Cottage vacation rentals in Bay Pines

Find and book unique cottages on Airbnb

0 of 0 items showing
1 of 3 pages
0 of 0 items showing
1 of 12 pages

Popular amenities for Bay Pines cottage rentals

Cottage rentals with a hot tub

Top guest favorite
A light-filled living area features a spacious sectional sofa and a cozy chair, complemented by a decorative area rug. A large television is positioned on a sleek white media console. Soft natural tones enhance the relaxed ambiance, with sunlight filtering through the window blinds.
Cottage in Safety Harbor
4.96 out of 5 average rating, 179 reviews

Harbor Oasis with Hot Tub

JillianRating, 5 stars5 days 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!
A charming duplex features a bright pink exterior with white awnings. A swing and patio chairs are located in the front yard, surrounded by potted plants. Bicycles are parked nearby, enhancing the inviting atmosphere of this beachside property.
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!
Top guest favorite
The exterior of a fully remodeled cottage is shown, featuring a gravel yard surrounded by various tropical palm trees. A light blue door adds a pop of color to the neutral siding, while a white picket fence partially borders the property.
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 stars2 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
A private hot tub is positioned on a wooden deck, outfitted with two black chairs and a small table. The cottage features a light blue exterior with a white door framed by two towels. A pergola with climbing plants is visible in the background.
Cottage in Safety Harbor
4.9 out of 5 average rating, 80 reviews

Downtown Luxe Comfort Cottage with Hot Tub!

ElonRating, 5 stars1 week ago
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.
Top guest favorite
A bright and airy seating area features a hanging chair and a cozy sofa, adorned with colorful cushions. Natural light floods in through large windows, complemented by light-toned wooden flooring and a textured pink area rug that adds warmth to the space.
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
A charming coastal cottage is depicted, featuring a welcoming front porch with rocking chairs and vibrant seating. Lush plants in decorative pots frame the entrance. The exterior is painted in soft grey tones, complemented by white shutters and a serene pathway leading to the door.
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
A vibrant outdoor area features a sparkling hot tub surrounded by lush greenery. Comfortable seating arrangements and a dining table create an inviting space for relaxation. A charming yellow cottage stands in the background, complemented by various tropical plants and trees.
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.
A private Jacuzzi is situated beneath a canopy, creating a shaded relaxation area. Above, a hanging basket filled with colorful flowers adds vibrancy. Surrounding greenery and a trellis provide a secluded and tranquil ambiance, inviting guests to unwind and enjoy the peaceful environment.
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

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
A spacious backyard is featured, bordered by a wooden fence for privacy and lined with tropical plants and trees. A concrete patio area is included, which features a grill covered for protection. The lawn is open and well-maintained, providing a serene outdoor space.
Cottage in Gulfport
4.96 out of 5 average rating, 152 reviews

The Pelicans Roost / Gulfport

KerryRating, 5 stars3 months ago
Excellent place to stay - had everything promised and was perfect for 3 people. Loved the backyard
Top guest favorite
A glass table is set with two wine glasses and a bottle of red wine, inviting relaxation. The backdrop features a picturesque view of the surroundings, with lush greenery and a sunset sky visible in the distance.
Cottage in Dunedin
5 out of 5 average rating, 15 reviews

Cozy Cottage Near Downtown + Waterfront

TimothyRating, 5 stars1 month ago
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.
Top guest favorite
A cozy living room features a tan sofa positioned across from a purple armchair. A round coffee table is centered on a light-colored rug. Colorful artwork adorns the wall, while a floor lamp provides warm lighting. The space is brightened by natural light through a window.
Cottage in St. Petersburg
4.96 out of 5 average rating, 122 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.
Superhost
A wide sandy beach stretches along the shoreline, with gentle waves lapping at the shore. Clear blue skies and a hint of distant buildings mark the horizon. The beach offers ample space for relaxation and recreation.
Cottage in Treasure Island
4.89 out of 5 average rating, 27 reviews

BEACH COTTAGE II

MelissaRating, 5 stars9 months ago
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.
Top guest favorite
A bright living area features a spacious sofa adorned with blue and green decorative pillows, complemented by a matching throw. A wooden coffee table with natural elements sits atop a woven rug. A piece of wall art depicting a serene beach scene adds a calming touch.
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.
Top guest favorite
An enclosed front porch features two white rocking chairs positioned on a patterned floor. A door with a large letter 'A' offers access, while windows provide natural light. Decorative elements include a small sailboat and hanging plants, complemented by a teal area rug.
Cottage in Gulfport
4.99 out of 5 average rating, 264 reviews

Gulfport Art District - One Block From Beach!

BrandonRating, 5 stars9 months ago
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!
Guest favorite
A spacious living area features a large sectional sofa in a neutral tone, accented by coastal-themed artwork on the walls. Light wood flooring complements the room, which includes a dining table and two bar stools, allowing for casual seating options. Bright natural light floods the space.
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! :)

Private cottage rentals

Superhost
A wooden picnic table with attached benches is shaded by a large red umbrella. Surrounding greenery enhances the outdoor space, while a white fence provides privacy. A sturdy tree trunk is prominently featured, offering a natural element to the area.
Cottage in Largo
4.79 out of 5 average rating, 68 reviews

Cottage by the Coast 2 bd - Pet Friendly

TaylorRating, 5 stars1 month ago
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.
Top guest favorite
A wooden boardwalk extends over the water, leading towards a calm bay. Boat slips line the sides, with several boats visible at the dock. A mix of clouds fills the sky, casting natural light over the serene scene.
Cottage in Dunedin
4.96 out of 5 average rating, 89 reviews

Adorable Villa 1 min to Downtown Dunedin

KailieRating, 5 stars3 weeks ago
Karina was extremely communicative. The location was perfect - walkable to all downtown!
Guest favorite
A modern living and dining area is highlighted by a round dining table surrounded by four white chairs. A sleek black lamp hangs above the table. A comfortable sitting area is adjacent, featuring a black sofa and a TV mounted on the wall. Natural light streams in from the screened porch.
Cottage in St. Petersburg
4.95 out of 5 average rating, 19 reviews

Modern Cottage

TammyRating, 5 stars3 months ago
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!
Guest favorite
The image captures a tranquil shoreline at sunset, with gentle waves lapping at the sandy beach. Silhouettes of palm fronds are seen on the left, while the horizon features a blend of warm colors as the sun sets over the water.
Cottage in Crystal Beach
4.71 out of 5 average rating, 77 reviews

Crystal Beach Yellow Cottage

SusanRating, 5 stars1 month ago
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.
Superhost
An aerial view captures the sandy shoreline meeting the calm green waters of the Gulf. A meandering path runs parallel to the beach, flanked by sparse vegetation. Nearby residences are visible along the street, providing a glimpse of the neighborhood's layout.
Cottage in Pass-a-Grille Beach
4.93 out of 5 average rating, 15 reviews

Beach Cottage- Pass a Grille- Steps to beach

JohnRating, 5 stars3 months ago
Very responsive, went above and beyond!
Top guest favorite
A contemporary cottage is illuminated at night, showcasing large glass panels that reveal a warm interior. Surrounding the cottage, a manicured lawn features stone pathways and lush greenery, creating a serene outdoor environment.
Cottage in Safety Harbor
5 out of 5 average rating, 52 reviews

Safety Harbor Cottage

NicoleRating, 5 stars1 week ago
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.
Guest favorite
A pathway is visible leading toward a tranquil waterfront, framed by lush greenery and palm trees. The sunlight filters through the leaves, casting dappled shadows on the ground. A sign can be seen in the background, indicating the proximity to the water.
Cottage in Crystal Beach
4.92 out of 5 average rating, 61 reviews

Mango Cottage, pet friendly, steps to gulf

AnneRating, 5 stars1 week ago
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!
Guest favorite
Cottage in Indian Rocks Beach
5 out of 5 average rating, 14 reviews

Beachside Historic Cottage – Steps to Sand!

JosephRating, 5 stars1 month ago
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.(

Destinations to explore

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