Entire home

Fishermen’s Paradise

Photo gallery for Fishermen’s Paradise

An aerial view of a resort with a large swimming pool, beach area, and a Ferris wheel.
An aerial view of a coastal resort with a swimming pool, beach area, and several buildings.
An aerial view of a sports complex with multiple tennis courts, a swimming pool, and a large building with a dome roof.
A waterfront property with a covered patio, outdoor seating, and a grill area.
A room with a brown quilted sofa, large windows with blinds, a view of a pool, and a sign reading "No Smoking".

Reviews

9.2 out of 10
Wonderful

Highlights

  • Top-rated for value
    Guests love how much they get for what they pay.
  • 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.

Popular amenities

  • Hot tub on site
  • Patio
  • Outdoor pool
  • Arcade/game room
  • Barbecue grill
  • Air-conditioning

Explore the area

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

Rooms & beds

2 bedrooms (sleeps 6)

Living Room 1

1 Double Sofa Bed

Upper kitchen bedroom

1 Double Bed

Upper level Master

1 Queen Bed

Bathroom

Towels provided · Toilet · Shower only · Hair dryer

Spaces

Deck or patio
Kitchen
Number of living rooms
Dining area

Add dates for prices

Similar properties

Property grounds
Our little slice of paradise
Breezeswept Beach Estates
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
10.0 out of 10, Exceptional, (2 reviews)
Our little slice of paradise

About the area

Summerland Key

Located in Summerland Key, this cottage 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. Jet skiing, scuba diving and snorkelling offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours nearby.
View more Cottages in Summerland KeyOpens in a new window
Map
Cudjoe Key, FL

What's nearby

  • Upper Sugarloaf Key - 7 min drive - 7.3 km
  • Florida Keys Beaches - 8 min drive - 7.4 km
  • Upper Sugarloaf Sound - 8 min drive - 8.6 km
  • Boondocks Grille & Draft House - 10 min drive - 11.7 km
  • Lower Sugarloaf Sound - 11 min drive - 12.1 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 31 min drive

Restaurants

  • ‪Boondock's Grille & Drafthouse - ‬9 min drive
  • ‪Morning Joint - ‬17 min walk
  • ‪Kiki's Sandbar - ‬12 min drive
  • ‪Looe Key Tiki Bar & Restaurant - ‬9 min drive
  • ‪Tonio's Seafood Shack & Tiki Bar - ‬6 min drive

Frequently asked questions

Does Fishermen’s Paradise have a pool?

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

Is Fishermen’s Paradise pet-friendly?

No, pets are not allowed at this property.

How much is parking at Fishermen’s Paradise ?

On-site parking is available at the property.

What time is check-in at Fishermen’s Paradise ?

Check-in begins at 3:00 PM.

What time is check-out at Fishermen’s Paradise ?

Checkout is at 10:00 AM.

Where is Fishermen’s Paradise located?

Situated on the waterfront, this cottage is within a 10-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

9.2

Wonderful

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. 71 out of 100 reviews
Rating 8 - Good. 20 out of 100 reviews
Rating 6 - Okay. 5 out of 100 reviews
Rating 4 - Poor. 1 out of 100 reviews
Rating 2 - Terrible. 3 out of 100 reviews

9.2/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

9.4/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

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

Loved our stay

The stay was awesome, had everything we needed.
Stayed 4 nights in Jul 2024
Verified review

10/10 Excellent

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

Fishing trip

Had a great time soaking up the sun and fishing. Great stay for me and my friend.
Stayed 7 nights in May 2023
Verified review

10/10 Excellent

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

Enjoyed Florida

We loved it. Very nice neighborhood.
Stayed 4 nights in Apr 2023
Verified review

10/10 Excellent

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

Special place

I love this spot. Everything was wonderful from the cool place yo stay to all the nice people in Venture out that we met. The location is perfect, I plan on being a regular 😎
Stayed 6 nights in Oct 2021
Response from VrboOwner on 9 Nov 2021
Can’t wait to have you back again Daniel!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great time staying here while in the area wanting to see the Keys. It is exactly as listed. It was fun to sit out the back door in the morning and evening watching the birds and different fish. Fit my family of three comfortably but I do think amymore pople it would be a tight fit. The air conditioners keep it comfortable inside and there were bikes waiting for us when we got there.
Stayed 4 nights in Dec 2025
Verified review

10/10 Excellent

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

Solid rental

I'm not big into leaving long reviews ill just say for the price I give 5 stars I'd book again and would recommend to anyone.This place is all you need if your like my family and plan on spending time out doors fishing, snorkeling, paddle boarding and site seeing as we did. Also the community pool is a nice perk pretty nice pool. Also the owner is very nice and laid back.
Stayed 5 nights in Apr 2025
Verified review

10/10 Excellent

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

Fisherman paradise

No complaints had the best experience here. Highly recommended
Stayed 4 nights in Feb 2023
Verified review

10/10 Excellent

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

Lovely Vacation!

This property was exactly what we were hoping for, a no-frills but very comfortable spot by the water in what is a really amazing resort community. Venture Out is a gem with great people, great facilities, and everything you could ask for for a week in the keys. We will definitely be back.
Stayed 6 nights in Mar 2024
Verified review

10/10 Excellent

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

Great week

Was very nice to have the boat only feet away and a quick shot out to the reefs. A/C struggled a bit during the day but at night was great! Overall was very pleased with place. Venture out was also very convenient with a store and pool area for the kids to enjoy. Would stay again for sure.
Stayed 6 nights in Jun 2023
Verified review

10/10 Excellent

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

Our Honeymoon

We LOVED this house! It was so clean, and welcoming. So many things to do in the area, and at the resort! We loved it! We will be back! :)
Stayed 6 nights in Jun 2022
Verified review

10/10 Excellent

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

Family spring break

Wonderful experience,beds very hard and noisy. But overall excellent choice
Stayed 5 nights in Mar 2024
Verified review

10/10 Excellent

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

Very nice

We had a very nice stay. Thank you. No problems
Stayed 6 nights in Mar 2024
Verified review

8/10 Good

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

Just as pictured

This property was exactly as shown. Perfect for my husband and I. It was clean and had all the household essentials. I loved being able to walk out the back door and fish the canal.
Stayed 14 nights in Feb 2023
Verified review

10/10 Excellent

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

Perfect fishing home!

We absolutely loved our stay with you! We actually look forward to planning our next trip down here and hopefully for a longer period of time! Accessibility to the Atlantic and to the gulf was so easy unlike on other keys were you have to navigate difficult channels or go extra long routes around. Everything was right there. We will be back, very soon!
Stayed 3 nights in Oct 2019
Response from VrboOwner on 31 Mar 2020
Hope to have you back sooner than later!
Verified review

10/10 Excellent

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

Wonderful location with tons of amenities!

A cute little house right on the water.. nothing fancy but everything you will need for a perfect stay. Was traveling with my hubby and our two teen daughters so mirror space was a battle, advice, add a mirror to other bedroom or to family room, to help with that lol! Host was very responsive! Venture out is a cool little community and everyone is so very friendly! Will stay again! Thanks a bunch!
Stayed 6 nights in Jan 2023
Verified review

10/10 Excellent

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

Great

The weather was wonderful my grandson loved us sitting by the pool. He read eight books altogether. This trip was all about him. He’s going to be a senior in college in the fall so this was his spring break with his grandma.
Stayed 7 nights in Feb 2024
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location

Peaceful

It had everything you needed and was close to stores and a half hour from Key West. A few suggestions, maybe a new grill, prune the palms on the east side as they made noise when it was windy while sleeping, replace the light bulb in the microwave for easier cooking and replace the broken mini blinds.
Stayed 7 nights in Dec 2023
Verified review

6/10 Okay

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

Update Air Conditioners

We were disappointed in the air conditioning as it was very warm during the day in the main room. We were able to sleep ok during the evening but would recommend better A/C. Location was great and lots of amenities, there is a boat ramp and saltwater swimming pool/jacuzzi.
Stayed 6 nights in Jun 2025
Response from VrboOwner on 8 Jul 2025
Hey! This is the first I’m hearing about it, as I would have brought over extra fans for you. I don’t think this calls for a 3 star review since everything else was great, Not much we can do on a island in the middle of July , there are 4 ACs units in a this 2 bed house, sorry the main living room by the front and back porch door was warmer than the rest of the house, when the sun is blistering hot and over a 100° the best to do is keep the blinds closed and all doors closed, as you said night is better because the sun goes down! Hope this helps for your next stay at an island!
Verified review

10/10 Excellent

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

Keys Getaway

Enjoyed our stay. Definitely a Florida Keys vibe. Nice location and an easy drive daily to attend a 5 day music festival in Key West. Kitchen was used for breakfast and lunch every day and had plenty of the essentials needed for basic meals. Even took advantage of the gas grill for one meal. We are fairly low key and the resort area was clean and quiet which made it enjoyable. We made use of some of the amenities as well. If you read the rules and are respectful of the many other residents/guests you will have a great stay! We did!
Stayed 4 nights in Jan 2023
Verified review

4/10 Poor

Liked: Check-in, location
Disliked: Cleanliness, listing accuracy

Owner Saves Vacation

This property is dated, hot, and not the cleanest. It was dark and depressing. The curtains had to stay closed the entire time to try and maintain coolness. The owner was made aware of issues and immediately moved us.The other property was great. The owner saved the day and our vacation by allowing us to move to other property.
Stayed 8 nights in Aug 2024
Verified review

10/10 Excellent

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

Family Vacation

This place is a very safe and fun gated community that we definitely enjoyed staying at. My kids loved being able to safely ride around the neighborhood just like they were at home. Everyone that worked there are super friendly, including the security guards at the front gate! We took full advantage of all the amenities that Venture Out had to offer. Our house was very cozy & had everything that we needed for our stay. Shawna was very pleasant & was very prompt in responding to any issues we had during our stay (which was super minor) All in all I would say this place is perfect if you are looking for an affordable getaway that is in a quite neighborhood that is literally minutes down the road from key west. We will definitely visit again.
Stayed 5 nights in Nov 2023
Verified review

10/10 Excellent

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

More than you pay for 01/24

This property was better than advertised. I was shopping for a affordable place that I planned to just sleep at and fishermans paradise was so much more. This place screamed florida keys and was exactly what my wife and adult son and his girlfriend wanted. Everything worked perfectly and we all enjoyed the patio on the water from coffee in the morning, drinks in the afternoon to fishing whenever we wanted. Fishing poles were provided also. The resort pool is heated and fun. The restaurants nearby are very good as well. To the next guest that stays here the light switches are not exactly where you think they should be, lol. Perfect stay for my group.
Stayed 4 nights in Jan 2024
Verified review

10/10 Excellent

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

Great host!

Overall this is a clean home in a safe community. When checking in we noticed the power was out to one of the rooms. The host was very responsive and diligent on getting things fixed, though it took 2 electricians over 2 days to finally get power back to the room the host was responsive the whole time and compensated us adequately for the inconvenience. If renting this home as a group know that you have to walk through the only bathroom to get to the main bedroom and can be a little inconvenient. I would absolutely recommend this rental and 1000% recommend this host.
Stayed 4 nights in Apr 2024
Verified review

6/10 Okay

Liked: Check-in, communication, location

Venture Out

Stay was o.k., had no hot water (and not much cold) for about 24 hours leaving us no choice but to eat out first night. Would like at least a refund for $100.00 for dinner for 4. Place has unusual set-up with bathroom, can’t get into master if someone in there. Folks friendly, heated pool a plus. Great if you have a boat, we didn’t. Probably wouldn’t book again. Had to buy a pillow and pans to cook with. There’s were in bad shape and need replaced. I bought a pillow for saggy couch and left all.
Stayed 9 nights in Feb 2022
Response from VrboOwner on 21 Feb 2022
Mary- obviously having no control over the water situation as things happen but I did have a emergency plumber come out and get it fixed immediately for you. Not sure why you had to go out to dinner because of the kitchen sink not running hot for a few hours. As that got fixed, I had brand new never ridden bikes dropped off for you , which you broke after 5 minutes of riding them. After speaking to my property manager she said there are NO new pots or pans in the house only the 2 sets we have bought 1/6/22. Did you not look at the pictures before booking to see that the bathroom is between the master and the kitchen- because the pictures are very accurate and detailed. You were full of complaints from the beginning. I try my absolute best to manage all my property’s and with 4.8 stars I think I do well. Sorry you had such a terrible experience ,as you “probably wouldn’t rent again” I probably would rent to you again either. Hope you find a better place in the Florida keys, have a great year .
Verified review

8/10 Good

Liked: Cleanliness, communication, location

Our Stay

Our stay on Cudjoe Key was definitely within our budget and close to Key West, which was our number one requirement. The checkin process with Venture Out was more than stated in the listing. We were charged $150 due to having 2 vehicles. While the inside was clean, there was a bit of a moldy smell. The floor is soft in numerous places, a few of the walls are bowed, and the ceiling in the queen size bedroom is detaching. This might be due to water damage(?) We were on Key West the majority of the time for a family member’s wedding, so we didn’t spend a lot of time at the property or use the amenities at Venture Out. Overall, your place fit our needs.
Stayed 5 nights in Mar 2024
Tell us how we can improve our siteShare feedback