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

Harbor Oasis with Hot Tub
Very responsive, helpful hosts and a wonderful location with lots to offer.

Sunny - Key West Vibe Cottage - Pool - Walkable
Antonia hosts a modern, cozy property featuring three cottages (each have two themed guest suites with a kitchenette). We stayed in the "Captain" cottage and definitely enjoyed our stay! There are also five themed guest rooms attached to a main "house". With eleven possible parties staying at any given time, everything seems to run very smoothly...like an intimate inn. There is ample parking, a Keurig machine in the lounge area, a mini fridge with a selection of sodas, and even towels for the hot tub/pool. They thought of everything to make our stay enjoyable. It certainly is a fantastic property just a few blocks from restaurants and activities in Dunedin. Thank you so much. We will be back to visit again!

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.

Are You Here Yet?
My boyfriend and I picked this place to visit his parents who live in Settlers Rest. This was a very clean and renovated place. Very easy to find and we arrived around 11pm as we drove from PA. Our packet with the key was easy to find and we did not have any issues. There were documents to fill out which I did not know about until I received a call from the office and they were understanding. We also brought our two dog's along and were asked for the vaccine records. I had these with me because my boyfriends parents told me to bring them otherwise I would not have had them. Otherwise everything was great and Kimberly responded quickly to all questions and everyone at the office was very nice. We would stay here again!

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.
Awesome place! Captain Al and housekeeping were great and very hospitable. Great location. Will definitely go back.

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

The Pelicans Roost / Gulfport
We really liked Bob’s place. So much we tried to book it for Christmas but it was already booked. We didn’t do any cooking as we were visiting with our boys and their family. Our pup loved exploring the backyard. Thank you again Bob for sharing your home.

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!

BEACH! Sunny Escape! Steps 2 Famous Beach w/2 Bike
Lisa was a great host, and paradise by the beach is an awesome place to stay. My family of 4 (2 adults and our older teens) just loved being able to have a lot of space (compared to the hotel rooms on st Pete beach) and a full kitchen and a close walk to the beach. The kids loved riding the bikes to get an ice cream at night, and it was so easy and convenient to pack up the chairs and umbrella and walk over to the beach. The walk is actually shorter than the resorts we have stayed at on spb. It was kind of like settling into our home by the beach—very comfy and convenient with everything we needed. Lots of tvs, lots of space, easy to get around. I also liked having a fully equipped kitchen—only made dinner one night, but everything we needed was there! We’d definitely again and prefer it to the other resorts we have stayed at. It’s less expensive, more convenient, and a lot more space. Thank you so much, Lisa! We hope your space is available next time we come down!

Adorable Dog-Friendly Cottage in Quaint Dunedin
We absolutely love staying at this property! It is our third time booking. The cottage is always impeccably clean and in a very safe area. It is stocked with everything you need. We love Coral Cottage! And Barbara is very friendly and so responsive. Dunedin is an amazing, quaint little town with so many wonderful food choices. Cafe' Alfresco is our personal favorite. Barbara's cottage is just a couple blocks from downtown Dunedin and only a 15 minute drive to Honeymoon Island State Park or Clearwater beach. I always pick up a piece of jewelry as a memento when we go on a trip. Just kitty-corner from the Airbnb is a charming jewelry store filled with beautiful, unique pieces that are reasonably priced. Romantique Jewelers. Just ask for Kimber, she's a doll! Don't hesitate to book this property for your next trip!!!

Vintage Florida Beach Cottage B
While staying in Indians Rock Beach, the apartment was just what we needed. It was a perfect size for the 3 of us. And so close to the beach. We took his recommendations and went to Cooky Coconut while the sun was setting. The neighborhood was quiet and peaceful. Great amenities for the beach we were grateful for. Overall great experience!! Hoping to visit again. Thank you Eric!

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!!

Alafia River Cottage
The Alafia River House did not disappoint. Check in was easy with helpful photos & directions. The neighborhood is pretty quiet but yet close to everything too. The house is tucked in right on the river, the yard is lush & Florida tropical, it is the perfect place to sit & read, eat a meal or take a nap. Watching the chickens and surrounding nature are an added bonus. The home is old with character, but so clean & refreshing. All the things you need and more are carefully stowed in antique furniture. Martha is easy to contact, but you shouldn’t need anything. The kitchen is up to date & has all of the extra things that you probably forgot to bring. My husband and I had a sweet trip & the Alafia River House was a gem. Thank you Martha.

Gulfport Art District - One Block From Beach!
Absolutely perfect Airbnb in every way! The location could not be better. We laughed because we had dinner reservations at Pia’s Italian restaurant and realized it was right across the street. Talk about convenience! This was hands down the cleanest Airbnb we’ve ever stayed in. Uncle Finley left us a thoughtful welcome package with a bottle of wine, beer, water, orange juice, and more. It’s clear he’s put real care into every detail to make the stay extra comfortable. Phone chargers were exactly where you needed them (no hunting for outlets), there were doggie bowls and doggie bags for our pup, Uncle Finley was super responsive to questions and genuinely committed to taking care of both his guests and this beautiful home. We’d come back in a heartbeat. Don’t hesitate just book it! Tip: In addition to Pia’s homemade pasta with pesto sauce, I’d also highly recommend the restaurant Pearl by Chef Karim for an unforgettable meal! The Pearl is a testament to culinary excellence.
Private cottage rentals

Tranquil Guesthouse Hideaway (Near MacDill AFB)
Was there weekend before last and enjoyed the privacy. The host gave great recommendations when there was a local internet outage. Great place from couples and 30-40 minutes to the beach, casino, and about 20 minutes from downtown. I recommend this place to any couple just looking for a peaceful getaway with tons to do

Adorable Villa 1 min to Downtown Dunedin
Amazing location & SUPER clean!! Quiet area, perfect for relaxing, biking, walking, restaurants & enjoying the cute town of Dunedin. Highly recommend & would book again next time we are in the area. Absolutely perfect!

"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.

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!

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!

Mango Cottage, pet friendly, steps to gulf
Very nice and quiet neighborhood. Crystal Beach sunset was beautiful. Well’s Spring park was a nice park for walking the dog. Everyone was friendly that we met while walking. Would book again.

Tampa-Retreat I Homestead with 5th Gen Floridians
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.

Carriage House 1893
Rick was such a kind helpful host! Checked on us to see if we needed anything. Had one request and he quickly fixed it! Upon entering, home was ready, music playing and a welcome note! He even had eggs and oatmeal available for breakfast! We would stay again.
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- Anna Maria Island
- Siesta Beach
- Weeki Wachee Springs
- Dunedin Beach
- Anna Maria Public Beach
- John's Pass
- Bean Point Beach
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Reunion West
- Gulfport Beach Recreation Area
- Vinoy Park
- ChampionsGate Golf Club
- North Beach
- Fort De Soto Park
- Island H2O Water Park
- Streamsong Resort
- Tampa Theatre
- Jannus Live
- Curtis Hixon Waterfront Park