Search Sugarloaf Key Condo Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Find holiday rentals that suit your style

Cottage image
Cottages
Cottages
apart-hotel image
Aparthotels
Aparthotels

Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Sugarloaf Key condo rentals

A wooden boardwalk leading to a hotel with a green roof, surrounded by palm trees and a water feature.

1. The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
Key West
10.0 out of 10, Exceptional, (35 reviews)
"Very nice clean place. Had a minor problem with the beds after checking in but property manager was quick to respond and correct issue. Would stay here again. "
United States
Teri K.
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
A wooden boardwalk leading to a hotel with a green roof, surrounded by lush greenery and palm trees.

2. The Andros | Incredible Views w/ Shared Pool

The Andros | Incredible Views w/ Shared Pool
Key West
9.0 out of 10, Wonderful, (45 reviews)
"Great place, location and reasonable price"
United States
Sujan K.
The Andros | Incredible Views w/ Shared Pool
A modern kitchen with a central island, bar stools, and pendant lighting.

3. The Tahiti Suite | Updated Key West Condo w/ Pool, Hot Tub, & Balcony!

The Tahiti Suite | Updated Key West Condo w/ Pool, Hot Tub, & Balcony!
Key West
10.0 out of 10, Exceptional, (2 reviews)
"This condo was perfect for our 2 day stay in the beautiful Key West. About 8 minutes from Duvall on the golf cart! The pool and hot tub was very clean as well!"
United States
Amy Jordan P.
The Tahiti Suite | Updated Key West Condo w/ Pool, Hot Tub, & Balcony!
A beachside resort with a wooden deck, palm trees, and a sunset view.

4. Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.2 out of 10, Wonderful, (26 reviews)
"Great stay"
United States
Dustin H.
The price is €827
includes taxes & fees
27 Nov - 28 Nov
Grand Marina Suite - Poolside & Waterfront Condo
A swimming pool area with multiple pools, palm trees, lounge chairs, and a clear blue sky.

5. Atlantic Parrot | Oceanfront Condo w/ Pool

Atlantic Parrot | Oceanfront Condo w/ Pool
Beachside
10.0 out of 10, Exceptional, (12 reviews)
"Very short stay (3 days), but worth it. Host was very communicative and even met us to show us how to use the locks (they can be trickey) Would recommend this for anyone who wants to vist the Keys!"
United States
Bill W.
Atlantic Parrot | Oceanfront Condo w/ Pool
A living room with a flat-screen TV, a ceiling fan, a teal sofa, and a view of the marina through large windows.

6. Waterfront Dock Pool Condo Near Duval St Pet OK

Waterfront Dock Pool Condo Near Duval St Pet OK
Meadows
9.4 out of 10, Exceptional, (48 reviews)
"Hosts are super responsive and helpful. Perfect location. Would absolutely stay here again! "
United States
Amber G.
Waterfront Dock Pool Condo Near Duval St Pet OK
A wooden boardwalk leading to a building with a green roof, surrounded by lush greenery and palm trees.

7. The Cat Island Suite | Charmingly Renovated w/ Pool

The Cat Island Suite | Charmingly Renovated w/ Pool
Key West
9.8 out of 10, Exceptional, (47 reviews)
"I liked that it was pretty centrally located to everything very nice Thank you we had a great time "
United States
Patti E.
The Cat Island Suite | Charmingly Renovated w/ Pool
A wooden bridge leading to a house with a sign indicating no swimming or diving.

8. The Tortuga at Sunrise Suites - Balcony & Pool

The Tortuga at Sunrise Suites - Balcony & Pool
Key West
8.6 out of 10, Excellent, (30 reviews)
"We were very impressed with the grounds. Loved the pool area. Was extremely clean"
United States
Margaret G.
The Tortuga at Sunrise Suites - Balcony & Pool
A tropical garden pathway leading to a building with a yellow facade and green shutters.

9. SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Old Town Key West
9.8 out of 10, Exceptional, (139 reviews)
"Great place to stay"
United States
walter l.
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
A waterfront property with a pool, a thatched-roof structure, and multiple buildings with balconies overlooking the water.

10. Pierre's Perch: Discover Charm and Convenience, Perfect Studio Retreat in Key West with Shared Pool

Pierre's Perch: Discover Charm and Convenience, Perfect Studio Retreat in Key West with Shared Pool
Old Town Key West
9.0 out of 10, Wonderful, (25 reviews)
"Super cute place. "
United States
Amanda M.
The price is €302
includes taxes & fees
23 Nov - 24 Nov
Pierre's Perch: Discover Charm and Convenience, Perfect Studio Retreat in Key West with Shared Pool
A street lined with palm trees and red flowering plants, with a fire hydrant and parked cars.

11. ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (115 reviews)
"Absolutely perfect! Great location, great property and great unit. Beautiful pool area with ice machine and filtered water dispenser was a highlight for the very hot and humid time we visited. Would return immediately and stay in the same spot. Thank you for a very enjoyable time in Key West!"
United States
Justin D.
The price is €326
includes taxes & fees
1 Dec - 2 Dec
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
A wooden boardwalk leading to a hotel with a pool and palm trees.

12. The Grenada at Sunrise Suites - Shared Pool

The Grenada at Sunrise Suites - Shared Pool
Naval Air Station Key West
8.8 out of 10, Excellent, (13 reviews)
"We had a lovely time- thank you"
United States
Jackie Y.
The price is €461
includes taxes & fees
30 Nov - 1 Dec
The Grenada at Sunrise Suites - Shared Pool
A narrow stone pathway flanked by a yellow building with a white fence and a wall-mounted electrical box.

13. Hidden Key West Cottage - Walk to Duval !!!

Hidden Key West Cottage - Walk to Duval !!!
Old Town Key West
10.0 out of 10, Exceptional, (4 reviews)
"Host was great! Fast response and easy to work with. Very, very, very clean! Quiet area A"
United States
Regina E.
The price is €233
includes taxes & fees
17 Nov - 18 Nov
Hidden Key West Cottage - Walk to Duval !!!
A covered balcony with wicker chairs, a view of palm trees, and multiple flags.

14. AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!

AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!
Old Town Key West
9.6 out of 10, Exceptional, (18 reviews)
"Friendly and clean place, love the look and location will be back"
United States
Amanda G.
AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!
A marina with boats docked, a clear sky, and a rainbow.

15. Waterfront Condo Dock Pool Near Duval St

Waterfront Condo Dock Pool Near Duval St
Meadows
9.8 out of 10, Exceptional, (30 reviews)
"Wonderful condo. Wonderful host. Wonderful location. Great for family of 6. Beautifully decorated and very spacious. Loved the large balcony. Host offered suggestions and responded almost immediately to any questions or needs. Very impressed."
United States
Patsy K.
Waterfront Condo Dock Pool Near Duval St
A bedroom with a large bed, a dresser, a television, and a door leading to a bathroom.

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

The Salt Cay | Updated! Stunning Sunset View, Pool
Key West
9.6 out of 10, Exceptional, (60 reviews)
"Good place to stay away from the crowds in Old Town. About a 15-20 minute golf cart ride into Old Town - very convenient! Unit was clean and had everything we needed. Beds and pillows were comfortable!"
United States
Dana P.
The Salt Cay | Updated! Stunning Sunset View, Pool
A modern living room with a sofa, coffee table, and a dining area with a table and chairs. There is a kitchen area with cabinets and appliances.

17. The Grand Cayman | Beautifully Remodeled Key West!

The Grand Cayman | Beautifully Remodeled Key West!
Key West
9.8 out of 10, Exceptional, (22 reviews)
"Great facility and loved the location! "
United States
Matt R.
The Grand Cayman | Beautifully Remodeled Key West!
A beachside resort with a wooden deck, palm trees, and a sunset view.

18. Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.6 out of 10, Exceptional, (35 reviews)
"Great property but not very walkable but all good"
United States
CAROL K.
The price is €827
includes taxes & fees
27 Nov - 28 Nov
Grand Marina Suite - Poolside & Waterfront Condo
A wide sandy beach with palm trees and a clear sky.

19. Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.

Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
Key West
9.2 out of 10, Wonderful, (115 reviews)
"I enjoyed my stay at the resort, highly recommend!"
United States
Michelaine a.
The price is €452
includes taxes & fees
15 Nov - 16 Nov
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
A modern living room with a sofa, coffee table, and a painting of a beach scene.

20. The Saint Kitts Suite | Breathtaking View, Heated Pool

The Saint Kitts Suite | Breathtaking View, Heated Pool
Key West
9.8 out of 10, Exceptional, (11 reviews)
"Excellent place to stay."
United States
Rolando
The Saint Kitts Suite | Breathtaking View, Heated 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.
View all properties

Learn more about Sugarloaf Key

Kayak through mangrove tunnels and spot colourful fish in the crystal-clear waters surrounding this laid-back island. Unwind on Sugarloaf Beach's white sands or explore Upper Sugarloaf Sound, where local boaters know the best snorkelling spots.

See all hotels in Sugarloaf Key
A coastal property with a white and yellow house, surrounded by palm trees and a rocky shoreline.

Frequently Asked Questions

Why book your condo in Sugarloaf Key with Expedia?

We think that getaways should be stress-free, so if you're seeking condos at a competitive rate, Expedia delivers. Save cash and choose something small and cosy, or splurge on a luxury condo and spoil your favourite people. Our search filters make it easy to find a place in Sugarloaf Key that checks your boxes.

How can I find cheap condos in Sugarloaf Key?

With Expedia's helpful filter tool, getting your hands on cheap condos in Sugarloaf Key is a piece of cake. To find properties that are easy on the wallet, refine your search by star rating, amenities and budget.

What is there to do in Sugarloaf Key near my condo?

The most useful travel accessory is a well-planned to-do list. Florida Keys Beaches is a wonderful place to begin your exploration of Sugarloaf Key.

Explore a world of travel with Expedia