Sugarloaf Key Vacation Rentals

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Vacation Rentals in Sugarloaf Key

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (253)
"I love ❤️ this place "
The price is CA $144
CA $356 total
includes taxes & fees
Sep 1 - Sep 2
Old Wooden Bridge Resort and Marina

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very good, (307)
"We had a nice stay. The property was in a great location."
The price is CA $311
CA $389 total
includes taxes & fees
Aug 10 - Aug 11
Hyatt Vacation Club at Sunset Harbor, Key West

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (160)
"The stay was beautiful "
The price is CA $81
CA $323 total
includes taxes & fees
Aug 11 - Aug 12
Aqua Lodges at Hurricane Hole Marina

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (818)
"Great place really nice rooms"
Coconut Mallory Resort And Marina By Kees Vacations

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (18)
"We had a wonderful stay here with our kids. Can’t beat the location."
The price is CA $134
CA $458 total
includes taxes & fees
Aug 12 - Aug 13
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (393)
"this was exactly as advertised and close to all the action"
The price is CA $123
CA $314 total
includes taxes & fees
Aug 12 - Aug 13
Steps from Duval, Pool on Site & Bikes Included!

Old Florida Style, wrap around porch, boat basin for dockage, open water

9.6 out of 10, Exceptional, (77)
"Very nice place to stay. Quick and efficient communication with host! Seemless check in and check out process. "
The price is CA $414
CA $962 total
includes taxes & fees
Aug 18 - Aug 19
Old Florida Style, wrap around porch, boat basin for dockage, open water

COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

9.6 out of 10, Exceptional, (137)
"We stayed in the Cohiba and it was so cute! Felt private and to ourselves. Everyone we met on site was so friendly. Having the pool on property and private was such a blessing. There was an incident in the main house bathroom that was quickly responded to by property management. Would stay again! Thank you! "
The price is CA $136
CA $347 total
includes taxes & fees
Aug 4 - Aug 5
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

7.4 out of 10, Good, (10)
"We were here celebrating 55th birthdays and had a blast. Great location and communication with Capt. We will return for sure, hoping to make it an annual get together."
The price is CA $385
CA $1,020 total
includes taxes & fees
Aug 12 - Aug 13
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (133)
"We very much enjoyed our stay at the cottage. Everything you need for a comfortable stay and a location that can't be beat. Also, the off-street parking was a time, money, and sanity saver. Thanks to Marcela and family!"
Heart of Downtown Key West Cottage With Off-Street Parking

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (178)
"Place is centrally located which is ideal for walking from place to place. House was very clean and had everything needed for my time spent there"
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!

9.6 out of 10, Exceptional, (13)
"Property was cute ... cleanly and in a great location for what we were looking for. Would definitely recommend to anyone and stay there again ourselves "
The price is CA $181
CA $583 total
includes taxes & fees
Aug 4 - Aug 5
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!

HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

9.6 out of 10, Exceptional, (141)
"Very clean, great location and wonderful amenities!"
The price is CA $132
CA $342 total
includes taxes & fees
Aug 6 - Aug 7
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!

10.0 out of 10, Exceptional, (1)
"We absolutely loved our stay at the Delaney house. The pool and outdoor area were lovely and private, the location was excellent and walking distance from fun Key West spots but quiet and cozy, and the beds were all incredibly comfortable! Would definitely recommend this place to everyone!"
DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (19)
"The Osprey Unit was terrific! Great location, clean, and most of all- the staff was incredibly kind and helpful."
The price is CA $134
CA $461 total
includes taxes & fees
Aug 4 - Aug 5
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

10.0 out of 10, Exceptional, (7)
"The ideal getaway, I brought a grill and a pan and did all the cooking outside on the deck. Took paddle boards through mangrove tunnels and saw tons of fish. Had a baby sea turtle swim up to the boat. "
The price is CA $223
CA $372 total
includes taxes & fees
Aug 7 - Aug 8
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

Scott's Cottage - Truman @ Duval | Perfect Location! Ideal for Solos &Couples

10.0 out of 10, Exceptional, (8)
"Great location, friendly and helpful hosts, clean, perfect spot for my solo trip!"
The price is CA $135
CA $407 total
includes taxes & fees
Aug 5 - Aug 6
Scott's Cottage - Truman @ Duval | Perfect Location! Ideal for Solos &Couples

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

10.0 out of 10, Exceptional, (18)
"Will stay here again "
The price is CA $134
CA $461 total
includes taxes & fees
Aug 4 - Aug 5
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

9.8 out of 10, Exceptional, (295)
"Excellent accommodations, gorgeous condon"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking

9.6 out of 10, Exceptional, (8)
"The units were perfect and the customer service was amazing. "
The price is CA $372
CA $1,168 total
includes taxes & fees
Aug 31 - Sep 1
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Sugarloaf Key Hotel Reviews

Frequently asked questions

Can I find vacation rentals in Sugarloaf Key?

Yes, we offer vacation rentals near popular sights in Sugarloaf Key, or you can go with a secluded option if you want a relaxing place to stay. Our travelers say Sugarloaf Key has a good selection of bars.

What's the top vacation rental in Sugarloaf Key?

Poinciana House in Key West: This vacation home rental outside Sugarloaf Key is located near the beach and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Sugarloaf Key?

Choose from 51 Expedia vacation rentals in Sugarloaf Key for a memorable vacation.

What’s there to see and do in Sugarloaf Key?

Florida Keys Beaches and Sugarloaf Beach are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Upper Sugarloaf Key and Saddlebunch Keys.

What’s a vacation rental in Sugarloaf Key like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Sugarloaf Key. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for family trips or small group gatherings.