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waterfront cottage near key west, sleeps 6

Waterfront cottage with kitchen and patio

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Calypso Cottage, a reimagined vintage style waterfront home, is your perfect haven in the Florida Keys. Enjoy kayaks, bikes, beach and snorkel gear on-site or explore community amenities like pools, a spa and sports courts nearby. Unwind on the lush screen porch or canal patio with drinks.

Reviews

9.4 out of 10
Exceptional

Entire home

2 bedrooms1 bathroomSleeps 6926 sq ft

Popular amenities

  • Hot tub
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

waterfront cottage near key west, sleeps 6

Waterfront cottage with kitchen and patio
Access to hot tub, laundry facilities and an arcade/games room are available at this smoke-free cottage. The cottage has 2 bedrooms and offers free WiFi and a patio. Guests can enjoy a fireplace, and other amenities include a kitchen with a fridge and an oven.
Air-conditioned accommodation at this cottage offers fireplaces and coffee/tea makers. Rooms open to patios. This accommodation is furnished with dining tables and kitchen islands. Kitchens offer fridges, stovetops, microwaves and kitchenware and utensils. Bathrooms include baths or showers and hairdryers.

This Summerland Key cottage provides complimentary wireless Internet access. Smart televisions are featured in guestrooms.

Recreational amenities at the cottage include Access to hot tub.

The recreational activities listed below are available either on-site or nearby; fees may apply.

Property amenities

Beach

  • Beach loungers

Pool/Spa

  • Communal pool
  • Hot tub

Internet

  • Available in the cottage: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room

Entertainment

  • Games
  • Smart TV

Outdoor areas

  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near the sea
  • On the waterfront

Things to do

  • Arcade/game room
  • Water sports equipment
  • Birdwatching nearby
  • Cycling nearby
  • Fishing nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkelling nearby
  • Swimming nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

General

  • Unit size: 926 square feet

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  • Kitchen
  • Washing machine
  • Dryer
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Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 21

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

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.

Pets

Pets not allowed

Children and extra beds

Children are welcome
Note from host: canal front property

Events

No events allowed

Smoking

Smoking is not permitted

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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

Property is also known as

Calypso Awaits Cudjoe Key
Calypso Cottage Awaits! Cottage
Calypso Cottage Awaits! Cudjoe Key
Calypso Cottage Awaits! Cottage Cudjoe Key
Last Minute Discounts for August September!

About the area

Located in Summerland Key, this cottage is on the waterfront. Florida Keys Beaches and Bahia Honda State Park 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. Visit our Summerland Key travel guide
View more Cottages in Summerland Key
Map
Cudjoe Key, FL

What's nearby

  • Beach and Pier at Sunset, Florida, USA
    Florida Keys Beaches
    10 min drive - 6.7 km
  • Lower Sugarloaf Sound
    Lower Sugarloaf Sound
    14 min drive - 12.1 km
  • Stopped by the sea on a ride down the Overseas Highway from Miami to Key West. The bike is a KZ750 lent to me by the guy living in the condo next door. #TheKeys #florida #beach #kawasaki
    Sugarloaf Beach
    21 min drive - 18.0 km
  • Upper Sugarloaf Key
    9 min drive - 6.9 km
  • Upper Sugarloaf Sound
    10 min drive - 8.2 km

Getting around

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

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

Does waterfront cottage near key west, sleeps 6 have a pool?

Yes, this property has a pool.

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

No, pets are not allowed at this property.

How much is parking at waterfront cottage near key west, sleeps 6?

On-site parking is available at the property.

What time is check-in at waterfront cottage near key west, sleeps 6?

Check-in begins at 4:00 PM.

What time is check-out at waterfront cottage near key west, sleeps 6?

Checkout is at 11:00 AM.

Where is waterfront cottage near key west, sleeps 6 located?

Situated on the waterfront, this cottage is within a 10-minute walk of Venture Out Keys, Venture Key and Out Key. Florida Keys Beaches and Upper Sugarloaf Key are also within 6 miles (10 km).

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waterfront cottage near key west, sleeps 6 Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 19 out of 26 reviews
Rating 8 - Good. 6 out of 26 reviews
Rating 6 - Okay. 1 out of 26 reviews
Rating 4 - Poor. 0 out of 26 reviews
Rating 2 - Terrible. 0 out of 26 reviews

9.2

Cleanliness

9.6

Location

8.0

Property conditions & facilities

Reviews

8/10 Good

Scott H.

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

Florida Key's Visit

Looking for a convenient location to stay while visiting the Florida Keys. This location was only about 30 minutes for Key West. We only used the home for sleeping since we spent the days sightseeing, but the home met our needs. It was clean and comfortable and a met our needs as a place to relax and get a good night's sleep.
Stayed 2 nights in Feb 2025

10/10 Excellent

Terry M.

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

Lovin life

The place was clean, and right on the water with access to both gulf and atlantic overall an awesome place to vacation
Stayed 6 nights in Aug 2023

10/10 Excellent

Therese B.

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

Getaway before Spring Break

Overall, a lovely property. Cozy would probably be the best word to describe. The location for where all we wanted to go was perfect...only downside, the pool closed the Monday through the week of our stay.
Stayed 6 nights in Mar 2024

10/10 Excellent

Stephanie S.

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

Great short stay

Our stay was short but sweet in this cute unit on Cudjoe Key. Plenty of sleeping space, beds were comfortable. The unit was well equipped with items for the beach, outside and use in the kitchen. Only complaint was that one of the bikes did not work. I am sure the o
Stayed 2 nights in Dec 2024

10/10 Excellent

shelby b.

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

Couples anniversary trip

We had a great stay! Other than the weather, everything was perfect! We had plans to dock our boat up at the house but it was too windy to take the boat out. We still enjoyed the patio and grilled out one night! We took showers across the street at the camp restrooms bc there were four of us and we would’ve ran out of hot water but that was no problem. We enjoyed our stay!
Stayed 4 nights in Jun 2024

6/10 Okay

Todd A

Liked: Communication
Disliked: Cleanliness
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.
Stayed 3 nights in Feb 2025

10/10 Excellent

Josh C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Comfortable little place on the water. Clean and kitchen stocked with everything you could need! The house did get pretty warm during the heat of the day but cooled nicely in the evenings. Was nice having coffee over looking the water. Recommend!
Stayed 3 nights in Aug 2025

10/10 Excellent

Bobby M.

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

4th annual bike trip

Great
Stayed 2 nights in Mar 2025

10/10 Excellent

Kelli M.

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

The Best

This place is exactly as described. The quirkiness was perfect for my husband and I to spend our anniversary. We had a day of rain and it was perfect!and
Stayed 5 nights in Mar 2025

10/10 Excellent

William S.

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

4 Friends came for Lobster Mini Season

This unit is old but very well maintained. It was very clean and actually well stocked with supplies that we brought because we didn’t expect to have. It was obvious that the owners really want you to enjoy the place. There were plenty of towels and beach towels, there were Kayaks ,Bicycles,Tennis Rackets, Games and everything worked well. I would definitely stay there again we had no complaints.
Stayed 6 nights in Jul 2025

10/10 Excellent

Karen A.

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

BFF Getaway

My friend and I love this little cottage. It was perfect for us! We enjoyed riding bikes in the canal neighborhood and sitting outside to watch the sun set with a glass of wine. Our host was responsive and helpful. It’s inside a gated community so we felt quite safe.
Stayed 3 nights in Jan 2023

10/10 Excellent

susannah c.

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

Great little place on a great little Key!

Our first Keys trip and calypso cottage in cudjoe key was exactly right! Only thing I’d change is a little bigger bathroom. Very comfortable and centrally located. Host was very communicative from booking through check out. Cudjoe Key is a great location if you want to be close to Key West for daily trips but want home base to be a quieter, slower pace. Venture Out was a quiet, friendly, relaxing community. We will definitely be returning!
Stayed 4 nights in Mar 2023

10/10 Excellent

John A.

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

Amazing Stay

We loved everything about this place. The cottage was well equipped with dishes, towels, even spices. Bed was comfortable. We spent most of our time on the front deck overlooking the channel. Even done a little fishing right off the porch. Caught some snapper, grunts and even a nurse shark. We enjoyed walking to the pool area overlooking the gulf and watching the sunrise every morning. Such a pleasant community. Everyone was so friendly. We can not wait to come back. We've found our perfect vacation spot.
Stayed 5 nights in Feb 2023

8/10 Good

Dan C.

Liked: Cleanliness, location, listing accuracy

Nice Floridian get away.

We had some difficulties checking in . We were not told the lot number, and the security desk didn’t have any info on our stay. Luckily things got ironed out quickly. Had no tv, the Ruku remote would not work . And couldn’t take a shower, Couldn’t get water to shower head. The unit Was clean and comfortable .
Stayed 4 nights in Apr 2023

8/10 Good

Edna Angeline F.

Liked: Cleanliness, communication, location, listing accuracy

Cute Place in the Keys!

Cute older manufactured home on canal. Relaxing to sit on back patio by the water. Host was extremely responsive when raised any questions or concerns. Close to marina and some awesome restaurants. Some clutter/disorganization under one of the beds and in closet near entryway/front porch. Having use of bikes and other amenities was great!
Stayed 4 nights in Jul 2022

10/10 Excellent

Linda M., CORINTH, Denton, TX

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

Safe harbor in Cudjoe Key

The cottage is comfortably and attractively furnished on a canal with bikes and even a motorized cart to use. It is located inside a resort property with controlled entry so we felt very safe there. The resort has a pool, small store, and other amenities to use, as well. We enjoyed our stay there.
Stayed 4 nights in Jun 2022

10/10 Excellent

Jason L.

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

Nice place

Great safe place with nice neighbors. Definitely recommend for the price and convenience
Stayed 3 nights in May 2022

8/10 Good

Paul W.

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

I like the convenience of staying at a fully furnished location

The nearby neighbors were friendly. They also enjoyed playing their music too loud, though I did not have the heart to tell them.
Stayed 6 nights in May 2022

8/10 Good

Jan K.

Liked: Cleanliness, check-in, location

Time at Venture Out

Venture out is a fun location . House could use some more amenities and sheets and mattresse pad that fit and stay on bed.
Stayed 5 nights in Jan 2022

10/10 Excellent

Norbert

Liked: Cleanliness, amenities, property conditions & facilities, communication
Liked how you can sit outside and take in fresh air next to water
Stayed 4 nights in Dec 2021

10/10 Excellent

Kristin W.

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

Charming property by the canal

A charming property with bohemian style, which backs right up to the canal. A great getaway to the Florida Keys
Stayed 5 nights in Aug 2021

10/10 Excellent

Yong Y.

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

Great location super nice host

Stayed 7 nights in Dec 2024

8/10 Good

lori m.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in May 2024

10/10 Excellent

kathleen

Stayed 7 nights in Feb 2023