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Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Waterfront holiday home in Summerland Key with an outdoor pool

Photo gallery for Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Shared pool
Private Kitchen
Private kitchen
living room over looking ocean
private laundry room

Reviews

8.8 out of 10
Excellent
3 bedrooms2 bathroomsSleeps 6118.2 sq m

Popular amenities

  • Dryer
  • Washer
  • Parking available
  • Pool
  • Barbecue grill

Explore the area

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

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 2

1 Queen Bed

Bedroom one

1 Queen Bed

Master Bedroom

1 King Bed

2 bathrooms

Bathroom 1

Bathtub or shower

Bathroom 2

Bathtub · Shower only

Spaces

Balcony

About this property

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Main House - You're in the tropics... listen to the waves, rest, relax or fish, and snorkel. Spacious three bedroom, two bath home, with direct ocean access, dockage, boat ramp and swimming pool. Sunrise view overlooking Cudjoe Bay. Fully furnished, linens, cable/internet. This home is on a compound, the swimming pools, dockage and property are shared with the other units on the property. The perfect spot for weddings, reunions, or large groups! Square Grouper restaurant and bar in the is down the street. Shuttle to Key West just steps from the home. Come and stay with us, you're sure to have a wonderful vacation.

Add dates for prices

Amenities

Pool
Washing machine
Dryer
Free WiFi
Air conditioning
Parking available

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Similar properties

Property grounds
Cudjoe Cottages, swimming pool, just 20 miles from Key West
  • Ocean view
  • Pool
  • Kitchen
  • Washer
8.8 out of 10, (147 reviews)
Cudjoe Cottages, swimming pool, just 20 miles from Key West

House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
Smoking allowed only outside

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 indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock

About the area

Summerland Key

Located in Summerland Key, this holiday home is on the waterfront. 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 Holiday homes in Summerland KeyOpens in a new window
Map
Cudjoe Key, FL

What's nearby

  • Upper Sugarloaf Key - 4 min drive - 3.3 km
  • Florida Keys Beaches - 12 min drive - 9.3 km
  • Sugarloaf Beach - 16 min drive - 14.4 km
  • Boca Chica Nude Beach - 36 min drive - 27.5 km
  • Duval Street - 48 min drive - 38.9 km

Getting around

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

Restaurants

  • ‪Boondock's Grille & Drafthouse - ‬9 min drive
  • ‪5 Brothers Two - ‬9 min drive
  • ‪Morning Joint - ‬2 min drive
  • ‪Broil - ‬4 min walk
  • ‪The Bent Prop - ‬19 min walk

Frequently asked questions

Does Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West have a pool?

Yes, this property has an outdoor pool.

Is Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West?

Check-in begins at 4:00 PM.

What time is check-out at Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West?

Checkout is at 10:00 AM.

Where is Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West located?

Situated on the waterfront, this holiday home 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).

Reviews

8.8

Excellent

8.4/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

9.6/10

Check-in

9.2/10

Communication

9.6/10

Location

8.8/10

Listing accuracy
Rating 10 - Excellent. 49 out of 87 reviews
Rating 8 - Good. 27 out of 87 reviews
Rating 6 - Okay. 4 out of 87 reviews
Rating 4 - Poor. 4 out of 87 reviews
Rating 2 - Terrible. 3 out of 87 reviews

Reviews

8/10 Good

Mitchell D O.

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

Great stay in in the Keys

Property was adequate but could use a few updates. The location was great. Easy to get to Key West near good local restaurants and beaches. Would stay again.
Stayed 3 nights in Feb 2025

10/10 Excellent

William E.

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

Great Cudjoe Bay Retreat

Excellent property for accessing Cudjoe Bay with skiffs and kayaks alike.
Stayed 8 nights in Apr 2023

10/10 Excellent

wade t.

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

Old friends relaxing in the sun, enjoying the water too.

Relaxing, enjoyingthe water
Stayed 7 nights in May 2024

10/10 Excellent

Mary W.

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

Relaxing with a Peaceful View

We were very happy with this VRBO and would stay again. Some attention to cleaning out drawers and dusting behind things should be addressed. Everything else was so nice we still give it 5 stars.
Stayed 5 nights in Jan 2025

8/10 Good

Olivia C.

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

Couple’s Getaway

We loved staying at this property and would definitely book it again! The view was beautiful and it was very convenient to what we wanted to do. The only thing I would say is for a sense of more privacy, I wish the blinds were repaired so that they covered the windows completely. Overall, we loved the property!
Stayed 4 nights in Mar 2024

8/10 Good

Michele H.

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

Winter vacation

Centrally located and had great views. Property was a little bit dated
Stayed 4 nights in Jan 2023

10/10 Excellent

Jeffrey W.

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

Good time

Loved our stay. This property works well for us, quiet but close enough to Key West to catch sunsets, shopping, and more dining options. Beautiful sunrises. Although quiet has pretty much everything you need nearby. Communication with Susan very easy
Stayed 7 nights in Jan 2024

10/10 Excellent

Roy H.

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

Retirement Fishing Trip

What a beautiful home and spectacular views. Just loved sitting out on the Adirondack chairs watching the sunrise and sunset to a cool breeze, nice music, and a cup of coffee or maybe a Margarita.
Stayed 4 nights in May 2023

10/10 Excellent

Grant H.

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

Cudjoe heaven

Perfect place on the water with a mini beach. Great for children. House is really nice and spacious with a great view. Big bummer the pool wasn’t heated! Enjoyed the stay and would stay there again!!
Stayed 9 nights in Jan 2023

8/10 Good

Catherine B.

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

Cudjoe Key - GORGEOUS and Acceptable Accomodations

The location and water access is excellent and we had an excellent 4-night stay, wishing it were longer. The house layout is good with very good views and it simply needs updating, including the AC. Cleanliness and well-stocked is important to us and owner did a good job with this. There are five cottages on property and we became well-acquainted with a group that was there.
Stayed 4 nights in Aug 2020

8/10 Good

Bergandi R., Port orange, Florida

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

Weekend getaway

We frequent the keys for fishing trips so we have stayed in quite a few homes. The location is great here. It was a little hard to navigate getting the boat in the channel but we figured it out the second day out. Manager was quick to respond. Home needs updates in order to keep up with the other homes around at similar pricing. Beds were all uncomfortable but home is clean and it works good for a fishing trip if you’re looking for a clean place without a ton of amenities. They could easily put some new mattresses in, kitchen amenities, and throw pillows to give it a nicer feel
Stayed 4 nights in May 2023

6/10 Okay

Ronald M.

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

3rd winter {5 week stay}

Once again for the first 10 days the pool heater needed to be replaced so we couldn't use the pool {it was cold}, The driveway in was full of ruts, the master bath shower door didn't close all the way, 2 of the drawers in the master vanity had the bottoms falling out so we couldn't use them, the deck facing the ocean has multiple rotten areas so we needed to watch where we walked so we didn't step thru them, the wicker furniture on the deck had mold(mushrooms} growing on them.When we ask the repair person which was next door to come over and fix some areas he said he can only fix what is absolutely necessary because the property is for sale and the owners do not want to spend any on repairs. We stayed here for 3 years and each year you can see there are more and more things that need to be repaired. The view is the best you'll see any where.
Stayed 35 nights in Feb 2024

8/10 Good

Tara G.

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

Decent

I thought the property was decent. It is an easy drive to Key West. You have everything you need the kitchen and living area are nice and open. It is wonderful having a washer and dryer there. They have dishwasher tabs and dish soap towels etc for your convenience, which is nice. It is a quiet setting. I thought communication was easy. Check in was easy also. We were in the main house. There are three queen bedrooms and two baths. We chose the master bedroom which we were very sorry we did. The bed is in DESPERATE need of new mattresses. Maybe this is normal for a VRBO I don’t know I have never stayed in one before. I literally didn’t sleep at all while we were there and I wasn’t going to kick my other guests out of their rooms and make someone else sleep in the bed. The springs in the bed must be broken and that doesn’t only make it uncomfortable but extremely noisy every time you turn over to try to get comfortable. The ceiling fans work off of remotes only and I think the batteries are dead in the living area so you cannot use them. Something easy for maintenance or the cleaning crew to look over or not realize. You need the fans for airflow but that is an easy fix which would help with keeping the house cool. All in all the place is a good value for the price and a nice quiet area.
Stayed 4 nights in May 2024

8/10 Good

Michael B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was good for what we wanted. The price point was really good. As others have stated, it is in need of some updates. The host was very communicative and very nice! We definitely enjoyed our stay and would consider staying there again.
Stayed 4 nights in Aug 2025

10/10 Excellent

Justin D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This house was the best water front with a pool in the lower keys for the money. We really enjoyed our stay, and look forward to booking again. I wouldn’t expect a brand new house and there was some things that were less then pristine about the house but isn’t most things in the Florida Keys. Side note accessing the slips by water is a bit of a challenge. Cudjoe Bay is shallow! 2 houses south has buoys use them and head out that way.
Stayed 3 nights in Jul 2025

10/10 Excellent

Yuselys C.

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

Grateful

Peace
Stayed 3 nights in Jun 2025

10/10 Excellent

Cheryl P.

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

Another wonderful family vacation!

We gather yearly at Cudjoe Cottages & have always enjoyed our stay. Jennifer is amazing & a great communicator!
Stayed 16 nights in Jun 2025

10/10 Excellent

Michelle K.

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

Keys Vacation

We had a great time and will be back.
Stayed 4 nights in May 2025

8/10 Good

Margie D.

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

Nice property

The home was neat and clean. There were a few items that needed to be repaired… Drawers in the primary bathroom vanity and master bedroom armoire. could’ve had more bath towels… We stayed one week the pool and dock area were very nice. Also, the kitchen amenities, including dishwasher worked very well for us… Would recommend
Stayed 6 nights in Mar 2025

8/10 Good

Eirene B.

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

Schöne aber in die Jahre gekommenende Unterkunft.

Für 4 Tage war es gut. Länger muss nicht sein ,da die Betten leider sehr weich sind . Das Haus und die Anlage war sicher mal top, aber ist sehr in die Jahre gekommen. Die Lage ist super.
Stayed 4 nights in Mar 2025

8/10 Good

Brian M.

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

Mac

The house was good for the five of us men. We were comfortable with the sleeping conditions. The kitchen lacked a couple essential pots and dishes to cook with. Yes the house could use some TLC but it was fine for what we needed. I would stay again
Stayed 3 nights in Mar 2025

8/10 Good

Lorilie L.

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

Beautiful water view

This has beautiful views, a pool that is heated. The house is in need of some maintenance. Two bedrooms are in desperate need of mattresses, specially if you’re using for adults, our guests were complaining. The house has plenty of kitchen supplies as in plates silverware cups coffee cup, The house was clean and we met the house keeper, she was very nice and we appreciated her. Our intentions were to enjoy our time away, and that we did.
Stayed 8 nights in Mar 2025

8/10 Good

lori c.

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

Nice views

The house was very clean. The pool was heated and clean. Great views. You have to share the dock and pool with the other guests. Need to bring your own pool towels. Two out of the three beds are not comfortable. There are things in the house that need fixing. The shower door in the bathroom comes off the track if you try to open it a certain direction. So had to step out of the shower next to the toilet. Danger of falling. The shower door in the master bathroom doesn't close right. Drawer in bathroom broken. Broken, taped up window in dining area. Drawer in a dresser broken. The deck needs some attention. No grill, although there are a couple propane tanks lying around. Lots of junk on the property which could easily be cleaned up. Kitchen has the very, very bare minimum. Check in was easy as the door was unlocked and key on counter, however, due to flight delays, we arrived after dark and it felt kind of creepy and dangerous just walking into an open place. We had a map but the house is not marked so we were not 100 percent sure we had the right unit until we could turn on a light. Overall, it was a nice rental and the inside was very clean but just can't give it a top rating due to listed problems.
Stayed 4 nights in Feb 2025

8/10 Good

Clive B.

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

Cudjoe Key

Property was very clean. Kitchen is well stocked with equipment. Location and pool were excellent. Pool furniture needed repair. Master bath needs some repair on shower door and vanity. First guest room bed needs replacement. Difficult to find the driveway entrance from the highway.
Stayed 2 nights in Feb 2025

2/10 Terrible

Carley O.

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

Health and Safety Warning! Mice Poop, Mold, Broken Windows, Holes in the Deck, Hair Everywhere

DO NOT STAY HERE! This is hands down the most inaccurate and deceptive listing on VRBO. The home and pool are in dangerous disrepair and an unlivable level of cleanliness. We found mouse poop, mold, and hair everywhere. We didn't think the cleaners had been to the home before our arrival and the sheets were clearly not changed. The owner assured us that they were and sent a cleaner back over. The cleaner vacuumed for a few minutes and left. We left the home after one night after opening a health and safety ticket with VRBO, the owners were not responsive to our request to cancel the remainder of our stay or offer any refund.
Stayed 3 nights in Jan 2025

About the host

Hosted by Susan Rich

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