Cottage holiday rentals in Longboat Key

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Popular amenities for Longboat Key cottage rentals

Cottage rentals with a hot tub

Guest favourite
Cottage in Palmetto
4.93 out of 5 average rating, 46 reviews

Charming Home w/ Hot Tub, 20 min to Beach + Garden

TimothyRating, 5 stars2 weeks ago
Great home and location with all the amenities that we needed. We walked and rode our bikes all over, and enjoyed the local restaurants.
Guest favourite
Cottage in Sarasota
4.84 out of 5 average rating, 45 reviews

Siesta Key Cottages Crescent 1C Beach/Pool/Hot Tub

TerriRating, 5 stars1 week ago
Marc and Dave were incredible. They were responsive and proactive! I will definitely be back. We had a family of 7 and even though it was small, we were comfortable. The bikes were an added bonus and amazing to use for our trips to the Daiquiri Deck! Although the weather didn’t cooperate we still had an amazing time and would 10000% recommend this place. Traveling with 5 kids can be stressful and they made accommodations seamless!
Top Guest favourite
Cottage in Safety Harbor
4.96 out of 5 average rating, 185 reviews

Harbor Oasis with Hot Tub

CalebRating, 5 stars2 days ago
Very responsive, helpful hosts and a wonderful location with lots to offer.
Guest favourite
Cottage in Indian Rocks Beach
4.97 out of 5 average rating, 39 reviews

Beachy Keen Cottage A only steps to the Beach

HannahRating, 5 starstoday
We absolutely loved it here. It was very clean and had everything we needed. Hot tub was a great amenity. The shed full of beach needs was amazing! Definitely would stay here again!
Guest favourite
Cottage in Tampa
4.94 out of 5 average rating, 125 reviews

Hot tub, 2 floors riverfront, Bush Gardens, kajaks

HanselRating, 5 stars1 month ago
Cozy, comfortable, yet two stories with plenty space to stretch out, scenic view with a hot tub, nice balcony view for coffee in the morning. Can’t go wrong.
Guest favourite
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 favourite
Cottage in Largo
4.98 out of 5 average rating, 57 reviews

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

TanyaRating, 5 stars3 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!
Guest favourite
Cottage in Largo
4.96 out of 5 average rating, 95 reviews

Hidden Oasis #1, hot tub near the beach

MadisonRating, 5 stars1 month ago
My boyfriend and I had a wonderful 5 night stay at Amy's for my first visit to Florida. The space was clean, the bed was comfortable, the kitchen was well stocked and the outside space was a peaceful area to spend our mornings. The hot tub in the evening was a perfect way to end the day of exploring. Short driving distance to the beach and other lovely neighbourhoods. We would absolutely recommend, and would be happy to stay again.

Pet-friendly cottage rentals

Top Guest favourite
Cottage in Gulfport
4.96 out of 5 average rating, 154 reviews

The Pelicans Roost / Gulfport

LindaRating, 5 stars1 month ago
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.
Guest favourite
Cottage in Englewood
4.96 out of 5 average rating, 159 reviews

Family-Friendly Beach Cottage Manasota Key

SarahRating, 5 stars2 weeks ago
Our family had a great stay! We traveled with a baby, toddler and two dogs and had plenty of space and everything we needed. Birgit was quick to respond when we had questions. The house is spacious and comfortable. We loved being able to walk across the street to the beach! And the convenience of having an outdoor shower to wash off the kids. There was lingering hurricane damage nearby, but Birgit’s place is pristine! We would definitely return in the future.
Top Guest favourite
Cottage in St. Petersburg
4.95 out of 5 average rating, 123 reviews

Artsy guest house; near downtown w/ private patio

PhoebeRating, 5 stars1 month 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.
Top Guest favourite
Cottage in Dunedin
4.96 out of 5 average rating, 207 reviews

Adorable Dog-Friendly Cottage in Quaint Dunedin

KikiRating, 5 stars2 weeks ago
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!!!
Guest favourite
Cottage in Indian Rocks Beach
4.89 out of 5 average rating, 295 reviews

Vintage Florida Beach Cottage B

HeatherRating, 5 stars1 week ago
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!
Superhost
Cottage in Bradenton
4.85 out of 5 average rating, 101 reviews

Casa Azul. 2 bed/2 bath on lake

SamanthaRating, 5 stars2 weeks ago
Cute spot!! Loved the lake! Actually caught a couple fish! Not a bad drive to the beach area. Would definitely stay again!
Superhost
Cottage in Indian Rocks Beach
4.7 out of 5 average rating, 214 reviews

Beachy Paradise

JoeyRating, 5 stars3 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 favourite
Cottage in Gulfport
4.99 out of 5 average rating, 267 reviews

Gulfport Art District - One Block From Beach!

RobbiRating, 5 starstoday
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

Guest favourite
Cottage in Bradenton
4.87 out of 5 average rating, 97 reviews

The Magical Mermaid Cottage

JoeRating, 5 stars3 weeks ago
We had a very pleasant stay. Sandra and Kim were great to deal with including special accommodations for a late night arrival. We really did feel like guests in every sense. I guess the best thing I can say is that we are back in Bradenton next week and looking forward to another stay.
Guest favourite
Cottage in Holmes Beach
5 out of 5 average rating, 7 reviews

Anna Maria Cottage w/Golf Cart

SarahRating, 5 stars1 week ago
My son and I had a wonderful stay at this cute little cottage. Everything was clean and well-decorated, and we had everything we needed in the kitchen. We loved having the golf cart to run around in! The host also provided beach chairs and a kayak to use, which was very handy. The area is pleasant, situated in a quiet neighborhood with public tennis and basketball courts across the street. Anna Maria is a happy little island, with a lot of good food and entertainment, and a number of beach areas to choose from. Lynda was very responsive to any questions we had, and provided a lot of easy -to-follow instructions for the house, as well as lots of helpful tips about the area. We will definitely be back!
Superhost
Cottage in Longboat Key
4.8 out of 5 average rating, 5 reviews

2BR Gulf Side Cottage: Longboat Key

AlRating, 5 stars2 months ago
A week of absolute relaxation. Literally 20 steps to the beach. Wonderful sunsets. The community was great extremely friendly people. Will be back again soon.
Top Guest favourite
Cottage in Bradenton
5 out of 5 average rating, 31 reviews

2/2 Charming Riverfront Cottage w Deck & Kayaks

KellyRating, 5 stars1 day ago
We stayed at this home for 2 weeks and the nature watching was fascinating. Alligators, turtles, birds and fish jumping out of the water. The home was comfortable and included everything one would need. The Wi-Fi was solid for zoom calls and remote work. The kitchen had every dish, pot, utensil for cooking. The AC worked great and the beds were super comfy. The host replied quickly to every question. I would stay here again. 5 stars. ⭐️ ⭐️⭐️⭐️⭐️
Guest favourite
Cottage in Holmes Beach
5 out of 5 average rating, 30 reviews

Hibiscus Villa by Beach Boutique Rentals

JodyRating, 5 stars2 months ago
Absolutely — here’s the updated version with that added: ⸻ Wonderful apartment. Very clean and nicely decorated. We didn’t cook more than coffee because the island’s restaurants were great, but the kitchen looked well equipped. The bed was very comfortable and there were plenty of soft towels. The private gardens and fountains were lovely. Walk right across the street to the beach and under a mile to good coffee and food. The management was quick, attentive, and detail-oriented with their responses to my questions. The beaches are very walkable, and the island is also super bike-friendly and you can easily reach beautiful, secluded beaches that way. Definitely try Mademoiselle’s Paris restaurant—great food, and Chuck played guitar the night we were there. I also liked Hurricane Hanks and The Sandbar. Really nice beach vacation. Great apartment in a beautiful location.
Guest favourite
Cottage in Holmes Beach
5 out of 5 average rating, 35 reviews

Sailfish Gulf Suites #4, Garden Views, Steps from

RichardRating, 5 stars2 months ago
The one issue with this rental was the cleaning and service fees. Upon checking out they asked for guests to clean up, meaning taking out the trash and empty the trash throughout the house, which was partially why am I going through the house and cleaning up when I’ve paid a hefty amount for cleaning fees. When we cleaned with the broom, we found left over food crumbles and pills (medication). Overall tho, a great experience.
Guest favourite
Cottage in Bradenton
4.97 out of 5 average rating, 39 reviews

NEW 3BR Home w/ grill | Near AMI, IMG & Beach

LouisRating, 5 stars1 week ago
We had a fantastic stay at Crysty’s place. The home was exactly as described—clean, cozy, and thoughtfully decorated. Check-in was seamless, and communication with the host was quick and helpful throughout the trip.
Top Guest favourite
Cottage in Indian Rocks Beach
5 out of 5 average rating, 13 reviews

Kamp Komfort Historic Family Beach House

HollyRating, 5 stars1 week ago
We can't say enough good things about our stay. Morgan was so friendly upon our arrival and made us feel right at home. The cottage was very cozy, and it was literally on the beach. The view from the patio was amazing. We sat out there until after dark every night. We would definitely love to make a return visit.

Quick stats about cottage rentals in Longboat Key

  • Total rentals

    20 properties

  • Nightly prices starting at

    $183 NZD before taxes and fees

  • Total number of reviews

    150 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with a pool

    20 properties have a pool

  • Wi-Fi availability

    20 properties include access to Wi-Fi

Destinations to explore

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