Cudjoe Bay Getaway In Paradise

Photo gallery for Cudjoe Bay Getaway In Paradise

A waterfront property with a covered deck, a dock, and a view of the marina and houses.
A marina with boats docked, a wooden walkway, and buildings with balconies.
A modern kitchen with a large island, stainless steel appliances, and wooden cabinets.
A living room with a sofa, a dining table, and a kitchen area with a microwave.
A two-story building with a green exterior, a white balcony, and a staircase leading to the upper floor.

Reviews

9.4 out of 10
Exceptional

Highlights

  • Beach, waves and sand
    Guests enjoy the stunning beach views at this property.
  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Balcony
  • Barbecue
  • Air-conditioning
  • Pet-friendly
  • Refrigerator
  • Washing machine

Explore the area

View map
Cudjoe Key, FL
  • Place, Upper Sugarloaf Key
    ‪6 min drive‬
  • Place, Florida Keys Beaches
    ‪7 min drive‬
  • Place, Upper Sugarloaf Sound
    ‪7 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪37 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Single Murphy Bed

1 bathroom

Bathroom 1

Bathtub or shower · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Outdoor play area
Dining area

Add dates for prices

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  • Kitchen
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10.0 out of 10, Exceptional, (32 reviews)
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About the area

Summerland Key

Located on the waterfront, this holiday home is in Cutthroat Harbor Estates, a neighbourhood in Summerland Key. Florida Keys Beaches and Coupon Bight Aquatic Preserve reflect the area's natural beauty and area attractions include Blue Hole and Wilhelmina Harvey Park. Big Munson Island and Looe Key National Marine Sanctuary are also worth visiting. Kayaking, scuba diving and snorkelling offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours nearby.
View more Holiday homes in Summerland KeyOpens in a new window
Map
Cudjoe Key, FL

What's nearby

  • Upper Sugarloaf Key - 6 min drive - 6.9 km
  • Florida Keys Beaches - 7 min drive - 7.0 km
  • Upper Sugarloaf Sound - 7 min drive - 8.2 km
  • Boondocks Grille & Draft House - 10 min drive - 11.4 km
  • Lower Sugarloaf Sound - 10 min drive - 11.8 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 31 min drive

Restaurants

  • ‪Morning Joint - ‬12 min walk
  • ‪Kiki's Sandbar - ‬11 min drive
  • ‪Boondock's Grille & Drafthouse - ‬8 min drive
  • ‪Tonio's Seafood Shack & Tiki Bar - ‬5 min drive
  • ‪Square Grouper Bar and Grill - ‬15 min walk

Frequently asked questions

Is Cudjoe Bay Getaway In Paradise pet-friendly?

Yes, this property allows pets (limit 2 total). Some restrictions may apply, so please contact the property for more details.

How much is parking at Cudjoe Bay Getaway In Paradise?

On-site parking is available at the property.

What time is check-in at Cudjoe Bay Getaway In Paradise?

Check-in begins at 3:00 PM.

What time is check-out at Cudjoe Bay Getaway In Paradise?

Checkout is at 11:00 AM.

Where is Cudjoe Bay Getaway In Paradise located?

Located in Cutthroat Harbor Estates, this holiday home is 0.7 mi (1.1 km) from Venture Out Keys and 2.4 mi (3.9 km) from Florida Keys Beaches. Venture Key and Out Key are also within 15 minutes.

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 6 out of 8 reviews
Rating 8 - Good. 1 out of 8 reviews
Rating 6 - Okay. 1 out of 8 reviews
Rating 4 - Poor. 0 out of 8 reviews
Rating 2 - Terrible. 0 out of 8 reviews

9.6/10

Cleanliness

9.6/10

Check-in

9.0/10

Communication

9.4/10

Location

8.6/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location, clean and attentive property manager

Great time, met all our needs Perfect location
Stayed 30 nights in Mar 2023
Response from VrboOwner on 11 July 2023
Thank you Mike for the great communication, suggestions and the booking! Please let us know of any future dates needed.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house in great location!

Great house in great location!
Stayed 2 nights in Aug 2022
Response from VrboOwner on 7 Feb 2023
Thank you! You're not listed as anyone we rented our house to but we are glad you like it!
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, listing accuracy

What a View

The Porch/Deck wraps around the whole house and there is a spectacular view of the bay from the back! Property manager was very nice and informative and almost never there! Great communication with manager and owner!
Stayed 29 nights in Jan 2024
Response from VrboOwner on 27 Aug 2024
We're glad you had a great time Mark! Please let us know if you'd like to book again. Thank you.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

BEAUTIFUL sunsets from this spot!

Our month here was great. Location of home was perfect for us. We spent the majority of our time on the upstairs patio that has fantastic views of the bay. The sunsets from this location are breathtaking (I have more pictures of the sunsets than I do my family! lol). Home has everything needed for a comfortable stay and communication with owner is great (easy to reach and responds quickly!).
Stayed 28 nights in Jan 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing stay

This canal property has an amazing west view only 3 houses from open water. Out of the 28 days I think there were only two nights without a sunset. The deck was where we spent the daytime. The inside tall ceiling made the place feel roomy. The mattress was more comfortable than my bed at home. Had all the modern appliances you could want. Will miss the outdoor shower. Wife did water aerobics right in the clean canal while I preferred to float on a raft and kayak. great stay.
Stayed 28 nights in Feb 2025
Response from VrboOwner on 12 Mar 2025
We're very happy to have hosted your wife and yourself for a winter get away. Your review means the world to us because of the work making the house comfortable, provide what people need and enjoyable for renting far from home. Please inquiry for future rentals anytime! Thank you!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
From check-in until check-out, our experience was smooth & seamless! We stayed for 2 months & truly were sad to leave. Property is totally as described in the listing, if not better.Very comfortable beds, including a Murphy style bed in the living area, plenty of towels & linens and convenient washer/dryer unit.The kitchen is top-notch within the spacious & open living and dining areas. Probably the over-all favorite feature was the wrap-around deck with multiple ceiling fans and comfortable outdoor furniture offering beautiful views of sunsets and canal leading to ocean. Our pets enjoyed hours running around the deck and viewing pelicans and other seabirds. The slow & relaxed way of life on Cudjoe Key and surrounding lower keys is easy to love! There are plenty of great local restaurants and areas to visit such as Bahia Honda state park and beach. Easy drive to Key West or Marathon if desired.We definitely would love to return and have nothing but positive things to say about the owner and property manager. Above and beyond in responsiveness to any questions!
Stayed 56 nights in Jan 2026
Verified review

6/10 Okay

Liked: Cleanliness, location
Disliked: Communication, listing accuracy

Shared residence with live in was most uncomfortable & deceitful

Property & westerly view of sunsets was very nice, but the fact that the owner had an individual living in the basement and occupied the downstairs deck & patio area, was not advertised nor anticipated until we arrived at the property. The owner was deceitful in failing to mention an individual lived at the residence and that the property was to be shared with that individual and her boyfriend during our stay. In talking to VRBO, they said that I should have contacted them during our stay there, but we tried to do that when we found out upon arrival, and the VRBO webpage stated for us to contact the Owner, which I did. A local real estate agent stated that there were no vacancies for alternative stays in the area, so we had little or no choice after driving 1000 miles to get there.
Stayed 28 nights in Jan 2023
Response from VrboOwner on 24 Feb 2023
Thank you so much for taking the time to review our home in paradise. We're happy to hear that you loved the sunsets as much as we do. As previously discussed, we are very sorry that we did not make the arrangement that we have with our property manager more clear. If we would have thought for one minute that we were all not on the same page, we would have been happy to answer any questions and discuss your reservation. Upon your arrival, we wanted to make sure that your stay was amazing. We sent in many items that were important to you including the new ironing board, iron, baking tins, additional towels, hand mixer, wine glasses and flutes. Our property manager, and her significant other brought you fresh fish, loaned you their personal items, filled 3 propane tanks and made themselves scarce. We really tried to do our best as a team, to make your stay awesome. During 2022 our home was reserved by three families for a total of 6 months. Each family appreciated the accessibility of a resource person at their finger tips. We hope that you did enjoy your time here in the Florida Keys and that you will make South Florida a winter destination each year. Thank you again.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Our keys vaca

We had a great rental experience. David was very easy to work with and was prompt with responses to any questions. Location and property were wonderful. Would stay here again!!
Stayed 28 nights in Feb 2022
Response from VrboOwner on 11 July 2023
Thank You Jack for the kind words! We look forward to your next stay at our place. Please reach out again for availability whenever. We're glad you had a great time and enjoyed the Keys!
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