Holiday Rentals in Sugarloaf Key

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Holiday Rentals in Sugarloaf Key

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (256)
"River boat houses, pool, kayak rentals. "
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, (310)
"EXCELENT LOCATION AND SUNSET VIEW"
The price is €261
includes taxes & fees
2 Sept - 3 Sept
Hyatt Vacation Club at Sunset Harbor, Key West

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (161)
"The stay was beautiful "
The price is €203
includes taxes & fees
19 Aug - 20 Aug
Aqua Lodges at Hurricane Hole Marina

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (397)
"this was exactly as advertised and close to all the action"
The price is €200
includes taxes & fees
21 Aug - 22 Aug
Steps from Duval, Pool on Site & Bikes Included!

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

9.6 out of 10, Exceptional, (139)
"This property was great, it had everything needed, extremely clean and walking distance to Davual st.The pool area is wonderful and it was the perfect temperature!Would highly recommend."
The price is €206
includes taxes & fees
20 Aug - 21 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)
"Took the team down to the keys for a little R&R"
The price is €612
includes taxes & fees
19 Aug - 20 Aug
Old Florida Style, wrap around porch, boat basin for dockage, open water

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

9.4 out of 10, Exceptional, (11)
"Great time staying there "
The price is €199
includes taxes & fees
19 Aug - 20 Aug
WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & 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 €282
includes taxes & fees
19 Aug - 20 Aug
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Claude Monet Suite | Cozy Studio with Pool & Patio Access!

9.4 out of 10, Exceptional, (20)
"Great location. Everything was perfect!"
The price is €237
includes taxes & fees
19 Aug - 20 Aug
Claude Monet Suite | Cozy Studio with Pool & Patio Access!

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (133)
"May not be a better location"
Heart of Downtown Key West Cottage With Off-Street Parking

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

9.6 out of 10, Exceptional, (14)
"Great place to stay! Very clean and steps to Duval Ave."
The price is €355
includes taxes & fees
19 Aug - 20 Aug
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!

GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor Suite w/Shared Pool!

9.2 out of 10, Wonderful, (16)
"We had a great time at this property. The owner is super attentive to detail and immediately responds to any questions or requests. You can really tell that they CARE about their property and guests. Property is well cared for and charming. Highly recommend!"
The price is €246
includes taxes & fees
20 Aug - 21 Aug
GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor Suite w/Shared Pool!

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

9.8 out of 10, Exceptional, (296)
"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 €709
includes taxes & fees
31 Aug - 1 Sept
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (179)
"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!

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

9.6 out of 10, Exceptional, (141)
"We had a great stay places is amazing"
The price is €201
includes taxes & fees
19 Aug - 20 Aug
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

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

10.0 out of 10, Exceptional, (19)
"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 location and very nice room"
The price is €282
includes taxes & fees
19 Aug - 20 Aug
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

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

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

10.0 out of 10, Exceptional, (2)
"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!

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

8.8 out of 10, Excellent, (55)
"Peaceful and paradise!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
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.