Entire home
$and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Private Pool, Dock & Pet-Friendly!
Holiday home in Summerland Key with private pool and kitchen
Photo gallery for $and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Private Pool, Dock & Pet-Friendly!





Reviews
10 out of 10
Exceptional
4 bedrooms 4 bathrooms Sleeps 12 273.4 sq m
Popular amenities
Explore the area

Sugarloaf Key, FL
- Place, Florida Keys Beaches5 min drive
- Place, Sugarloaf Beach6 min drive
- Place, Upper Sugarloaf Key8 min drive
- Airport, Key West, FL (EYW-Key West Intl.)32 min drive
Rooms & beds
4 bedrooms (sleeps 12)
Bedroom 1
1 King Bed
Bedroom 2
1 King Bed
Bedroom 3
1 King Bed
Bedroom 4
1 Queen Bed
Flex Room
1 Queen Bed and 1 Single Bunk Bed
4 bathrooms
Bathroom 1
Bathtub · Toilet · Shower only
Bathroom 2
Toilet · Shower only
Bathroom 3
Toilet · Shower only
Bathroom 4
Toilet · Shower only
Spaces
Deck or patio
Kitchen
About this property
$and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Private Pool, Dock & Pet-Friendly!
County zoning requires a minimum rental period of 28 nights, no exceptions can be made. Please review additional policies below.
Welcome to $and D0llar$, your ultimate waterfront escape in the heart of the Florida Keys! This extraordinary property promises an unforgettable retreat, where every moment is adorned with the beauty of the open water and the charm of tropical living. Step onto the second-floor deck and immerse yourself in the magic of breathtaking sunset views, a perfect backdrop for sipping cocktails and creating timeless memories with loved ones. The backyard of $and D0llar$ transforms into a tropical oasis, complete with a heated saltwater pool where laughter echoes as children splash about, and the dock becomes a haven for fishing enthusiasts. Whether you're an avid angler or just seeking tranquility by the water, this retreat caters to every whim. For those with a passion for boating, the possibilities are endless. Embark on thrilling adventures to the backcountry sandbars or venture out to the Atlantic for world-famous fishing excursions. The waters are your playground, and the experiences are as diverse as the marine life that surrounds you. While $and D0llar$ offers a myriad of activities within arm's reach, the allure of the Florida Keys beckons exploration. Conveniently located just 20 minutes from the vibrant energy of Key West and 45 minutes from the allure of Marathon, you're perfectly positioned to dive into the rich culture, dining, and entertainment the Keys have to offer. $and D0llar$ isn't just a vacation rental; it's a gateway to a world of tropical wonders and endless possibilities.
Sleeps Maximum of 12 Guests:
Bedroom 1 (2nd Floor): King Bed, En-Suite Bathroom, Smart TV (no cable/satellite TV)
Bedroom 2 (2nd Floor): King Bed, Smart TV (no cable/satellite TV)
Bedroom 3 (1st Floor): King Bed, Smart TV (no cable/satellite TV)
Bedroom 4 (1st Floor): Queen Bed, Smart TV (no cable/satellite TV)
Flex Room: Queen Bed, Queen Bunk Beds
Living Room: Sofa, Loveseat, Two Chairs, Smart TV (no cable/satellite TV)
Kitchen: Nicely equipped (all things necessary to prepare and serve a meal)
AMENITIES:
- Saltwater Heated Pool (heated to ~83-87 degrees Nov-Apr)
- 26' of Dockage
- Exterior Elevator
- Fish Cleaning Station W/ Water
- Bait Freezer
- Outdoor Seating
- Propane BBQ Grill
- Parking for a maximum of 4 vehicles (including boat trailers) on the property. RVs may not be parked on the property.
- Linen's and towels provided
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 $10/night 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, three exterior security cameras monitor the front door entry, driveway, and boat dock/lift. These cameras are for security purposes only and do not monitor any private interior or outdoor living spaces.
Welcome to $and D0llar$, your ultimate waterfront escape in the heart of the Florida Keys! This extraordinary property promises an unforgettable retreat, where every moment is adorned with the beauty of the open water and the charm of tropical living. Step onto the second-floor deck and immerse yourself in the magic of breathtaking sunset views, a perfect backdrop for sipping cocktails and creating timeless memories with loved ones. The backyard of $and D0llar$ transforms into a tropical oasis, complete with a heated saltwater pool where laughter echoes as children splash about, and the dock becomes a haven for fishing enthusiasts. Whether you're an avid angler or just seeking tranquility by the water, this retreat caters to every whim. For those with a passion for boating, the possibilities are endless. Embark on thrilling adventures to the backcountry sandbars or venture out to the Atlantic for world-famous fishing excursions. The waters are your playground, and the experiences are as diverse as the marine life that surrounds you. While $and D0llar$ offers a myriad of activities within arm's reach, the allure of the Florida Keys beckons exploration. Conveniently located just 20 minutes from the vibrant energy of Key West and 45 minutes from the allure of Marathon, you're perfectly positioned to dive into the rich culture, dining, and entertainment the Keys have to offer. $and D0llar$ isn't just a vacation rental; it's a gateway to a world of tropical wonders and endless possibilities.
Sleeps Maximum of 12 Guests:
Bedroom 1 (2nd Floor): King Bed, En-Suite Bathroom, Smart TV (no cable/satellite TV)
Bedroom 2 (2nd Floor): King Bed, Smart TV (no cable/satellite TV)
Bedroom 3 (1st Floor): King Bed, Smart TV (no cable/satellite TV)
Bedroom 4 (1st Floor): Queen Bed, Smart TV (no cable/satellite TV)
Flex Room: Queen Bed, Queen Bunk Beds
Living Room: Sofa, Loveseat, Two Chairs, Smart TV (no cable/satellite TV)
Kitchen: Nicely equipped (all things necessary to prepare and serve a meal)
AMENITIES:
- Saltwater Heated Pool (heated to ~83-87 degrees Nov-Apr)
- 26' of Dockage
- Exterior Elevator
- Fish Cleaning Station W/ Water
- Bait Freezer
- Outdoor Seating
- Propane BBQ Grill
- Parking for a maximum of 4 vehicles (including boat trailers) on the property. RVs may not be parked on the property.
- Linen's and towels provided
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 $10/night 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, three exterior security cameras monitor the front door entry, driveway, and boat dock/lift. These cameras are for security purposes only and do not monitor any private interior or outdoor living spaces.
Add dates for prices
Amenities
Pool
Kitchen
Washing machine
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
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 not indicated whether there is a smoke detector on the property
About the area
Summerland Key
Summerland Key is home to this holiday home. Coupon Bight Aquatic Preserve and Lower Sugarloaf Sound reflect the area's natural beauty and area attractions include Wilhelmina Harvey Park and Blue Hole. Big Munson Island and Looe Key National Marine Sanctuary are also worth visiting.

Sugarloaf Key, FL
What's nearby
- Florida Keys Beaches - 5 min drive - 3.0 km
- Sugarloaf Beach - 6 min drive - 3.7 km
- Upper Sugarloaf Key - 8 min drive - 7.2 km
- Boca Chica Nude Beach - 32 min drive - 23.4 km
- Duval Street - 36 min drive - 36.9 km
Getting around
Restaurants
- Baby's Coffee - 7 min drive
- Morning Joint - 13 min drive
- Broil - 11 min drive
- The Bent Prop - 12 min drive
- Square Grouper Bar and Grill - 13 min drive
Frequently asked questions
About the host
Hosted by iTrip Vacations Key West

Premier Host
They consistently provide great experiences for their guests
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