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Cottage vacation rentals in Sunset Key

Find and book unique cottages on Airbnb

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Popular amenities for Sunset Key cottage rentals

Cottage rentals with a hot tub

A bright living area features light-colored furnishings with nautical accents. Large windows offer views of the water, while a flat-screen TV is positioned on a stylish stand. The adjoining dining area showcases a white table with matching chairs surrounded by plants, enhancing the airy environment.
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
An outdoor seating area features a round table surrounded by iron chairs, overlooking tranquil waters. Lounge chairs are positioned along the railing. The covered porch provides shade, with lush greenery visible across the waterway, enhancing the serene setting.
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!
The exterior of the Conch Cottage features a light green facade with large windows allowing natural light. Palm trees frame the entrance, and a clear driveway leads to the door marked with the number 315. A window air conditioning unit is also visible.
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!
An aerial view presents a light blue cottage alongside a canal, with white lounge chairs positioned on the deck. A kayak rests in the water, surrounded by lush palm trees and calm, clear waters reflecting a bright blue sky.
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.
A charming green cottage is surrounded by a landscaped area featuring palm trees. A wooden deck leads to the front entrance, and bright blue chairs are positioned on the gravel patio. A neighboring structure is partially visible in the background.
Cottage in Marathon
4.77 out of 5 average rating, 31 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.
The spacious cottage interior showcases two queen size beds with light bedding, set against soft blue walls. A ceiling fan adds to the airiness, while a small dining table with black chairs sits nearby. A kitchenette area is visible in the background.
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
A charming outdoor space is shown with a small circular table and two chairs set on a stone patio. Lush greenery surrounds the area, and wooden steps lead to the entrance of the cottage. A tree provides shade, enhancing the serene ambiance.
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.
A charming yellow cottage is visible, featuring a white door and a small window above it. Two blue chairs are positioned in front, surrounded by lush greenery and palm trees. The pathway is made of brick, enhancing the inviting exterior of the cottage.
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!
A bright sleeping area features a spacious bed adorned with floral bedding. Soft blue walls create a serene backdrop, while natural light filters through the partially open blinds. Nightstands with lamps stand beside the bed, and a dresser is positioned against the opposite wall.
Private room in Marathon
4.36 out of 5 average rating, 113 reviews

Tropical Cottages - Room # 11

GabrielRating, 5 stars1 month ago
It was an amazing experience in this atypical accommodation! Really in love with the outdoor bathroom. The organization is perfect. Recommended

Private cottage rentals

Superhost
The living area features a high, vaulted ceiling with exposed beams and large windows letting in natural light. A comfortable sofa and armchair provide seating options around a round coffee table. Decor includes tasteful artwork and fresh plants, creating a relaxed environment.
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
The exterior view features a charming cottage framed by lush greenery and tropical plants. French doors open onto a wooden deck, inviting guests into the living space. A stone pathway leads to the entrance, while seating is offered nearby under the natural shade of palm trees.
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 favorite
A long wooden dock extends into clear blue water, flanked by palm trees and lush greenery. Two turquoise chairs are positioned at the dock’s end, providing an ideal spot for relaxation and enjoying scenic water views under a bright sky dotted with clouds.
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
A view of the serene ocean waters with palm trees lining the shore. A sandy beach area leads to a marina with docks, while thatched umbrellas provide shaded spots. Clear blue skies and a few clouds complete the inviting coastal landscape.
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 favorite
A charming entrance features double French doors framed by lush greenery. The brick pathway leads to the entrance, with soft lighting from wall sconces accentuating the space. Latticework indicates nearby outdoor areas, while bike racks complete the inviting entry.
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 favorite
A wall-mounted dispenser is shown, featuring two clear bottles labeled 'WAVE sensation.' One bottle contains a green citrus and sea foam body wash, while the other holds a liquid for conditioning hair. The bottles are secured on a metallic holder against a brown stone backdrop.
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 favorite
An outdoor deck extends from the cottage, featuring a table with four yellow chairs, a blue umbrella, and a gas grill. Lush greenery surrounds the space, with a comfortable sitting area visible in the background, creating a relaxed outdoor environment.
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 favorite
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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