Sugarloaf Key Vacation Rental

Welcome to "Tropical Serenity in Sugarloaf," a delightful canal front home located in the scenic paradise of Sugarloaf Key. This charming getaway offers you the convenience of easy access to both the Atlantic Ocean and the Gulf of Mexico, making it a haven for water enthusiasts. Relax and rejuvenate by taking a dip in the pool or finding respite in.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Sugarloaf Key

Sugarloaf Key Vacation Rental 5.0 Star Review

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 .......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Sugarloaf Key

Sugarloaf Key Vacation Rental 5.0 Star Review

3 Bedroom / 2 Bath Upstairs
1 King Bed, 2 Queen
Spacious office with open water views
2 Bedroom/ 1 Bath Down
1 King, 2 twin
2 Separate living room areas, up and down, each with large flat screen TV's and DVD players
Large screened porch up and down
Heated Pool w/ outdoor shower and pergola
(**pool heat additional $200 per mo.......read more

5 Bedrooms - Sleeps 8
Vacation Rental Home in Sugarloaf Key

Sugarloaf Key Vacation Rental

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 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 floati.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Sugarloaf Key

Sugarloaf Key Vacation Rental 5.0 Star Review

Welcome to Paradise! This beautiful open water open features panoramic views. 4 bedrooms and 3.5 baths provides tons of indoor living space. Outside entertains even bigger and better! Porches off of every bedroom and a large porch overlooking your own private pool and crystal clear water. This home also features a dock on the canal great for boatin.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Sugarloaf Key

Sugarloaf Key Vacation Rental 5.0 Star Review

‘Ohana House
Nestled in a quiet, friendly Sugarloaf Key (MM17) neighborhood, the ‘Ohana house is equipped with all the amenities needed for the perfect Florida Keys getaway. This house sits on a double lot for great privacy. In addition, there are no residences on the other side of the canal for the entire block which makes the house feel li.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Sugarloaf Key

SUGARLOAF KEY Vacation Rental 5.0 Star Review

The best time of the year to visit us is now!!
The temperature is amazing and the seaweed is at a minimum.

Off the beaten path you will find a unique location and a beach front bungalow with endless unobstructed views of the ocean from every bedroom. Featuring an open family area, full kitchen, deck and its own tiki, excellent for grilli.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in SUGARLOAF KEY

Sugarloaf Key Vacation Rental 4.6 Star Review

Beautiful 3 bedroom 2 bath spacious Caribbean-style waterfront home in Sugarloaf Shores. Complete privacy w/lush landscaped grounds, gated and pool. Large screened in porch to enjoy the outside living. Plenty of space to dock your boat. One property in from open waters.


-Pool Heater charge $125.00 per week
-2 Queen beds
-2 sing.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Sugarloaf Key

Upper Sugarloaf Key Vacation Rental

The best time of the year to visit us is now!!
The temperature is amazing and the seaweed is at a minimum.

One of a kind two bedroom beach bungalow right on the beach, deck with direct ocean views, sandy beach, a tropical ambiance and a family friendly setting that will make you feel like you are in your own private island and where memo.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Upper Sugarloaf Key

Sugarloaf Key Vacation Rental

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 wo.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Sugarloaf Key

Sugarloaf Key Vacation Rental 4.9 Star Review

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 .......read more

3 Bedrooms - Sleeps 10
Vacation Rental Home in Sugarloaf Key

Upper Sugarloaf Key Vacation Rental

Escape to Sugarloaf Key!! Waterfront Home. Enjoy your vacation from this 2 bedroom 2 bath ground level home. You won't want to leave this rental. Endless water views with beautiful SUNRISES . The open floor plan is ideal for entertaining. Sliding glass doors open from the living room to the screen patio so you can enjoy the water views from in.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Upper Sugarloaf Key

Sugarloaf Key Vacation Rental

The best time of the year to visit us is now!!
The temperature is amazing and the seaweed is at a minimum.

Part of the Bungalows at Sugarloaf Beach Collection, The Hammock House features an open family area and three bedrooms, all with ocean views. Our one of a kind master bedroom will not disappoint with mesmerizing ocean views, enjoy t.......read more

3 Bedrooms - Sleeps 10
Vacation Rental Home in Sugarloaf Key

Upper Sugarloaf Key Vacation Rental 4.5 Star Review

Castaway to Sugarloaf Key for a vacation home like no other. This large corner lot 4 bedroom / 3-bathroom home offers unobstructed panoramic views of the Gulf of Mexico.

Surrounded by water as far as the eye can see. Bring your boat and water toys and make Castaway your home away from home.
The homes interior is full of oversized floor.......read more

4 Bedrooms - Sleeps 12
Vacation Rental Home in Upper Sugarloaf Key

Sugarloaf Key Vacation Rental 4.0 Star Review

WE have LOBSTER SEASON July 15 to Aug 15 still available and room for a boat here. 3 foot control depth to the gulf or ocean! This is where you can live the Keys as it should be lived! Mostly ground level expansive 2400 sf home and with only stairs upon entry and down to large living area. Located in Sugarloaf Shores one of the best neighborhoo.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Sugarloaf Key

Upper Sugarloaf Key Vacation Rental 4.3 Star Review

The best time of the year to visit us is now!!
The temperature is amazing and the seaweed is at a minimum.

Our Lighthouse is a 2 bedroom 1 bath loft Bungalow sitting just feet from our private beach. The master bedroom loft is accessed by a spiral stair, and has a beautiful bird’s eye view of the Atlantic Ocean. Our cozy nautical ins.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Upper Sugarloaf Key

SUGARLOAF KEY Vacation Rental 4.1 Star Review

The best time of the year to visit us is now!!
The temperature is amazing and the seaweed is at a minimum.

One of a kind beach house with a private sandy beach, dock and boat dockage . A modern tropical ambiance and a family friendly setting that will make you feel like you are in your own private island. Clear blue Florida Keys waters,.......read more

2 Bedrooms - Sleeps 8
Vacation Rental Home in SUGARLOAF KEY

Upper Sugarloaf Key Vacation Rental 4.8 Star Review

The best time of the year to visit us is now!!
The temperature is amazing and the seaweed is at a minimum.

Enjoy breathtaking vistas of our sandy beach, palm trees and the Atlantic Ocean from this amazing Beach House. As you step inside, you walk into a newly renovated home with a chic island vibe. Enjoy decks on all levels with sweepi.......read more

5 Bedrooms - Sleeps 12
Vacation Rental Home in Upper Sugarloaf Key

Upper Sugarloaf Key Vacation Rental 5.0 Star Review

Kick back, leave it all behind, escape to island style living and enjoy this private secluded ocean front estate with breathtaking open water views from every room. The estate boasts meticulously maintained four bedrooms, perfect for the entire family. Well-appointed chef’s kitchen, oasis infinity edge pool and spa overlooking the private white s.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Upper Sugarloaf Key

Sugarloaf Key Vacation Rental

Welcome to Tiki Palms!

Your tropical Keys paradise awaits! Enjoy water views and swaying palm trees while relaxing under the tiki with your favorite cocktail. Cool off in your private pool or take the boat out for the world famous fishing that is only minutes away. There is plenty to do at this house, but if you want to explore the Keys, you.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Sugarloaf Key

Sugarloaf Key Vacation Rental 4.9 Star Review

Villa of the Setting Sun

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'

Recline with a beverage on your own private beach, or take a dip in the private heated pool with a view. You've just arrived at this beautiful home by the sea, surrounded by .......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Sugarloaf Key

Sugarloaf Key Vacation Rental 4.9 Star Review

Lush, tropical home!

Located in upscale South Point, overlooking Sugarloaf Sound and just 12 miles from Key West, this beautiful home offers you a totally tropical experience. From the Tommy Bahama inspired interior furnishings to the spectacular foliage that graces every view, this home is a visual delight. The open floor plan and soaring.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Sugarloaf Key