Cottage vacation rentals in Key West

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Popular amenities for Key West 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.
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, 154 reviews

ATLANTIS...Ocean Front Cottage Retreat!

WendyRating, 5 stars3 weeks ago
We had an amazing 6-night stay at this waterfront Airbnb! The location is perfect—right on the water with gorgeous sunrise views. We used the provided kayaks every day, and my husband loved fishing off the deck while I relaxed in the sun. The house is super cute, clean, and beachy. The bed was very comfortable, and the kitchen was well-stocked with basics like spices and oil, making it easy to cook most of our meals. We also appreciated the strong, hot shower and provided toiletries. Extras like beach towels, umbrellas, fishing gear, and a washer/dryer made our stay even better. The area is peaceful, clean, and friendly—plus, Key West is just a short drive away. We’d definitely stay here 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!
A bright living area features a comfortable gray sofa and an upholstered ottoman. Large sliding doors open to a water view, letting in natural light. A small dining table with patterned chairs is positioned near the window, complemented by a ceiling fan and modern decor.
Cottage in Key Colony Beach
4.55 out of 5 average rating, 11 reviews

2BR dog-friendly water view stay, resort amenities

StephanieRating, 5 stars6 months ago
Perfect location for boaters and fishermen. Clean and mostly quiet canal with minimal low wake zone. House had all basics and very comfortable for my husband and I. Loved having the park nearby to take our dog, would recommend!
Guest favorite
An aerial view captures the vibrant community of Venture Out Residential Condominium, showcasing homes along the canal. Boats are docked nearby, and palm trees surround the outdoor seating areas. The clear water reflects the buildings, creating a serene waterfront atmosphere.
Cottage in Cudjoe Key
4.9 out of 5 average rating, 29 reviews

Conch Cabana in Paradise 23 miles outside Key West

MelodyRating, 5 stars4 days ago
Eliane was very easy to communicate with before and during our stay. She suggested some great things to do too! The place was clean and had everything we needed and more during our stay. I will absolutely stay here again!

Cottage rentals with a pool

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 living room features high vaulted ceilings and large windows allowing natural light to fill the space. A comfortable sofa and chairs are arranged around a glass coffee table. Artwork adorns the walls, and a small dining area is visible in the background.
Cottage in Key West
4.78 out of 5 average rating, 9 reviews

Ann Street Cottage

PaigeRating, 5 stars2 months 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
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
4.73 out of 5 average rating, 15 reviews

Colony Poolside: A charming bungalow near Duval

BrianRating, 5 stars3 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 kidney-shaped pool glistens under a partly cloudy sky, surrounded by lush tropical greenery. The pool features built-in seating areas and is framed by a clean white border. Nearby, wooden decking provides space for lounging and enjoying the serene outdoor environment.
Cottage in Key West
5 out of 5 average rating, 31 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!
Superhost
A kidney-shaped pool with a waterfall is surrounded by lush tropical plants and palm trees. The water features a bright blue hue, inviting relaxation, while a deck with lounge chairs and a wooden fence creates a private atmosphere.
Cottage in Key West
4.83 out of 5 average rating, 23 reviews

Pete's East Cottage: Cypress east cottage steps

AmberRating, 5 stars2 weeks ago
We had a great stay. The pool was perfect in the heat of the afternoons, and so many great restaurants and sites to see within walking distance.
A tiki patio is visible with a thatched roof, surrounded by tropical palm trees. The setting features a private pool, inviting outdoor seating, and a hammock. Bright sunlight highlights the serene atmosphere, with views toward the home through sliding glass doors.
Cottage in Key Colony Beach
5 out of 5 average rating, 11 reviews

Luxurious Oasis: 2BR w/Pool, Tiki, Dock & Beach

MatthewRating, 5 stars1 month ago
What a fantastic place to stay in Marathon! LeeAnn really makes sure you feel right at home. Forgot a toothbrush? Didn't pack or want to buy shampoo? No problem, it's there! The pool is amazing, house is spotless, and the Key Colony Beach community is the best. It is quiet and relaxing while also being in the heart of everything to do in the Florida Keys. LeeAnn is so nice and responsive, she got back to us quickly with any questions that we had. Overall, this was one of the nicest places that my family and I have ever stayed on a vacation. 10/10 would recommend to anyone!
Guest favorite
A private deck area features two gray chairs and a small glass table, surrounded by lush tropical foliage. The deck offers an inviting exterior view of the cottage, with a white lattice screen providing added privacy.
Cottage in Key West
4.79 out of 5 average rating, 14 reviews

Colony Calypso - A quaint 1 Bedroom Cottage

DianeRating, 5 stars1 month ago
Nice little space for 2. Spacious rooms, great location. Privacy, quiet street Easy to walk or bike to many restaurants, museums, shops Nice little pool, there are beach towels available to use We would definitely recommend and stay again if in the area b
A covered outdoor seating area features a round glass table and two chairs overlooking the blue ocean, framed by vibrant green palm trees. The tranquil beachfront path can be seen in the distance, promoting an inviting atmosphere for relaxation.
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.

Pet-friendly cottage rentals

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 stars2 weeks ago
The location was great. We parked our car and walked to everything. The condo was very nice and we loved the pool!
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
4.88 out of 5 average rating, 8 reviews

The Southern Cross

JohnRating, 5 stars1 month ago
Place was just as advertised and pictured. Close to everything on Duval St. The pool is beautiful with lots of vegetation and wild life near it. Only thing to be aware of is that second bedroom upstairs would be a challenge for a tall person. Overall a great stay and I would definitely recommend and stay there again.
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, 82 reviews

Hidden Oasis @ the Colony ~ Great location

HiedyRating, 5 stars1 month ago
We had an amazing stay! Beautiful hideaway, felt like we were at home! Very clean and had everything we needed and more! The grounds were well kept and the pool was perfect! This is DEFINITELY a gem!! And we will 100% rebook in the future! We had a small issue with the mini split and it was handled quickly and never gave us another issue!
Guest favorite
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 stars3 months ago
Comfortable accommodations, located in a quiet neighborhood. Pool was nice and we enjoyed the private courtyard. Beds were very comfortable as well!
Guest favorite
A cozy living area features a gray sofa adorned with pirate-themed cushions, complemented by a decorative throw. Two large windows framed by red curtains allow natural light to brighten the space. A round rug with a compass design anchors the room, accompanied by a side table and lamp.
Cottage in Islamorada
4.84 out of 5 average rating, 32 reviews

Floating 2 BD, 1 BATH Private Villa Pirates Lair

SondraRating, 5 stars1 month ago
We are definitely planning on coming back to stay. We only spent 2 nights here and I’m disappointed we booked another spot in the lower keys for the rest of our trip. The guys at the front desk were very friendly and helpful! We grabbed some local shrimp and bbq’d on the grill. Totally a comfortable, peaceful, and relaxing place to stay, but very close to everything
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 stars2 months 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 cozy living area features a brown leather sofa and a low wooden coffee table, set against a backdrop of wooden paneling. Large glass doors reveal a scenic view outside. A television is mounted on the wall, and decorative items are arranged on a nearby shelf.
Cottage in Islamorada
4.82 out of 5 average rating, 155 reviews

1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON

T LRating, 5 stars3 months ago
Toni was very nice. She went out of her way to make sure we were satisfied with everything. The bed was comfortable and we got a great night's sleep there on the water. Watching the fish jump and pelicans dive as we sat on the front deck was very relaxing.
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, 30 reviews

Prime Location 1B/1B Home

MelissaRating, 5 stars2 weeks ago
We enjoyed our stay very much. Beautiful grounds, the home had everything we needed. The AC kept us very cool, even in the loft. The location was great for our planned activities from Islamorada to Key West. It is about 20-30 minutes to public beaches. We loved and highly recommend Bahia Honda State Park for beaches, snorkeling. We only used the pool once but it was very clean. Sunset was beautiful by the dock. Would definitely stay here again.

Quick stats about cottage rentals in Key West

  • Total rentals

    40 properties

  • Nightly prices starting at

    ﺩ.ﺇ294 before taxes and fees

  • Total number of reviews

    1.1K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with a pool

    20 properties have a pool

Destinations to explore

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  2. United States
  3. Florida
  4. Monroe County
  5. Key West
  6. Cottage rentals