Entire home

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

Cottage in Summerland Key with kitchen

Overview
Amenities
Policies
Location

Excellent

2 bedrooms1 bathroomSleeps 4785 sq ft

Popular amenities

Dryer
Washer
Pet-friendly

Place, Venture Out Keys
Place, Upper Sugarloaf Key
Place, Florida Keys Beaches
Airport, Key West, FL (EYW-Key West Intl.)

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

2 Single Beds

1 bathroom

Bathroom 1

Toilet · Shower only

Spaces

Kitchen

Dining area

About this property

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.

Add dates for prices

Amenities

Pool

Kitchen

Washing machine

Dryer

Pet-friendly

Air conditioning

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Pool
Pet-friendly
Parking included
Free WiFi

House Rules

Check in after 3:00 PM

Minimum age to rent: 25

Check out before 10:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

Pets allowed: dogs (limit 2 total)

Smoking

Smoking is not permitted

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.

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 indicated that there is a smoke detector on the property

Safety features at this property include a fire extinguisher

About the area

Summerland Key

Summerland Key is home to this cottage. Florida Keys Beaches and Coupon Bight Aquatic Preserve 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.

View more Cottages in Summerland Key

Cudjoe Key, FL

What's nearby

Upper Sugarloaf Key - 3 min drive - 3.3 km
Florida Keys Beaches - 11 min drive - 10.4 km
Sugarloaf Beach - 17 min drive - 14.4 km
Boca Chica Nude Beach - 35 min drive - 27.9 km
Duval Street - 39 min drive - 41.4 km

Getting around

Key West, FL (EYW-Key West Intl.) - 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

Frequently asked questions

Does Charming cottages, dockage, pool, just minutes to Key West have a pool?

Yes, this property has a pool.

Is Charming cottages, dockage, pool, just minutes to Key West pet-friendly?

Yes, this property allows dogs (limit 2 total).

What time is check-in at Charming cottages, dockage, pool, just minutes to Key West?

Check-in begins at 3:00 PM.

What time is check-out at Charming cottages, dockage, pool, just minutes to Key West?

Checkout is at 10:00 AM.

Where is Charming cottages, dockage, pool, just minutes to Key West located?

Situated in Summerland Key, this cottage is within 3 miles (5 km) of Upper Sugarloaf Key, Upper Sugarloaf Sound and Venture Key. Venture Out Keys and Out Key are also within 3 miles (5 km).

8.6

Excellent

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

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8.4/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Eco-friendliness

9.6/10

Check-in

9.4/10

Communication

9.2/10

Location

8.6/10

Listing accuracy

10/10 Excellent

Tommy K.

23 Feb, 2025

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

Peaceful

Enjoyed the serenity of your place

Stayed 6 nights in Feb 2025

10/10 Excellent

Jerie F., Altamonte Springs Florida

10 Jul, 2023

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

Quaint Cottage

Nice Location, has a dock, pool and allows Dogs.

Stayed 4 nights in Jul 2023

10/10 Excellent

Jennifer C.

1 Apr, 2023

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

Great Location

We have stayed at this property multiple times. It is a super convenient location. We bring our boat and it's only a short ride out to either the Gulf or Ocean.

Stayed 7 nights in Mar 2023

10/10 Excellent

Terra P.

29 Jul, 2024

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

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

6/10 Okay

Pat H.

15 Feb, 2025

Liked: Check-in, communication

Disliked: Listing accuracy

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

8/10 Good

Randy G.

25 Jul, 2025

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

Jennifer was very nice and accommodating.

Stayed 4 nights in Jul 2025

6/10 Okay

amanda l.

24 Jun, 2025

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

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.

6 Jun, 2025

Liked: Location

Disliked: Listing accuracy

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

ANJANA

26 Apr, 2025

Liked: Cleanliness, amenities, property conditions & facilities, communication

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.

15 Apr, 2025

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

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.

13 Apr, 2025

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

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

Sheila G.

30 Mar, 2025

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

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

27 Mar, 2025

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

Perfect

30 minutes from Key West. No problems finding the place. No traffic.

Stayed 3 nights in Mar 2025

8/10 Good

nicholas p.

9 Mar, 2025

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

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

Amy O.

29 Jan, 2025

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

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

6/10 Okay

Brendan M.

27 Oct, 2024

Liked: Location, listing accuracy

Disliked: Cleanliness, communication

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

Tom J.

17 Jul, 2024

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

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.

4 Jun, 2024

Liked: Check-in, communication

Disliked: Cleanliness, listing accuracy

?

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

8/10 Good

Heike H.

5 Apr, 2024

Liked: Check-in, communication, location

OK, aber Raum für Verbesserung, Achtung keine Kajaks

Es gab auf der Anlage 6 Ferienhäuser, wobei man bei der Buchung nicht auswählen konnte. Wir bekamen das Appartment Nr. 6, welches direkt an der Hauptstraße der Insel gelegen war und die minderwertigste Ausstattung von allen hatte. So hatten wir z. B. keine Veranda zum Draußensitzen. Das Appartement ist insgesamt OK, aber in die Jahre gekommen und war auch nicht sehr sauber, vor allem der Küchenboden. Beim Einchecken fehlte der Schlüssel. Auf Nachfrage stellte sich heraus, dass die Vorgänger diesen wohl mitgenommen hatten. Wir bekamen dann aber schnell einen neuen Schlüssel. Die Kajaks, die sogar im Titel der Anzeige angepriesen werden, gab es leider auch nicht. Ich hatte das Appartment u. a. wegen der Möglichkeit Kajaks auszuleihen, gebucht. Wir waren dann viel unterwegs und hatten unterm Strich einen schönen Aufenthalt.

Stayed 5 nights in Mar 2024

10/10 Excellent

Michael W.

27 Mar, 2024

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

Good place

Couldn’t beat the price

Stayed 3 nights in Mar 2024

10/10 Excellent

CINDY L.

25 Mar, 2024

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

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.

14 Feb, 2024

Liked: Communication, location

Disliked: Cleanliness, check-in

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.

16 Jan, 2024

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

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

10/10 Excellent

Hollison P.

2 Jul, 2023

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

Cudjoe Cottages

We absolutely love staying here at this location! It’s a nice/safe location with so many things to access while you stay. The house is clean and perfect whether you stay there all day or are just there to sleep. We always look forward to coming back!

Stayed 5 nights in Jun 2023

10/10 Excellent

Florida P., Stuart, Florida

17 Jun, 2023

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

Nice Location; Old Keys Feel

Our large family group is renting six units here for a long vacation. We rented Unit 6 for my daughter and son-in-law. They enjoyed staying on the same property as the rest of us. The cottage is older but roomy. They enjoyed the pool and going out in the boats. They also appreciated the short drive (25 minutes) to Key West for a day trip.

Stayed 6 nights in Jun 2023