Cottage vacation rentals in Bay Pines

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Popular amenities for Bay Pines cottage rentals

Cottage rentals with a hot tub

Top guest favorite
Cottage in Safety Harbor
4.96 out of 5 average rating, 183 reviews

Harbor Oasis with Hot Tub

JavhelRating, 5 stars4 days ago
We enjoyed our stay, it was a very pleasant, clean, and a practical location. We give thanks to the host!
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
4.77 out of 5 average rating, 149 reviews

Pink Gulfside Cottage, Steps to Beach, Pets OK

MarkRating, 5 stars3 days ago
Great old school beach cottage. Perfect for my Son and me. The Capt. and especially the First mate made it 5 stars!
Guest favorite
The outdoor pool area features a clear water pool surrounded by lounge chairs and vibrant umbrellas. A bright blue building is visible in the background, complemented by colorful accents along the poolside. Lush greenery adds to the relaxed atmosphere.
Cottage in Dunedin
4.89 out of 5 average rating, 101 reviews

Sunny - Key West Vibe Cottage - Pool - Walkable

DorothyRating, 5 stars4 days ago
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.
Guest favorite
A shared hot tub is surrounded by palm trees and lush greenery. Sunlight filters through the leaves, creating a serene atmosphere. A small seating area with chairs is visible in the background, offering a spot for relaxation.
Cottage in Indian Rocks Beach
4.97 out of 5 average rating, 38 reviews

Beachy Keen Cottage A only steps to the Beach

Natthakarn (Emma)Rating, 5 stars1 month 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
4.91 out of 5 average rating, 87 reviews

Downtown Luxe Comfort Cottage + Hot Tub!

ChelseyRating, 5 stars3 days ago
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!
The exterior view of a charming blue cottage is presented, featuring white accents and shutters. Two light-colored lounge chairs are positioned on the paved front area. Lush greenery surrounds the property, enhancing the inviting beach house vibe.
Cottage in Clearwater Beach
4.77 out of 5 average rating, 151 reviews

Corner Cottage Sleeps 5, Steps to Beach, Pets OK.

JoseRating, 5 stars2 weeks ago
Our trip was short but Captain Al went above and beyond expectations! Family felt right at home in his cozy cottage. Thanks again Captain Al, we’ll definitely be returning!
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 stars8 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 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, 57 reviews

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

TanyaRating, 5 stars2 weeks ago
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

Superhost
A spacious living area features a light-colored couch and a coordinating armchair, positioned on a decorative area rug. A wooden TV stand holds a flat-screen television. Wall art adds color, while a ceiling fan provides comfort. Natural light filters through the windows.
Cottage in Largo
4.8 out of 5 average rating, 70 reviews

Cottage by the Coast 2 bd - Pet Friendly

GerardRating, 5 stars1 month ago
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.
Guest favorite
A comfortable seating area features two light-colored sofas with throw pillows, arranged around a rustic wooden coffee table. A decorative screen provides partial division from other spaces, and a textured rug is laid beneath the furniture, enhancing the warm ambiance of the room.
Cottage in Bayshore Beautiful
4.76 out of 5 average rating, 162 reviews

Good Vibes Cozy Cottage on Million $ Row

KaylynRating, 5 stars3 weeks ago
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!
Guest favorite
A charming entryway features a wooden front door with a decorative handle. Two patterned chairs are positioned on a small porch, surrounded by lush greenery and potted plants. A concrete path leads up to the entrance, highlighting the inviting exterior of the cottage.
Cottage in St. Petersburg
4.95 out of 5 average rating, 19 reviews

Modern Cottage

TammyRating, 5 stars5 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!
Top guest favorite
A dining area is showcased with a white table set for four, featuring floral tableware and a decorative centerpiece. A large window allows natural light to illuminate the space, which is complemented by a cozy seating area in the background and a TV mounted on the wall.
Cottage in Dunedin
4.96 out of 5 average rating, 206 reviews

Adorable Dog-Friendly Cottage in Quaint Dunedin

MicheleRating, 5 stars4 weeks ago
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!!
Guest favorite
A single-story cottage features a pink exterior with large windows allowing natural light. A landscaped garden with decorative stones is visible in the front. White chairs are placed near the entrance, and ample parking spaces are provided in the driveway.
Cottage in Indian Rocks Beach
4.89 out of 5 average rating, 294 reviews

Vintage Florida Beach Cottage B

MollyRating, 5 stars5 days ago
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
Guest favorite
A cozy interior space features a neutral color palette with a striped bedspread. A serving tray holds two white cups beside a small dish of candy. Natural light fills the room, highlighting a kitchenette in the background, complemented by white cabinetry and a subtle decor.
Cottage in Dunedin
4.85 out of 5 average rating, 362 reviews

Cozy up in a French Country nest NEAR EVERYTHING

RileyRating, 5 stars1 month ago
The location was great. Place was tidy and clean also checking in was super easy. Tons of things to do nearby. Neighborhood was quiet. Host was super responsive and made our stay perfect! Would book this again it’s just as you see!!!
Guest favorite
A charming cottage exterior is highlighted by vibrant blue accents on the door and window frames. Lush palm trees surround the property, and a pathway of red bricks leads to the entrance. Gravel landscaping complements the home, enhancing its welcoming appearance.
Cottage in Indian Rocks Beach
4.7 out of 5 average rating, 211 reviews

Beachy Paradise

JoeyRating, 5 stars2 weeks ago
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!!
Top guest favorite
Cottage in Gulfport
4.99 out of 5 average rating, 266 reviews

Gulfport Art District - One Block From Beach!

MatthewRating, 5 starstoday
This may be my one of favorite vacation rentals we’ve done! The owner is super attentive and quick with responding. The place itself is adorable. Amazing location, clean and so charmingly decorated. They have the fridge and cabinets stocked with essentials which is an amazing touch. Already thinking about booking again for a trip in the winter!

Private cottage rentals

Superhost
A wide expanse of soft, white sand stretches along the shoreline, meeting calm blue waters. Tall grasses are visible in the foreground, and the horizon is clear under a bright blue sky, creating a serene coastal environment.
Cottage in Redington Shores
4.91 out of 5 average rating, 11 reviews

2 Bedroom Turtle’s Nest Beach Cottage,

MarinaRating, 5 stars23 months ago
Staying at Shane's place was wonderful! Our family stayed for 8 nights. It was just as described, and the pictures were extremely acurate. The place was very clean and it really was just a short walk (maybe 3 minutes) to the beach. We had everything we needed for our stay. Diane was extremely helpful and responsive and she answered all of our questions in a very timely manner. The neighborhood is beautiful, quiet and very safe. Another family was staying upstairs during our stay, and although you could hear them a little bit, we had no issues with the shared access areas because they were super nice and friendly, too. The beach is absolutely gorgeous and not crowded at all. We had access to beach equipment (chairs, unbrellas, etc, which was a bonus for us). It was a perfect beach vacation for our family of 4 and we can't wait to stay at Shane's place again!
Guest favorite
A wooden boardwalk is framed by lush greenery and colorful foliage leading towards a serene beach. A sign reading 'Please Leave Nothing But Your' is visible on the left. The tranquil ocean is visible in the distance under a partly cloudy sky.
Cottage in Indian Rocks Beach
4.93 out of 5 average rating, 14 reviews

Seaside Retreat Cottages #4

DavidRating, 5 stars3 weeks ago
A perfect spot to enjoy a solo vacation. Lazy mornings by the pool, followed up by a 3 minute walk l (if that) to the beach for an afternoon of sand and ocean time. Dinner at Cocos Crush right around the corner was perfect. I can't wait to get back to this perfect place.
Guest favorite
A cozy outdoor seating area features two woven chairs positioned around a modern gas fire pit. Flame dances above colorful glass stones, casting a warm glow. A small wooden table sits between the chairs, complemented by decorative cushions on the seats.
Cottage in Tampa
4.96 out of 5 average rating, 90 reviews

River adjacent, Quiet neighborhood, King bed

VictoriaRating, 5 stars6 days ago
We loved our stay at Hew’s place. The location was perfect and Hew was super helpful and responsive to all questions asked. So happy we found this place for our stay!
Guest favorite
Cottage in Redington Shores
4.86 out of 5 average rating, 50 reviews

Palm Cottage- Escape to Paradise!

MeghanRating, 5 stars5 days ago
I’ve stayed in many AirBnBs, in many countries, and this is by far one of my favorites. Pros: - incredibly well appointed with everything you could need while on vacation (beach gear, kitchen utensils and pantry basics, games, etc.) - walkable to beach and restaurants - very comfy beds - laundry! - a private, fenced yard — great for small children! - a kitchen you can actually cook in - a large communal family room space and comfy couch Cons: Very few, if I’m being honest. They likely had to do a complete reboot after the hurricane so the bathroom and bedrooms could use a few more hooks to place towels and robes on. Also, when you’re accessing the back and front, it can take a bit for the living room to cool back down. Pretty typical, though. There isn’t a large communal dining space inside (just the two bar chairs on the island) but we didn’t find that to be an issue.
Top guest favorite
A tranquil backyard area is illuminated by soft lighting, featuring several comfortable chairs arranged around a central fire pit. The space is surrounded by a wooden fence, with gravel underfoot and a few plants adding a touch of greenery.
Cottage in Safety Harbor
5 out of 5 average rating, 57 reviews

"Sweet Harbor Cottage" Walk to Downtown

AlexisRating, 5 stars6 days ago
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.
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 stars4 months ago
Very responsive, went above and beyond!
Top guest favorite
Cottage in Safety Harbor
5 out of 5 average rating, 54 reviews

Safety Harbor Cottage

WendyRating, 5 stars3 weeks ago
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!
Guest favorite
A waterfront pathway is lined with palm trees swaying gently in the breeze. Colorful flowers are planted along the edge of the walkway, while a calm waterway reflects the clear blue sky. Parked cars are visible in the background, adding to the lively atmosphere.
Cottage in Gulfport
4.73 out of 5 average rating, 51 reviews

The Cottage at Wishing Well, Gulfport

TonyRating, 5 stars2 months ago
Second time staying at the beautiful place! Will again!

Destinations to explore

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