Entire home
Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and Dog-Friendly Perks!
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Reviews
9.8 out of 10, Loved by Guests
Top 10% based on
4 bedrooms3+ bathroomsSleeps 102668 sq ft
Popular amenities
Explore the area

Sugarloaf, FL
- Place, Lower Sugarloaf Sound1 min walk
- Place, Upper Sugarloaf Sound3 min drive
- Place, Florida Keys Beaches9 min drive
- Airport, Key West, FL (EYW-Key West Intl.)27 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:
- 37' Private Dockage (boat lift not available for guest use)
- Fish Cleaning Station with Lights and Water
- Heated Saltwater Pool
- Tiki & Outdoor Seating
- Keurig, Drip Coffee Maker, Toaster, Blender
- Propane BBQ Grill
- Corn Hole Boards and Bags
- Horseshoe Pits and Horseshoes
- 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 a $10/night pet fee. To help maintain a safe and welcoming environment for all, we require every guest to submit pet or assistance animal information through BetterPet Passport. Guests will simply submit "household pet" information, request an accommodation for an assistance animal, or confirm they are not bringing a pet/animal. It's free, and only requires creating an account if you're bringing a pet or animal. After booking, you'll receive a link to complete the process.
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.
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:
- 37' Private Dockage (boat lift not available for guest use)
- Fish Cleaning Station with Lights and Water
- Heated Saltwater Pool
- Tiki & Outdoor Seating
- Keurig, Drip Coffee Maker, Toaster, Blender
- Propane BBQ Grill
- Corn Hole Boards and Bags
- Horseshoe Pits and Horseshoes
- 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 a $10/night pet fee. To help maintain a safe and welcoming environment for all, we require every guest to submit pet or assistance animal information through BetterPet Passport. Guests will simply submit "household pet" information, request an accommodation for an assistance animal, or confirm they are not bringing a pet/animal. It's free, and only requires creating an account if you're bringing a pet or animal. After booking, you'll receive a link to complete the process.
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.
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- Washing machine
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10.0 out of 10, Exceptional, (206 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
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 no 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 Lower Sugarloaf Sound reflect the area's natural beauty and area attractions include Wilhelmina Harvey Park and Big Munson Island.

Sugarloaf, FL
What's nearby
- Lower Sugarloaf Sound - 1 min walk - 0.0 km
- Upper Sugarloaf Sound - 3 min drive - 2.4 km
- Florida Keys Beaches - 9 min drive - 8.0 km
- Duval Street - 35 min drive - 33.9 km
- Southernmost Point - 37 min drive - 34.2 km
Getting around
Restaurants
- Circle K - 10 min drive
- Baby's Coffee - 4 min drive
- Morning Joint - 11 min drive
- Broil - 9 min drive
- Mangrove Mama's - 7 min drive
Frequently asked questions
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 window10/10
Cleanliness
10/10
Check-in
9.6/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
Verified
30 Jun, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 28 nights in Jun 2024
Verified
10/10 Excellent
David G.
13 Dec, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Outstanding stay at paradise point
David G.
Stayed 32 nights in Oct 2024
From a partner site
10/10 Excellent
Emily G.
25 Jul, 2023
Truly "home away from home"
Emily G.
Stayed 28 nights in Jun 2023
Verified
10/10 Excellent
timothy p.
29 May, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing Everything!!
timothy p.
Stayed 28 nights in May 2021
From a partner site
10/10 Excellent
Savannah B.
28 Aug, 2023
Peaceful Paradise
Savannah B.
Verified
10/10 Excellent
tom d.
26 Jun, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent
tom d.
Stayed 28 nights in May 2023
Verified
10/10 Excellent
Karla P.
24 Mar, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
An Excellent Property and the Best Vacation
Karla P.
Stayed 28 nights in Feb 2024
From a partner site
10/10 Excellent
Shelley M.
7 Feb, 2025
Paradise Point is Paradise
Shelley M.
Verified
6/10 Okay
Alan L.
2 Mar, 2023
Liked: Cleanliness, check-in, location, listing accuracy
Disliked: Communication
Paradise Point Sugarloaf Key
Alan L.
Stayed 28 nights in Feb 2023
Verified
10/10 Excellent
Adam T.
19 Jan, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Paradise Point is on point!!
Adam T.
Stayed 28 nights in Dec 2023
Verified
10/10 Excellent
James A.
11 Feb, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Idyllic getaway from the frozen North
James A.
Stayed 28 nights in Jan 2022
Verified
10/10 Excellent
Dora J.
31 Dec, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Paradise Found
Dora J.
Stayed 31 nights in Nov 2021
Verified
10/10 Excellent
Kelsay W.
10 Aug, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Annual July Family Trip
Kelsay W.
Stayed 28 nights in Jul 2021
Verified
10/10 Excellent
Kassondra c.
30 Jul, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Kassondra c.
Stayed 28 nights in May 2025
About the host
Hosted by iTrip Vacations Key West
Premier Host
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