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

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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.
An aerial view of a sports complex with multiple tennis courts, a basketball court, and a large circular structure.
A coastal area with a beach, clear blue waters, and a line of wind turbines in the background.
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.

Reviews

9.4 out of 10
Exceptional

Entire home

2 bedrooms1 bathroomSleeps 6864 sq ft

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi

Explore the area

View in a 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

Room options

About the neighborhood

Summerland Key

This vacation home places you within a leisurely stroll of Venture Out Keys and Venture Key. The vacation home includes a kitchen, a patio, and a sofa bed.
View more Vacation Homes in Summerland KeyOpens in a new window

What's nearby

  • Upper Sugarloaf Key - 6 min drive - 4.1 miles
  • Florida Keys Beaches - 6 min drive - 4.2 miles
  • Upper Sugarloaf Sound - 7 min drive - 4.9 miles
  • Boondocks Grille & Draft House - 9 min drive - 6.9 miles
  • Lower Sugarloaf Sound - 10 min drive - 7.1 miles

Getting around

  • Key West Intl. Airport (EYW) - 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

About this property

Entire place

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

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

We have a big bright eat in fully stocked kitchen. Kitchen has many pots and pans, keurig, blender, glassware and most things that you’ll be looking for while relaxing in the beautiful Keys!! The main bedroom has a KING size bed, lots of storage space and TV with YouTube Live TV & Roku.

The second bedroom has a twin trundle, when the two twin beds are side by side it's like another King Size Bed and TV with Roku & streaming YouTube Live TV.

We're provided lots of fluffy cotton towels in the bathroom. We have a grill in our backyard along with cement patio furniture for you to enjoy the beautiful keys weather. The front porch has a large deck, seating for 6. You can enjoy the sunrise and your morning coffee, family dinners and evening cocktails!

Bring your boat! We are on a dry lot but there is no charge for launching in at the Venture Out Marina, your boat can be stored in the 'overflow' lot for a small fee ($5-10 day subject to first come first serve availability). Conveniently located near the marina, picnic area, pool, tennis and rec hall. The Florida Keys have some of the best fishing in the world! (Boat and trailer parking is an additional daily charge by the park.) It is also a great spot for Kayaks. Take your choice to relax in the heated Olympic size salt water pool, hot tub or open Atlantic swimming area all nearby. You can fish from our open water areas. There is a big TIKI HUT on the open water where picnicking is perfect!

Unfortunately due to some bad experiences pets are no longer allowed.

OUR HOME IS NO SMOKING. Smoking outside is obviously permitted.

The GATED COMMUNITY we own in is AWESOME & a very friendly place to stay & enjoy. The amenities include: 24 hour security, Lighted tennis courts (2 rackets available at the house) Olympic-sized heated pool, kiddie pool, spa Jacuzzi, ping pong, bocce ball courts (set of bocce balls in the closet), pickle ball, lighted basketball court, children's playground, pool table, darts, Marina complete with 2 ramps, gas, store, ATM and fish cleaning station, boat trailer parking onsite, open water picnic areas, ocean front tiki hut, lending library, post office - and MORE - ALL IN A GATED COMMUNITY with a mixture of RV sites and manufactured homes where you can feel safe and secure.

We're only 19 miles from Key West, but do not think you HAVE to go anywhere - lay by the HUGE POOL right on the OPEN WATER and watch the elegant seagulls float overhead as the palms sway. Sun yourself and read a good book and simply relax! Plunge into the BIG JACUZZI and soak your troubles away. Or spend some time with someone you love - holding hands and watching the herons fishing along the waterside! And you do not even have to get in your car to do any of these!

Adventure beyond the gates for a bite to eat at some of Florida Key's favorite restaurants such as, Square Grouper, Morning Joint, The Bent Prop, Mangrove Mamas, Kiki's Sandbar or Boondocks Draft house and Miniature Golf course, all within a 10 minute drive. Or head a little further to Key West for even more fun only 20 minutes away! What are You waiting for??? Send an email and we'll fill you in on any of your questions to make certain your family and friends are going to have a great vacation getaway in the Keys!

Make sure you check our availability calendar as it is updated after each reservation is placed. Plan it now, before someone else gets YOUR Place!

Our home has parking for one vehicle but extra may be able to be stored in the nearby overflow lot for an additional fee of $5-10/night subject to availability. FYI a full size pick up will not fit in the driveway (we fit a Titan) and will need to go in the overflow lot with a nightly charge. There is an additional one time fee of $125 payable to the community at the time of entrance which is separate from anything paid to me through Vrbo. Would be willing to book direct if asked for discounted rate. Contact me at five zero eight 826-six two seven one. My phone number is also on rental agreement.

Arrival time is 3:00 PM, Departure is 10:00 AM

Keywords: House, home, bungalow, cottage
The vacation home is air-conditioned and features a kitchen and a patio, and there's space to spread out with 2 bedrooms. Guests can expect to find free WiFi and a Smart TV with a DVD player. Other standard amenities include a washing machine, a sofa bed, and a coffee maker.

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Property amenities

Beach

  • Beach loungers
  • Beach towels

Pool/Spa

  • Communal pool
  • Fenced private pool
  • Hot tub
  • Outdoor pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bed sheets provided
  • Sofa bed

Bathroom

  • 1 bathroom
  • Hair dryer
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • DVD player
  • Smart TV with cable/satellite channels
  • Stereo
  • Video games

Outdoor areas

  • Barbecue grill
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Cobblestone flooring in public areas
  • No elevator
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near a health/beauty spa

Things to do

  • Bicycles
  • Billiards/pool table
  • Table tennis
  • Basketball nearby
  • Birdwatching nearby
  • Fishing nearby
  • Golfing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Mountain biking nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby
  • Whale watching nearby
  • Wildlife walks nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Bicycles
  • Unit size: 864 square feet

Policies

Check-in

Check-in time starts at 3:00 PM

Check-out

Check-out before 10:00 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 complete the following before checking out:
Start the dishwasher
Gather used towels
Remove personal items, remove leftover food and drinks, and take out the trash
Turn off the lights
Failure to complete these may result in a negative review from the host.

Rules

Cancellations within 60 days will not be refunded unless we're able to rebook the dates. Travel Protection Insurance is recommended.

Pets

  • This property doesn't allow pets
  • Note from host: 2 pets subject notification at booking & $50 fee

Children and extra beds

Children allowed: ages 0-17

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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
  • Check-in: 3:00 PM
  • Check-out: 10:00 AM

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, and a smoke detector.

Additional information about polices, regulations, and more:

  • There are no elevators.

Frequently asked questions

What's there to see around this vacation home?

This vacation home is located in Summerland Key, a short 13-minute walk from Venture Out Keys and also 13 minutes on foot from Venture Key. You'll also find Florida Keys Beaches and Upper Sugarloaf Key within a short drive.

Is there parking available at Enjoy Caribbean weather in the USA. Openings August 2026 forward! ?

No, this vacation home doesn't offer parking.

Is this vacation home associated with a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, this vacation home doesn't have an indoor pool; however, there are an outdoor pool and a hot tub.

What amenities will couples enjoy at Enjoy Caribbean weather in the USA. Openings August 2026 forward! ?

Couples staying at this vacation home will appreciate amenities like a smart TV and a kitchen as well as an outdoor pool.

Does Enjoy Caribbean weather in the USA. Openings August 2026 forward! have a hot tub?

No, there isn't a spa tub at this vacation home.

Does this vacation home provide breakfast?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay for free?

No, pets aren't allowed at this vacation home.

Does Enjoy Caribbean weather in the USA. Openings August 2026 forward! have connecting rooms available?

No, this vacation home doesn't feature connecting guestrooms.

How close is the airport from this vacation home?

The closest major airport to this vacation home is Key West Intl. Airport (EYW), which is 21 mi away (30 minutes by car). Another top airport is Marathon, FL (MTH-Florida Keys Marathon), which is located 28.9 mi away (41-minute drive).

Are there rooms with balconies at Enjoy Caribbean weather in the USA. Openings August 2026 forward! ?

Yes, every house at Enjoy Caribbean weather in the USA. Openings August 2026 forward! comes with a patio and some offer water views.

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

Reviews

9.4

Exceptional

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

Reviews

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
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

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 place to stay

The
Stayed 7 nights in Mar 2024
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!
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.
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
Verified review

10/10 Excellent

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

Cute cottage

Nice, quiet neighborhood. Close to amenities. Only downside, entrance door is hard to open and close; very little shade during the day. Will definitely consider in the future.
Stayed 3 nights in May 2024