
Cottage vacation rentals in Bay Pines
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Top-rated cottage rentals in Bay Pines
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Popular amenities for Bay Pines cottage rentals
Cottage rentals with a hot tub

Harbor Oasis with Hot Tub
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!

Pink Gulfside Cottage, Steps to Beach, Pets OK
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!

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.

Downtown Luxe Comfort Cottage with Hot Tub!
The cottage was perfectly located in Safety Harbor, close to everything and had all the amenities to enjoy every experience the area has to offer.

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

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!

Hidden Oasis #1, hot tub near the beach
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.

Castle Keep Guest House
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

Yachtsman Gulf front on sand, Sleeps 6 Heated Pool
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.

The Pelicans Roost / Gulfport
Excellent place to stay - had everything promised and was perfect for 3 people. Loved the backyard

Cozy Cottage Near Downtown + Waterfront
Michael’s Citrus Cottage was perfect for our 6 day stay in Dunedin! It had all the amenities we needed. The bed was extremely comfortable, and the shower was one of the best I have seen in all the Airbnbs I have been to. The location is perfect also. Less than a 10 min walk to many restaurants, to 7 microbreweries, and many stores to satisfy your shopping itch. I would stay at Michel’s place again should we travel to Dunedin again.

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.

BEACH COTTAGE II
The house was very nice, not huge, but very accurate with what the pictures showed, and it was actually a lot brighter inside than I expected based on the pictures. Everything was clean and with 5 people, there was plenty of space. They provided beach chairs and an umbrella which was wonderful. We also used the grill which we enjoyed having access to. The only thing we would recommend is more pots/pans/serving bowls, etc. for use in the kitchen - that was a little lacking. Otherwise, communication with the host was outstanding. We had a couple of minor issues that were resolved immediately. They let us check in early and stay late based on our schedule and the fact that no one was coming in behind us. Finally, the location is awesome - right across the street from the beach with easy beach access. We had a great time and would definitely recommend this house.

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

Gulfport Art District - One Block From Beach!
This is probably our favorite Airbnb to date! The location is fantastic, on a street full of restaurants and bars, about a block from the beach. Yet, it was quiet! The place is very comfortable, with awesome and quirky decor, two bedrooms, and an air-conditioned, screened-in front porch, which was our dog’s favorite part! Great value!

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

Cottage by the Coast 2 bd - Pet Friendly
Very happy with Jennifer’s responsiveness and helpfulness. She went above and beyond, and had almost everything we could’ve possibly asked for available. The place was very close to all nearby beaches ~ 10-20 minutes. Everything was clean and the furniture was comfortable, which is rare for these airbnb’s. Definitely looking forward to staying in more of Jennifer’s airbnb’s in the future.

Adorable Villa 1 min to Downtown Dunedin
Karina was extremely communicative. The location was perfect - walkable to all downtown!

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!

Crystal Beach Yellow Cottage
My husband and I enjoyed our stay at the cozy cottage. The location to Crystal Beach is great! We loved sitting on the screen porch. The house is just like the pictures. We had everything we needed to spend one month. Joni is a responsive host. We would be happy to stay again.

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

Safety Harbor Cottage
This was our third stay so that itself should speak for how much we enjoy Lisa's place. Our favorite part is the quiet private backyard. And we love the outdoor shower. Beds and pillows are comfortable. Everything in the kitchen you need. Lots of tv viewing options. Lisa is very responsive and great to deal with. Always makes you feel welcome both in messages and at the cottage.

Mango Cottage, pet friendly, steps to gulf
We had a wonderful relaxing stay. The home was as pictured and had a cozy welcoming feel. It had everything we needed, included lots of towels and linens, and extra toiletries for any forgotten items. We also enjoyed the morning show of bunnies and birds! A quiet neighborhood and we slept great in very comfortable beds. Thanks for a nice break!

Beachside Historic Cottage – Steps to Sand!
We really enjoyed our stay, walk to beach, comfortable deck, close access to restaurants and shops. We were a little apprehensive of the circular stairs at first but were no issue at all. Only downside was the spotty Wi-Fi which both Jude and Jenni tried to help with, but it was a Spectrum issue. Both were available and extremely accessible, helpful and friendly.(
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- John's Pass
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