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Charming cottages, dockage, pool, just minutes to Key West

Cottage in Summerland Key with kitchen

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Fridge, microwave, oven, stovetop
Marina
Exterior detail
TV
Pool

Reviews

8.6 out of 10
Excellent

Entire home

2 bedrooms1 bathroom785 sq ft

Popular amenities

  • Dryer
  • Pet friendly
  • Washer

Explore the area

View in a map
Cudjoe Key, FL
  • Place, Upper Sugarloaf Key
    ‪4 min drive‬
  • Place, Upper Sugarloaf Sound
    ‪5 min drive‬
  • Place, Florida Keys Beaches
    ‪12 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪41 min drive‬

Room options

About the neighborhood

Summerland Key

This cottage places you within a few miles (5 km) of Upper Sugarloaf Key and Upper Sugarloaf Sound. The cottage includes a kitchen, a refrigerator, and a microwave.
View more Cottages in Summerland KeyOpens in a new window

What's nearby

  • Upper Sugarloaf Key - 4 min drive - 2.1 miles
  • Upper Sugarloaf Sound - 5 min drive - 2.9 miles
  • Lower Sugarloaf Sound - 9 min drive - 5.3 miles
  • Florida Keys Beaches - 12 min drive - 5.2 miles
  • Sugarloaf Beach - 16 min drive - 9.0 miles

Getting around

  • Key West Intl. Airport (EYW) - 27 min drive

Restaurants

  • ‪Boondock's Grille & Drafthouse - ‬9 min drive
  • ‪5 Brothers Two - ‬8 min drive
  • ‪Morning Joint - ‬2 min drive
  • ‪Broil - ‬1 min walk
  • ‪The Bent Prop - ‬19 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.

Charming cottages, dockage, pool, just minutes to Key West

Cottage #6 - Only 20 miles from Key West, but a world away from the hustle and bustle. Come experience a truly relaxing Keys experience. Our fully equipped cottages mean all you need is your swimsuit and sunscreen! Anglers will find easy access to crystal clear waters using our small boat launch and convenient dock and sea wall. Runners and cyclists will find easy access to the Florida Keys Overseas Heritage Trail - 75 miles of paved trail tracing the original route of the Flagler Railroad. When you're ready for tourist activities make the short drive to Key West and visit the Aquarium or hop on the Conch Tour Train. Big Pine offers nature enthusiasts the Blue Hole with Key Deer lots of wildlife.
The cottage is air-conditioned and features a kitchen and space to spread out with 2 bedrooms. Other standard amenities include a washing machine and a coffee maker.

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Property amenities

Pool/Spa

  • Communal pool

Internet

  • Available in the cottage: Internet access

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Living room

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Barbecue grill

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total

Suitability/Accessibility

  • Smoking not allowed

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

General

  • Unit size: 785 square feet

Policies

Check-in

Check-in time starts at 3:00 PM
Contactless check-in available
Minimum check-in age: 25

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

Rates are subject to change until reservation is confirmed. Occupancy limits strictly enforced. This unit accommodates a maximum of 4 guests.
ONLY registered guests permitted to use Cudjoe Cottage amenities to include pool, boat launch, kayaks, seawall and dock.

Pets

  • This property welcomes pets
  • Dogs only
  • 2 total pets
  • Service animals exempt from fees

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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
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
  • Minimum check-in age: 25

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.
  • 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 fire extinguisher and a smoke detector.

Frequently asked questions

What's there to do close to this cottage?

This cottage is located in Summerland Key, close to Florida Keys Beaches, Upper Sugarloaf Key, and Venture Out Keys. You'll also find Upper Sugarloaf Sound and Crab Key within a short drive.

Will I be able to park at this cottage?

No, there isn't parking available at the cottage.

Is this cottage associated with a casino?

No, this cottage is not connected to a casino.

Is there an indoor pool at this cottage?

No, there is no indoor pool at this cottage.

What amenities will couples enjoy at Charming cottages, dockage, pool, just minutes to Key West?

Couples staying at this historic cottage will appreciate amenities such as a kitchen in each accommodation with kitchens in some.

Are there hot tubs at Charming cottages, dockage, pool, just minutes to Key West?

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

Does this cottage include breakfast service?

No, this cottage doesn't offer breakfast.

Does this cottage allow pets to stay free of charge?

Although dogs can't stay for free, they are welcome at this cottage.

Are there connecting rooms at this cottage?

No, this cottage doesn't feature connecting guestrooms.

What is the closest airport to this cottage?

The closest major airport to this cottage is Key West Intl. Airport (EYW), which is 19.2 mi away (27 minutes by car). Another top airport is Marathon, FL (MTH-Florida Keys Marathon), which is around 28.3 mi away.

Are there rooms with balconies at Charming cottages, dockage, pool, just minutes to Key West?

No, there aren't any accommodations with balconies at Charming cottages, dockage, pool, just minutes to Key West.

Reviews

Charming cottages, dockage, pool, just minutes to Key West Reviews

8.6

Excellent

8.4/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Eco-friendliness
Rating 10 - Excellent. 68 out of 119 reviews
Rating 8 - Good. 27 out of 119 reviews
Rating 6 - Okay. 14 out of 119 reviews
Rating 4 - Poor. 8 out of 119 reviews
Rating 2 - Terrible. 2 out of 119 reviews

Reviews

8/10 Good

Randy G.

Liked: Cleanliness
Jennifer was very nice and accommodating.
Stayed 4 nights in Jul 2025

6/10 Okay

amanda l.

Liked: Cleanliness

Very "rustic"

We enjoyed staying in Cudjoe Key, but we will not be staying in this same property again. I will list the pros and cons to make it easier. Pros: pool was nice. Outside yard was nice and shady with plenty of parking. Boat ramp on site. Nice neighborhood and close to restaurants. The owner is very nice and responsive. Cons: The bedroom door did not close. It hit the wall instead of the doorframe. There was zero water pressure in the kitchen sink so we had to wash dishes in the shower. There is no A/C vent in the bathroom, so if you shut the door it turns into a sauna because the sun hits that window. The internet connection was all over the place. The whole unit needs serious updates. To put your boat in at the boat ramp, you have to back all the way down the road beside the other houses. I do not normally leave lengthy reviews, but I felt it was warranted with this place.
Stayed 4 nights in Jun 2025

6/10 Okay

Ruth M.

Memorial Day getaway

The accommodations were good. We are fisherman. I would describe this as a nice fish camp type accommodations. Our problem was accessibility for the boat. Water is really shallow. We needed to time our trips around the tide. On one trip out water was more shallow than indicated on GPS and we bent both our props. We like the accommodations and the location but just doesn't work for our boat.
Stayed 3 nights in May 2025

10/10 Excellent

Barbara P.

Liked: Cleanliness
Stayed 5 nights in Apr 2025

10/10 Excellent

ANJANA, Charlottesville

Traveled with partner, Traveled with family
Liked: Cleanliness, amenities, property conditions & facilities
Amazing place for a getaway. Very calm quiet area and close to 2 nice beaches.
Stayed 6 nights in Apr 2025

8/10 Good

Peter M.

Liked: Cleanliness

Cottage

This is a no frills get away. It is clean albeit a bit run down. Bring your own everything and you will need coins for the laundry machines. Nice place to crash after active days.
Stayed 3 nights in Apr 2025

8/10 Good

PJ H.

Liked: Cleanliness

Good Value

Great value. Really enjoyed the location. The apartment could use some attention to detail but overall was a great experience.
Stayed 6 nights in Apr 2025

10/10 Excellent

James R.

Liked: Cleanliness
Stayed 5 nights in Mar 2025

10/10 Excellent

Sheila G.

Liked: Cleanliness

Perfect for family.

We enjoyed are stay. The customer service was great. The area was quiet and had access to the water for a boat.
Stayed 4 nights in Mar 2025

10/10 Excellent

S

Liked: Cleanliness

Perfect

30 minutes from Key West. No problems finding the place. No traffic.
Stayed 3 nights in Mar 2025

8/10 Good

nicholas p.

Liked: Cleanliness

Great Location

We launched our kayaks right from the property and found great fishing and paddling moments from the dock. The bay and dockage are very shallow--I wouldn't bring my power boat to this property. Easy drive into Key West and to all the lower keys. Nice little grocery store within minutes had everything we needed. The property is older and could use some maintenance, but if you don't mind a little fraying at the edges, this is a comfortable, beautiful and quiet corner of the keys. We loved it.
Stayed 4 nights in Mar 2025

10/10 Excellent

Tommy K.

Liked: Cleanliness

Peaceful

Enjoyed the serenity of your place
Stayed 6 nights in Feb 2025

6/10 Okay

Pat H.

Expectations

Property was misrepresented in pictures online. Unit was in poor condition and needed updating and minor repairs. Furniture in living room is old and very uncomfortable. Lack of maintenance was evident. Kitchen was poorly equipped.
Stayed 4 nights in Feb 2025

6/10 Okay

Rahul I.

Liked: Cleanliness
Stayed 3 nights in Dec 2024

10/10 Excellent

Amy O.

Liked: Cleanliness

Much needed RnR

Drove From CLE to The Keys with my dog and enjoyed the quietness of the property. 30 an hour from Key West. Great rate. Would recommend.
Stayed 5 nights in Jan 2025

10/10 Excellent

Luke A.

Liked: Cleanliness

Nice quiet and budget friendly

Stayed 3 nights in Dec 2024

6/10 Okay

Brendan M.

Disliked: Cleanliness

So close to perfect...

With just a little bit of touch up and increased responsiveness, this would be a five star for me. The property is much larger than pictures suggest, and very quiet while conveniently next to route 1. Furniture was comfortable and price was just right. So so close to perfect. The host wasn't unresponsive, but responded very slowly. Whether to vrbo messages, texts, or email the responses took hours or days to arrive. This didn't cause any major issues, but should there have been one it's pretty disheartening to know I likely wouldn't hear anything back for ages. The cleanliness was questionable. Windowsills were noticeablely dirty, and I couldn't help but wonder how that's been missed when the place is cleaned regularly. I don't regularly clean mine at home and they've never been like that. There was also a dirty coffee mug in the cupboard [along with a broken one] and coffee grounds in the water basin of the coffeemaker. Not the end of the world, but I felt silly making coffee in a saucepan at a rental I payed hundreds for. Again, how was this all missed? The paint could use touch up. Lots of places it is noticeably scratched off. Seems like a quick & easy fix that I'm not sure why they hadn't yet. Hand soap in the bathroom was refilled with water, making it difficult and unpleasant to use. This I did find upsetting, since handsoap is incredibly inexpensive. I can't imagine why this was the solution. Overall, wonderful property. Just needs some love.
Stayed 3 nights in Oct 2024

10/10 Excellent

Randy G.

Liked: Cleanliness
Stayed 3 nights in Jul 2024

10/10 Excellent

Terra P.

Liked: Cleanliness

Great location

This particular unit needs some updates as other reviews have mentioned, but it was clean and quiet. There were enough dishes and utensils to cook meals. The AC and internet worked well. We enjoyed using the pool each day and watched the sunset by the water. The kayaks looked clean and new. Other guests had dogs that were no issue, all were quiet and kept on a leash. We spent most of our time in Bahia Honda State Park and Key West, this property was easy to get to both areas.
Stayed 3 nights in Jul 2024

10/10 Excellent

Tom J.

Liked: Cleanliness

Wonderful cottage for fishing stay

The cottage was wonderful as a base-camp for a fishing stay. The kitchen was well stocked for breakfasts preparation, big refrigerator w ice maker, very roomy and comfortable. Air conditioning and ceiling fans were a blessing. The property is very nice w added perk of nice pool. Great location, quiet and convenient.
Stayed 3 nights in Jul 2024

4/10 Poor

Cathy S.

Disliked: Cleanliness

?

2 Q-tips in the toilet, so not sure how it got past house cleaning. Other guest had dog off leash, charged us (Not the management’s fault, I suppose). My fault for not looking at the website more thoroughly.
Stayed 4 nights in May 2024

10/10 Excellent

Michael W.

Liked: Cleanliness

Good place

Couldn’t beat the price
Stayed 3 nights in Mar 2024

10/10 Excellent

CINDY L.

Liked: Cleanliness

Realtor

Great quite location but close enough to Key West to go to dinner or the day
Stayed 2 nights in Mar 2024

4/10 Poor

James L.

Disliked: Cleanliness

Maintenance issues

On arrival at 4:20 PM, I had to contact host, unit was not cleaned yet. The cleaner arrive within 20 minutes and required us to leave unit for an additional 30 minutes. The garbage can in the laundry room was overflowing on arrival and was never emptied our week long stay. The cable wires were a spaghetti mess tripping hazard on the ground outside the unit. The outdoor chairs in need of repair. The location, grounds and other guest were great. It appeared a maintenance person was missing to handle easy issues.
Stayed 6 nights in Jan 2024

10/10 Excellent

Nathaniel G.

Liked: Cleanliness

Easy access

Great small place for fisherman to crash… prob wouldn’t count on docking anything but flats boat..great location
Stayed 3 nights in Jan 2024