Cottage vacation rentals in Cudjoe Key

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Popular amenities for Cudjoe 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.
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 two-story cottage is framed by lush tropical vegetation, with prominent palm leaves. Illuminated doorways reveal a welcoming interior, while a balcony overlooks the entrance, suggesting a space for relaxation. The exterior features light-colored walls that harmonize with the natural surroundings.
Cottage in Key West
4.74 out of 5 average rating, 31 reviews

Darling of Duval at Old Town

JoeRating, 5 stars1 month ago
What a great place to stay for a Key West trip! Perfect location, lots to do, super short walk to Duval St. Very easy check in, and Last Key were easily available for questions.
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
4.88 out of 5 average rating, 59 reviews

NAUTILUS...ocean front cottage retreat ~

JessicaRating, 5 stars2 weeks ago
Super responsive host! Place was great if you’re looking for a relaxed vibe. Close enough to key west but much less crowded relaxing vacation. My kids loved the pool and ocean being so close.
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
4.56 out of 5 average rating, 9 reviews

2BR dog-friendly water view stay, resort amenities

StephanieRating, 5 stars4 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!

Pet-friendly cottage rentals

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
An outdoor seating area is highlighted by a round wooden table surrounded by Adirondack chairs. A ceiling fan adds comfort, and the scene features expansive views of the water, with a dock visible in the background under a clear blue sky.
Cottage in Marathon
4.67 out of 5 average rating, 6 reviews

Waterfront 1B/1B Tiny Home

MatthewRating, 5 stars4 weeks 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.
The overhead loft area features a cozy sleeping space with soft pillows arranged on a spacious bed. Natural light enters through multiple windows, illuminating the area. A wooden safety railing provides a safe transition to the open space below, which contains additional sleeping arrangements.
Cottage in Marathon
4.67 out of 5 average rating, 33 reviews

Cute 1B/1B Lofted Cottage

AmyRating, 5 stars1 week ago
What a beautiful, peaceful spot to stay! Family friendly and exceeded expectations. Great location to explore all of the Keys but always a nice, private and quiet place to come back to. Would absolutely stay here again!
Cottage in Marathon
4.75 out of 5 average rating, 12 reviews

Waterview 1B/1B Tiny Home

RuthRating, 5 stars2 weeks 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 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.
A bright living area features a large flat-screen TV mounted beneath a stylish white cabinet. Natural light pours in through multiple windows, illuminating the modern gray sofa and round seating options. Air conditioning units are visible in the ceiling, providing comfort to the space.
Cottage in Marathon
4.72 out of 5 average rating, 25 reviews

Prime Location 1B/1B Home

AbbyRating, 5 stars2 weeks ago
We thoroughly enjoyed our stay! The cottage was very clean and comfortable with plenty of space for three adults. We especially loved the pool and proximity to the ocean - the views were stunning! Just a quick note about parking: the house rules state that parking for one vehicle is included with each reservation, but we were able to park both of our cars with no issue.
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!
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, 236 reviews

Tropical Cottages - Cottage # 8

ChereeRating, 5 stars4 months ago
We loved that it was a true cottage and not attached to another house especially since we had our dog with us. Having food and drinks within feet of the cottage was a huge plus. We brought our kayak with us and never felt that we needed to check if it was still there during the night.

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 stars4 months ago
This charming unit exceeded our expectations and was wonderfully walkable yet totally private.
Superhost
A wooden door opens to a lush garden pathway, framed by tropical foliage and vibrant flowers. An ornate table with decorative plants is positioned to the left, while a charming outdoor dining area is visible in the background, surrounded by greenery.
Cottage in Key West
4.86 out of 5 average rating, 44 reviews

Namaste: A blissful one bedroom cottage

JorgeRating, 5 stars2 months ago
This was, by far, the best Airbnb I’ve ever stayed at, and I’ve been at Airbnb’s since 2012. It was the perfect place for our honeymoon stay, very VERY easy walk to Duval (under 2 minutes to Sloppy Joe’s). Seriously, this place is IT.
A communal heated swimming pool is surrounded by lush greenery and palm trees. Comfortable lounge chairs are positioned along the poolside, complemented by two blue umbrellas providing shade. A serene atmosphere is created by the clear blue skies above and the vibrant landscaping surrounding the area.
Cottage in Islamorada
4.78 out of 5 average rating, 79 reviews

Serene Cozy Cottage in Islamorada with Heated Pool

JustinRating, 5 stars2 weeks ago
The place and location were perfect. We were looking for a no frills type of place so my kids would have to spend time without devices and just be outside. This little place is exactly what we needed, it’s just big enough to sleep, eat a quick breakfast and head out for the day on the keys. The pool area is really nice and everything was great. It does not come with any extras..like beach bike, beach chairs or extra beach towels so you may want to bring your own. We left a few behind for the next family to enjoy. Over all this was a very clean and nice place to stay in a good neighborhood located to almost everything.
Superhost
A sparkling shared pool is framed by tropical landscaping, with lounge chairs arranged nearby for relaxation. A nearby bungalow is visible in the background, enhancing the sense of privacy in this serene outdoor space.
Cottage in Key West
4.71 out of 5 average rating, 14 reviews

Colony Poolside: A charming bungalow near Duval

EricaRating, 5 stars16 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!
Superhost
A cozy studio features a queen-size bed adorned with patterned bedding. Comfortable seating is provided by two armchairs near a window overlooking tropical foliage. Warm light is emitted by ceiling fixtures, and shelves display decorative items, contributing to the inviting decor.
Cottage in Key West
4.77 out of 5 average rating, 22 reviews

Bali Hideaway: A studio cottage that's perfect

GailRating, 5 stars1 month ago
Loved our stay here. Close to everything yet did not hear the noise or sounds of the town. Great studio and fantastic little garden/yard. Loved the vibe and the privacy. Pool was great too!
Cottage in Key Colony Beach
5 out of 5 average rating, 10 reviews

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

DawnRating, 5 stars12 months ago
Leeann’s place exceeded our expectations! She was incredibly responsive to any concerns or inquiries we had throughout our stay. The added perk of access to Glunz Beach Resort with its beach, pool, and gym made our experience even more delightful. The house was equipped with everything we needed for a comfortable stay. Thank you, Leeann!

Quick stats about cottage rentals in Cudjoe Key

  • Total rentals

    10 properties

  • Nightly prices starting at

    ﺩ.ﺇ624 before taxes and fees

  • Total number of reviews

    770 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with a pool

    10 properties have a pool

  • Wifi availability

    10 properties include access to wifi

Destinations to explore

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  4. Monroe County
  5. Cudjoe Key
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