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water at your back door

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A marina with boats docked, a small dock with a barbecue grill, and houses with palm trees in the background.
A bedroom with a bed, two nightstands, a dresser, and a framed picture on the wall.
A living room with a dining table, chairs, a sofa, a TV, and a ceiling fan.
A house with a covered patio, outdoor seating, and a barbecue grill.
A kitchen with white cabinets, a stainless steel sink, and a microwave.

Reviews

8.8 out of 10
Excellent

Entire home

2 bedrooms2 bathroomsSleeps 6

Popular amenities

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

Explore the area

View in a map
Cudjoe Key, FL
  • Place, Upper Sugarloaf Key
    ‪7 min drive‬
  • Place, Florida Keys Beaches
    ‪8 min drive‬
  • Place, Upper Sugarloaf Sound
    ‪8 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪38 min drive‬

Room options

About the neighborhood

Summerland Key

This cottage places you within a 10-minute stroll of Venture Out Keys and Venture Key. The cottage includes a kitchen, a patio, and a sofa bed.
View more Cottages in Summerland KeyOpens in a new window

What's nearby

  • Upper Sugarloaf Key - 7 min drive - 4.5 miles
  • Florida Keys Beaches - 8 min drive - 4.6 miles
  • Upper Sugarloaf Sound - 8 min drive - 5.3 miles
  • Boondocks Grille & Draft House - 10 min drive - 7.3 miles
  • Lower Sugarloaf Sound - 11 min drive - 7.6 miles

Getting around

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

Restaurants

  • ‪Boondock's Grille & Drafthouse - ‬9 min drive
  • ‪Morning Joint - ‬16 min walk
  • ‪Kiki's Sandbar - ‬11 min drive
  • ‪Looe Key Tiki Bar & Restaurant - ‬9 min drive
  • ‪Square Grouper Bar and Grill - ‬20 min walk

About this property

Entire place

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

water at your back door

**We Have Everything You Need For A lovely Getaway**
We welcome you to our Beautifully Furnished 2 bedroom, 2 bath home located in Cudjoe Key Florida. (Also Known As Venture Out & It's Gated Community )
Located just 23 miles from downtown key west, with a 30 minute drive to either key west or marathon, This house Has direct ocean access for the serious fisherman & is located on a 60 ft Wide Canal, with a 35ft dock space at your backdoor & an outdoor cleaning station. Washer & Dryer available. The 2 bedrooms include 2 Queen size beds with both having access to the bathrooms.
Both bathrooms have stand up walk-in showers, Kitchen includes all the necessity's.
Living room has a sleeper sofa & a 55 inch smart Tv with over 5000 channels to choose from. The resort has a beautiful large Olympic size Swimming pool, or a area marked for swimming if you prefer salt water & snorkeling, hot tub, tennis courts, basketball court, Children's playground, Pool Tables, & a marina with two boat ramps, snacks & fuel. There is room to park one vehicle in the driveway at the property anything else is
** A VENTURE OUT REGISTRATION FEE**
**Per Registration for no more than 6 guest (MAX) ($125.00) payable at the gate upon arrival
via cash or credit card. This Fee is Paid directly to venture out;

Only one car is permitted at each unit. Transportation vehicles must fit in the driveway or will have to be moved into overflow parking for a small nightly fee. If you have an extra car you will need to park in the overflow parking lot and pay the appropriate nightly fee up to 14 days maximum pending availability.

There is no jet ski trailer parking available. Boat trailer parking may be available, subject to availability and for a fee. The rates are $5-$10 per night depending on size.
The cottage is air-conditioned and features a kitchen, 2 bathrooms, and a patio, and there's space to spread out with 2 bedrooms. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a washing machine, a sofa bed, and a coffee maker.

Similar properties

Exterior
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
  • Ocean view
  • Pool
  • Kitchen
  • Washer
9.8 out of 10, 96, 96 reviews
$354 nightly
The price is $395
Sep 16 - Sep 17
Total with taxes and fees
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Property amenities

Beach

  • Beach loungers

Pool/Spa

  • Fenced private pool
  • Heated pool
  • Hot tub
  • Outdoor pool

Internet

  • Available in the cottage: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

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

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Sofa bed

Bathroom

  • 2 bathrooms
  • Hair dryer
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • Smart TV with cable/satellite channels

Outdoor areas

  • Barbecue grill
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Printer

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • On the waterfront

Things to do

  • Billiards/pool table
  • Heated pool
  • Tennis

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)

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

Rules

NO FROZEN BAIT IN KITCHEN FREEZER
Absolutely no more than 6 guest..

Pets

  • This property doesn't allow pets

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
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 professional host. The provision of housing is linked to their trade, business, or profession.
  • 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 and a smoke detector.

Frequently asked questions

What can I see within easy reach of this cottage?

This cottage in Summerland Key is within a 10-minute walk of Venture Out Keys, Venture Key, and Out Key. You'll also find Florida Keys Beaches and Upper Sugarloaf Key within a short drive.

Is there parking available at water at your back door?

No, there isn't parking at this cottage.

Is this cottage next to a casino?

No, this cottage is not connected to a casino.

Will I find an indoor pool at this cottage?

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

What do couples enjoy most about water at your back door?

Amenities that appeal to couples at this waterfront cottage include a smart TV and a kitchen along with an outdoor pool.

Are there hot tubs at water at your back door?

No, but this cottage does have a heated pool.

Does this cottage include breakfast service?

No, this cottage doesn't offer breakfast.

Will this cottage allow pets to stay free of charge?

No, pets aren't allowed at this cottage.

Are there connecting rooms at water at your back door?

No, this cottage doesn't feature connecting guestrooms.

How close is the airport from this cottage?

The closest major airport to this cottage is Key West Intl. Airport (EYW), which is 21.3 mi away (31 minutes by car). Another top airport is Marathon, FL (MTH-Florida Keys Marathon), which is located 29.2 mi away (42-minute drive).

Are there rooms with balconies at water at your back door?

Yes, every cottage at water at your back door comes with a patio.

water at your back door Reviews

Reviews

8.8

Excellent

Rating 10 - Excellent. 21 out of 34 reviews
Rating 8 - Good. 8 out of 34 reviews
Rating 6 - Okay. 2 out of 34 reviews
Rating 4 - Poor. 1 out of 34 reviews
Rating 2 - Terrible. 2 out of 34 reviews

9.4/10

Cleanliness

10/10

Property conditions & facilities

Reviews

Verified review

10/10 Excellent

Verified traveler

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

Great Stay!

Host was great!!
Stayed 4 nights in Feb 2023
Verified review

10/10 Excellent

Jeanne D.

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

Great time!

Beautiful and safe place to stay!
Stayed 4 nights in Apr 2022
Verified review

10/10 Excellent

Erik M.

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

Great Host - Great Property

Overall Great Stay. Excellent Host and the property was great. Would highly recommend it.
Stayed 6 nights in Jul 2023
Verified review

10/10 Excellent

Gerry S.

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

Family time

Wonderful experience neighbors and community very helpful and plessant
Stayed 7 nights in Mar 2025
Verified review

10/10 Excellent

Shaun M.

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

Cute place

We had a great stay. Loved that both bedrooms had bathrooms. Its a beautiful property. All we need for our stay.
Stayed 6 nights in Mar 2023
Verified review

10/10 Excellent

Alex N.

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

Paradise on a private canal.

Great house. Great neighbors. Close to pretty much anything you want.
Stayed 4 nights in Dec 2024
Verified review

10/10 Excellent

Jen T.

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

Excellent

The house was cute, clean and in a great community. We loved it!
Stayed 5 nights in Mar 2023
Verified review

10/10 Excellent

Megan A.

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

Nice Getaway

Our family enjoyed this cute little cottage while exploring the keys. Everything was as advertised and communication with the owner was easy. We would definitely recommend.
Stayed 4 nights in Apr 2023
Verified review

10/10 Excellent

Kevin C.

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

Great time in a beautiful place!

We checked in and had a great time while staying in the Keys! Clean, and friendly !!! neighbors were very friendly and welcoming! pool was great and this rental was amazing! All things available for a weeks stay! Definitely hope to return in the future!!
Stayed 5 nights in Feb 2022
Verified review

10/10 Excellent

Jerri B.

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

Cute Water View

This property has was you need and than some. Kitchen is well stocked. Ample room for 4 people. Heated pool in the community is awesome. Water view from property is relaxing.
Stayed 4 nights in Jan 2022
Verified review

10/10 Excellent

Mark G.

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

Nice place.

House was much nicer than expected. Very clean. Property manager Jessica was awesome at check in & check out. She went out of her way to make sure that we felt welcome & taken care of.
Stayed 6 nights in Feb 2023
Verified review

10/10 Excellent

lynn z.

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

very clean and safe community

very clean and safe community. It is quiet too. I cannot live in hotel because I cannot bear noise. This is a very quiet community. The house is clean too.
Stayed 4 nights in Feb 2023
Verified review

10/10 Excellent

Ricky A.

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

Got no yacht?

Aside from hot bedrooms and bathrooms (despite fan unit cooling), place was clean, tidy and cosy. Small by American standards, but acceptable for short stays. Resort has nice pool and spa and is aimed at the RV and boating community as a priority.
Stayed 4 nights in Dec 2022
Verified review

8/10 Good

Joan S.

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

Fantastic stay in Cudjoe Key

We (2 couples) had a wonderful time in Cudjoe Key/The Keys. Property was even better than described. It was perfect for us. Great views, comfortable and well stocked for us to cook the evenings we decided to stay in. We made use of the pool, hot tub, ping pong table and Pickleball court. Everything is very well maintained and everyone is very friendly. Property manager was really nice and helpful! We’re already planning to return next year!!
Stayed 5 nights in Feb 2023
Verified review

8/10 Good

Luis V.

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

Storm Vacation

Because of the storm we were locked into the house for two days that’s when we discovered that the TV in the master bedroom did not work, we tried going for a bike ride. One of the tires popped as soon as we tried to ride down the street aside from that, the place was very comfortable.
Stayed 5 nights in Aug 2024
Verified review

8/10 Good

Karen F.

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

Girls trip to the Keys

The rental was the perfect size for the 4 of us, being right on the canal was a bonus. We had no problem finding the place and after a 5 minute check in at the gate where they explained the rules of the resort - which we didn't think were out of line - we were unpacking. The place was clean and the air conditioning was thankfully cold! From the rental we could easily get to activities in Marathon and Big Pine as well as all the fun in Key West. The host, Jessica was always available and quick to respond, we had a wonderful time and would stay here again
Stayed 5 nights in May 2023
Verified review

10/10 Excellent

Ellen S.

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

Everything and more..

This rental had everything that we needed from a blender for margaritas to a kitchen aid mixer for killer brownies and a gas grill for our steaks. Everything was fantastic! This was our first stay with VRBO and Jessica, the property mgr made the process so easy. She answered all of our questions and more! We will be back! Ellen & Jim S.
Stayed 4 nights in Jan 2022
Verified review

10/10 Excellent

Therese G.

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

Cudjoe Key Luxury

Five Star. Comfortable. Clean. Well appointed. Bright. Morning sun off patio. Enjoyed a run/walk/ salt water swim every morning. Safe. Friendly neighbors. Would go back tomorrow!
Stayed 14 nights in Feb 2022
Verified review

8/10 Good

Kathy

Liked: Property conditions & facilities, communication
Firstly, the communication and helpfulness of Jessica, the property manager, was excellent. We appreciated her. The house has been re-done recently, and worked well for us. The kitchen was great and well-supplied with utensils, and all the appliances work well. We felt we needed to re-wash all the dishes and wipe down other things in the kitchen before using it. Also, the floor wasn't the cleanest, I think they forgot to mop before. The laundry machines were greatly appreciated, and the showers are perfectly clean and new. Finally, the grounds are well maintained and it's a very nice pool area and picnic grounds.
Verified review

6/10 Okay

Shane H.

Liked: Cleanliness, check-in, communication, location

Short trip

Property was clean. This place is Much smaller than pics show. Tv is a pain to operate. Tv in bedroom did not work, light flickering when on in main bedroom and shower had NO pressure. Parking in driveway was for a compact car much to small for my truck (stuck out in the road). Living room fan is so low its dangerous especially walking out the bedroom. Neighbors were nice and helpful. Venture out is an awesome place to stay as a community. My 3rd year renting different houses here. Definitely wont rent this one again. For the price it was not a good deal especially since it was so small and off season!!!
Stayed 6 nights in Jan 2024
Verified review

4/10 Poor

Verified traveler

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

Great place but boat docking not maintained

The place was as described, very clean and great air conditioner, which is needed in south Florida. More utensils, pots, pans, small appliances than you will ever need which is rare in a rental. The place is right on a canal with a place to keep your boat right at your back door. However, a bumper on the dock is missing with two large screws sticking out that caused significant damage to my paint and fiberglass. When the property owner or manager was notified of the damage his only reply was “sorry for your inconvenience.” It’s not an inconvenience it’s a lack of maintenance of the property that caused several hundred dollars of damage to my boat. This tells me that the owner/manager has no integrity and doesn’t care about my damage.
Stayed 6 nights in Jun 2024
Verified review

6/10 Okay

Barb C.

Liked: Communication, location
Disliked: Check-in

Property lacks attention to detail

I want to start with the positive things about the property. The gated community is beyond friendly and as the owner states safe. The kitchen had literally every gadget you could ever use. Jessica was friendly and was quick to respond to text messages while we were on property. The gate fee is not clearly communicated in the listing so it was confusing why it wasn't part of the rental agreement. Jessica contacted us the day of our arrival wanting to know what time we would be there. She contacted us 3 more times as we made our way through the keys. When we arrived on property she told us at first it was to "show us how to use the TV", but then later said that the owner wanted her to meet everyone that rented the place? She also told us a story of why the owner wanted her to do that, which we all took offense to, and wondered why someone would repeat that. As for the attention to detail, the main thing was the bed linens and pillows didn't feel or smell fresh. Which when you are paying close to $400 per night is something you expect. The property is small, which I would not mind if it was also cozy and comfortable, but there is not comfortable seating for 4 guests so I am not sure where their max guests of 6 would sit, not to mention sleep. The last night we were on property we were sitting on the outside patio when a large rat ran out from the property and across the patio. When I texted Jessica in the morning about it as we made our way to the airport, she said "oh great, I hate rats. I will call the owner now." "Down here there are a lot of "palm rats". Not, oh I'm terribly sorry. I hope it didn't ruin your stay, we really try hard to avoid them. So, I think it could be a good property, but I will not be giving it a second chance. The cost to value ratio is just not there.
Stayed 4 nights in Feb 2022
Verified review

2/10 Terrible

william t.

Liked: Cleanliness, location
Disliked: Check-in, listing accuracy

Was less then Satisfied

(Not allowed to post fee prices) Once you arrive the place is amazing, however the first thing you find out hours before arrival is an additional large fee that is not in listing, then as soon as you arrive, you find out there was no longer boat trailer parking available, which you pay for with your reservation and the closest available parking was 7 miles away for another large fee, the add said they did have available parking for significantly less, so there were more surprise fees, followed by the fact we came with 2 vehicles as well as the boat and trailer and the second vehicle was yet a another additional fee a day that was quite far away from the rented location. Then yet again got a ticket on my truck saying it’s to big for the only one included and that I’d have to pay yet another additional fee per day to park my truck (our main vehicle) so more fees which I did not accept and about had it at that point. The house was nice only real issue which was a very big issue was the ac, we came back from being on the boat everyday to 82 degree inside temperatures while set at 70. Called and had no solution to the problem after being told that someone would be sent to check it out, as well as the parking situation coming back with sorry we can’t help you. We didn’t pay 3xxx$ to have all these extra fees and not even having cold ac when we get back from burning offshore all day. For the price of all the extra fees we could’ve just got a nicer place with extra room and could’ve parked the trailer at the house itself along with our second vehicle and most likely would’ve had sufficient ac. And yet the last issue we ran into was we went to grill for the first time on our second night and propane ran out right after grill heated up and food was placed on the grill so had to take it off and cook all the food in the kitchen. Security employees were very rude and entitled and made our whole vacation a hassle and way less enjoyable then I’d have liked and planned for it to be. They were unhelpful and disrespectful.Definitely will not ever stay here again we made the best of it, but way over priced and should’ve never have all these issues. God forbid if we came on a strict budget once we paid the rental fee. This place isn’t for the faint of pocket, we came across over a thousand dollars in extra fees, fuel going back and forth to our trailer, our second vehicle, etc. not to mention the loss of sleep due to our house being over 80 degrees.
Stayed 6 nights in Jun 2022
Verified review

10/10 Excellent

Glenda G.

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

5 day stay at venture out

Very much enjoyed place. Excellent communication and responses.
Stayed 5 nights in Dec 2022
Verified review

2/10 Terrible

Justin L.

Liked: Check-in, communication, location, listing accuracy

Summer trip

When we arrived check in was a breeze. We launched our boat put the trailer in storage. When we got to the house the inside temperature was 90 degrees. We unpacked our things and left when we came back it was still hot inside. We called to complain and the response we got that it’s just hot out and that the house will cool down. Well the whole week we stayed it never did at night time it would not get any cooler then 80 degrees and during the day it would stay around 90 degrees. We asked if they could send a A/C technician out and they said no that the A/C works fine. My father that has health problems had a hard time we went and bought fans to keep him comfortable but still didn’t help. The other thing is if you are over 6’ tall you won’t fit in the bathroom because of low ceilings. We had other issues with things to like the tv and parking.
Stayed 7 nights in Jul 2022

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