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Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and Dog-Friendly Perks!

Photo gallery for Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and Dog-Friendly Perks!

Lounge by the pool and take in the amazing view of the surroundings.
The open layout between the kitchen and living room encourages effortless and engaging conversations to flow freely throughout the space.
Open water views as far as the eye can see – the epitome of a true Florida Keys paradise.
Four comfortable seats at the kitchen island provide an inviting space for enjoying meals or sharing conversations.
Enjoy a cocktail while watching the sun set – the perfect ending to your day in paradise.

Reviews

9.8 out of 10
Exceptional
4 bedrooms3+ bathroomsSleeps 102668 sq ft

Popular amenities

  • Dryer
  • Washer
  • Kitchen
  • Pet-friendly
  • Pool
  • Barbecue grill

Explore the area

Map
Sugarloaf, FL
  • Upper Sugarloaf Key
    ‪6 min drive‬
  • Florida Keys Beaches
    ‪12 min drive‬
  • Sugarloaf Beach
    ‪13 min drive‬
  • Key West, FL (EYW-Key West Intl.)
    ‪21 min drive‬

Rooms & beds

4 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 Queen Bed

Bedroom 4

1 Queen Bed

3 bathrooms, 1 half bathroom

Bathroom 1

Bathtub · Toilet · Shower only

Bathroom 2

Bathtub · Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet

Spaces

Deck or patio
Kitchen
Balcony

About this property

Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and Dog-Friendly Perks!

County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below.

Escape to your personal open water paradise at Paradise Point!

This fantastic waterfront retreat invites you to experience breathtaking sunset views, enjoy a splash in the heated saltwater pool, and set out on unforgettable fishing adventures just minutes from your doorstep. You'll find endless activities right at this house, but if you're eager to explore the Florida Keys, you're conveniently located just 20 minutes from Key West and 45 minutes from Marathon.

SLEEPS MAXIMUM OF 10 GUESTS:

Bedroom 1 (1st Floor): King Bed, En-Suite Full Bathroom, Flat Screen TV with DirecTV

Bedroom 2 (2nd Floor):King Bed, En-Suite Full Bathroom, Flat Screen TV with DirecTV

Bedroom 3 (2nd Floor): Queen Bed, Flat Screen TV with DirecTV

Bedroom 4 (2nd Floor): Queen Bed, Flat Screen TV with DirecTV

Living Room: Sofa, Loveseat, Two Chairs, Flat Screen TV with DirecTV

Kitchen: Nicely equipped (all things necessary to prepare and serve a meal)

AMENITIES:

- 45' Private Dockage

- Fish Cleaning Station with Lights and Water

- Heated Saltwater Pool

- Corn Hole Boards and Bags

- Horseshoe Pits and Horseshoes

- Tiki

- Outdoor Seating

- Propane BBQ Grill

- Parking for a maximum of 4 vehicles (including boat trailers) on the property. Recreational Vehicles may not be parked on the property.

- Linen's and towels provided

- 2 Rollaway Twin Beds available

IMPORTANT POLICIES FOR YOUR STAY:

Age & Occupancy: The booking tenant must be 25 years or older and must occupy the property for the entire duration of the stay. This property is exclusively available as a vacation rental and not for worker housing.

Peak Season Monthly Bookings: All bookings from December through March must be for the entire month, starting at the beginning and ending at the end of the month. Consecutive months may be booked if they follow this requirement. Bookings that do not adhere to this policy are subject to cancellation. If you are interested in alternative dates, please contact us for approval before booking.

Pet Policy: Up to two friendly and well-behaved dogs will be considered with prior approval, payment of a $300 pet fee, and registration with a third-party pet screening service (fee applies for pets, free for service animals). Please review our pet policy before booking—we will provide the registration link after you confirm your reservation.

Smoking Policy: Smoking is strictly prohibited to maintain a smoke-free environment.

Mid-Stay Cleaning: For stays of 28 nights or more, we reserve the right to require a mid-stay cleaning to maintain the quality of the property. For longer stays, a mid-stay cleaning will be required every 28 nights thereafter. The cost will be collected separately, and the number of cleanings depends on the length of your stay.

Boating & Dockage Advisory: Due to bridges and varying water depths, it is your responsibility to ensure that your boat can safely navigate local waters, access the canal, and fit the listed dockage before booking. While we are happy to provide general information based on our knowledge of the area, guests must exercise extreme caution when boating and ensure all activities comply with local regulations.

Local Wildlife & Pest Control: The Florida Keys are home to various insects (mosquitoes, no-see-ums, termites), reptiles, chickens, Key deer, and other wildlife. While routine pest control is in place, complete elimination is not possible. Guests should take precautions, such as using insect repellent and keeping doors closed, to minimize exposure.

Construction & Renovation Notice: Due to ongoing growth in the Florida Keys, renovations, construction, and road repairs may occur without prior notice. While we strive to provide a peaceful stay, iTrip Key West is not liable for any inconveniences caused by nearby construction.

Photo Disclaimer: All images are for illustrative purposes only. Individual features such as bed sizes, bedding, décor, appliances, colors, and amenities may vary, as these are privately owned homes and updates occur regularly. Lighting conditions and screen settings may also affect how colors appear. Please refer to the written description and reach out with any specific questions or concerns. All furnishings and décor are subject to change at any time.

Security Cameras: For the safety and security of our guests and property, two exterior security cameras monitor the front driveway, and pool. These cameras are for security purposes and only viewable from inside the house.

Property manager

iTrip Vacations Key West
Premier Host
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Amenities

Pool
Kitchen
Washer
Dryer
Pet-friendly
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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 security system

About the area

Summerland Key

Located on the waterfront, this holiday home is in Sugarloaf Shores, a neighbourhood in Summerland Key. Florida Keys Beaches and Coupon Bight Aquatic Preserve reflect the area's natural beauty and area attractions include Wilhelmina Harvey Park and Big Munson Island. Take the opportunity to explore the area for water adventures such as fishing.
Map
Sugarloaf, FL

What's nearby

  • Lower Sugarloaf Sound - 1 min walk - 0.0 km
  • Upper Sugarloaf Sound - 4 min drive - 2.5 km
  • Upper Sugarloaf Key - 6 min drive - 5.7 km
  • Florida Keys Beaches - 12 min drive - 8.1 km
  • Sugarloaf Beach - 13 min drive - 8.6 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 21 min drive

Restaurants

  • ‪Mangrove Mama's - ‬7 min drive
  • ‪Baby's Coffee - ‬4 min drive
  • ‪The Square Grouper Bar & Grill - ‬11 min drive
  • ‪My New Joint - ‬11 min drive
  • ‪South Of The Seven - ‬3 min drive

Frequently asked questions

Does Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and Dog-Friendly Perks! have a pool?

Yes, this property has a pool.

Is Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and Dog-Friendly Perks! pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and Dog-Friendly Perks!?

Check-in begins at 4:00 PM.

What time is check-out at Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and Dog-Friendly Perks!?

Checkout is at 10:00 AM.

Where is Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and Dog-Friendly Perks! located?

Located in Sugarloaf Shores, this holiday home is steps from Lower Sugarloaf Sound and 1.6 mi (2.5 km) from Upper Sugarloaf Sound. Upper Sugarloaf Key and Florida Keys Beaches 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. 12 out of 13 reviews
Rating 8 - Good. 0 out of 13 reviews
Rating 6 - Okay. 1 out of 13 reviews
Rating 4 - Poor. 0 out of 13 reviews
Rating 2 - Terrible. 0 out of 13 reviews

9.8/10

Cleanliness

10/10

Check-in

9.4/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Shelley M.

Paradise Point is Paradise

We are early retirees and this was our first home away from home to get out of the cold North Dakota weather in January. The house and grounds had everything we needed. Our pets Mac & Jack felt at home immediately. We kayaked daily and also used the pool almost every day. Our children were able to come stay with us for a week and enjoy the fun and sun. Thank you Paradise Point for the memories. We will be back.

10/10 Excellent

David G.

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

Outstanding stay at paradise point

High recommend , we will be back for sure , very responsive host/manager and lovely property . Pet friendly and fully fenced . Wonderful views . 5 stars.
Stayed 32 nights in Oct 2024

10/10 Excellent

Emily G.

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

Our 2nd time back to Paradise Point!

Our family enjoyed staying at Paradise Point for a 2nd time! We love the area, fishing, diving and snorkeling. This is a great location and so relaxing!
Stayed 28 nights in Jun 2024

10/10 Excellent

Karla P.

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

An Excellent Property and the Best Vacation

Thank you so much for your hospitality- This was the absolute best vacation for us in all the years we have been enjoying the Keys - Your home is beautiful, and the property management and staff were terrific - We will be back :) Thank you again, Sincerely, Karla
Stayed 28 nights in Feb 2024

10/10 Excellent

Adam T.

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

Paradise Point is on point!!

We were very excited prior to our stay at this property. We typically come down to the keys every year and stay in the upper keys. For this year we thought we would change things up a bit. Upon arrival we were beyond impressed. Home is absolutely beautiful and the property was very clean and well kept. The pool and tiki are great and dock was brand new! Pool was a bit cold for our liking when arriving so we reached out to the management company with immediate response. Could not recommend this place more!! Only thing we will warn is the channels needed to take to get out on the open water on the boat are a bit lengthy and a good quality maps overlay on your navigation system is very important. Overall very pleased with the stay and hope to make it back by this property again in the future!
Stayed 28 nights in Dec 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Savannah B.

Peaceful Paradise

We had so much fun & loved the house! The location was perfect & peaceful. The house had plenty of room for our guests & was clean. Tina did a great job with what we we needed making our stay that much better!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Emily G.

Truly "home away from home"

Paradise Point was a fantastic location for our family!! We stayed for one month and thoroughly enjoyed the house, pool, and dock. It had everything we needed to enjoy our stay. We love the area and we plan to return!!!
Stayed 28 nights in Jun 2023

10/10 Excellent

tom d.

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

Excellent

Everything was awesome!
Stayed 28 nights in May 2023

6/10 Okay

Alan L.

Liked: Cleanliness, check-in, location, listing accuracy
Disliked: Communication

Paradise Point Sugarloaf Key

Loved the home and outside. Only problem was the pool circulation did not work for one week of our stay.
Stayed 28 nights in Feb 2023

10/10 Excellent

James A.

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

Idyllic getaway from the frozen North

We were so happy to have found Paradise Point. It is an ideal location - close enough to enjoy everything that Key West has to offer, and yet just far enough away to provide serenity when wanted. The property itself is located at the end of a spit of land that provides stunning views over the water. The landscaping has been thoughtfully arranged and allows for a good amount of privacy. A few things I’d like to call out: 1. Overall, the house is very well provisioned. Lots of towels and 2 sets of sheets for each of the 4 bedrooms. Having two master bedrooms is a plus - not to mention extensive closet space! The washer and dryer and laundry room set-up was very appreciated! 2. The pots and pans in the kitchen were not left very clean by the previous renters, and I assume not checked by the cleaning service. This was surprising as the rest of the house was well tended. 3. One day about halfway through our stay, the fire alarm low battery beeped - it was very thoughtful to have extra batteries in the kitchen. 4. Having kayaks, paddleboards and bikes at our disposal was a bonus! A minor point - one of the bicycle seats needed to be tightened, and it would be helpful to have a few basic tools available to renters so that minor fixes could be actioned efficiently. 5. There were a few issues with some broken and malfunctioning pool equipment (salt chlorinator/filter/heat pump) that prevented our use of the pool for a few days. Tina from the management company was very responsive to our needs and was wonderful to work with. Paradise Point was a great place to escape the Northeast winter! We spent a blissful month there and hope to return.
Stayed 28 nights in Jan 2022

10/10 Excellent

Dora J.

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

Paradise Found

Great home with all amenities needed for our one month on Sugarloaf. Hope to visit again.
Stayed 31 nights in Nov 2021

10/10 Excellent

Kelsay W.

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

Annual July Family Trip

We visit the Keys with our family & friends each year for the month of July. The house we usually stay in sold, which lead us to finding this gem! The house is very nice, great space, pool is perfect & plenty of room for a large boat to be docked. We are looking forward to visiting this place again very soon!
Stayed 28 nights in Jul 2021

10/10 Excellent

timothy p., chesapeake

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

Amazing Everything!!

Amazing house Amazing view Amazing location Amazing Management Amazing FL keys Wanted to stay forever!
Stayed 28 nights in May 2021

About the host

Hosted by iTrip Vacations Key West

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Premier Host

They consistently provide great experiences for their guests