
Vacation rentals with outdoor seating in Cudjoe Key
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Top-rated accommodations with outdoor seating in Cudjoe Key
Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Cudjoe Key outdoor seating rentals
House rentals with outdoor seating

Key West Paradise
Sharon was an excellent host that answered any of our questions promptly. The place was even better than what the photos showed. Comfortable enough for 7 people to stay for a long weekend. We didn't use the pool, but it was nice to have the option. Easy to get into the gated community, and we didn't struggle to find parking with our rental car. Easy to get to many different popular spots around Key West with rideshare. Convenient to have some convenience stores like CVS within walking distance, and a Publix not too far via car. Only thing I would improve is having more toilet paper and hand soap refills in each bathroom, especially with 7 people staying over a long weekend.

Luxury Waterfront Retreat with Dockage & Pool
We enjoyed our stay. The home was comfortable and very clean. It was nice to have a view of the water and a heated pool! The rooms were comfortable and accommodating for our family. Naomi was quick to respond when we had questions. I would stay here again! This spot was close to many restaurants, grocery stores, and right on bike paths!

Waterfront Home 37.5-ft dock, Cabana Club Included
We loved our stay! The house was super clean and the back patio was beautiful. We loved the back canal area and saw lots of very cool wildlife and enjoyed fishing right there. Having the kayaks to use was also great. Beds were very comfy and the rooms were spacious. The house had everything we needed. We loved the key colony area. The cabana club was a great space and the house is in walking distance to Sunset Beach, which was beautiful. The whole area is super close to fun things to do and great restaurants. We would absolutely stay here again!

Lower Keys Paradise
Great place to stay. It’s a house in a community with a lot of activities available. There’s an extra $125 fee for that, but it’s worth it.

Beachfront Villa - Florida Keys
This is a fantastic property! Right across from Sombrero Beach but still peaceful and private. The house and yard is like an oasis. Host and management company are WONDERFUL! Highly recommend!

Dream Vacation KCB Marathon with private pool !
Alfonso is a very responsive host who provided clear details, local recommendations (multiple of which we used), and provided a place in a great location. Neighbors are friendly. Place was clean. Perfect for our family with a 14 and 6 year old.

Kittyhouse on Catherine, Tropical Pool, Parking
Thank you for sharing your beautiful home. We appreciate your wonderful suggestions and thoroughly enjoyed our dinner at El Siboney restaurant. Unfortunately the rain kept us from using the pool but we still had a fantastic time.

Pelico Palms Sunset Suites
fantastic cottage and pool with plenty of privacy, close to the water. basically 3 master suites with adjoining bathrooms, one living area and a kitchen. really big pool deck with seating and cornhole, Webber grill and outdoor dining table. (bring bug spray). we had a great time, close to key West and Bahia Honda, a great cottage!
Apartment rentals with outdoor seating

Ocean Breeze Gated Community
The condo and the whole condo complex was beautiful. The pool was great, with an awesome view. Plenty of places to sit at the pool and in the surrounding areas. One thing to note is that the condo has no closets and no place to hang clothes. Wasn’t a huge deal for us, as we were able to put things on shelves. Frank was very responsive when we needed something. The Marathon area has plenty of things to do and it’s close enough for a day trip to Key West.

Beachside Unit 22 - Private Beach on Atlantic
Had a great stay here. Very nice and great location in the keys.

At Mine | Key West Suite steps from Duval Street
Great location and great service/communication. Will definitely come back.

Studio Near Downtown - The Bartlum
Excellent location, very walkable to everything we wanted to do and see! Clean, well kept, and cute. Would visit again!

Duval Street Suites full kitchen, free parking, &
Exactly as listed. Megan was very helpful and responsive. You are right in Duval street. If you are coming for a few days, this is the place to stay at.

Duval Balcony - Suite Mischief
Reached out later on in the day for a sporadic trip to key west, immediate response from thomas with clear instructions. Quaint room in the best location, lots to do within walking distance. Really enjoyed our stay, we recommend it!

Beachfront Condo w/ Ocean Views in Marathon
This is a beautiful ocean-front condo!! It is equipped with everything needed to spend a week or many weeks. The view is incredible, the beach is very nice and walkable. It is quiet, relaxing and the pool is at least 85 in January!! Enjoyed our week very much and hope to come back for a few weeks next time!!

New Deluxe Duplex Unit, 1 Queen Bed, Unit C
We were on a girls trip and this was just enough room for four of us! Not a ton of amenities included, which host was clear about. Location is away from the hustle and bustle and we had lots of key deer come by! Bahia Honda was fabulous and a short drive away.
Condo rentals with outdoor seating

La Dolce Vita, Old Town Steps to Duval! 3 blks bch
Great location and accommodations, friendly and prompt communications.

Villa 5027 on Duck Key BOAT SLIP available
Fantastic Last-Minute Stay! We decided last minute—just the night before—to extend our stay in the Keys, as our kids were having a blast during their break. Our original place of stay in Marathon wasn’t available for another night, but thankfully, Frank’s place was. Even with our 11 p.m. booking, Frank was incredibly accommodating. He welcomed us warmly and communicated everything clearly, making check-in a breeze. If we take another family trip to the Keys, Frank’s place will be my first choice—I only wish we had found it sooner! The views of the water were stunning, and watching the sunset from the porch was truly exhilarating. Highly recommend!

Oceanfront 3 bed condo Ocean Edge w/ optional slip
Carrie's place was absolutely beautiful! it was so clean, the beds were insanely comfortable, and there were tons of linens and towels for everyone. We very comfortably fit 8 people into the home with no problems. The view from the balcony is absolutely amazing and we were all blown away. Carrie was extremely responsive and friendly. We were here for our wedding and had our wedding party stay here so it was extra magical. The pool and hot tub is super close, elevator to help with our bags, and the resort itself is gorgeous. 10/10 would stay again. We loved it so so much! Don't miss out.

Affordable Beachfront Luxury Condo Sleeps 6
Everything was perfect for our stay at Airbnb, the pool felt amazing, the views were stunning, and the Uber drivers were incredibly fast. Even the locals agree that this is the best place to stay in Key West, and I couldn't agree more - I'll definitely be back. Our host, Traci, was absolutely top-notch!

A Perfect Getaway
This condo was in the perfect place in Key West. Very walkable to all the great places we wanted to see. The condo was comfortable and set up well. The people in the complex were very friendly and we enjoyed “afternoon pool time” with everyone, meeting wonderful people from all over! Loni was very friendly and extremely responsive - although we didn’t need her for anything through the week. We’d definitely stay in this location again!

Fully renovated 2/2 bath condo w/ shared pool!
We had a great stay at Chris’s place in Key West! The property was exactly what we needed for a relaxing getaway. Chris is an excellent communicator—his instructions were clear, detailed, and made everything super easy from check-in to check-out. We felt well taken care of and really appreciated the smooth experience. I’d definitely recommend this place to anyone planning a trip to Key West!

Downtown Key West 2BR/2BA•Pool, Dock, Pet "Aruba"
Went for a quick fishing trip. Great location. Enjoyed it so much

Slip, Ramp, Pool, Trailer Parking, Bait Freezer
Great little place for our family of 4! Very clean and the location was perfect for us. Would definitely stay again!
Quick stats about vacation rentals with outdoor seating in Cudjoe Key
Total rentals
140 properties
Nightly prices starting at
$138 CAD before taxes and fees
Total number of reviews
3.1K reviews
Family-friendly rentals
110 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
120 properties have a pool
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