
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
We enjoyed our stay, it was a very pleasant, clean, and a practical location. We give thanks to the host!

Pink Gulfside Cottage, Steps to Beach, Pets OK
Great old school beach cottage. Perfect for my Son and me. The Capt. and especially the First mate made it 5 stars!

Sunny - Key West Vibe Cottage - Pool - Walkable
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.

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 + 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.
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!

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
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

Cottage by the Coast 2 bd - Pet Friendly
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.

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!

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!

Adorable Dog-Friendly Cottage in Quaint Dunedin
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!!

Vintage Florida Beach Cottage B
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

Cozy up in a French Country nest NEAR EVERYTHING
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!!!

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!
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

2 Bedroom Turtle’s Nest Beach Cottage,
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!

Seaside Retreat Cottages #4
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.

River adjacent, Quiet neighborhood, King bed
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!

Palm Cottage- Escape to Paradise!
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.

"Sweet Harbor Cottage" Walk to Downtown
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.

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

Safety Harbor Cottage
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!

The Cottage at Wishing Well, Gulfport
Second time staying at the beautiful place! Will again!
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- Anna Maria Island
- Siesta Beach
- Dunedin Beach
- Anna Maria Public Beach
- John's Pass
- Crescent Beach
- Turtle Beach
- Bean Point Beach
- Busch Gardens Tampa Bay
- Cortez Beach
- Lido Key Beach
- Raymond James Stadium
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- Clearwater Beach
- Vinoy Park
- North Beach
- Fort De Soto Park
- Tampa Theatre
- Curtis Hixon Waterfront Park
- ZooTampa at Lowry Park
- Jannus Live
- Splash Harbour Water Park