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Cottage holiday rentals in Sunset Key

Find and book unique cottages on Airbnb

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Popular amenities for cottage rentals in Sunset Key

Cottage rentals with a hot tub

Cottage in Cudjoe Key
4.82 out of 5 average rating, 98 reviews

OCEANIA... water front cottage retreat ~

DeniseRating, 5 stars1 month ago
Place was great. We loved the kayaks and Bikes that were there. Very clean and spacious. Beautiful view being on the canal. my negative I would say, which has nothing to do with the host, We were aware of the $125 resort fee, And our fee was increased to $145 cause my son’s large pickup. Curious as to what that fee actually pays for. We would definitely stay again.
Superhost
Cottage in Cudjoe Key
4.86 out of 5 average rating, 37 reviews

Tidewater Views at Venture Out

KatieRating, 5 stars1 month ago
Great location, and a very practical and cute little house. The neighbor who resides on the ocean side was wonderful and inviting, which made the stay so much better. Well stocked kitchen. Lots of clean towels and name brand starter essentials. The down side, there was a bag of (assumed??) dirty bedding left by the door, which I contacted our concierge about when we arrived, and it went ignored until I brought it up at check out again. It worked out fine though, my kids brought their own blankets and used them instead. Everything else was great though!
Cottage in Cudjoe Key

Cozy, Perfect Conch Cottage! - VO315

StephanieRating, 5 stars2 months ago
Loved our stay! Clean place, great location and the community at VO is so nice. Great place to stay. Clean and cozy spot. Had everything we needed. Would definitely stay here again!
Cottage in Cudjoe Key
4.85 out of 5 average rating, 61 reviews

NAUTILUS...ocean front cottage retreat ~

AngelaRating, 5 stars1 month ago
Manuel was so kind and responsive! This place was sooo cute and perfect to stay in! The community felt super safe with the constant security, and he had so many amenities for us such as kayaks, fishing poles, bikes, kitchen supplies, hair dryer, etc. We had a slight issue with the wifi and he accommodated us to an extra day! It was soo sweet of him to do that and it made our stay extra fun:) Overall, I recommend 100% for anyone to stay here! It’s awesome. The pool and hot tub are so nice as well!

Pet-friendly cottage rentals

Cottage in Marathon
4.62 out of 5 average rating, 13 reviews

Waterview 1B/1B Tiny Home

RuthRating, 5 stars2 months ago
We absolutely loved it here and would've happily stayed for weeks! The tiny house was cute, clean and comfy with everything we needed. The location was perfect, would give it 110%. Beautiful sea view, amazing sunsets and the children enjoyed the games in the clubhouse and the pool. There are also lots of things to do nearby. Probably the best place we've ever stayed.
Cottage in Marathon
4.67 out of 5 average rating, 6 reviews

Waterfront 1B/1B Tiny Home

MatthewRating, 5 stars2 months ago
We had a great stay in their tiny house. The neighbor’s were all nice and friendly. The locals that live inside the campground are absolutely wonderful very nice and full of local information where to go and what to do.
Cottage in Marathon
4.78 out of 5 average rating, 32 reviews

Prime Location 1B/1B Home

AngelaRating, 5 stars6 days ago
The resort itself is great with plenty of amenities and a perfect area to watch sunsets. The boat ramp is small and not very wide so if you’re bringing a boat be prepared to launch elsewhere and then parking your boat in a slip. It is at the top of Marathon and all the activities and restaurants are at the bottom part of the island, which is 10 miles away. Our cottage was roomy but in need of a coffee table or an ottoman and more side tables. The bed was not super hard and not super soft. There is no dishwasher so if you don’t want to do dishes bring paper plates, cups and plastic wear with you. I would consider staying here again, however, I would be sure to bring cleaning supplies with me as our cottage was dirty. There was dog hair all over the floor, the side table and trash left in the bathroom shower on top of the shampoo dispenser. Unless you are shorter than five feet you also won’t fit under the shower head so washing hair is challenging. Go to the comfort station instead.
Cottage in Marathon
4.42 out of 5 average rating, 219 reviews

Tropical Cottages - Cottage # 03

AndrewRating, 5 stars2 months ago
The cottage was cute, comfortable and made a great central location for all our excursions. Loved having a tiki bar and taco truck waiting for us after a long day. We loved our stay.
Superhost
Cottage in Key West
4.83 out of 5 average rating, 84 reviews

Hidden Oasis @ the Colony ~ Great location

EricRating, 5 stars4 days ago
Great place for 2 people for a week. Very peaceful and quiet. Parking was easy and there was a park within walking distance for pets which was great. The cottage was very clean and the grounds were well maintained. Would stay again.
Cottage in Marathon
4.61 out of 5 average rating, 238 reviews

Tropical Cottages - Cottage # 8

RebeccaRating, 5 stars4 weeks ago
It was very cozy and peaceful. It literally made me feel like home! Outside shower was nice!
Private room in Marathon
4.36 out of 5 average rating, 113 reviews

Tropical Cottages - Room # 11

GabrielRating, 5 stars1 month ago
This was an awesome experience at this one-of-a-kind place! A real favorite for the bathroom outside. The organization is perfect. I would recommend it.

Private cottage rentals

Superhost
Cottage in Key West
4.64 out of 5 average rating, 11 reviews

Ann Street Tranquility

LisaRating, 5 stars6 months ago
This charming unit exceeded our expectations and was wonderfully walkable yet totally private.
Superhost
Cottage in Key West
4.8 out of 5 average rating, 20 reviews

Colony Sunset- Bright and airy cottage

PollyRating, 5 stars3 weeks ago
The location was great. We parked our car and walked to everything. The condo was very nice and we loved the pool!
Guest favourite
Cottage in Little Torch Key
4.9 out of 5 average rating, 167 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

NicoleRating, 5 stars3 months ago
Wish we could’ve stayed longer. It was a perfect home!
Superhost
Cottage in Cudjoe Key
4.8 out of 5 average rating, 5 reviews

Ocean Breeze at Venture Out 537

MelissaRating, 5 stars2 weeks ago
I had a wonderful stay at this Airbnb! The home was perfect for our occasion—just as advertised, and even more charming in person. The vibrant and inviting colors gave the space a warm, welcoming feel. There was a slight delay with check-in, but our host, John, responded quickly and resolved the issue right away, which we really appreciated. We also took full advantage of the amenities, which added to the overall experience. Everything was clean, comfortable, and well thought out. I would definitely stay here again and highly recommend it to others!
Guest favourite
Cottage in Key West
4.75 out of 5 average rating, 16 reviews

Colony Poolside: A charming bungalow near Duval

BrianRating, 5 stars4 weeks ago
GREAT location. Our poolside location was fantastic and the staff were very helpful. My only complaint would be the bed. Rather thin mattress and the frame felt a little on the cheap side. This is the only bad thing I can say about our stay. Highly recommend
Guest favourite
Cottage in Key West
5 out of 5 average rating, 32 reviews

Pete's West Cottage steps from Duval

EmilyRating, 5 stars1 month ago
One of my favorite Airbnb’s and I’ve been to at least 20. Nicely decorated with comfortable furnishings and artwork. Kitchen well equipped and plenty of paper goods. Convenient to restaurants, beaches and shopping but not in the noisy bar area. The main bedroom was super quiet and the bed was comfortable. The pool is shared with just two units and never saw the other guests - so essentially a private landscaped pool/patio area with plenty of lounge chairs. Would love to return!
Guest favourite
Cottage in Key West
4.71 out of 5 average rating, 90 reviews

Stay at Hidden Treasure for a relaxing vacation!

JenniferRating, 5 stars1 week ago
We loved everything about the location and the accommodations. Beds were extremely comfortable. It was my daughter and her friend first time in KW and they loved it too. I would rent this place again as I have stayed in other areas of KW before and while they were good too, I just liked the vibe of this area. Thank you for the hospitality.
Guest favourite
Cottage in Cudjoe Key
4.93 out of 5 average rating, 129 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

DonnaRating, 5 stars1 month ago
We brought another couple with us. Had a relaxing enjoyable time. Felt like home. Definitely be back. Thank you

Destinations to explore

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  4. Monroe County
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