
Vacation rentals with outdoor seating in Cudjoe Key
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Top-rated accommodations with outdoor seating in Cudjoe Key
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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.

Seaside Sunrise. Newly remodeled waterfront
Everything was excellent. Only complaint would be the bicycles. One bike was usable but the seat was loose and we didn’t have tools to fix it. The other adult bike’s chain was rusted so bad it wasn’t usable. We still had an excellent experience.

Luxury Waterfront Retreat with Dockage & Pool
Had an amazing stay at this house with my husband and 4 small kids. The house was spacious and clean, with lots of natural light at soon as the sun came up. The pool was so warm and had a large shallow area that was perfect for our 3 year old. Naomi was a wonderful communicator. It was so sad to have to leave.. Would definitely recommend staying here.

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!

Paradise Ocean Front 4/3Home Heated Pool
We had a 5 star stay at Isabella’s Airbnb home! We had 10 guests and all had a place to sleep, place to sit and eat if we all wanted to sit together at the dining table and plenty of room there! We loved her home and our stay there!! Isabella remembered that we were there on vacation celebrating our mom’s 80th birthday and went out of her way to buy a key lime pie and balloon to have waiting for us/my mom when we arrived! That was very thoughtful and sweet of her!! Thank you for sharing your home with us!!!

Cozi home with dock
Look no further for the place to stay with kids and or dogs! Cabana club is super nice!! They should update the pics of the place because it’s way nicer than the pics!! Instacart and door dash works well!! Really can’t say enough good!
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
Key Colony Beach is truly the gem of the Florida Keys. Staying at Cindy's apartment in the Continental was the perfect fit for my husband and I. The private beach was clean, easy to access, and just steps from the accommodation. The overall vibe here was quiet and peaceful, and the apartment had all the amenities we needed for a 5-day stay. Cindy's space is very clean and well-appointed. This location is perfect for morning walks around the immaculate and safe neighborhood, or short jaunts to Key Colony Inn or Havana Jack's for dinner/drinks. Honestly now, you're already here! What's your hurry? :)

At Mine | Key West Suite steps from Duval Street
This tucked away place is in a sneaky great location, walkable to everything but away from the hustle & bustle. The customer service was excellent from start to finish, would definitely recommend!

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, &
This place was an idea location, everything we wanted to do was in walking distance. The pool was quite and hardly used by others while we were there. The pull out couch bed was very comfortable. Will return!

Duval Balcony - Suite Mischief
This was a lovely place to stay. Thomas was very responsive offering us tips on parking! the area is perfect if you are into bar hopping, and the culture that Duval street has to offer. Balcony was nice for people watching and having a glass of wine! I would highly recommend staying here if you are ok with stairs (1 full flight). P.S. coffee shop right downstairs in the shop..very convenient:)

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
Great space with everything you need. Patio is a perfect place to relax. The house is well stocked. Plenty of room for a group. Access to hotel pools/restaurant with transportation into town if you need it. Great host communication. All you could want!

Beach/Docks Avail/3 Pools/Hot tub/Gym/Restaurants
Great experience, great host and accommodations. Hot tub wasn't working while we were there, but repair was delayed over the holiday week which was out of the hosts' control. Very communicative and responsive.

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!

Den Suite Two Balconies- Islamorada
Great spot to spend days for vacation. Great service by office staff. They took care of all requests we had in the most friendly manner. The hotel is located right on the water, so views were great. Nice pool and great vibe. Would highly recommend.

A Perfect Getaway
We had a great stay at Lori’s place. It was within walking distance to everything but we did use the Duval Loop to go to places that were about a mile away. A pick up spot for the loop bus was super close. The condo was nice and we sat on the back deck with our coffee every morning. There were 4 of us and we had plenty of room. The only negative is no reflection on Lori or her condo. We chose this rental because it had a pool. We attempted to use the pool one day. Since we were on vacation, we were ready to hang at the pool with some music playing and wanted a pool party vibe. But when we walked into the pool area, about 20 people (we assume snowbirds, residents, retirees) all turned and stared at us. We were very uncomfortable so we just turned around and left. We didn’t attempt to go to the pool again. No fun to be had there! Adding to this review so others are aware, this is not a party atmosphere. Overall, it’s a great place to stay when visiting Key West!

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!
Quick stats about vacation rentals with outdoor seating in Cudjoe Key
Total rentals
140 properties
Nightly prices starting at
$139 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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