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

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A two-story house with a balcony, a staircase, and a view of the beach.
A waterfront property with a pool, palm trees, and a house with a balcony.
A kitchen with a window, a sink, and wooden cabinets.
A bedroom with a wooden bed, a dresser, a TV, and a mirror.
A beach view with a swimming pool, palm trees, and lounge chairs.

Reviews

8.6 out of 10
Excellent

Highlights

  • Dive into relaxation
    Unwind in the top-rated pool, your perfect spot for relaxation.
  • Outdoor pool
    The outdoor pool is a refreshing retreat under the open sky - a rare gem in this area.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
3 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Balcony
  • Outdoor pool
  • Barbecue grill
  • Air conditioning
  • Refrigerator
  • Washer

Explore the area

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

Where you'll sleep

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

Kitchen
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.
Our prices include all fees. No hidden fees.

Add dates for prices

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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

Property # 2037544
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 and a deadbolt lock
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

About the neighborhood

Summerland Key

Located in Summerland Key, this vacation 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 Vacation Homes in Summerland KeyOpens in a new window
Map
Cudjoe Key, FL

What's nearby

  • Upper Sugarloaf Key - 3 min drive - 3.3 km
  • Upper Sugarloaf Sound - 4 min drive - 4.6 km
  • Lower Sugarloaf Sound - 7 min drive - 8.2 km
  • Florida Keys Beaches - 8 min drive - 8.6 km
  • Great White Heron National Wildlife Refuge - 10 min drive - 8.0 km

Getting around

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

Restaurants

  • ‪Boondock's Grille & Drafthouse - ‬9 min drive
  • ‪Morning Joint - ‬2 min drive
  • ‪Looe Key Tiki Bar & Restaurant - ‬9 min drive
  • ‪Square Grouper Bar and Grill - ‬2 min drive
  • ‪Tonio's Seafood Shack & Tiki Bar - ‬6 min drive

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.

How much does it cost to stay at Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West?

As of Sep 27, 2026, prices found for a 1-night stay for 2 adults at Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West on Oct 9, 2026 start from $645, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the 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?

Check-out 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 vacation home is within 3 mi (5 km) of Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key. Venture Out Keys and Out Key are also within 3 mi (5 km).

Reviews

8.6

Excellent

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
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Rating 10 - Excellent. 57 out of 103 reviews
Rating 8 - Good. 30 out of 103 reviews
Rating 6 - Okay. 6 out of 103 reviews
Rating 4 - Poor. 6 out of 103 reviews
Rating 2 - Terrible. 4 out of 103 reviews

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

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
short drive to downtown of course as long as traffic allows it...quiet stay beautiful views...bring mosquito repellent.
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location plenty of room for 4 adults and 2 kids
Stayed 3 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful location and as described. Hope to be back soon.
Stayed 4 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fun place. Awesome pool , patio , and ocean access. Check in was easy. Had no issues and enjoyed ourselves
Stayed 4 nights in Apr 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was perfect except the beds need replaced.Loved the view!
Stayed 4 nights in Feb 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice place. Very comfortable. Gorgeous view. Host was responsive.
Stayed 3 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location for us, liked the secluded feeling. Little overgrown and outdated. Clean, ease of checking in. Worked just right for us.
Stayed 4 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay at this charming home on Cudjoe Key! The location is perfect, quiet, peaceful, and just a short drive to groceries/gas everything we needed. The house itself was clean, with a bright, airy feel that immediately made us feel at home.The outdoor space was the highlight; great for morning coffee, pool in the afternoon returning from our days fishing, and perfect evening relaxation. The kitchen was a great size, and we loved being able to cook fresh catches from the day. Everything was spotless upon arrival, which we really appreciated.The beds are a bit dated (they could use an update as they are concave), but we still slept well overall thanks to the quiet neighborhood and great AC.We’d definitely recommend this property for anyone looking for a relaxed Florida Keys getaway. The host was responsive and helpful throughout. Thank you for a great stay!
Stayed 6 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect place to stay to experience Key West but away from all the noise when you need a break. Beds were comfy, pool was perfect & loved watching wildlife on land and sea from the backyard. Easy drive into Key West. Host was very resposinve & helpful with recommendations & resturants. I noticed a bit of a mildew smell or first night & realized the dishwasher had not been emptied. Ran it & smell went away. We did not hang out on the deck much, as it was really soft in several places. Honestly didn't bother us much as we would rather be at the pool or out by the water. Would definitely stay here again!
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This location was better than the pictures. My family and I truly enjoyed every minute we spent here and will definitely return if we’re back in the area. The backyard……..pictures can not do this kind of beauty justice!!! Sunrise and sunsets are gorgeous. Coconuts everywhere, we swam in the pool in February…….just amazing. Highly recommend
This is what we woke up to and was able to relax, read a chapter, and watch the sunrise
Stayed 3 nights in Feb 2026
Verified review

10/10 Excellent

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
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a nice stay at Cudjoe key. We like the location of the home (in between Key West and Marathon). Views were beautiful! We enjoyed the local wildlife neighbors (lizards, pelicans, a one legged cormorant and jelly fish). Great restaurants nearby. Pool was nice and plenty of outdoor chairs for relaxing. Inside the home was as expected based on prior reviews. I would like to have had more bath towels provided. Communication and instruction from the managers good. Washer and dryer very efficient.
Stayed 7 nights in Mar 2026
Verified review

10/10 Excellent

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

We LOVE this piece of paradise! This was our second stay and hope to stay again!

Relaxing in paradise!
Stayed 9 nights in Nov 2022
Verified review

10/10 Excellent

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
Verified review

8/10 Good

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
Verified review

10/10 Excellent

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

Amazing as usual

Always a great stay!!
Stayed 6 nights in Mar 2023
Verified review

10/10 Excellent

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
Verified review

2/10 Terrible

Liked: Check-in, communication
Disliked: Cleanliness, listing accuracy
Both front and back decks had pholes a small Manatee could have fallen through, contacted owner and got a 'we are aware of the deck" . The grill I will just leave picture of that for you to decide. When I contacted owner, I was told we have multiple grills at the other houses why is this grill even here then and it's the one in the picture on the listing. I will provide a photo of the other option. Which is a "borrowed" from a local park public charcoal grill on the ground. All dishes were greasy, probally because no dishwasher pods provide so previous guest just ran the dishwasher sans soap. Many broken tiles, the front of the kitchen sinks falling off (in video) . AC barely worked, took 5 hours to go down 5 degrees, pictures and videos to back up all I'm reporting. Long hairs wound around the urine smelling master bath. Just dirty, old and in desperate need of safety repairs. We dealt with it as we were 3 guys just there to dive for lobster. But the hairs, grills and blatant not caring about the safety of guests pushed me over the limit. At what works out to be 800 a night this is not worth it at all till repairs are done and the house is completely cleaned top to bottom. No need to belive me, just look at the pictures. I'm embarrassed I paid this much for this. I contacted the owner made, made my case was told I should have dealt with it then. She later acknowledged knowing about the deck but still dodnt care and rented it.
Stayed 3 nights in Aug 2026
Verified review

4/10 Poor

Liked: Cleanliness, check-in, communication, location
I have been coming to the Keys for 30 years, renting many properties. This property is nearing the end of its' lifespan without significant repairs. Multiple holes in the second floor outside deck, some on the stairs right before you enter the property. The inside is reasonable - nice mattress on the master bed. AC works well. We had to borrow a toaster from one of the other properties as the main home's didn't stay down. The pool is good. We fish - had to bring my own cleaning table to the dock. There is no ice maker on property. Boat dockage is a big deal. I have a 26" CC - got stuck on the sand bar just past the channel. It was advertised a 2.5 foot of depth - that is inaccurate at low tide. There is a slight "channel" marked with 4 white buoys - hit bottom there several times as well. Had to clean out my engine's pee hole several times. If you have a small boat (23' cc or smaller) and don't mind a minimal experience, this property is fine. Our family rented three of the properties and were the only ones using the pool; however, it is listed as a community pool. The water around the dock is brown - visibility 3-5 inches. My usual Keys experience is seeing mangrove snappers and parrot fish cruising alongside the dock. Also ,the dockage requires you to pull in either bow or stern first - you can't pull alongside the dock. So, for families, we had to bring and use a step ladder to get in the boat each time. This is cumbersome. Be aware when renting.
Stayed 7 nights in Aug 2026
Response from VrboOwner on Sep 18, 2026
Thank you for staying with us. This is a wonderful property, we are always making improvements and doing maintenance. The deck has since been replaced. Thank you for letting us know about the toaster, that has also been replaced. We do not have a fish cleaning table and we do not provide an ice machine for fishing. We have 2 swimming pools that are shared with the other units on the property. And addressing the water color, unfortunately, that is from sargassum, it was really bad this year, all over Florida. It comes and goes. And there is 2 1/2 feet of draft at low tide, for a 26 foot boat, depending on how many engines, this could be challenging. We have boats here every week with no problem.
Verified review

8/10 Good

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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

Beautiful Location

How was clean and well equipped. Host was very quick to respond any time we had questions. Beautiful house and great location
Stayed 3 nights in Aug 2024
Verified review

10/10 Excellent

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

Quiet place

Very quiet, clean, and overall great experience. I’ve been staying at properties in the Keys for over 20 years and this is one of the best experiences I have had.
Stayed 6 nights in Aug 2024
Verified review

10/10 Excellent

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

Great stay

Perfect property. Clise to key west but nice and quiet. Right on the water. Clean and comfortable.
Stayed 4 nights in Jan 2023
Verified review

10/10 Excellent

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

Vacation

My family and I had a great time. The property is nice and everything was as described. Easy check in and great communication with the owner.
Stayed 7 nights in Jul 2023

About the host

Hosted by Susan Rich

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