Entire home

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

Photo gallery for Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

A beachside area with picnic tables and palm trees.
A beachside area with a wooden gazebo, a bench, and a rope barrier.
A coastal building with a balcony, surrounded by palm trees and a boat.
A row of bicycles parked outside a building.
A kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a stove.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Dive into relaxation
    Unwind in the top-rated pool, your perfect spot for relaxation.
  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Balcony
  • Spa pool on site
  • Outdoor pool
  • Toys
  • Gas barbecue
  • Air-conditioning

Explore the area

View map
Cudjoe Key, FL
  • Place, Upper Sugarloaf Key
    ‪6 min drive‬
  • Place, Florida Keys Beaches
    ‪6 min drive‬
  • Place, Upper Sugarloaf Sound
    ‪7 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪37 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Convertible bed(s)

1 Queen Sofa Bed

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Outdoor play area
Dining area

Add dates for prices

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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 Big Munson Island. Consider Boondocks Grille & Draft House for a night out or Looe Key National Marine Sanctuary if you're travelling with kids. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with cycling and ecotours.
View more Holiday homes in Summerland KeyOpens in a new window
Map
Cudjoe Key, FL

What's nearby

  • Upper Sugarloaf Key - 6 min drive - 6.6 km
  • Florida Keys Beaches - 6 min drive - 6.7 km
  • Upper Sugarloaf Sound - 7 min drive - 7.9 km
  • Boondocks Grille & Draft House - 9 min drive - 11.0 km
  • Lower Sugarloaf Sound - 10 min drive - 11.5 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 30 min drive

Restaurants

  • ‪Morning Joint - ‬3 min drive
  • ‪Kiki's Sandbar - ‬12 min drive
  • ‪Boondock's Grille & Drafthouse - ‬10 min drive
  • ‪Tonio's Seafood Shack & Tiki Bar - ‬7 min drive
  • ‪Square Grouper Bar and Grill - ‬4 min drive

Frequently asked questions

Does Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security have a pool?

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

Is Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security pet-friendly?

No, pets are not allowed at this property.

How much is parking at Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security?

On-site parking is available at the property.

What time is check-in at Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security?

Check-in begins at 3:00 PM.

What time is check-out at Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security?

Checkout is at 10:00 AM.

Where is Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security located?

This family-friendly Summerland Key holiday home is located on the waterfront, within a 15-minute walk of Venture Out Keys, Venture Key and Out Key. Florida Keys Beaches and Upper Sugarloaf Key are also within 6 miles (10 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 238 out of 276 reviews
Rating 8 - Good. 34 out of 276 reviews
Rating 6 - Okay. 2 out of 276 reviews
Rating 4 - Poor. 1 out of 276 reviews
Rating 2 - Terrible. 1 out of 276 reviews

9.8/10

Cleanliness

9.6/10

Amenities

9.6/10

Property conditions & facilities

9.8/10

Check-in

9.6/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great communication with host, very nice resort amenities.
Stayed 9 nights in Sep 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice property with access to a great swimming pool and other amenities (tennis courts, soccer courts, etc.)I really appreciated that the basic amenities (coffee, sugar, shampoo, body wash, etc.) were provided. The unit was clean and comfortable. The sheets need to be thrown out but otherwise the beds were comfortable. We loved the large washer and dryer!It was great to have bicycles to use and it made getting around the community really nice.
Stayed 3 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome
Stayed 7 nights in Aug 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had an amazing time kayaking and biking around the area. Even saw a dead shark hunk up in the Venture key. It was clean and beautiful.
Stayed 6 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This house was great for our whole family! Easy to get to. Quick and easy check in process. Tons to do and the host provided a lot to use if wanted (bikes for kids/adults, kayaks..). Our kids loved the pool more than anything, which was great!! Our host had all the amenities. Full kitchen with all we needed. Sheets/blankets pillows provided; washer/dryer worked well. We loved sitting out on the balcony while there. Overall, great experience!!
Stayed 8 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great stay at Venture out, the facilities were great. Location to everything was nice. We would definitely stay again.
Stayed 7 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great Vacation stay. The house was well stocked with what we needed. The house was clean. We loved the location on the keys. Cudjoe was perfect. The pool was nice in the afternoon. Thanks for a great stay!
Stayed 7 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property was clean and comfortable and had everything we needed. The best part was access to the Kayaks, multiple bikes, beach umbrellas, chairs, towels and fishing gear. The appliances were new and everything worked great. There are (2) bedrooms and the beds are a bit small but they were comfortable.
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property and Venture Out community were as described and very well maintained. The check in process was smooth and the whole experience is turn key. The house itself was very clean with several extras supplied, including linens, towels, and daily use kitchen items, in addition to Kayaks and bicycles. Highly recommend this home and the community as a base camp if you’re looking for a peaceful setting with an easy commute to Key West or the middle keys
Stayed 7 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
This place was perfect for Our Christmas Vacation. It really was paradise. When i come back this place is where ill be staying
Stayed 4 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place to stay in Venture Out
Stayed 8 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean and awesome location
Stayed 5 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Spent most of my time out on the Deck, both day and night. Weather fantastic!! Loved having kayaks & bicycles at anytime. Host takes extreme pride in their property and it shows!!! Neighbors very friendly and helpful! Loved having paper instructions to activate TV and learn about activities within the complex. Definitely a 20 out of 10 property and I’d love to stay again!!! Thank you!!
Stayed 30 nights in Mar 2026
Verified review

10/10 Excellent

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

Great place to stay!

Home was clean and great location! Would definitely stay here again!
Stayed 3 nights in Mar 2025
Verified review

10/10 Excellent

Liked: Cleanliness, property conditions & facilities, communication
Absolutely love love love Venture Out! This unit is phenomenal! We had an amazing family vacay!
Stayed 6 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great House and amenities
Stayed 3 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great vacation. House was wonderful.
Stayed 7 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was great from check in to the venture out community and facilities to the actual home we loved it all.
Stayed 3 nights in Jul 2025
Verified review

10/10 Excellent

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

Clean, affordable vacay rental

The home was clean, well decorated and has everything we needed plus some for our vacation. Highly recommended for families.
Stayed 6 nights in Jul 2025
Verified review

10/10 Excellent

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

Great homebase in Keys

Wonderful place to stay in the Keys for our family. All the items you need and great location. Would return again!
Stayed 3 nights in Apr 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property was spacious, clean and as listed. We had a very nice day.
Stayed 4 nights in Aug 2025
Verified review

10/10 Excellent

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

Spring break getaway

Had a great time at the property many amenities to enjoy. Perfect location to bounce from key to key would definitely come back again.
Stayed 5 nights in Mar 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was very clean when we arrived. There was every cooking item available for cooking. The distance to Key West was very nice.
Stayed 4 nights in Oct 2025
Verified review

8/10 Good

Liked: Cleanliness, amenities, property conditions & facilities, communication
It was located where we wanted to stay
Stayed 3 nights in Aug 2022
Verified review

10/10 Excellent

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

Girls trip

Had a great time. And the pool was excellent.
Stayed 7 nights in Apr 2025
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