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waterfront cottage near key west, sleeps 6
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Reviews
9.4 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 686.0 sq m
Popular amenities
Rooms & beds
2 bedrooms (sleeps 6)
bedroom 2
1 Queen Bed
main
1 King Bed
1 bathroom
Bathroom 1
Bathtub or shower · Toilet
Spaces
Deck or patio
Porch or lanai
Kitchen
About this property
waterfront cottage near key west, sleeps 6
This reimagined vintage style waterfront home is everything! With the ability to tie up to 17f boat right outside your door, you will be able to enjoy the many amenities of the home (kayaks, bikes, beach & snorkel gear, pickle ball, board games, wifi & roku) and of the community (Pools, spa, boat launch, sports courts, even a library and a general store!). You can use this magical location to launch all your Florida keys adventures! Canal patio for drinks? Lush screen porch for coffee? It's on!About this space
This reimagined vintage style waterfront home is everything! With the ability to tie up to 17f boat right outside your door, you will be able to enjoy the many amenities of the home (kayaks, bikes, beach & snorkel gear, pickle ball, board games, wifi & roku) and of the community (Pools, spa, boat launch, sports courts, even a library and a general store!). You can use this magical location to launch all your Florida keys adventures! Canal patio for drinks? Lush screen porch for coffee? It's on!
The space:
Calypso Cottage is a re-imagined Florida-style mobile home. It is spacious and well appointed, with a jaunty tropical motif. The open floor plan provides perfect entertaining space with sight lines between common rooms as well as the canal front patio. The roomy screen porch offers comfortable seating amidst a lush, tropical setting. The master bedroom is oversize while the smaller bedroom still has plenty of space and lots of storage. Both beds are equipped with thick, new memory foam mattresses and there are also a queen size sofa bed and a smaller futon. The bathroom is small but fully outfitted, and for extra bathroom space there is a 24 hour bath house (absolutely immaculate!) directly across the way. Whole family need to shower at once? perfect solution. Need to do a load of laundry? there is a laundry niche with a modern washer and dryer in the cottage. Free use of Kayaks, bikes, beach gear and everything in the cottage means you'll never want to leave!
Guest access:
Parking at the unit is for one vehicle only. Guests can park additional vehicles in the overflow lot on a first-come first-serve basis for a small fee. This is arranged through the front gate. boat trailers are also parked in the overflow lot.
It is a short walk to the common areas or guests can bike the community or travel by boat, float or other vessels in the abundant canals.
Other things to note:
100.00 plus tax entrance fee to the community paid on arrival. This is a flat fee no matter what the duration. This is a fee charged of every group admitted to Venture Out and has nothing to do with VRBO
About Venture Out:
Venture Out is a gated resort community located at mile marker 22 which makes it less than 20 miles to Key West and close to the key deer refuge, Bahia Honda State park and much much more. Amenities in the community include 2 pools, a hot tub, a protected swimming area, a boat launch, general store, community center with a post office and reading library, game room, tennis, pickle ball and bocce ball courts, multiple bath houses and so much more!
This reimagined vintage style waterfront home is everything! With the ability to tie up to 17f boat right outside your door, you will be able to enjoy the many amenities of the home (kayaks, bikes, beach & snorkel gear, pickle ball, board games, wifi & roku) and of the community (Pools, spa, boat launch, sports courts, even a library and a general store!). You can use this magical location to launch all your Florida keys adventures! Canal patio for drinks? Lush screen porch for coffee? It's on!
The space:
Calypso Cottage is a re-imagined Florida-style mobile home. It is spacious and well appointed, with a jaunty tropical motif. The open floor plan provides perfect entertaining space with sight lines between common rooms as well as the canal front patio. The roomy screen porch offers comfortable seating amidst a lush, tropical setting. The master bedroom is oversize while the smaller bedroom still has plenty of space and lots of storage. Both beds are equipped with thick, new memory foam mattresses and there are also a queen size sofa bed and a smaller futon. The bathroom is small but fully outfitted, and for extra bathroom space there is a 24 hour bath house (absolutely immaculate!) directly across the way. Whole family need to shower at once? perfect solution. Need to do a load of laundry? there is a laundry niche with a modern washer and dryer in the cottage. Free use of Kayaks, bikes, beach gear and everything in the cottage means you'll never want to leave!
Guest access:
Parking at the unit is for one vehicle only. Guests can park additional vehicles in the overflow lot on a first-come first-serve basis for a small fee. This is arranged through the front gate. boat trailers are also parked in the overflow lot.
It is a short walk to the common areas or guests can bike the community or travel by boat, float or other vessels in the abundant canals.
Other things to note:
100.00 plus tax entrance fee to the community paid on arrival. This is a flat fee no matter what the duration. This is a fee charged of every group admitted to Venture Out and has nothing to do with VRBO
About Venture Out:
Venture Out is a gated resort community located at mile marker 22 which makes it less than 20 miles to Key West and close to the key deer refuge, Bahia Honda State park and much much more. Amenities in the community include 2 pools, a hot tub, a protected swimming area, a boat launch, general store, community center with a post office and reading library, game room, tennis, pickle ball and bocce ball courts, multiple bath houses and so much more!
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Oceanfront 2BR/2BA in Cudjoe Key | 50' Seawall, Dock, Open Porch, Stunning Views
Oceanfront 2BR/2BA in Cudjoe Key | 50' Seawall, Dock, Open Porch, Stunning Views
- Pool
- Spa pool
- Kitchen
- Washing machine
8.0 out of 10, Very good, (1 review)
House Rules
Check in after 4:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Canal front property
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Check-out instructions
The host requires you to complete the following before checking out:
Start the dishwasher
Gather used towels
Remove leftover food and drinks and take out the rubbish
Failure to complete these may result in a negative review from the host.
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
About the area
Summerland Key
Located in Summerland Key, this cottage is on the waterfront. 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. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Cudjoe Key, FL
What's nearby
- Florida Keys Beaches - 7 min drive - 7.1 km
- Upper Sugarloaf Key - 7 min drive - 7.3 km
- Upper Sugarloaf Sound - 8 min drive - 8.6 km
- Lower Sugarloaf Sound - 12 min drive - 12.1 km
- National Key Deer Refuge Visitor Center - 16 min drive - 17.9 km
Getting around
Restaurants
- Boondock's Grille & Drafthouse - 9 min drive
- Kiki's Sandbar - 11 min drive
- Morning Joint - 16 min walk
- Broil - 4 min drive
- 5 Brothers Two - 8 min drive
Frequently asked questions
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 window9.2/10
Cleanliness
10/10
Amenities
8.0/10
Property conditions & facilities
9.4/10
Check-in
9.2/10
Communication
9.6/10
Location
9.6/10
Listing accuracy
Reviews
Verified
30 Nov 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in Nov 2025
Verified
10/10 Excellent
mark m.
6 Jan 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
mark m.
Stayed 2 nights in Dec 2025
Verified
10/10 Excellent
Josh C.
7 Aug 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Josh C.
Stayed 3 nights in Aug 2025
Verified
10/10 Excellent
Bobby M.
25 Mar 2025
Liked: Cleanliness, check-in, location, listing accuracy
4th annual bike trip
Bobby M.
Stayed 2 nights in Mar 2025
Verified
10/10 Excellent
Kelli M.
1 Apr 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
The Best
Kelli M.
Stayed 5 nights in Mar 2025
Verified
10/10 Excellent
Terry M.
11 Aug 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovin life
Terry M.
Stayed 6 nights in Aug 2023
Verified
8/10 Good
Scott H.
23 Feb 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Florida Key's Visit
Scott H.
Stayed 2 nights in Feb 2025
Verified
10/10 Excellent
William S.
1 Aug 2025
Liked: Cleanliness, check-in, location, listing accuracy
4 Friends came for Lobster Mini Season

William S.
Stayed 6 nights in Jul 2025
Verified
10/10 Excellent
Therese B.
19 Mar 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Getaway before Spring Break
Therese B.
Stayed 6 nights in Mar 2024
Verified
10/10 Excellent
Stephanie S.
26 Jan 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great short stay
Stephanie S.
Stayed 2 nights in Dec 2024
Verified
10/10 Excellent
Karen A.
15 Jan 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
BFF Getaway
Karen A.
Stayed 3 nights in Jan 2023
Verified
10/10 Excellent
shelby b.
4 July 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Couples anniversary trip
shelby b.
Stayed 4 nights in Jun 2024
Verified
10/10 Excellent
susannah c.
18 Mar 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great little place on a great little Key!
susannah c.
Stayed 4 nights in Mar 2023
Verified
10/10 Excellent
John A.
6 Feb 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing Stay
John A.
Stayed 5 nights in Feb 2023
Verified
8/10 Good
Dan C.
7 Apr 2023
Liked: Cleanliness, location, listing accuracy
Nice Floridian get away.
Dan C.
Stayed 4 nights in Apr 2023
Verified
6/10 Okay
Todd A
16 Feb 2025
Liked: Communication
Disliked: Cleanliness
Todd A
Stayed 3 nights in Feb 2025
Verified
8/10 Good
Debbie A.
30 Jan 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Debbie A.
Stayed 7 nights in Jan 2026
Verified
8/10 Good
Edna Angeline F.
3 Aug 2022
Liked: Cleanliness, communication, location, listing accuracy
Cute Place in the Keys!
Edna Angeline F.
Stayed 4 nights in Jul 2022
Verified
10/10 Excellent
Linda M.
10 June 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Safe harbor in Cudjoe Key
Linda M.
Stayed 4 nights in Jun 2022
Verified
10/10 Excellent
Jason L.
16 May 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice place
Jason L.
Stayed 3 nights in May 2022
Verified
8/10 Good
Paul W.
16 May 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
I like the convenience of staying at a fully furnished location
Paul W.
Stayed 6 nights in May 2022
Verified
8/10 Good
Jan K.
30 Jan 2022
Liked: Cleanliness, check-in, location
Time at Venture Out
Jan K.
Stayed 5 nights in Jan 2022
Verified
10/10 Excellent
Norbert
3 Jan 2022
Liked: Cleanliness, amenities, property conditions & facilities, communication
Norbert
Stayed 4 nights in Dec 2021
Verified
10/10 Excellent
Kristin W.
17 Aug 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Charming property by the canal
Kristin W.
Stayed 5 nights in Aug 2021
Verified
10/10 Excellent
Yong Y.
16 Feb 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location super nice host
Yong Y.
Stayed 7 nights in Dec 2024
About the host
Hosted by Jennifer Neal
We are Jenny and Doug; a couple who enjoys travel and like to share our adventures with others. If we can make it happen for you, trust me , we will! So please enjoy this property as much as we do by kicking off your shoes, settling into you lounge chairs, and watching the water roll by.
Why they chose this property
A few years ago we started traveling by cruise ship and jet plane, to a variety of exotic locations. We made a life decision to discover our forever home on an island and begin living our best life upon retirement. (still a few years away). Last year we were sipping cold beverages on a wharf in key west, and one of us made a unique observation. "you know" I said to Doug. "Key West IS pretty much a Caribbean Island." Fast forward a few months and here we are! We hope you can enjoy the location for the same reason, and also discover some reasons of your own.
What makes this property unique
Keys life is the BEST life. Between the salt air, the abundant wildlife, the ever present sunshine and the turquoise waters of the Gulf and Atlantic, this area has it all! Key deer and other wildlife abound, there are hundreds of miles of channels and waterways, and untold seashells to be found. Once you discover the keys you'll never want to vacation anywhere else. With Calypso Cottage you can enjoy all this through the lens of the "Old Florida" vantage point. Back when Florida's architecture was pastel and simple, the landscape was unspoiled and still relatively untouched by modern times. But you will have all the modern amenities as well. with an unrivaled resort experience!
Languages:
English
Premier Host
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