Sugarloaf Key Holiday Rentals

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Holiday Rentals in Sugarloaf Key

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very good, (306)
"We had a nice stay. The property was in a great location."
The price is NZ$489
includes taxes & fees
24 Aug - 25 Aug
Hyatt Vacation Club at Sunset Harbor, Key West

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (250)
"I love ❤️ this place "
Old Wooden Bridge Resort and Marina

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (158)
"Such a unique stay and affordable!"
The price is NZ$390
includes taxes & fees
31 July - 1 Aug
Aqua Lodges at Hurricane Hole Marina

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (391)
"this was exactly as advertised and close to all the action"
The price is NZ$370
includes taxes & fees
3 Aug - 4 Aug
Steps from Duval, Pool on Site & Bikes Included!

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

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 NZ$1,389
includes taxes & fees
18 Aug - 19 Aug
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, (131)
"Cute little cottage perfect for my wife and I. Location is ideal for those who want to be in the heart of old town , only a block from Duval and within a stone’s throw of several great places to get drinks or food. The home is older , but was clean and comfortable. We had to reach out to the owners for two small issues which were addressed very quickly. "
Heart of Downtown Key West Cottage With Off-Street Parking

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

9.6 out of 10, Exceptional, (136)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great getaway, far enough away from noise, but close enough to enjoy all Key West has to offer. Place was just what we were looking for."
The price is NZ$408
includes taxes & fees
3 Aug - 4 Aug
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

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

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!

Living the Dream Key West Style

10.0 out of 10, Exceptional, (19)
"Great hosts and great accommodations!"
The price is NZ$564
includes taxes & fees
2 Aug - 3 Aug
Living the Dream Key West Style

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 NZ$446
includes taxes & fees
27 July - 28 July
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

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

9.8 out of 10, Exceptional, (11)
"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 NZ$711
includes taxes & fees
3 Aug - 4 Aug
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!

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

10.0 out of 10, Exceptional, (16)
"The Osprey Unit was terrific! Great location, clean, and most of all- the staff was incredibly kind and helpful."
The price is NZ$502
includes taxes & fees
30 July - 31 July
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

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

9.2 out of 10, Wonderful, (5)
"The units were perfect and the customer service was amazing. "
The price is NZ$1,533
includes taxes & fees
4 Aug - 5 Aug
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking

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 NZ$460
includes taxes & fees
27 July - 28 July
Scott's Cottage - Truman @ Duval | Perfect Location! Ideal for Solos &Couples

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

9.6 out of 10, Exceptional, (138)
"Very clean, great location and wonderful amenities!"
The price is NZ$407
includes taxes & fees
28 July - 29 July
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

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 NZ$496
includes taxes & fees
27 July - 28 July
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool

9.2 out of 10, Wonderful, (10)
"Great time staying there "
The price is NZ$402
includes taxes & fees
4 Aug - 5 Aug
WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool

JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!

9.6 out of 10, Exceptional, (161)
"Clean, comfortable and close to everything fun! "
JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!
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 holiday rentals in Sugarloaf Key?

Yes, there are holiday rentals close to the most popular sights in Sugarloaf Key, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Sugarloaf Key has a good selection of bars.

What are some of the best holiday rentals that Sugarloaf Key has to offer?

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

How many holiday rentals are there in Sugarloaf Key?

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

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 holiday rental in Sugarloaf Key like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sugarloaf Key. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a small group gathering.