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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 beach view with a swimming pool, palm trees, and lounge chairs.
A beach with palm trees, a wooden dock, and lounge chairs.
A waterfront property with a pool, palm trees, and a house with a balcony.
A kitchen with a window, a sink, and wooden cabinets.

Reviews

8.8 out of 10
Excellent

Entire home

3 bedrooms2 bathroomsSleeps 61272 sq ft

Popular amenities

  • Ocean view
  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
The current price is $761
$686 nightly
$761 total
Total with taxes and fees
Sep 23 - Sep 24

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

Room options

Similar properties

Exterior
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
  • Ocean view
  • Pool
  • Kitchen
  • Washer
4.9 out of 5, Exceptional, 96 reviews
$388 nightly
The price is $431
Sep 7 - Sep 8
Total with taxes and fees
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

About the neighborhood

Summerland Key

With a stay at this vacation home in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key. .This vacation home is 2.2 mi (3.6 km) from Upper Sugarloaf Sound and 2.7 mi (4.3 km) from Venture Key.
View more Vacation Homes in Summerland KeyOpens in a new window

What's nearby

  • Upper Sugarloaf Key - 3 min drive - 2.1 miles
  • Upper Sugarloaf Sound - 4 min drive - 2.9 miles
  • Lower Sugarloaf Sound - 7 min drive - 5.1 miles
  • Florida Keys Beaches - 8 min drive - 5.4 miles
  • Great White Heron National Wildlife Refuge - 10 min drive - 5.0 miles

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

About this property

Entire place

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

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.
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony. Complimentary wireless internet access keeps you connected, and a Smart television is provided for your entertainment. Conveniences include a microwave and a coffee/tea maker.
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including barbecue grills.
Guests will find features like internet access and onsite parking.

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Communal pool
  • Outdoor pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Bedrooms

  • 3 bedrooms

Bathroom

  • 2 bathrooms
  • Bathtub
  • Bathtub or shower
  • Hair dryer
  • Shower

Entertainment

  • Smart TV

Outdoor areas

  • Balcony
  • Barbecue grill
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Upper floors accessible by stairs only
  • Smoking not allowed
  • Note from host: Smoking allowed only outside

Location highlights

  • Near the ocean
  • On the waterfront

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)
  • Fire extinguisher
  • Deadbolt lock

General

  • Unit size: 1,272 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM
Contactless check-out available

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

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

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
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
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

We should mention

This property does not have elevators

Property is also known as

Vrbo Property

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

Reviews

8.8

Excellent

Rating 10 - Excellent. 57 out of 101 reviews
Rating 8 - Good. 30 out of 101 reviews
Rating 6 - Okay. 6 out of 101 reviews
Rating 4 - Poor. 5 out of 101 reviews
Rating 2 - Terrible. 3 out of 101 reviews

8.4/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

Reviews

Verified review

10/10 Excellent

Lismary D.

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

Bob B.

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

Clay M.

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

10/10 Excellent

Anne H.

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

8/10 Good

Valerie T.

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

10/10 Excellent

Ryan L.

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

8/10 Good

Jan H.

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

Denise B.

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

Trina M.

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

James G.

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

8/10 Good

Jen S.

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

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
Verified review

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
Verified review

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
Verified review

10/10 Excellent

Holly G.

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

Michael D.

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

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
Verified review

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
Verified review

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
Verified review

10/10 Excellent

Katie H.

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

Patrick K.

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

Amy K.

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

Michael M.

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
Verified review

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
Verified review

10/10 Excellent

Yuselys C.

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

Grateful

Peace
Stayed 3 nights in Jun 2025