Cottage vacation rentals in Sunset Key

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Popular amenities for Sunset Key cottage rentals

Cottage rentals with a hot tub

Superhost
An outdoor dining area is situated on a covered porch overlooking expansive water views. A large table is set with colorful dishware in blue and turquoise. Yellow kayaks are visible on the dock, complementing the serene backdrop of the water and sky.
Cottage in Cudjoe Key
4.87 out of 5 average rating, 67 reviews

Turtle Cove Views at Venture Out

CooganRating, 5 stars1 month ago
Enjoyed the stay - the cottage was cute and nicely decorated - met all of our needs. Great athletic facilities. Nice being on the water and watching the sun rise every morning.
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 week 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!
Guest favorite
A clear view of the waterfront features a well-maintained seawall alongside tranquil blue waters. Palm trees line the shore, offering a tropical feel. The space is enhanced by direct access for boating activities, emphasizing the serene and inviting coastal environment.
Cottage in Cudjoe Key
4.93 out of 5 average rating, 121 reviews

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

TjRating, 5 stars1 month ago
What a fantastically beautiful place. right on the canals leading to the sea with spectacular views. Great hosts who were super responsive. Highly recommended
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
4.81 out of 5 average rating, 95 reviews

OCEANIA... water front cottage retreat ~

RachelRating, 5 stars7 months ago
If we could rate this 6+ stars out of 5, we would! Manuel was super easy to reach, he provided simple and clear instructions, the guards at the gate were easy to work with and available for 24/7 entry and check in.. the location is unbeatable for a boat owner! You dock right at your back door, clean your fish at the back door OR at the marina, immediate access to the Atlantic.. perfection. The home itself is extremely clean & beautiful. The kitchen and bathrooms were all stocked with anything you’d need as well as even the laundry room! We truly felt at home but twice as relaxed! Thanks Manuel!!
Superhost
The exterior of a mid-rise home is shown, featuring a light-colored facade and a set of stairs leading to an elevated porch. The porch area is equipped with a table and umbrella, surrounded by tropical landscaping and a gravel driveway.
Cottage in Cudjoe Key
4.64 out of 5 average rating, 111 reviews

VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck

Elizabeth CarmenRating, 5 stars1 month ago
Jason’s place was a great place to stay in the keys!! Jason is great at responding great location, clean house only the couch could use a cleaning. It would have been nice if there were trash bags, extra hand soap and extra toilet paper. Other then that it was perfect!!
Superhost
A bright window offers views of the canal and vibrant outdoor scenery. Two stools are positioned in front of the window, inviting guests to relax and enjoy the surroundings. Colorful decorations add a charming touch to the space, enhancing the coastal atmosphere.
Cottage in Cudjoe Key
4.7 out of 5 average rating, 145 reviews

Calypso Cottage

CourtneyRating, 5 stars2 weeks ago
Place was exactly like described, super quaint and had a great homey cottage feel. Neighbors were all super friendly as well. We really enjoyed being able to sit outside on the canal and enjoy our breakfast/dinner as well as playing any games. Would highly recommend this place, not far from key west a matter of 35-45 min depending on traffic
An American flag is displayed on a balcony, gently waving in the ocean breeze. The calm waters are reflected under a cloudy blue sky, creating a serene atmosphere. White railings and chairs frame the view, emphasizing the oceanfront location.
Cottage in Cudjoe Key
4.9 out of 5 average rating, 152 reviews

ATLANTIS...Ocean Front Cottage Retreat!

JeanRating, 5 stars1 month ago
Manuel's home was clean, bright, quiet, and peaceful with a million dollar view. It sits directly on big open water which we enjoyed from the nice open porch. We ate meals on the porch while relaxing and savoring the amazing view of the blue water and the two islands beyond. We never tired of the view. The whole neighborhood is quiet and clean, and there is a small beach and a pool. The check in/check out process was simple and Manuel was responsive with all communications. We enjoyed exploring Key West (about a 30-35 minute drive) and walking the old train/then road Old Seven Mile Bridge from Marathon Key to Pigeon Key. The Bridge is a beautiful 4 mile round trip walk to small Pigeon Key where we swam and participated in a guided walking tour and shark feeding. If you're looking for a peaceful, relaxing, home with an amazing view to get away from it all, Manuel's home is the answer! It was perfect for my husband and me.

Pet-friendly cottage rentals

Superhost
The living area features a gray sofa complemented by a colorful area rug. A flat-screen television is mounted on the wall. A small bar with seating connects to the kitchen area, adorned with bamboo window treatments, enhancing the bright and airy ambiance.
Cottage in Key West
4.79 out of 5 average rating, 19 reviews

Colony Sunset- Bright and airy cottage

MaureenRating, 5 stars12 months ago
What a great find! Everything we needed was there! Quick walk to everywhere: beach, Duval street fun, restaurants and grocery store. So glad we went with this air bnb and not the hotel we normally go to. Saved so much money. Loved the privacy!
Superhost
The outdoor deck provides a spacious area for dining and relaxation, framed by lush greenery. Two flags flutter gently in the breeze, while a mix of natural wood and beige gravel enhance the serene atmosphere of this tropical retreat.
Cottage in Key West
4.83 out of 5 average rating, 6 reviews

The Southern Cross

AllisonRating, 5 stars5 months ago
We enjoyed our stay. Very close to Duval and southernmost point. Plenty of space for 2 couples. Enjoyed having a kitchen. Host was responsive. Had issue with front gate but it was promptly taken care of. Wish upstairs room had small set of drawers and full length mirror somewhere in house. Would rent again!
Superhost
An outdoor seating area features a round table with four yellow chairs beneath a large umbrella. A gas grill is positioned nearby on a wooden deck surrounded by lush greenery and tropical plants. Large French doors lead into the cottage.
Cottage in Key West
4.71 out of 5 average rating, 89 reviews

Stay at Hidden Treasure for a relaxing vacation!

LisaRating, 5 stars1 month ago
Comfortable accommodations, located in a quiet neighborhood. Pool was nice and we enjoyed the private courtyard. Beds were very comfortable as well!
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
4.84 out of 5 average rating, 80 reviews

Hidden Oasis @ the Colony ~ Great location

GeorgeRating, 5 stars4 months ago
Great stay and perfect location to all I wanted to do and see. Very let friendly as well. I will be back
Superhost
An open studio layout features high ceilings and light blue walls. A queen bed is positioned near the window, with a comfortable couch and a coffee table in the seating area. French doors lead to an outdoor deck, enhancing natural light in the room.
Cottage in Key West
4.67 out of 5 average rating, 30 reviews

Osprey @ Colony

FrancesRating, 5 stars1 month ago
Perfect place for two. Awesome location, within walking distance of Duval but far enough away that it’s nice and quiet at night. Beautiful little pool. Will 100% stay here again next visit to Key West
A charming cottage exterior features light blue siding and is accented by vibrant pink Adirondack chairs. Lush greenery surrounds the entrance, and flowering plants add color to the setting. A clear blue sky and tropical palm trees complete the welcoming atmosphere.
Cottage in Marathon
4.62 out of 5 average rating, 116 reviews

Tropical Cottages - Cottage # 10

LoriRating, 5 stars1 month ago
The Airbnb had a great location. My husband enjoyed the local fishing, which was a block away. The Airbnb was clean and very comfortable. We also enjoyed the taco truck and Tiki bar located on the premises. The most important thing was that we could bring our dog Chloe and felt comfortable and safe. We will come back again to the cottage.
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, 218 reviews

Tropical Cottages - Cottage # 03

HilaryRating, 5 stars3 months ago
I thought that our tiny house (cottage) was adorable. The grounds are great, and the food truck and bar every evening was super! We couldn’t figure out how to turn back to air conditioning after heat kicked on. Maybe just include a little info sheet on this on the kitchen counter. Parking on site is great! And the toiletries were very nice as well. Super close to Sombrero Beach. Loved it!
Private room in Marathon
4.39 out of 5 average rating, 111 reviews

Tropical Cottages - Room # 11

EmmaRating, 5 stars3 months ago
Really nice place

Private cottage rentals

Superhost
A shared swimming pool is framed by lush tropical landscaping, with several lounge chairs positioned around the water. Shaded by tall greenery, the pool area creates a relaxed ambiance, inviting guests to enjoy the serene environment.
Cottage in Key West
4.79 out of 5 average rating, 19 reviews

Colony Sunset- Bright and airy cottage

MaureenRating, 5 stars12 months ago
What a great find! Everything we needed was there! Quick walk to everywhere: beach, Duval street fun, restaurants and grocery store. So glad we went with this air bnb and not the hotel we normally go to. Saved so much money. Loved the privacy!
Superhost
An outdoor dining area is situated on a covered porch overlooking expansive water views. A large table is set with colorful dishware in blue and turquoise. Yellow kayaks are visible on the dock, complementing the serene backdrop of the water and sky.
Cottage in Cudjoe Key
4.87 out of 5 average rating, 67 reviews

Turtle Cove Views at Venture Out

CooganRating, 5 stars1 month ago
Enjoyed the stay - the cottage was cute and nicely decorated - met all of our needs. Great athletic facilities. Nice being on the water and watching the sun rise every morning.
Superhost
A winding brick pathway leads through lush tropical foliage and vibrant flowers, creating a serene and inviting entrance to the cottage. Sunlight filters through the leaves, illuminating the greenery that surrounds the path, offering a tranquil atmosphere for guests.
Cottage in Key West
4.78 out of 5 average rating, 9 reviews

Ann Street Cottage

PaigeRating, 5 stars1 month ago
Comfortable cottage for 2 adults. Cooked dinner in a few nights, breakfast as well. Clean rooms, kitchen, bathrooms & bedding. Took a day to figure out where laundry was, but once we did more snooping, we found it across the small deck area. Only complaint/attention to maintenance: the decking off the living rm/bedroom is rotted. Extremely soft and about to break thru walking across it. Someone's likely to get hurt if the boards give way. Also the patio table on the deck should be replaced with something a little sturdier. It's shaky and legs are wobbling on the table. Our stay was very comfy and enjoyable. Easy walk to activities/bars/restaurants, yet tucked away enough that it was mostly quiet & definitely private our entire stay.
Guest favorite
Two turquoise Adirondack chairs are positioned on a sunlit dock overlooking clear blue water. The dock is surrounded by green palm trees and a bright sky, creating a relaxing outdoor space for enjoying the views.
Cottage in Little Torch Key
4.9 out of 5 average rating, 167 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

NicoleRating, 5 stars1 month ago
Wish we could’ve stayed longer. It was a perfect home!
Superhost
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
4.71 out of 5 average rating, 14 reviews

Colony Poolside: A charming bungalow near Duval

EricaRating, 5 stars17 months ago
We loved our time at Colony Poolside! We spent a long weekend at Colony Poolside (it was our second stay in this location). The rental was exactly like the pictures, clean and comfortable. The kitchen was well stocked, and there were even beach towels, sunblock and a workout mat. The pool was clean and quiet. Short walk to Duval and lots of great restaurants. We would highly recommend!
Top guest favorite
An outdoor deck is visible along the canal, featuring a picnic table and two sun loungers. A kayak in bright orange and white rests on the surface. The sky is clear, with a few clouds, and a calm waterway is seen in the background.
Cottage in Marathon
4.97 out of 5 average rating, 32 reviews

Catch n' Relax Canalfront Cottage in Marathon

SandyRating, 5 stars1 month ago
We stayed for 11 nights at Wendy's beautiful home. We had everything we needed for our entire stay. The area is very quiet and peaceful. It was so lovely walking up on the water and enjoying breakfast outside. Extra touches like having bikes and kayaks to use were also sooo nice! Wendy was very helpful with local spots to check out as well. We will definitely be back!
Superhost
A cozy living room features a dark leather sofa and a unique, modern art piece on the wall. A spiral staircase with white railings leads to a loft area. Natural wood beams and a warm light enhance the inviting space.
Cottage in Key West
4.8 out of 5 average rating, 5 reviews

Pete's Cottages: Twin Cypress cottages steps from

SteveRating, 5 stars3 months ago
We had a family gathering. My wife and I and our older daughter and husband in one house with our younger daughter, husband and two sons in the adjacent house. Absolutely perfect. Loved the pool in the shared back garden. Would love to stay here again and again. Thank you
Guest favorite
A kidney-shaped pool is surrounded by a white deck, featuring steps that lead into the water. Two lounge chairs are positioned beside the pool, and lush greenery creates a private atmosphere.
Cottage in Key West
5 out of 5 average rating, 31 reviews

Pete's West Cottage steps from Duval

EmilyRating, 5 stars1 week 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!

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Key West
  6. Sunset Key
  7. Cottage rentals