Cottage holiday rentals in Cudjoe Key

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Popular amenities for cottage rentals in Cudjoe Key

Cottage rentals with a hot tub

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.
Cottage in Cudjoe Key
4.9 out of 5 average rating, 154 reviews

ATLANTIS...Ocean Front Cottage Retreat!

WendyRating, 5 stars1 month 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
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!
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!
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!
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!

Pet-friendly cottage rentals

Superhost
Cottage in Key West
4.83 out of 5 average rating, 84 reviews

Hidden Oasis @ the Colony ~ Great location

EricRating, 5 stars3 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.
Guest favourite
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
Cottage in Islamorada
4.75 out of 5 average rating, 175 reviews

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

JaceyRating, 5 stars4 months ago
We loved staying here for the two nights we were on the Keys. The patio outside was great for looking at the stars or sipping coffee and watching manatees. We would definitely return!
Cottage in Marathon
4.67 out of 5 average rating, 6 reviews

Waterfront 1B/1B Tiny Home

MatthewRating, 5 stars2 months 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.
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.
Cottage in Islamorada
4.79 out of 5 average rating, 156 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.
Cottage in Marathon
4.66 out of 5 average rating, 38 reviews

Cute 1B/1B Lofted Cottage

JenniferRating, 5 stars4 days ago
Great distance to everything in the Keys. We stayed for several days and was able to hit all the spots- snorkeling, Key West, national parks. Close to restaurants, fishing and much more. Manager and maintenance were very responsive to questions, within minutes. Would stay here again!
Cottage in Marathon
4.62 out of 5 average rating, 117 reviews

Tropical Cottages - Cottage # 10

ChrisRating, 5 stars2 months ago
Perfect getaway for a couple, very quaint cottages. Bonus is the taco food truck on property as well as the covered bar area. Would definitely stay again!

Private cottage rentals

Superhost
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.
Cottage in Islamorada
4.78 out of 5 average rating, 82 reviews

Serene Cozy Cottage in Islamorada with Heated Pool

DonnaRating, 5 stars2 weeks ago
Great choice! Very close to everything, central. Pool was so nice & our own mostly. Cottage is modern clean & comfortable. Perfect for a girls trip!
Guest favourite
Cottage in Key West
4.75 out of 5 average rating, 16 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 favourite
Cottage in Key West
4.79 out of 5 average rating, 24 reviews

Bali Hideaway: A studio cottage that's perfect

JessRating, 5 stars2 weeks ago
Very happy with our week at the Bali Hideaway! Safe and beautiful gated gardens between the cottage and the road. Surprisingly quiet and peaceful at all hours despite being so close to Duval. Bed was comfortable and everything was clean and maintained. Decor was lovely and kept us in the tropical spirits. Would stay again!
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!

Quick stats about cottage rentals in Cudjoe Key

  • Total rentals

    10 properties

  • Nightly prices starting at

    ₹14,633 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

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