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Tree Top Paradise

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Photo gallery for Tree Top Paradise

An aerial view of a resort with a large swimming pool, palm trees, and a beach.
A beachside area with picnic tables, palm trees, and a building with a blue roof.
A beach with a pool, palm trees, and thatched-roof structures.
An aerial view of a coastal area with a marina, a small island with a dock, and a building with a white roof.
A wooden staircase with white railings, leading to a covered area.

Reviews

9.8 out of 10
Exceptional

Entire home

2 bedrooms2 bathroomsSleeps 6865 sq ft

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly

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
    ‪9 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪38 min drive‬

Room options

About the neighborhood

Summerland Key

This vacation home places you within a 5-minute walk of Venture Out Keys and Venture Key. The vacation home includes a kitchen, a patio, and a sofa bed.
View more Vacation Homes in Summerland KeyOpens in a new window

What's nearby

  • Upper Sugarloaf Key - 7 min drive - 4.8 miles
  • Florida Keys Beaches - 8 min drive - 4.8 miles
  • Upper Sugarloaf Sound - 9 min drive - 5.6 miles
  • Lower Sugarloaf Sound - 12 min drive - 7.8 miles
  • Key West Visitors Center - 18 min drive - 13.0 miles

Getting around

  • Key West Intl. Airport (EYW) - 32 min drive

Restaurants

  • ‪Boondock's Grille & Drafthouse - ‬9 min drive
  • ‪Morning Joint - ‬18 min walk
  • ‪Kiki's Sandbar - ‬12 min drive
  • ‪Looe Key Tiki Bar & Restaurant - ‬9 min drive
  • ‪Square Grouper Bar and Grill - ‬3 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.

Tree Top Paradise

On 7/6/24 I have bought a new oven, microwave, dishwasher, washer and dryer and barbeque to make your vacation very comfortable.
Unit #179 - At the “Tree Top Paradise” we have spared no expense to make sure your vacation is not just a vacation but an experience of your life with a peak a boo view of the canal. This home is a fantastic 2 bedrooms (Queen beds) and 2 baths. You have a large lovely screened in porch with comfy furniture to enjoy your morning coffee. A bright open concept kitchen is fully stocked with pots, pans, dishes, etc. Open concept allows you to socialize with those in the living room and dining room while preparing your fresh caught fish. The living room has a sleeper sofa and a new 55-inch flat screen crystal smart tv. The cable/internet is Xfinity Comcast Cable with, Movie channels, News channels. Watching the big game has never been better. There is also a work station with a 27 inch screen that your lap top can connect to if you had to do some work on vacation. Down the hallway there is a stackable washer and dryer. Under the home is a picnic table, hammock, barbeque, Kayaks, pickle ball paddles, fishing poles and gear and bicycles. Key West is only 20 minutes south and Bahia Honda State Park is 16 miles north. “Venture Out” is a wonderful gated resort that provides a host of amenities - large heated Salted Swimming Pool, Saltwater lagoon, Hot Tub, Playground, Tennis courts, Basketball, Pickle ball, and Bocce ball. There is a Marina store, boat launch and rinse station. The Rec Hall offers a Pool Table, Ping Pong Table, games and an air-conditioned place to hang out.
Venture Out is a gated community and there is a $125.00 one-time resort fee payable on arrival at the guard shack. (This charge is not included in the listing) Also note that there is a strict maximum of 6 people including children. One car is allowed to park at the house. Overflow parking for more than one vehicle that is an additional charge, but not guaranteed. Please leave the trash can at the street. The garbage men will not go on my property to dump it. Just fill it where it is. They come Monday and Thursday early so put it out Sunday night and Wednesday night.
IF YOU’RE BRINGING A BOAT
• Venture Out Resort has decided that renters staying there need to park their boat and trailer off site. They WILL NOT provide any parking for a trailer with or without a boat. You may have to park your boat and trailer on the street overnight at your own risk or please make arrangements on your own. I can provide you with some places that rent spots.
Please treat our home as your home and not a hotel room. Tidy up when you leave. If you use excessive towels please wash them. Don't leave trash inside the home when you leave. There are trash bins in overflow parking lot if needed. There is a ring camera above garage doors.

Trust me you’re not going want to leave but you have to so a new group can experience the “Tree Top Paradise”. The good news you can always come back!
The vacation home is air-conditioned and features a kitchen, 2 bathrooms, and a patio, and there's space to spread out with 2 bedrooms. Guests can expect to find free WiFi and a Smart TV with a DVD player. Other standard amenities include a washing machine, a sofa bed, and a coffee maker.

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Exterior
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
  • Ocean view
  • Pool
  • Kitchen
  • Washer
9.8 out of 10, 96, 96 reviews
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Total with taxes and fees
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Property amenities

Beach

  • Beach towels

Pool/Spa

  • Communal pool
  • Fenced private pool
  • Heated pool
  • Hot tub
  • 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
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 2 bathrooms
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • DVD player
  • Games
  • Smart TV with cable/satellite channels

Outdoor areas

  • Barbecue grill
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total (up to 20 lbs per pet)

Suitability/Accessibility

  • Designated smoking areas

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near the marina
  • Near the ocean

Things to do

  • Arcade/game room
  • Bicycles
  • Billiards/pool table
  • Heated pool
  • Kayak
  • Table tennis
  • Tennis
  • Basketball nearby
  • Cycling nearby
  • Fishing nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby
  • Windsurfing nearby

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

General

  • Bicycles
  • Property located in a resort
  • Unit size: 865 square feet

Policies

Check-in

Check-in time starts at 4:00 PM

Check-out

Check-out before 10:00 AM

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

  • This property welcomes pets
  • Dogs only
  • 2 total (20 lbs is the maximum weight per pet)
  • Service animals exempt from fees

Children and extra beds

Children allowed: ages 3-17

Events

Events allowed

Smoking

Smoking allowed: in designated areas

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
Parties and events are allowed on site; maximum attendees: 6
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
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
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • 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.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Parties and events are allowed on site. Maximum attendees: 6.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, and a smoke detector.

Property is also known as

Vrbo Property
Tree Top Paradise Cudjoe Key
Tree Top Paradise Private vacation home
Tree Top Paradise Private vacation home Cudjoe Key

Frequently asked questions

What's there to do close to this vacation home?

This vacation home in Summerland Key is within a 10-minute walk of Venture Out Keys, Venture Key, and Out Key. You'll also find Florida Keys Beaches and Upper Sugarloaf Key within a short drive.

Will I be able to park at Tree Top Paradise?

No, there isn't parking at this vacation home.

Is this vacation home associated with a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, this vacation home doesn't have an indoor pool; however, there are an outdoor pool and a hot tub.

Is Tree Top Paradise a good place to stay for couples?

Couples staying at this vacation home will appreciate amenities like a smart TV and a kitchen as well as an outdoor pool.

Does Tree Top Paradise have a hot tub?

No, but this vacation home does have a heated pool.

Does this vacation home include breakfast service?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay free of charge?

Although dogs can't stay for free, they are welcome at this vacation home.

Does Tree Top Paradise have connecting rooms available?

No, there aren't connecting guestrooms at this vacation home.

What is the closest airport to this vacation home?

The closest major airport to this vacation home is Key West Intl. Airport (EYW), which is 21.4 mi away (32 minutes by car). Another top airport is Marathon, FL (MTH-Florida Keys Marathon), which is located 29.3 mi away (43-minute drive).

Can I book a room with a balcony at Tree Top Paradise?

Yes, every house at Tree Top Paradise comes with a patio and some offer water views.

Tree Top Paradise Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 18 out of 21 reviews
Rating 8 - Good. 3 out of 21 reviews
Rating 6 - Okay. 0 out of 21 reviews
Rating 4 - Poor. 0 out of 21 reviews
Rating 2 - Terrible. 0 out of 21 reviews

9.6/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Barbara S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great stay at Treetop Paradise. The pool and views were amazing and the house is in a great location.
Stayed 28 nights in Mar 2026
Verified review

10/10 Excellent

Scott F.

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

great getaway

Good time and close to all accommodations
Stayed 10 nights in Feb 2024
Verified review

10/10 Excellent

Chris B.

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

Tree Top

Great place! Great location!
Stayed 4 nights in Jan 2024
Verified review

8/10 Good

Elizabeth L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The screened porch with the beautiful trees all around. Very tropical feeling.
Stayed 7 nights in Nov 2025
Verified review

10/10 Excellent

Karen and Eric G.

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

Great Vacation Location

The house was very comfortable and in a great location, as we were not only visiting Key West, but several other Keys too. Beds were comfortable and loved all the extras, including the pool! Thank you for helping us make great memories!!
Stayed 4 nights in Jul 2023
Verified review

10/10 Excellent

Washington F.

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

We have a nice weekend

Had good accommodation . Well recommend
Stayed 3 nights in Sep 2021
Verified review

10/10 Excellent

Brigette P.

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

Safe and Homey

Thanks Keith for a wonderful place to stay and great communication!
Stayed 3 nights in Oct 2022
Verified review

10/10 Excellent

William C.

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

Nice stay, especially the screened in porch!

Nice rental, and everything was available for the kitchen, etc. The landlord was accessible and very helpful
Stayed 25 nights in Feb 2022
Verified review

10/10 Excellent

Michael S.

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

5 Star Accomodations

This was an amazing, well appointed, and 5 star accommodation. I would stay again in a heartbeat. Special thank you to Keith for all the communications.
Stayed 4 nights in Feb 2023
Verified review

10/10 Excellent

Casey M.

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

Don’t think twice

Awesome experience, this place met all expectations! Property owner was great and kept up with you about any questions you may have! This place was super clean and very comfortable! Staff at the neighborhood was very helpful! We had a great vacation.we will be back!
Stayed 4 nights in May 2023
Verified review

10/10 Excellent

Kim G.

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

Spring Break

We enjoyed our stay at Keiths! Fully stocked with anything we needed to grill, cook and clean! Access in and out was a breeze and the amenities were amazing. Heated pool, jacuzzi, boat ramp, store, laundry, huts, and lagoon. We used it all! So safe to walk around any time of the day and an easy drive to anything we needed. Groceries, pizza, entertainment!
Stayed 3 nights in Apr 2023
Verified review

8/10 Good

William N.

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

Mostly Positive

Great property overall. Dryer was broken during my stay which was disappointing. Recommend asking about this prior to booking.
Stayed 6 nights in May 2024
Verified review

10/10 Excellent

Linda B.

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

Tree top Pradise

We were close to great food , boat rentals, biking, and Key West. We had kayaks. Played tennis etc. our unit was dog friendly and well furnished. The only negative was not being able to walk our dog in common areas. Had to go outside gate entrance to do potty breaks etc. we were at least pretty close to this entrance. Staff was very friendly and we really enjoyed our stay
Stayed 4 nights in Nov 2023
Verified review

8/10 Good

tyree p.

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

Short stay

My stay was short. Purpose of the stay was work related. Would stay again if it was more for pleasure.
Stayed 4 nights in Sep 2022
Verified review

10/10 Excellent

Richard B.

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

Great Place

Excellent rental in a great resort. Will rent again!
Stayed 7 nights in Jul 2022
Verified review

10/10 Excellent

Amber B.

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

Great!

We really enjoyed the location and the small community feel. It is so close to everything and we could have stayed forever :) The property is in a very clean golf cart/bike riding community of small homes and RV’s. Everyone waves and/or smiles. The property owner is very responsive and kind! We are looking forward to planning a trip back!
Stayed 5 nights in Mar 2022
Verified review

10/10 Excellent

Jessica S.

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

Very accommodating and nice place

My husband and my adult children and I just stayed. It was a very nice experience. Love the heated community pool and hot tub. House was clean and stocked with amenities.
Stayed 4 nights in Jan 2022
Verified review

10/10 Excellent

Amy B.

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

Relaxing and fun

Great clean place. We enjoyed our stay and will be back our next visit
Stayed 4 nights in Dec 2021
Verified review

10/10 Excellent

Kelley J.

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

The Keys

We had a great time and it was in a great location.
Stayed 6 nights in Oct 2021
Verified review

10/10 Excellent

Elizabeth W.

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

Truly Treehouse Paradise

We enjoyed the house so much! Clean, plenty of amenities, communication with owner was great as well. The whole community was very friendly and the area was clean and well kept. Will likely stay here again!
Stayed 3 nights in Nov 2021
Verified review

10/10 Excellent

Sandy C.

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

Fit our needs

Great communication with the owner. Very clean and nice place to stay. Lots of great amenities (You do need to have your own equipment for most) Would definitely recommend this place for family.
Stayed 4 nights in Sep 2021