
Cottage vacation rentals in Madeira Beach
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Top-rated cottage rentals in Madeira Beach
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Madeira Beach cottage rentals
Cottage rentals with a pool

Coral Cottage pool/firepit 2 bedr 2 bth sleeps 6
Coral cottage was the perfect place to get to our favorite locations on the suncoast - being 10 minutes from Hellas is a godsend

Mermaid Cottage
We took our boys on their first trip to the beach and it did not disappoint! If you are looking for a host that communicates extremely well, a house VERY close to the beach, and a cozy quaint space this is your house! I cannot say enough good things about our stay. This was the perfect house for a small group and so close to all things fun!

Tropical Coquina Cove Studio #1 5min Walk to Beach
This place was so cute, great location quiet and relaxing vibe. Highly recommend!

Tampa Bay Area Cottage w/ Gas Grill and Fire Pit!
Great place to stay with pets. Great backyard.

6B Newly Renovated Casita at Coastal Cottages!
Vielen Dank für die schone Zeit bei euch. Das Apartment war so wie beschrieben. Sehr ruhig. Ich hatte es nur 15 min 15 Minuten zur Arbeit. Geschäfte und Lokale in der Gegend alles wie es sein soll. Danke! Ich hoffe bis bald.

1 Bedroom / 1 Bath Ground Level, Gulf-View Cottage
It's a great value. It's a motel but because you're renting via this platform they go above and beyond making sure you're happy and making it feel like you're renting from a home owner. It's right on the beach and the location is amazing. The room itself was ok, it was a good value. I did expect it to be owned by someone which usually those places are kept in better condition and cleaner since it's more personal. However, I have no complaints. Yes I will stay there again. The front desk clerk was great to us. Right before check-in, expect to receive a link from The Molloy motel asking you to provide some details including a picture of your DL.

Endless Summer Cottage 2
Excellent accommodations. Very well maintained and comfortable with all the accomodations for a relaxing and enjoyable stay. Great location close to beaches, restaurants, ancd other attractions. I am looking forward to a return visit. Marie Karine was a friendly and responsive host.

Seaside Retreat Cottages #1
We absolutely love our stay. We had a wonderful weekend getaway and the location was within 5-10 minutes to some great restaurants and the beach. We also love the fact that beach towels, chairs, wagon, and umbrella was included for us to use. Walking up and being able to take 5 steps outside the door and into the courtroom pool was wonderful. I will say the hot tub was more of a spa as never got hot but I may have misread how it was listed. Honestly, though it didn’t matter because the atmosphere was so quiet and relaxing. We are already looking for the next date where we can come back with friends.
Cottage rentals with a hot tub

Harbor Oasis - Hot Tub - Private
Very responsive, helpful hosts and a wonderful location with lots to offer.

Sunny - Key West Vibe Cottage - Pool - Walkable
Really enjoyed our stay at the Captain’s Cottage! Nicely kept, with thoughtful amenities. Hope to be back someday to explore more of Dunedin.

Beachy Keen Cottage A only steps to the Beach
We absolutely loved it here. It was very clean and had everything we needed. Hot tub was a great amenity. The shed full of beach needs was amazing! Definitely would stay here again!

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.
The corner cottage was cozy and we love the location! Walking distance to the beach was perfect. Lots of family memories made and would definitely go back to this location!!

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
The house was cute, cozy and beautifully decorated. Laura was very responsive when communicating. Our family of 4 stayed for 3 nights and enjoyed the outdoor space and game room a lot. Plenty to do and lacked nothing. Just be warned about the mosquitoes if you plan on spending long periods of time in back patio area. Bug repellent was provided, however we were still eaten alive. This however did not ruin our overall experience. I would totally recommend this location to anyone and would definitely like to visit again.

Hidden Oasis #1, hot tub near the beach
This Airbnb was in a great location within 12-15 minutes of numerous beaches. It was also easy to get around. Many restaurants were close by as well as grocery shopping options. The Airbnb is on a quiet street. The outside patio of the property was shaded and quiet. Amy had a great recommendation booklet with helpful information. The house was spacious, and worked well for my trip. Lots of bath towels were provided as well as chairs, cooler, umbrella for the beach which was extremely appreciated!
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!

The Pelicans Roost / Gulfport
Great home in a very quiet neighborhood. The town of Gulfport is a short drive, and has some great places to eat. It was very close to our fishing guides home marina.. One of the quietest places I've stayed.. A great place for 3 or 4 people. Two comfortable beds. Good TV and internet. Kitchen appliances looked showroom. Small screened porch and outdoor grill and picnic table looked.very inviting, but the heat kept us in the good A/C. I would return.

Artsy guest house; near downtown w/ private patio
We LOVED staying at Christopher’s. The apartment was exactly what we needed. The neighborhood is adorable and so close to downtown. Christopher was an absolute gem of a host who went above and beyond to make sure we had a great stay. So grateful! Would return.

Palm Cottage- Escape to Paradise!
I highly recommend Sandy Feet. It was well appointed, decorated and spotless. We had one very minor issue and they responded and resolved it immediately. I only mention it because I was very impressed with their customer service.

Cozy up in a French Country nest NEAR EVERYTHING
Such a vibe! The location is perfect. Close enough to walk to downtown, but far enough to feel like you've got privacy.

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!!

Gulfport Art District - One Block From Beach!
Absolutely perfect Airbnb in every way! The location could not be better. We laughed because we had dinner reservations at Pia’s Italian restaurant and realized it was right across the street. Talk about convenience! This was hands down the cleanest Airbnb we’ve ever stayed in. Uncle Finley left us a thoughtful welcome package with a bottle of wine, beer, water, orange juice, and more. It’s clear he’s put real care into every detail to make the stay extra comfortable. Phone chargers were exactly where you needed them (no hunting for outlets), there were doggie bowls and doggie bags for our pup, Uncle Finley was super responsive to questions and genuinely committed to taking care of both his guests and this beautiful home. We’d come back in a heartbeat. Don’t hesitate just book it! Tip: In addition to Pia’s homemade pasta with pesto sauce, I’d also highly recommend the restaurant Pearl by Chef Karim for an unforgettable meal! The Pearl is a testament to culinary excellence.

Walk Downtown and Waterfront Barefoot Parrot 3
Hands down this was the best stop of our vacation. The space was pristine and felt luxurious with great attention to detail throughout the unit. It’s in a great location and walkable to all that Dunedin has to offer. We felt right at home and had an awesome stay. Our hosts were proactive and responsive. Wish we could have stayed longer. Thanks for sharing your gorgeous space!
Quick stats about cottage rentals in Madeira Beach
Total rentals
10 properties
Nightly prices starting at
G$25,092 GYD before taxes and fees
Total number of reviews
1K reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
John's Pass, Madeira Beach Access, and Hubbard's Marina
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- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- Dunedin Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Bean Point Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Lido Key Beach
- Cortez Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- North Beach
- Fort De Soto Park
- Vinoy Park
- Jannus Live
- Tampa Theatre
- ZooTampa at Lowry Park
- Curtis Hixon Waterfront Park
- Adventure Island
- Splash Harbour Water Park