Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise

Photo gallery for Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise

A balcony with a white railing, a wicker sofa, a glass table with a bottle and fruit, and a palm tree.
Property video
A spacious living area with a sofa, dining table, chairs, and a balcony with a view.
A modern kitchen with white cabinets, stainless steel appliances, a large island with stools, and pendant lighting.
A dining area with a round table, chairs, a hanging light fixture, a framed picture, and a view of the sea through large windows.

Reviews

9.6 out of 10
Exceptional

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • Ping pong on-site
    A rare find — challenge friends and family to endless matches.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Balcony
  • Spa pool on site
  • Swimming pool
  • Barbecue
  • Air-conditioning
  • Pet-friendly

Explore the area

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

Rooms & beds

2 bedrooms (sleeps 4)

Guest Bedroom

1 King Bed

Primary Bedroom

1 King Bed

2 bathrooms

Guest Bathroom

Bathtub · Toilet

Primary Bathroom

Bathtub · Toilet

Spaces

Deck or patio
Kitchen
Balcony
Separate dining area
Outdoor play area
Dining area

Add dates for prices

Similar properties

About the area

Summerland Key

Located in Summerland Key, this holiday home is on the waterfront. Florida Keys Beaches and Upper Sugarloaf Key reflect the area's natural beauty and area attractions include Blue Hole and Big Munson Island. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and cycling nearby.
Map
Cudjoe Key, FL

What's nearby

  • Upper Sugarloaf Key - 7 min drive - 7.6 km
  • Florida Keys Beaches - 8 min drive - 7.7 km
  • Upper Sugarloaf Sound - 9 min drive - 8.9 km
  • Boondocks Grille & Draft House - 11 min drive - 12.1 km
  • Lower Sugarloaf Sound - 12 min drive - 12.5 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 32 min drive

Restaurants

  • Boondock's Grille & Drafthouse
  • Morning Joint
  • Kiki's Sandbar
  • Looe Key Tiki Bar & Restaurant
  • Tonio's Seafood Shack & Tiki Bar

Frequently asked questions

Does Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise have a pool?

Yes, this property has a pool. Pool types include heated pools.

How much does it cost to stay at Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise?

As of 2 November 2026, prices found for a 1-night stay for 2 adults at Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise on 3 November 2026 start from NZ$1,221, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise pet-friendly?

Yes, pets are allowed at this property.

How much is parking at Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise?

On-site parking is available at the property.

What time is check-in at Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise?

Check-in begins at 4:00 PM.

What time is check-out at Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise?

Checkout is at 10:00 AM.

Where is Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise located?

Situated on the waterfront, this holiday home is within 6 miles (10 km) of Upper Sugarloaf Key, Florida Keys Beaches and Boondocks Grille & Draft House. Lower Sugarloaf Sound and Big Pine Key Flea Market are also within 9 miles (15 km).

Reviews

9.6

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. 44 out of 53 reviews
Rating 8 - Good. 7 out of 53 reviews
Rating 6 - Okay. 0 out of 53 reviews
Rating 4 - Poor. 2 out of 53 reviews
Rating 2 - Terrible. 0 out of 53 reviews

9.8/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our stay was wonderful. Accommodations were as described and very comfortable. Location was great and the best views for the sunrise.
Stayed 4 nights in Mar 2026
Response from VrboOwner on 26 March 2026
Thank you so much for this glowing review Kathy! We are thrilled that you loved the excellent accommodations and location. Yes, the sunrise views are incredible and we hope you'll return soon to experience them again!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place!
Stayed 6 nights in Nov 2025
Response from VrboOwner on 16 December 2025
Thanks so much for the lovely feedback! We’re happy to hear you enjoyed the property and would love to host you again in the future.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our stay here! The home is very clean and well-kept, the beds and linens were comfortable, and the kitchen had everything we needed for our short stay. We appreciated the soft shower towels and pool towels as well. We would gladly return to this property again in the future.
Stayed 2 nights in Feb 2026
Response from VrboOwner on 10 March 2026
We’re grateful for your glowing review Nathan! It was such a pleasure to host you, and we’re already looking forward to your return to the island.
Verified review

10/10 Excellent

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

Great place

Great place to stay. Very secure and comfortable.
Stayed 6 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was amazing! Right on the water and very comfortable!
Stayed 6 nights in Nov 2025
Response from VrboOwner on 2 December 2025
Dana, so glad to hear you had such a positive experience! We’d love nothing more than to welcome you back for another wonderful stay.
Verified review

10/10 Excellent

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

Fantastic place to stay!

We had an awesome week at this property. I highly recommend this property ... fantastic communication, clean and exactly as described on the listing.
Stayed 7 nights in Jul 2025
Response from VrboOwner on 11 September 2025
We’re so glad you had a great time with us, Mandy! It was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful house, great boating and lobster area
Stayed 5 nights in Sep 2025
Response from VrboOwner on 6 October 2025
Karen, we truly appreciate your review! It makes us happy to know you loved this home, and we’d be delighted to host you again anytime.
Verified review

8/10 Good

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

Enjoyed our stay

Very clean and comfortable property
Stayed 3 nights in Nov 2023
Response from VrboOwner on 3 June 2024
Thank you for your review. We are thrilled you loved this home and hope to host you again soon!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is one of the best rental units in venture out. The location on the canal looking out at the bay is very nice and gets a breeze. The furnishing and layout are great too. Would love to stay here again.
Stayed 7 nights in Oct 2025
Response from VrboOwner on 3 November 2025
Ben, we’re grateful for your glowing review! It was such a pleasure to host you, and we’re already looking forward to your return to the island.
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was nicely decorated. Appreciated the coffee maker, nightlights etc
Stayed 5 nights in Oct 2025
Response from VrboOwner on 19 November 2025
Alice, we’re grateful for your glowing review! It was such a pleasure to host you, and we’re already looking forward to your return to the island.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house is really nice. I did not get to enjoy the amenities in the park since we traveled to key west. I would stay here again! It’s forcing me to do a rating on pool and facilities but I don’t know. Disregard that.
Stayed 2 nights in Feb 2026
Response from VrboOwner on 5 March 2026
Thank you so much for the excellent rating and kind review Mary! We love that you enjoyed the home and would stay with us again. Please come back soon!
Verified review

10/10 Excellent

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

Enjoyed very much!

Perfect place to stay in the keys! Close to attractractions and very accommodating!
Stayed 3 nights in Oct 2022
Response from VrboOwner on 13 September 2023
We are so happy to hear that you enjoyed your stay with us Amy! Thank you so much for the positive review. We hope we get the chance to host you again in the future! One of One Stays
Verified review

10/10 Excellent

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

Superb!

Property exceeded expectations, and the view was spectacular! Absolutely would recommend staying here. It has everything you need for a comfy stay.
Stayed 7 nights in Mar 2025
Verified review

10/10 Excellent

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

Venture out

Very nice place to stay!
Stayed 3 nights in Jun 2023
Response from VrboOwner on 8 September 2023
Thank you for your review! We are happy to hear you enjoyed our location! Come stay with us again! Isa Brightwild
Verified review

10/10 Excellent

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

Great spot!

The House, is beautiful, comfortable, clean and quiet!!
Stayed 9 nights in Aug 2024
Verified review

8/10 Good

Liked: Cleanliness, location, listing accuracy
Disliked: Check-in

stay

great location and amenities
Stayed 6 nights in May 2024
Verified review

10/10 Excellent

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

Vacation Getaway

Short trip to the Keys! Very pleased with the rental company and their communication! Would definitely rent again!
Stayed 5 nights in May 2025
Verified review

10/10 Excellent

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

Perfect vacation spot

We really enjoyed everything at this house , newer home , very clean , the patio is right by the water , good neighborhood to stay , great food close by ! Definitely going back 😊
Stayed 4 nights in Feb 2023
Response from VrboOwner on 13 September 2023
Thank you so much for the kind review Reuben! I hope we get the chance to host you again in the future. Cheers!
Verified review

10/10 Excellent

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

Comfort In paradise

Super nice place Comfortable Couch Comfortable Bed
Stayed 2 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved it! The view is unbelievable! Such a such place and tastefully decorated. Beds were comfy and it had just what we needed to cook. Nice big table to play games. We will definitely book again!
Stayed 5 nights in Jul 2025
Response from VrboOwner on 6 October 2025
Jennifer, we’re grateful for your glowing review! It was such a pleasure to host you, and we’re already looking forward to your return to the island.
Verified review

10/10 Excellent

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

Amazing

Great time and location! Beds were the most comfy ever!
Stayed 4 nights in Mar 2023
Response from VrboOwner on 13 September 2023
We are so happy you enjoyed our location! Thanks for staying with us! We hope to host you again in the future! Brightwild
Verified review

10/10 Excellent

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

Coconut typhoon

Excellent views, very quiet, pool was outstanding
Stayed 7 nights in Dec 2024
Verified review

4/10 Poor

Disliked: Cleanliness, communication, location, listing accuracy
The view was excellent. The house itself was in horrible disrepair. Lights didn’t work, appliances broke, the window treatments were broken, the toilet seat handles cracked,the stair railings were broken and dangerous,the laundry door was off the hinges and the furniture was scratched.
Stayed 8 nights in Feb 2026
Response from VrboOwner on 25 March 2026
Thank you for taking the time to share your feedback Michael. We’re glad to hear you enjoyed the view—that’s something many of our guests truly appreciate. That said, we take concerns about the condition of the home very seriously. We want to clarify that prior to your arrival, all lighting and major systems were fully inspected and in working order. During your stay, we responded immediately to the items you reported, including repairing the toilet handle and addressing the laundry door. These types of issues, while unfortunate, can occasionally occur in any well-used home and were not an indication of "horrible disrepair". We also understand there was some confusion regarding the window treatments. Instructions were provided, and additional in-person assistance was given to ensure they were functioning properly for you. Regarding the stair railings, our records and follow-up inspection indicated damage occurred during the stay. Regardless, repairs were arranged as quickly as possible to maintain safety and the quality of the home. We strive to provide a well-maintained and comfortable experience for every guest and we regret that your stay did not meet your expectations. At the same time, we stand by the condition of the property and the responsiveness of our management team in addressing concerns as they arose. We appreciate your feedback and we wish you the best in your future travels.
From a partner site

10/10 Excellent

Beautiful view

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: House was very clean!! Great location not far from key west and good food and drinks only slept on the master bed was very comfy and I’m pretty picky about my bed our property management rep. Alli was also great!!! Quick response if I had any questions just an overall great experience!
Response from VrboOwner on 17 January 2026
What a joy to read your review—thank you so much Howard! We’re so glad you loved your time in Key West and can’t wait to have you back on the island soon.
Verified review

10/10 Excellent

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

Cudjoe Key

Very nice rental! Beautiful location!
Stayed 3 nights in Jan 2024
Response from VrboOwner on 3 June 2024
We are so happy you found this property and its location ideal for your get away in Key West. We hope you'll stay with us again next time you visit!
Tell us how we can improve our siteShare feedback