Vacation Rentals in Sugarloaf Key, Florida.

Lush, tropical open water home that offers everything you want for a fabulous Keys vacation. Enjoy your own private beach with swimming, snorkeling, and fishing on the canal side, as well as a dock for your boat. Afterwards, you can rinse off in one of the two outdoor showers, and then gather for cocktails on the beach or the front patio which is surrounded by lush foliage. You can even shoot hoops on the basketball court!

The interior boasts beautiful views from every room, with an upst.......

10.0 Star Review

4 Bedrooms - Sleeps 8
Sugarloaf Key Vacation Rental

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!

Life in the Florida Keys is all about spending time outdoors, indulging in the things you love with the ones you love; and BLUE HORIZON is the perfect vacation home to experience Keys living for yourself. Whether your ideal day is floating around the large pool with a cold drink in hand, cruising the waters of the Lower Keys in your boat, or gathering your loved ones around the firepi.......

4 Bedrooms - Sleeps 8
Sugarloaf Key Vacation Rental
Pets Allowed

Casa Verde - the open water views from every room of this gorgeous home will leave you breathless! This is truly an escape from the hustle bustle.

Located on direct open water in a very quiet neighborhood, you can enjoy many resort activities - without ever leaving home! Snorkel, fish, or swim right off the deck, in the warm, crystal-clear waters of the Florida Keys. Or, you may choose to lounge or swim in the waterfront, 30-foot by 15-foot, heated pool. The view from the screened in por.......

9.8 Star Review

3 Bedrooms - Sleeps 10
Sugarloaf Key Vacation Rental

The best time to visit is right now — and yes, we’re pet friendly!

Welcome to The Hammock House, part of the exclusive and private Beach Houses Key West Collection— a serene escape with panoramic ocean views from every room.

This three-bedroom retreat offers a bright, open-concept living space and a show-stopping master suite where you can wake up to stunning sunrises from your king-sized bed. The fully stocked kitchen is perfect for crafting your favorite meals, island-style.......

8.0 Star Review

3 Bedrooms - Sleeps 8
Sugarloaf Key Vacation Rental
Pets Allowed

Mi Azucar is one of five secluded bungalows nestled within a private 10-acre oceanfront paradise. This unique property offers nearly 1,000 feet of private sandy beach, along with two docks extending 450 feet into the water—perfect for docking boats or jet skis, or enjoying excellent fishing right from the pier.

At the heart of the resort is our signature amenity: a grotto-style pool inspired by the natural coral coasts of South Florida. The pool area features two pools—a smaller, rela.......

10.0 Star Review

2 Bedrooms - Sleeps 8
Sugarloaf Key Vacation Rental

One of a kind beach house with a private sandy beach, dock and boat dockage . Featuring a tropical ambiance and a family friendly setting that will make you feel like you are in your own private island. Gorgeous ocean views. natural Florida Keys private beach, great for swimming, snorkeling, kayaking, paddle boarding or just reading a book by a palm tree.

Also great for weddings, corporate retreats, family reunions, and romantic getaways (venue fee applies).

Our guests are our to.......

8.4 Star Review

2 Bedrooms - Sleeps 8
SUGARLOAF KEY Vacation Rental
Pets Allowed

Escape to a beachfront oasis where the beauty of the ocean meets luxury and comfort. This stunning beach house offers breathtaking views of powdery sand, swaying palms, and endless blue waters. Step inside to a newly renovated haven, designed with a chic island vibe that blends relaxation with modern elegance. Lounge on spacious decks at every level, soaking in panoramic ocean views and the soothing sound of waves. Whether you`re sipping your morning coffee at sunrise or enjoying a starlit eveni.......

9.8 Star Review

5 Bedrooms - Sleeps 12
Sugarloaf Key Vacation Rental
Pets Allowed

Welcome to this delightful house in Sugarloaf Key. With three bedrooms featuring two king beds and one queen bed, you will find plenty of space to relax. The Main Suite is situated on the opposite side from the other rooms and boasts a huge walk-in closet, private toilet, steam shower, over-sized claw foot tub and french doors exiting onto a private balcony. All rooms are fully appointed and ready for visitors.
The custom kitchen is decked in copper with a convection stove-top. All applianc.......

3 Bedrooms - Sleeps 6
Sugarloaf Key Vacation Rental

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



Welcome to Ocean Acres, a truly rare and private oceanfront retreat set on 20 expansive acres on Sugarloaf Key. Offering unmatched space, serenity, and direct views of the Atlantic Ocean, this 3-bedroom estate is the perfect escape for those seeking both luxury and seclusion in the Florida Keys.



Surrounded by natural beauty, Ocean .......

3 Bedrooms - Sleeps 8
Sugarloaf Key Vacation Rental
Pets Allowed

Welcome to a rare luxury oceanfront estate in the Florida Keys, offering total privacy, panoramic water views, and resort-style amenities, just 18 miles from Key West. This exclusive waterfront compound is more than a vacation home—it's a private destination designed for luxury travelers, milestone celebrations, and unforgettable coastal escapes. Whether you're searching for a Key West luxury vacation rental, a private beachfront villa, or an event-ready oceanfront estate, this one-of-a-kind p.......

9.4 Star Review

4 Bedrooms - Sleeps 8
Sugarloaf Key Vacation Rental

Summary:
Loggerhead Lagoon is a stunning, tropically themed, 3-bed 2-bath home located on a large private lot that offers covered parking, a boat dock, and direct access to the Gulf of Mexico.

This rare find boasts a lush outdoor area, full of beautiful palms, sun loungers, and tons of FL sunshine! Located in Sugarloaf Key, 19 miles from Key West and world famous Duval Street.

Looking to unwind? You won't find a better option for your month-long (or more) stay in paradise

3 Bedrooms - Sleeps 8
Sugarloaf Key Vacation Rental
Pets Allowed

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

Escape to the Green Turtle Oasis, a haven nestled on Sugarloaf Key where your tropical paradise dreams come true!

Revel in mesmerizing water vistas and the gentle rustling of palm trees as you unwind beneath the charming tiki hut with your preferred libation. Embrace refreshing dips in your secluded pool or set sail on your boat for unparalleled world.......

4 Bedrooms - Sleeps 10
Sugarloaf Key Vacation Rental
Pets Allowed

RARE SINGLE STORY 2500 sq. ft Canal Front Home with gorgeous POOL!
Relax in this spacious and serene space with 3 large bedrooms with 3 en-suite baths, plus additional full bath near pool. Kayaks, paddle boards, ping pong, bicycles and pool table! 8 guests only, 6 adults & 2 children. 28 night minimum rental . 12 miles north of Key West. Located on a crystal clear 70’ wide canal. Easy access to ocean and Gulf -Snipes & Marvin sandbars! Park your boat in your backyard! We allow boats up 26.......

1 Bedrooms - Sleeps 8
Sugarloaf Key Vacation Rental

Welcome to Reel Wahoo — your private slice of paradise in the heart of beautiful Sugarloaf Key. This newly updated canal-front retreat offers 100 feet of waterfront, a private pool, exceptional boating access, and all the comforts you need for the ultimate Florida Keys getaway.
Perfectly situated on a deep-water boating canal with approximately 3' draft and space for up to a 35-foot boat, Reel Wahoo is a dream destination for boaters, anglers, and outdoor lovers alike. Spend your days on th.......

3 Bedrooms - Sleeps 6
Sugarloaf Key Vacation Rental
Pets Allowed

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!

Drop anchor and let the good life begin. Situated on the waterfront shores of Sugarloaf Key, THE COMMODORE'S REFUGE puts you in the heart of the Lower Keys — a quieter, more authentic slice of island life. With direct water access, serious dock space, private tiki hut, a sparkling pool, and a private pickleball court, this is the kind of place where your only hard decision is whethe.......

4 Bedrooms - Sleeps 10
Sugarloaf Key Vacation Rental
Pets Allowed

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 perf.......

10.0 Star Review

4 Bedrooms - Sleeps 12
Sugarloaf Key Vacation Rental
Pets Allowed

Spectacular Sunset View Waterfront Home w/ Dock, Tiki Hut & More!
Experience the ultimate Florida Keys getaway at this 2-bedroom, 2-bath waterfront retreat on Sugarloaf Key—designed to comfortably accommodate up to 6 guests. Set on an oversized, private point lot with over 280 feet of open-water frontage, this home offers year-round panoramic sunset views that will take your breath away.
Inside, the spacious great room features wall-to-wall water views and a bright, open kitchen, perfect.......

2 Bedrooms - Sleeps 6
Sugarloaf Key Vacation Rental
Pets Allowed