Tropical Lochloosa-Enjoy Caribbean weather in the USA. Fall & Jan 2027 dates!

Photo gallery for Tropical Lochloosa-Enjoy Caribbean weather in the USA. Fall & Jan 2027 dates!

A sunset over a body of water with a structure that appears to be a gazebo or pavilion.
A tropical beach resort with a pool, palm trees, and a boat in the water.
A resort with a pool, lounge chairs, palm trees, and a view of the water.
A coastal resort with multiple swimming pools, a beach area, and a parking lot.
An aerial view of a sports complex with multiple tennis courts, a basketball court, and a large circular structure.

Reviews

9.4 out of 10
Exceptional

Highlights

  • Dive into relaxation
    Unwind in the top-rated pool, your perfect spot for relaxation.
  • 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

  • Spa pool on site
  • Patio
  • Outdoor pool
  • Barbecue
  • Air-conditioning
  • Refrigerator

Explore the area

View map
Cudjoe Key, FL
  • Place, Upper Sugarloaf Key
    ‪6 min drive‬
  • Place, Florida Keys Beaches
    ‪6 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 2

2 Single Beds

Master

1 King Bed

Sofa pulls out to a bed which has a foam topper and is very

1 Double Futon

1 bathroom

Bathroom 1

Spaces

Deck or patio
Porch or lanai
Kitchen
Dining area

Add dates for prices

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About the area

Summerland Key

Summerland Key is home to this holiday home. Florida Keys Beaches and Coupon Bight Aquatic Preserve reflect the area's natural beauty and area attractions include Blue Hole and Big Munson Island. Kayaking, scuba diving and snorkelling offer great chances to get out on the surrounding water, or you can seek out an adventure with mountain biking 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 - 6.6 km
  • Florida Keys Beaches - 6 min drive - 6.7 km
  • Upper Sugarloaf Sound - 7 min drive - 7.9 km
  • Boondocks Grille & Draft House - 9 min drive - 11.0 km
  • Lower Sugarloaf Sound - 10 min drive - 11.5 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 30 min drive

Restaurants

  • ‪Boondock's Grille & Drafthouse - ‬10 min drive
  • ‪Morning Joint - ‬4 min drive
  • ‪Kiki's Sandbar - ‬12 min drive
  • ‪Looe Key Tiki Bar & Restaurant - ‬10 min drive
  • ‪Tonio's Seafood Shack & Tiki Bar - ‬7 min drive

Frequently asked questions

Does Tropical Lochloosa-Enjoy Caribbean weather in the USA. Fall & Jan 2027 dates! have a pool?

Yes, this property has an outdoor pool.

How much does it cost to stay at Tropical Lochloosa-Enjoy Caribbean weather in the USA. Fall & Jan 2027 dates!?

As of 2 Nov 2026, prices found for a 1-night stay for 2 adults at Tropical Lochloosa-Enjoy Caribbean weather in the USA. Fall & Jan 2027 dates! on 3 Nov 2026 start from AU$1,063, 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 Tropical Lochloosa-Enjoy Caribbean weather in the USA. Fall & Jan 2027 dates! pet-friendly?

No, pets are not allowed at this property.

How much is parking at Tropical Lochloosa-Enjoy Caribbean weather in the USA. Fall & Jan 2027 dates!?

On-site parking is available at the property.

What time is check-in at Tropical Lochloosa-Enjoy Caribbean weather in the USA. Fall & Jan 2027 dates!?

Check-in begins at 3:00 PM.

What time is check-out at Tropical Lochloosa-Enjoy Caribbean weather in the USA. Fall & Jan 2027 dates!?

Checkout is at 10:00 AM.

Where is Tropical Lochloosa-Enjoy Caribbean weather in the USA. Fall & Jan 2027 dates! located?

Situated in Summerland Key, this holiday home is within a 15-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).

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. 108 out of 144 reviews
Rating 8 - Good. 24 out of 144 reviews
Rating 6 - Okay. 9 out of 144 reviews
Rating 4 - Poor. 1 out of 144 reviews
Rating 2 - Terrible. 2 out of 144 reviews

9.2/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

9.8/10

Check-in

9.8/10

Communication

9.8/10

Location

9.2/10

Listing accuracy

Reviews

Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, listing accuracy
Cute, clean property. Only
Stayed 4 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was very clean and had everything we needed for our stay!
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

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

Great place

Great place to stay.
Stayed 6 nights in Apr 2023
Verified review

10/10 Excellent

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

Awesome stay

Great location
Stayed 3 nights in May 2023
Verified review

10/10 Excellent

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

Perfect location and perfect stay!

We love this little cottage! The proximity to the pool the Jacuzzi, the beach access and the rec center is perfect!We had the best time and will definitely try and be back! Try all the local restaurants they are so good!
Stayed 5 nights in May 2025
Verified review

8/10 Good

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

Good place to stay, well located in the Keys

We enjoyed our stay here. However 125 usd fee to pay at arrival even for a few days.
Stayed 3 nights in Aug 2024
Response from VrboOwner on 29 Aug 2024
Unfortunately that’s beyond my control as is payable at the gate to the facility. But I hear you!!
Verified review

10/10 Excellent

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

Great place

Great stay. Comfy beds. Everything you need.
Stayed 5 nights in Apr 2024
Verified review

10/10 Excellent

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

Excellent place !

Great location! Fabulous pool! Well be back again for sure !
Stayed 4 nights in Sep 2024
Verified review

10/10 Excellent

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

Cozy Stay

Cozy stay just a short drive from Key West. Fully functioning kitchen and comfortable lounging and sleeping areas.
Stayed 5 nights in May 2023
Verified review

10/10 Excellent

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

Cudjoe Paradise

Great place to get away for a week!
Stayed 9 nights in Jun 2024
Verified review

10/10 Excellent

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

Wonderful place to stay

The
Stayed 7 nights in Mar 2024
Verified review

10/10 Excellent

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

Great place for a short stay!

Had a great stay in April. Place was just as described, plenty of kitchen counter space for cooking and variety of utensils. Venture Out community was nice, just be sure to include the 125 fee at gate in your budget.Would rent again!
Stayed 4 nights in Apr 2025
Verified review

10/10 Excellent

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

Wonderful time

Definitely will come back again. Great location to everything. Secure property with all the amenities. Beach was great Host was so wonderful answering all our questions. We absolutely loved it
Stayed 5 nights in Nov 2024
Verified review

10/10 Excellent

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

Nice home base as we explored the keys.

The home was centraly located to loads of activities in the keys. The community is nice and well maintained. We enjoyed the tenis courts with the family and lounging by the tiki huts.
Stayed 4 nights in Jun 2023
Verified review

10/10 Excellent

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

Our stay

Honestly it was all described and on point. Super easy to sign in with Venture Out, parking was easily accessible. I’ll be back for sure!
Stayed 6 nights in May 2023
Verified review

8/10 Good

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

Decent place for a quick getaway

Pool security is silly!
Stayed 3 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
They had everything that we would need for our stay. Plenty of pots and pans and all the cooking utensils that you would need. There was plenty of room in the kitchen, front room, and living room. The master bedroom was a little small but it had a king size bed in it so we didn't mind at all. Second bedroom had a trundle bed and room even with bed pulled out. All in all it suited our family of 5 perfect. We all enjoyed all the resort amenities. My boys stayed at the basketball court. The pool is warmed, so even if it wasn't super hot out the pool was still perfect.
Stayed 9 nights in Dec 2025
Archival

10/10 Excellent

great place

great home and development. master bedroom a little warm but other than that we thoroughly enjoyed ourselves. thanks!
Response from VrboOwner on 23 Mar 2020
I'm glad you had a great time Erika, we are here now. We checked the a/c service and the trick is to keep the ceiling fans going at all times where the vents are in the floor. That way everything stats nice and comfortable. Hopefully you'll come back and see for yourself!!! Thanks for renting our home!!
Verified review

10/10 Excellent

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

Vacation

As advertised. Clean and good AC!
Stayed 4 nights in Jun 2024
Verified review

10/10 Excellent

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

Very good experience.

Excellent communication with owner and property caregiver, Malcolm.
Stayed 4 nights in Jun 2019
Verified review

10/10 Excellent

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

Great stay!

Perfect place to escape the heat and rest our heads. We spent most of the time on the boat. Close to key west and drove down and back in 1 day. Host was extremely helpful when I needed to ship a package to the home. We will def be rebooking this place!
Stayed 8 nights in Jul 2023
Archival

10/10 Excellent

from Louisville

This is a beautifully kept property with all the amenities anyone could ask for. This place has all the comforts of home, We loved it and hope to return some day. Thank you so much for opening your beauiful home to us.
Response from VrboOwner on 23 Mar 2020
Barbara, I'm glad to hear you enjoyed your stay at our home! Please come back-repeat renters get a 10% discount! Appreciate your kind words!
Verified review

10/10 Excellent

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

Great place to stay in the keys!

This is a very nice place to stay in the lower keys. Very comfortable with all of the amenities of being in your own home. The complex it's in has all the amenities, pool, tennis, laundry, etc. Great bridge fishing close by. Everyone is very friendly and accommodating. This is the second time we have stayed at venture out on cudjoe key and have been very happy with it.
Stayed 7 nights in Dec 2023
Verified review

10/10 Excellent

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

Sunrise in Paradise

Had an amazing time! The hosts were very responsive and hospitable. The location was beautiful and perfect for our vacation. We were able to experience a gorgeous sunrise literally right outside our door. The house itself was homey and comfortable. We had everything we needed. I’d definitely stay there again .
Stayed 3 nights in Apr 2023
Verified review

10/10 Excellent

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

Christmas vacation

My family loved staying here. We had a wonderful time. Thank you for making a space welcoming and stocked with items (spices for cooking, superglue, feminine products, ect.) items that you dont think about when traveling but this place thought of it for you. Thank you for being thoughtful it was a wonderful time.
Stayed 10 nights in Dec 2024
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