Cottage vacation rentals in Clearwater

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Popular amenities for Clearwater cottage rentals

Cottage rentals with a pool

Guest favorite
Cottage in Palm Harbor
4.89 out of 5 average rating, 27 reviews

Coral Cottage pool/firepit 2 bedr 2 bth sleeps 6

SoniaRating, 5 stars7 months ago
Everything was LOVELY! The kitchen was fully stocked with everything needed, much appreciated! The home was super clean and peaceful. The pool was warm and clean ... the shower outside was amazing! Our stay was truly amazing and peaceful ... a home away from home.
Superhost
Cottage in Indian Rocks Beach
4.74 out of 5 average rating, 31 reviews

Yachtsman Gulf front on sand, Sleeps 6 Heated Pool

LaurieRating, 5 stars2 months ago
The Yachtsman is a charming cottage in a perfect location, with a lovely view of the ocean. Open the front door and you're right on the beach to go for a walk, sit on the patio and see a beautiful sunset every night. It was impressive how quickly and well the Management restored everything after the hurricanes. Staying at The Yachtsman was a special and unique experience; I would do it again in a heartbeat if I could.
Top guest favorite
Cottage in Indian Rocks Beach
4.99 out of 5 average rating, 169 reviews

Pool | King Bed | Art Mural | Steps to the Beach

Mary AnnRating, 5 stars7 months ago
The cottage was immaculately clean and comfortable. It was stocked with everything you would need such as kitchen necessities, toiletries, extra towels and beach items. The pool was beautiful and even lit up at night. It is a three minute walk to the beach and some of the bars and restaurants. It is a very quiet neighborhood. The host was extremely nice and responsive with everything. We would stay there again. And I loved the free library out front. I left a book in there ☺️If you are thinking about renting this cottage, you definitely should, you won't be disappointed.
Cottage in Madeira Beach
4.81 out of 5 average rating, 53 reviews

Beach cottage, 30 second walk to the sand !

SaraRating, 5 stars7 months ago
Very clean cute place to stay. Easy beach access. Restaurants are within walking distance. Pool is clean and perfect to cool off in. Great place. We’d stay again.
Superhost
Cottage in Safety Harbor
4.89 out of 5 average rating, 44 reviews

5B Newly Renovated Casita at Coastal Cottages!

RayRating, 5 stars1 month ago
Great location to Main St. in Safety Harbor. The unit was very clean upon arrival. Nice facilities and quiet. The staff was most helpful in sorting a few extra things. Would highly recommend a look at booking here. Cheers
Guest favorite
Cottage in Thonotosassa
4.96 out of 5 average rating, 26 reviews

Tampa-Retreat I Homestead with 5th Gen Floridians

Jennifer MihalRating, 5 stars2 months ago
We arrived at night days late due to flight cancellations from home weather. Ashley and Josh were very understanding and welcoming. They were responsive and kind throughout our stay. Their daughter showed our kids around the property and shared her toys, making everyone feel welcome. The back house was comfortable, clean, and well stocked. The area is beautiful and we felt very safe with our small children. We enjoyed walks to feed the cows, playing with the dogs, finding frogs, watching lizard play, listening to birds, dipping out feet in the pool, and collecting eggs from the chickens. The location was convenient for getting to many locations in and around Tampa.
Guest favorite
Cottage in Indian Rocks Beach
4.88 out of 5 average rating, 42 reviews

Backyard Oasis with sand and private pool

Deidre MarieRating, 5 stars7 months ago
This was the first time staying in an Airbnb and I highly recommend this property and the management company, 5 stars ⭐️ . The home was just as advertised but better. Home was sparkling clean and I own a cleaning business in Tampa, so that says a lot! It was walkable to the beach, great restaurants and grocery stores. Everything you need for the first day/night to get you started on your getaway. The pool was clean and we loved the beach sand area of the pool area! The host and his associates were very responsive. We look forward to staying at this house or any of the other 29 properties the host has!
Cottage in Treasure Island
4.87 out of 5 average rating, 39 reviews

1 Bedroom / 1 Bath Ground Level, Gulf-View Cottage

CinthiaRating, 5 stars19 months ago
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.

Cottage rentals with a hot tub

Top guest favorite
Cottage in Safety Harbor
4.96 out of 5 average rating, 179 reviews

Harbor Oasis with Hot Tub

JillianRating, 5 stars1 week ago
I’ve found my new favorite staycation spot and where I will enthusiastically recommend to friends and family visiting the area. The space was thoughtfully designed, clean, and comfortable. I will miss my morning coffee on the patio amongst all the plants and birds, my daily work sessions in the small quiet office, and the evening dips in the hot tub. Thanks for your thoughtfulness in creating this space!
Cottage in Clearwater Beach
4.76 out of 5 average rating, 146 reviews

Pink Gulfside Cottage, Steps to Beach, Pets OK

LoniRating, 5 stars3 months ago
Our cottage wasn’t ready when we arrived but Captain Al was very responsive and accommodating! He provided us another cottage in a timely manner and generously took care of our dinner tab while we waited. It was very chilly in Florida during our stay and Captain Al brought us an additional space heater to use during our stay. The location is amazing and the cottages are very unique! We’d definitely come back!
Guest favorite
Cottage in Indian Rocks Beach
4.97 out of 5 average rating, 37 reviews

Beachy Keen Cottage A only steps to the Beach

Natthakarn (Emma)Rating, 5 stars6 days ago
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.
Guest favorite
Cottage in Tampa
4.95 out of 5 average rating, 121 reviews

Hot tub, 2 floors riverfront, Bush Gardens, kajaks

Kemp Signs & ServiceRating, 5 stars5 days ago
Hosts was accommodating and quick to respond. Nice, quiet, hidden, place to kick back and relax after a long day!
Top guest favorite
Cottage in Largo
4.98 out of 5 average rating, 50 reviews

Family FUN~Pool, GameRoom+Bikes, Near Beach/Trail

KellaRating, 5 stars1 week ago
Great stay for our family! The home is very clean and decorated with a beachy, fun vibe! Great bathroom, comfy beds and lots of places to hang out! The dryer was very helpful with wet towels and beach gear was great. Our favorite part of the home was the backyard. The plunge pool was so fun and we loved the game room and golf. Private yard and we enjoyed the birds over coffee each morning! Recommend for any family!
Guest favorite
Cottage in Crystal Beach
4.83 out of 5 average rating, 90 reviews

Happy Camper Cottage | Cozy Oasis with Hot Tub

JasonRating, 5 stars7 months ago
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!
Top guest favorite
Cottage in Largo
4.96 out of 5 average rating, 92 reviews

Hidden Oasis #1, hot tub near the beach

MicheleRating, 5 stars3 weeks ago
Ame is a wonderful host! This is the cutest little house, stocked with everything you might need for a stay in sunny Florida! Clean as a whistle, too. Location was perfect, groceries, the beach, pizza and shopping all close by.
Cottage in North Downtown
4.56 out of 5 average rating, 36 reviews

Castle Keep Guest House

PeterRating, 5 stars24 months ago
Tim and Jeannie are the best hosts ever! Communication and local recommendations are top notch! If you are like us, you’ll be on the go because Saint Petersburg offers so much with arts, culture and outdoor recreation that most of the time was being out and about. However, when you get back, you’ll feel like you’re at home and everything you need is right there! Sleep in and eat breakfast at the cottage, come back early and watch a movie or hit the hot tub or just do another load of laundry and hit the beach one more time! It’s so convenient and the best location ever! Thank you Tim and Jeannie :)

Pet-friendly cottage rentals

Guest favorite
Cottage in Bayshore Beautiful
4.76 out of 5 average rating, 156 reviews

Good Vibes Cozy Cottage on Million $ Row

JessicaRating, 5 stars3 weeks ago
Place and location were great! And host was super communicative. It is small but that is expected based on the listing information. Would definitely go back!
Top guest favorite
Cottage in Gulfport
4.96 out of 5 average rating, 153 reviews

The Pelicans Roost / Gulfport

CatherineRating, 5 stars1 day ago
Bob was very accommodating, easy to communicate with and very friendly. Everything went smoothly, from entry to instructions for leaving. Adorable place, all new appliances, nice bedrooms, even great water pressure in the shower! Can’t wait to come back!
Top guest favorite
Cottage in Dunedin
5 out of 5 average rating, 16 reviews

Cozy Cottage Near Downtown + Waterfront

ThomasRating, 5 stars1 day ago
Citrus Cottage 2 was the perfect size for my wife and I. The location can't be beat. Dunedin is a walkable town, and the cottage was right in the center of everything. We were a 5-minute walk to numerous restaurants and breweries and to the Pinellas Trail. Michael provided a clean and comfortable home for us to relax in. The shower was amazing and felt so good after a 13+ mile bike ride. We have been to Dunedin several times and this was, by far, the best place we've stayed in. We highly recommend Citrus Cottage 2, and we will definitely look to stay here again the next time we visit Dunedin!
Top guest favorite
Cottage in St. Petersburg
4.95 out of 5 average rating, 123 reviews

Artsy guest house; near downtown w/ private patio

PhoebeRating, 5 stars1 week ago
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.
Guest favorite
Cottage in Pass-a-Grille Beach
4.87 out of 5 average rating, 166 reviews

BEACH! Sunny Escape! Steps 2 Famous Beach w/2 Bike

CindyRating, 5 stars4 months ago
If you are looking for a historic, old-school Florida home, this is it. The only reason it isn’t a perfect score is that the hurricane closed most of the shops that make Pass-a-Grille quaint. We were able to support a few local restaurants, and the local traffic was very light. We wouldn’t have changed our trip, but it would have been good to know. It seems like businesses are working hard to get back on their feet. Overall a good experience. I appreciate Lisa’s great responsiveness.
Guest favorite
Cottage in Redington Shores
4.85 out of 5 average rating, 48 reviews

Palm Cottage- Book now for Spring Break!

VirginiaRating, 5 stars8 months ago
What a cozy, comfortable and quaint little house right by the beach! The house was well appointed with all the initial essentials & was very clean. The bedrooms were spacious and the beds were very comfortable (we actually slept like we were at home, a rarity!). Communication was flawless and the host was accommodating at check-in which we really appreciated. Located steps from the beach, it was the perfect amount of house for our family of four. Lots of space for our things and easy to use laundry facilities were helpful. Beautifully landscaped back yard and deck, with clean outdoor furniture and bbq, as well as beach accoutrements (chairs, wagon, inflatables) the host definitely takes pride in their rental. Would recommend and will definitely be back! Thank you for a great little vacation.
Top guest favorite
Cottage in Gulfport
4.99 out of 5 average rating, 265 reviews

Gulfport Art District - One Block From Beach!

ChristinaRating, 5 stars1 day ago
Whenever I visit Gulfport, Uncle Finley’s is the first place I check for availability. The house is well situated with all the right touches to make you feel at home. There have been some recent improvements to the inside and outside of the home that add even more value to the stay.
Guest favorite
Cottage in Indian Rocks Beach
4.91 out of 5 average rating, 122 reviews

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

JessRating, 5 stars3 months ago
We really enjoyed our stay at the Indian Shores Beach Cottage! Property was exactly as the photos describe, easy check-in, cute minimal decor which is always helpful traveling with children (less to babyproof), host was friendly and responsive, and best of all.. Location is just one block walk to the beach! A quiet, relaxing, tropical stay for our annual FL getaway! :)

Quick stats about cottage rentals in Clearwater

  • Total rentals

    70 properties

  • Nightly prices starting at

    ﺩ.ﺇ184 before taxes and fees

  • Total number of reviews

    6.1K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with a pool

    20 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Pinellas County
  5. Clearwater
  6. Cottage rentals