Cottage holiday rentals in Sunset Key

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Popular amenities for cottage rentals in Sunset Key

Cottage rentals with a hot tub

Superhost
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
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 favourite
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
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
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
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
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
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!
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.
Superhost
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!
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!
Superhost
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
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
Superhost
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
Superhost
Cottage in Key West
New place to stay

Coming July 1! - The Jolly Rooster - Walk to Duval

Private cottage rentals

Superhost
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
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
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 favourite
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!
Top guest favourite
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!
Guest favourite
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!
Superhost
Cottage in Key West
4.82 out of 5 average rating, 22 reviews

Pete's East Cottage: Cypress east cottage steps

SaraRating, 5 stars1 month ago
Great location! Pool was great! We enjoyed our stay!
Superhost
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!

Destinations to explore

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