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, (224)
"Very nice and quiet! "
The price is CA $192
CA $354 total
includes taxes & fees
May 6 - May 7
Old Wooden Bridge Resort and Marina

Aqua Lodges at Hurricane Hole Marina

2.0 star property
9.0 out of 10, Wonderful, (134)
"Would definitely stay here again! "
The price is CA $191
CA $447 total
includes taxes & fees
May 31 - Jun 1
Aqua Lodges at Hurricane Hole Marina

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very good, (295)
"We had a nice stay. The property was in a great location."
The price is CA $387
CA $474 total
includes taxes & fees
May 4 - May 5
Hyatt Vacation Club at Sunset Harbor, Key West

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (808)
"Very tropical, on the water. Everything u need in amenities. Pools were great!"
Coconut Mallory Resort And Marina By Kees Vacations

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (382)
"very clean, was able to park the car and walk to where we wanted to go. I would stay again."
The price is CA $150
CA $349 total
includes taxes & fees
May 11 - May 12
Steps from Duval, Pool on Site & Bikes Included!

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

9.6 out of 10, Exceptional, (7)
"Kevin and Capt. Phil were great hosts. Would definitely stay there again. "
The price is CA $207
CA $804 total
includes taxes & fees
May 12 - May 13
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

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

10.0 out of 10, Exceptional, (6)
"My wife and I have been to Key West many times, and Liam's house boat has to be the coolest place we've stayed yet! "
The price is CA $233
CA $377 total
includes taxes & fees
May 28 - May 29
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (121)
"Perfect spot for small group or couple to stay one block over from Duval St. Highly recommend staying here!"
Heart of Downtown Key West Cottage With Off-Street Parking

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (174)
"Very comfortable and clean place right by water, had a great stay "
Direct Oceanfront Cottage-Sunrise View- #2,

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

9.8 out of 10, Exceptional, (8)
"Everything was great"
The price is CA $240
CA $498 total
includes taxes & fees
May 11 - May 12
Claude Monet Suite | Cozy Studio with Pool & Patio Access!

Poolside Cottage #411

10.0 out of 10, Exceptional, (42)
"Lovely home to stay in for a couple of nights on Key West"
The price is CA $309
CA $523 total
includes taxes & fees
May 7 - May 8
Poolside Cottage #411

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

9.8 out of 10, Exceptional, (286)
"Great time!! Great place!!"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

The Salt Cay | Updated! Stunning Sunset View, Pool!

10.0 out of 10, Exceptional, (12)
"We loved our condo. Perfect location for spring break with our kids and grandchild. Very clean. Would stay here again. Pool day was great! "
The price is CA $336
CA $799 total
includes taxes & fees
May 11 - May 12
The Salt Cay | Updated! Stunning Sunset View, Pool!

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

9.8 out of 10, Exceptional, (10)
"My wife and I stay at many places and I personally travel extensively for business. I've stayed in all sorts of accommodations and the most important aspect of my travel is the customer support and caliber of the people hosting my stay. I have to say, Rick is amazing, ready to accommodate and help in every way. Polite, professional and a pleasure to talk to. We highly recommend and are already planning a family trip for Easter. Thanks so much..."
The price is CA $217
CA $521 total
includes taxes & fees
May 5 - May 6
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

9.4 out of 10, Exceptional, (218)
"Everything walking distance!!"
The price is CA $313
CA $691 total
includes taxes & fees
May 16 - May 17
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!

9.2 out of 10, Wonderful, (265)
"The room was great with the biggest plus being that it was in walking distance to many attractions. The bathrooms were tiny!"
The price is CA $412
CA $798 total
includes taxes & fees
Jun 1 - Jun 2
Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!

VanGogh Studio | Updated, Old Town, Heated Pool

8.4 out of 10, Very good, (18)
"This rental is well appointed, and has everything you could need for your stay in Key West, short or long, with small desk/table space, kitchenware and appliances, ironing tools. High ceilings and great AC were a plus. The host was excellent at communicating and accommodating. Location was unbeatable, close to the Southernmost Point and nearby beaches, Fort Taylor State Park and its beautiful beaches, and the restaurants, shopping and entertainment of Duval Street. We highly recommend and...
The price is CA $240
CA $503 total
includes taxes & fees
May 7 - May 8
VanGogh Studio | Updated, Old Town, Heated Pool

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (173)
"We would definitely stay here again! Great location, exactly as described, overall great place."
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

Cottage with Pool and Boat Dockage just minutes to Key West!

8.6 out of 10, Excellent, (135)
"Perfect location for us 23 miles to key west. Restaurants near by, pool, fishing pier. Can't wait to come back and do it all over again!"
Cottage with Pool and Boat Dockage just minutes to Key West!

Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

9.2 out of 10, Wonderful, (12)
"Great location. Walkable to everywhere we wanted to go. Comfortable beds"
The price is CA $217
CA $521 total
includes taxes & fees
May 5 - May 6
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
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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Other types of properties in Sugarloaf Key you may be interested in

Southernmost Beach Resort and Guesthouses

4.0 star property
8.6 out of 10, Excellent, (2456)
"Great stay"
The price is CA $395
CA $537 total
includes taxes & fees
May 20 - May 21
Southernmost Beach Resort and Guesthouses

Margaritaville Beach House Key West

4.0 star property
8.6 out of 10, Excellent, (1710)
"We’ve stayed here multiple times always a great trip "
The price is CA $332
CA $461 total
includes taxes & fees
May 18 - May 19
Margaritaville Beach House Key West

Fairfield Inn and Suites by Marriott Key West

3.0 star property
7.8 out of 10, Good, (1100)
"Staff is professional and pool is very nice."
The price is CA $252
CA $323 total
includes taxes & fees
Jun 1 - Jun 2
Fairfield Inn and Suites by Marriott Key West
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.

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.