waterfront cottage near key west, sleeps 6

Top rated by guests
pools, a spa and the ocean, what more do you need?
Interior
whimsical decor is our superpower
a screen porch entry makes your arrival super easy
loungers can be moved from sun to shade
review stars
9.3Outstanding
(29 Ratings)
"Place was perfect for us, beach feel and very clean, loved the kayaks. Pool was nice to take a break, all in all 10 stars. "
Mike S.
Don't miss out! Price and availability may change
9.3 / 10
Outstanding(29 Ratings)

Cottage in Cudjoe Key, FL

6 guests · 2 bedrooms · 1 bath

Reasons to book

Guests love it hereGuests give this property a top rating
Well priced for this locationPriced under area average
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this cottage rental

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!

Amenities

Non-smoking
No pets allowed

Map of Cudjoe Key, FL


Ratings and reviews

9.3 / 10
Outstanding(29 Ratings)
10 / 10Outstanding·Mar 2026
Place was perfect for us, beach feel and very clean, loved the kayaks. Pool was nice to take a break, all in all 10 stars.
8 / 10Excellent·Jan 2026
The host was easy to communicate with and accommodating! The community that we stayed in had wonderful amenities, and the location was perfectly between Key West and Miami.
10 / 10Outstanding·Jan 2026
Great back patio. Nice development. Loved the open floor plan
6 / 10Average·Feb 2025
Location was good, nice pool and amenities. 1. We arrived and the property was not turned over( trash, dirty towels, beds slept in) 2. Cleaning lady came, removed our things. She did bring some back, but threw away our candies/ food. Promised to replace, never done. 3. Bedroom air conditioning unit was moldy, foul smell. We had to leave it off or sleep on the couch as it was very very smelly. 4. Neighbor’s boat blocks the kayak launch making it unusable. Out door chairs are broken, cannot sit in them. ( there were additional chairs in the front we were able to move to the back) 5. Bathroom door is off the hinge, multiple members of our group required extrication.

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FAQs

Is parking included with this cottage?

Parking is not specified as an available amenity at waterfront cottage near key west, sleeps 6. For more information, we encourage you to contact the property about where to park.

Is there a pool at this cottage?

We didn’t find pool listed as an amenity for this cottage. It may be worth double checking if a pool is important for your stay.

Is waterfront cottage near key west, sleeps 6 pet friendly?

Unfortunately, this cottage is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at waterfront cottage near key west, sleeps 6?

We found 2 amenities for this rental. This includes non-smoking, and no pets allowed.


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