Sugarloaf Key Vacation Rentals

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Jul 30 - Jul 31
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Jul 31 - Aug 1
This weekend
Aug 1 - Aug 3
Next weekend
Aug 8 - Aug 10

Vacation Rentals in Sugarloaf Key

Hyatt Vacation Club at Sunset Harbor, Key West
Surrounded by lush tropical vegetation and a serene waterfall, this tranquil oasis offers a peaceful escape with a mountain view.

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."
$262 nightly
The price is $295
Aug 24 - Aug 25
Total includes taxes and fees
Hyatt Vacation Club at Sunset Harbor, Key West
Old Wooden Bridge Resort and Marina
Relax in a cozy seating area with a sofa and small table, and enjoy a fully equipped kitchenette with microwave, coffee maker, and refrigerator.

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (252)
"I love ❤️ this place "
$238 nightly
The price is $268
Aug 12 - Aug 13
Total includes taxes and fees
Old Wooden Bridge Resort and Marina
Aqua Lodges at Hurricane Hole Marina
Relax by the marina with a casual meal or snack at this tranquil waterfront spot.

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (161)
"It was a great place to stay! There were a few bugs in the aqua Lodge in the kitchen area, but other than that awesome place!"
$229 nightly
The price is $258
Aug 11 - Aug 12
Total includes taxes and fees
Aqua Lodges at Hurricane Hole Marina
Steps from Duval, Pool on Site & Bikes Included!
Bicycles line the quiet street, surrounded by lush greenery and a charming white building with green shutters.

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"
$199 nightly
The price is $222
Aug 3 - Aug 4
Total includes taxes and fees
Steps from Duval, Pool on Site & Bikes Included!
Coconut Mallory Resort And Marina By Kees Vacations
Relax in a serene outdoor oasis surrounded by lush greenery and a wooden pergola.

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
Guests can enjoy stunning marina views from the hotel's elevated balconies.

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."
$667 nightly
The price is $740
Aug 11 - Aug 12
Total includes taxes and fees
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Heart of Downtown Key West Cottage With Off-Street Parking
Cozy home with a front porch and garden, perfect for relaxation.

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
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!
Escape to a secluded beach paradise with tall palm trees and soft sandy shores.

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."
$220 nightly
The price is $245
Aug 3 - Aug 4
Total includes taxes and fees
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!
Old Florida Style, wrap around porch, boat basin for dockage, open water
Relax on the waterfront with Adirondack chairs and a small dining table.

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
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Comfortable bedroom with two beds, a wall-mounted TV, and a ceiling fan.

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."
$302 nightly
The price is $332
Aug 12 - Aug 13
Total includes taxes and fees
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
Surrounded by lush greenery, this charming home offers a serene escape with a front porch and staircase.

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!
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!
Enjoy the serene view of the calm body of water from the comfort of your room.

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. "
$241 nightly
The price is $268
Aug 3 - Aug 4
Total includes taxes and fees
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!
Welcome to this charming home with a beautifully maintained garden and a cozy porch.

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 "
$374 nightly
The price is $412
Aug 3 - Aug 4
Total includes taxes and fees
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Relax in a serene oasis with a hot tub surrounded by lush tropical plants and a wooden fence.

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

10.0 out of 10, Exceptional, (18)
"Will stay here again "
$299 nightly
The price is $329
Aug 3 - Aug 4
Total includes taxes and fees
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Enjoy a serene outdoor space surrounded by lush plants and a charming seating area.

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."
$299 nightly
The price is $329
Aug 3 - Aug 4
Total includes taxes and fees
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking
Relax in style with a hot tub and outdoor seating area, perfect for social gatherings or a peaceful retreat.

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. "
$770 nightly
The price is $848
Aug 31 - Sep 1
Total includes taxes and fees
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking
Resort View 1BR Suite
Relax on the beach with sun loungers aligned along the shoreline, surrounded by palm trees and a tranquil atmosphere.

Resort View 1BR Suite

2.0 star property
10.0 out of 10, Exceptional, (2)
"Cleanliness "
$303 nightly
The price is $341
Aug 26 - Aug 27
Total includes taxes and fees
Resort View 1BR Suite
Scott's Cottage - Truman @ Duval | Perfect Location! Ideal for Solos &Couples
Situated in a sunny location, this charming building features a gabled roof and white exterior, complete with shutters and a covered outdoor seating area perfect for dining or socializing.

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!"
$268 nightly
The price is $295
Aug 5 - Aug 6
Total includes taxes and fees
Scott's Cottage - Truman @ Duval | Perfect Location! Ideal for Solos &Couples
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!
Escape to a serene beach setting surrounded by tall palm trees and a vast expanse of sandy shores.

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

9.6 out of 10, Exceptional, (141)
"Very clean, great location and wonderful amenities!"
$222 nightly
The price is $246
Aug 6 - Aug 7
Total includes taxes and fees
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!
GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor Suite w/Shared Pool!
Beach nearby

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

9.2 out of 10, Wonderful, (15)
"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!"
$273 nightly
The price is $303
Aug 4 - Aug 5
Total includes taxes and fees
GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor Suite w/Shared Pool!
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

The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

10/10 Excellent
"Nice place. Friendly staff. Nice breakfast. Nice pools and outdoor area. Room was basic, but clean and the ac worked good. I was in an attic room, very small but cheap!!"
thomas 4-night trip
Posted 6 hours ago
The Southernmost Inn - Adults Only

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.