Amazing Waterfront Home with Fabulous Pool and Sunset Views
Welcome to the Sugarloaf Guest House, the perfect Florida Keys Island Getaway. As you enter the gate to this charming seaside cottage, you will experience its charm and relaxing vibes. A gorgeous new pool with graceful waterfalls make it the perfect getaway!! Fully renovated, you’ll find all you need to enjoy a piece of paradise, on one of the most desirable keys-Sugarloaf. This house has it all and is beautifully furnished, from a well-equipped kitchen to 3 lovely bedrooms with 3 ensuite baths. After a sun soaked day outdoors, a convenient outdoor shower is available under the swaying palms. A cute bunk room is perfect for visiting children. For grandparents and older visitors, this one story home makes staying here a breeze. Portable ramps are available for wheelchair access. (For more info contact rental agent.) An open living area opens onto an enclosed porch overlooking the water where you can enjoy coffee or cocktails with a beautiful bay view. Sunsets are fabulous here and can be enjoyed inside or out and now especially as you relax in your own tropical pool overlooking paradise.
Located on a deep canal and open bay, the house offers swimming, snorkeling, kayaking, or fishing right off the dock. Outside, is a covered bar that overlooks horseshoe pits and a lovely garden. Bikes are also available and the Sugarloaf neighborhood has a wonderful bike and walking path. There are also extended bike paths in the area. With its excellent location, serious fishermen can jump in their boats and in minutes be fishing in the backcountry (Gulf) or the Atlantic Ocean. Nearby Sugarloaf Marina has all your fishing needs, including rentals (and ice cream too).
This beautiful home is located on the ocean side of US1 and is only minutes from Key West and all it offers-shopping, fine dining, and entertainment. Available for Lobster Season and has room for a boat.
For those with a larger family and need more room we have the perfect solution. The Sugarloaf Guest House becomes the Sugarloaf Family Compound with the house next door which also has a beautiful new pool and lanai area. Through the gate you’ll find another lovely home with 4 Bedrooms and 3.5 Baths. Perfect for in-laws, grandkids, friends and special events. See the Sugarloaf Family Compound for full property details.
swimming
snorkeling
kayaking
Fishing
Bikes
shopping
Fine dining
Entertainment
Canal
Tiki Hut
Fish Cleaning Station
BBQ (gas)
No Booking or Service Fees
Save up to 25% compared to other websites - no hidden costs.
Connect Directly with Hosts
Book with confidence and get the best rates.
Florida's #1 Vacation Rental Site
Trusted by millions - your go-to for the perfect Florida getaway.
| Rate Period | Nightly | Weekend Night | Weekly | Monthly | Min Stay |
|---|---|---|---|---|---|
May 01 - Nov 30 2025 | $11,850 | 28 nights | |||
Dec 01 2025 - Apr 30 2026 | $11,850 | 28 nights | |||
May 01 - Nov 30 2026 | $11,850 | 28 nights | |||
Jul 01 - Aug 31 2026 | $11,850 | 28 nights |
Fees:
Notes:
Deposits and subsequent payments are accepted in the form of personal checks. 50% of remaining balance is due 60 days prior to arrival. The full balance must be received 30 days prior to arrival. Please note that rates are subject to change without notice and that seasonal, holiday and special events may be higher.
Regarding cancellations: 60 days prior to arrival, deposits will be refunded in full, less a $75 administration fee – this fee will be retained. If the cancellation occurs within 59 days, any and all deposits and or rents will be forfeited.
Last updated on November 05, 2025