-15 minute drive, allowing me to catch a sunset. There are plenty of DoorDash options for those that don't want to mess up the spotless kitchen. Highly recommend for business or pleasure. Will be back soon!
Quick stats about cottage rentals in Gulfport
Total rentals
10 properties
Nightly prices starting at
₹6,851 before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
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- Anna Maria Island
- Siesta Beach
- Dunedin Beach
- Anna Maria Public Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Bean Point Beach
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- Vinoy Park
- North Beach
- Fort De Soto Park
- Streamsong Resort
- Tampa Theatre
- Jannus Live
- Curtis Hixon Waterfront Park
- ZooTampa at Lowry Park
- Splash Harbour Water Park