Oceanside home, dock,kayaks,bikes,pool,fishing,109

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Entire home

Overview
Amenities
Policies
Location
Host

Exceptional

2 bedrooms3 bathroomsSleeps 61194.8 sq ft

Popular amenities

Kitchen
Dryer
Washer
Parking available
Pool
Barbecue grill

Explore the area

Cudjoe Key, FL

Venture Out Keys
Upper Sugarloaf Key
‪3 min drive‬
Florida Keys Beaches
‪10 min drive‬
Key West, FL (EYW-Key West Intl.)
‪35 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

Common spaces

1 Double Sofa Bed

3 bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Spaces

Kitchen

Balcony

Garden

Dining area

About this property

This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. I also rent units 111 and 107 on VRBO 4441714 and 342851) in case you need more than one home. We are 80 feet the water's edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on one of two balconies, dock or poolside, where you can soak up the sun steps from the house. Breathtaking southwest views of the blue-green ocean and sunsets can be seen from either balcony.

PLEASE NOTE: Beginning in 2023 the cleaning fee is to be left for housekeeping upon departure. Current amount is $225. This is in addition to the price you pay via this site.

Your boat, up to 25 feet, can be kept at the dock for your entire stay in the calm waters directly behind the house. I pay for you to store your trailer off-site at Cudjoe Gardens Marina where the ramp is. Looe Key and American Shoal Reef can be seen from the house where you’ll find the most beautiful snorkeling and diving reefs in the keys, along with the excellent fishing. Fish or kayak right off the end of the dock or you can venture out to experience the history and action in Key West located only 17 miles away. In the immediate area you’ll find several very good restaurants, a gym/wellness center, and Cudjoe Garden’s Marina, a full service marina offering boat rentals. The only 18-hole miniature golf course in the keys is located 15 minutes away. Bahia Honda State Park and the Dolphin Research Center, which offers dolphin encounters, are other area attractions.

This casually elegant home has:
* high ceilings with crown molding and ceiling fans
* bamboo wood floors
* a gourmet kitchen with stainless appliances and granite countertops
* Two master suites with king beds and full private baths
* a third full bathroom downstairs
* 3 flat screen HDTV’s with full U-Verse cable package
* Free WIFI
* covered parking for 2 vehicles
* I pay for you to store your trailer at the local marina to give you maximum space under home
* walk in closet and luxury king beds and furniture
* Beach chairs, cooler, beach toys,
* Fishing poles
* Kayaks
* Bicycles

This is the perfect vacation home for families or couples looking for relaxing ambiance in tropical setting and for those who want it all – beach, pool, boat dock, kayaks and views.

Property manager

John Benckenstein

Premier Host

Languages

English

Add dates for prices

Amenities

Pool

Kitchen

Washer

Dryer

Free WiFi

Air conditioning

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Sea view
Pool
Kitchen
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House Rules

Check in after 4:00 PM

Minimum age to rent: 22

Check out before 10:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

No pets 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

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, a first aid kit and a deadlock

We should mention

A car is recommended for transport to and from this property

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. Looking to get your feet wet? Jet skiing, kayaking and scuba diving adventures can be found near the property.

Cudjoe Key, FL

What's nearby

Upper Sugarloaf Key - 3 min drive - 3.6 km
Florida Keys Beaches - 10 min drive - 10.1 km
Sugarloaf Beach - 18 min drive - 14.7 km
Boca Chica Nude Beach - 35 min drive - 28.2 km
Duval Street - 39 min drive - 41.7 km

Getting around

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

Restaurants

‪Mangrove Mama's - ‬3 min drive
‪Boondocks Grille & Draft House - ‬8 min drive
‪The Square Grouper Bar & Grill - ‬2 min drive
‪Looe Key Tiki Bar & Grill - ‬9 min drive
‪Five Brothers Grocery Two - ‬8 min drive

Frequently asked questions

Does Oceanside home, dock,kayaks,bikes,pool,fishing,109 have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is Oceanside home, dock,kayaks,bikes,pool,fishing,109 pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Oceanside home, dock,kayaks,bikes,pool,fishing,109?

Check-in begins at 4:00 PM.

What time is check-out at Oceanside home, dock,kayaks,bikes,pool,fishing,109?

Checkout is at 10:00 AM.

Where is Oceanside home, dock,kayaks,bikes,pool,fishing,109 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).

Exceptional

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

Learn more

10/10

Cleanliness

10/10

Amenities

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

10/10 Excellent

Srdjan M.

29 Apr, 2025

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

Nice vacation complex

Well maintained and clean. Close to beaches and Key West. It has a small beach of it's own that maybe doesn't look too appealing. But if you jump on a kayak and row away a few hundred feet, the water is beautiful. Our unit was great. I wuld just add more utensils. There were around 4-5 spoons, wich for a group of 5 is not that much.

Stayed 5 nights in Apr 2025

10/10 Excellent

Jason A.

2 Apr, 2025

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

Perfection

Everything was great, very nice property. Clean and beautiful!! Highly recommended

Stayed 4 nights in Mar 2025

10/10 Excellent

Terese H.

11 Mar, 2025

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

Great location

Location was great. Excellent space for 4 people. Very pretty setting. Nice amenities.

Stayed 7 nights in Mar 2025

10/10 Excellent

Sara D.

31 Jan, 2025

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

Beautiful Condo

John's condo is really gorgeous. It is spotless, well decorated, and very comfortable. The beds are comfy with lovely linens, the chairs and sofa for watching TV are also comfortable. All the mechanicals work well and you have calming water views.We went to Key West a couple times but were so happy to come home to the quiet relaxation of our condo.We visited the Turtle Hospital and walked the beach of Bahia Honda.There are really good restaurants within a few minute drive. Broil and Square Grouper were both exceptional.John is a great host! He communicates well and is very responsive.I would definitely be a repeat visitor here!

Stayed 7 nights in Jan 2025

10/10 Excellent

Tommy and Cheryl E.

15 Jul, 2024

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

Weekend Fishing Trip

Property was very clean suited our needs perfectly. Great location.

Stayed 3 nights in Jul 2024

10/10 Excellent

Callie M.

8 Jul, 2024

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

Great Family Spot

My family of five (kids aged 9, 12, 13) had a great time! The girls split one king bed + an air mattress. We loved the location, as well as the paddleboards and kayaks. We visited both Key West and Marathon and enjoyed being in between the two. Great communication, comfy beds, super clean, highly recommend!

Stayed 4 nights in Jul 2024

10/10 Excellent

Louanna A.

18 Jun, 2024

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

Best of Both Worlds

I was a little concerned when I initially reserved this property. My husband and I were traveling with 3, 15 year-old boys and I was concerned the boys would prefer to stay directly in Key West with all of the more touristy activities and find Cudjoe Key and this property boring after a few days, but surprisingly I was wrong! The boys absolutely loved it! They thoroughly enjoyed all of the amenities this property offered. They took advantage of using the fishing poles, bikes, kayaks and pool. It was nice to see them enjoy being kids and not captive to their electronic devices!! Most of the neighboring properties were occupied but we had no issues with any of the other renters. The units are extremely close to one another so one may feel as though they don’t have a lot of privacy especially when enjoying the outdoor space each unit offers but again this wasn’t a bother to us. The unit is exactly as displayed in the pics and offered working appliances that we benefited from. Cudjoe Key is a more relaxed environment with a seemingly smaller population than Key West but a close 20 minute drive that allows you to visit as often as you’d like. This really is the best of both worlds and satisfied all of us. We will definitely look to stay here if we visit the Florida Keys again.

Stayed 5 nights in May 2024

10/10 Excellent

Rachel B.

30 May, 2024

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

Excellent, Relaxing Location

The property is very well maintained, clean and comes stocked with everything you need. Great location for paddle boarding/kayaking and within close proximity to local beaches, restaurants and Key West.

Stayed 3 nights in May 2024

10/10 Excellent

Lisa G.

5 May, 2024

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

Excellent stay in the lower keys

We loved this place. Very beautiful property on the ocean. Great docks, beds, furnishings. Excellent host!

Stayed 4 nights in May 2024

10/10 Excellent

Charles D.

29 Apr, 2024

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

Sunrise beach resort

I thoroughly enjoyed every aspect of our stay! Clean, roomy accommodations with plenty to do or not to do! Close to great restaurants and essentials for making your own meals as well. I would give it 10 stars if i could! Great place!

Stayed 4 nights in Apr 2024

10/10 Excellent

Alfred G.

28 Apr, 2024

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

Keys

Very comfortable and clean. Highly recommend it

Stayed 5 nights in Apr 2024

10/10 Excellent

karen s.

24 Apr, 2024

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

Cudjoe Stay

Property was great—clean, comfortable and has everything that you need!

Stayed 3 nights in Apr 2024

10/10 Excellent

Erin A.

6 Apr, 2024

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

Perfect as usual

This is the second time we have stayed in this gated community at one of Johns properties. Once again, it did not disappoint. You are on the water with plenty availability for kids to swim or fish. The chairs along the pool and waters edge are so comfortable. There is even an added bench at the far end of the dock, perfect for watching sunsets. The house is your own. 2 floors. Plenty of space. The beds are super comfortable with an array of pillows, hard and soft, for whatever you like. Extra linens, beach towels, anything you could need in the kitchen. We enjoyed using the kyacks but there are bikes for use also. The underside of the house has a cool relaxing seating area with table and gas grill. We used these often. The houses that John owns in this gated community are also unique in that they have stained glass windows and none of the other homes have that. Very beautiful. Highly recommend this property and owner. You wont be sorry. We also explored Bahai Honda State Park, 20 minutes from the property and spent 2 different days going into Key West, one of which was to go to Ft. Jefferson on Yankee Freedom. You are 30 minutes from Key West as well, but not in all the crazy.

Stayed 4 nights in Mar 2024

10/10 Excellent

Jennifer B.

18 Mar, 2024

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

Perfect House

The sunsets were amazing! Fishing was fun. It was a very nice, clean house and we would definitely stay again!

Stayed 5 nights in Mar 2024

10/10 Excellent

Adam S.

15 Mar, 2024

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

Florida Keys Vacation

Our family thoroughly enjoyed everything about our stay at this property. John, the host, provided great resources and advice prior to our drive from Ft. Lauderdale to the house. We dipped in the pool every day, used the kayaks - very easy access, dined at several recommended restaurants, absolutely LOVED Looe Key Resort for the snorkel tour, and enjoyed Bahia Honda’s Sandspur Beach twice (easy to rent beach chairs!) We adventured to Key West one day and sadly missed the Florida Eco-Discovery Center (open Wed-Sat only), but caught the sunset from Mallory Square. There is nothing missing from this property. Its location, cleanliness, pool/amenities, and being so well stocked were excellent. We highly recommend, and thank you so much John for sharing your gem!

Stayed 5 nights in Mar 2024

10/10 Excellent

Jeanne C.

30 Jan, 2024

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

Fabulous property in the keys

We loved our stay! Everything was provided that we would need, it was just like being at home. Everything was clean, pool was great and we tied up our boat at the dock. We also used the bikes. We look forward to staying here again.

Stayed 5 nights in Jan 2024

10/10 Excellent

Tracy B., St. Louis

25 Jan, 2024

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

Fabulous property with all the amenities

Clean, clean, clean! Everything you could possibly need in the kitchen. Detailed instructions with lots of recommendations on places to eat and visit. Location was primo! Pool was fabulous, just a few steps from the ocean.

Stayed 6 nights in Jan 2024

10/10 Excellent

Liz P.

16 Jan, 2024

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

Perfect family trip

This was the perfect family trip. Our host sent us a packet that included a ton of information that allowed us to know where we could find things on our way to our rental and it included places we might enjoy. The rental and what was offered was perfect. We had a wonderful family trip. We would definitely would do it again. Thank you!!

Stayed 4 nights in Jan 2024

10/10 Excellent

Ann A.

28 Dec, 2023

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

Pre Christmas getaway

My daughters and I enjoyed our stay here. The condo was beautiful with plenty of amenities to enjoy. Communication with owner was very good. Location was nice. Easy access to Key West, Bahia Honda State Park, many restaurants and coffee joints. We would highly recommend.

Stayed 5 nights in Dec 2023

10/10 Excellent

Jessica C.

3 Dec, 2023

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

Great place!

Loved our stay! Great home in a great location.

Stayed 7 nights in Nov 2023

10/10 Excellent

Kristen T.

28 Aug, 2023

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

Perfection!

We had a fantastic stay on Cudjoe Key! The house was beautiful and very clean, and the amenities were great. We loved having the pool and the little beach for the kids, as well as the bikes and water toys. The kitchen was very well equipped for a rental property, which allowed us to have a lot of meals at home. The location was perfect, too. We felt super close to Key West and activities on other islands, but had a quiet home to retreat to when needed. The grill and fire table under the house were great, and the sunsets on the dock were amazing! We had one very minor problem during our stay, and the owner was so responsive and helpful. He had a solution for us in minutes. We will definitely be staying here again!

Stayed 5 nights in Aug 2023

10/10 Excellent

Deana H., Missouri City, Texas

3 Aug, 2023

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

perfect spot

worked out great. location to all things lower keys related.

Stayed 7 nights in Jul 2023

8/10 Good

Tim S.

24 Jul, 2023

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

Great family spot in the lower keys

We spent the week of the 4th at the unit. The property manager was very responsive and very accommodating. The unit was very clean and comfortable. The docks and cleaning station was nice and the folks at the marina were very helpful. We enjoyed every minute of our stay and are looking forward to our trip next summer!

Stayed 5 nights in Jul 2023

10/10 Excellent

Pam B.

13 Jun, 2023

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

The Sweet Key Life

Wonderful experience from start to finish. Sparkling clean, comfortable & cozy with spectacular views. Close to everything you could need or want. Easy drive to Key West and grocery stores. Great restaurants are nearby. We took the owner, John's, recommendations on a couple of places and Kiki's Sandbar was the absolute best! Owner provided enough trash bags, hand/dish soap & laundry detergent to last an entire week. This was unusual & very much appreciated. The entire resort felt very secure. My only caution is beware there are many steps if they are an issue for anyone in your party. I HIGHLY recommend this property for an amazing vacation in the Keys!

Stayed 7 nights in Jun 2023

10/10 Excellent

Brett D.

3 Jun, 2023

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

Great quiet location

Took our 21 foot boat, 1/2 mile from boat launch. Put in early to store trailer there. The second option is just up the road and has plenty of storage. Boat docks are nice. Very shallow coming and going depending on tide. Dock area is quite deep. Rooms were extremely clean and comfortable. Very close to key west. Great additional items at location to enjoy exploring (kayaks and SUP). Good fishing all around. Not sure I would recommend the square grouper maybe bad day for them but food was not good and staff were very rude. The 420 lounge above it was much better but adults only. Going north from Vrbo about five miles on left side is a tiki bar that had great food and many locals and music. All in all we had a wonderful stay and will be back

Stayed 4 nights in May 2023

About the host

Hosted by John Benckenstein

We are married and the kids are all out of the house so we have the time to spend on vacations like our Cudjoe Key getaway house. We enjoy being on the water, touring Key West, eating out and then have a quiet place to sleep and relax.

Why they chose this property

We fell in love with the Keys and purchased these properties to make it that much easier to visit. Sunrise Beach Resort is the perfect blend of Keys life. It is just close enough to Key West when you want action and secluded enough for relaxing anytime.

What makes this property unique

Sunrise Beach is always a quiet place to relax. With nearby dive companies, or your own boat, you can explore some of the most beautiful reefs in the Keys just a few miles off shore. Nearby Key West (17 miles) is always a fun trip for a wide variety of food and entertainment. However, three of my top five favorite restaurants anywhere in the keys are less than 5 miles away. You will be staying in one of eleven stilt homes in this secluded gated community.