A waterfront with a pier, calm water, and houses with palm trees in the background.

Search and Rent Sugarloaf Key Condos

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Sugarloaf Key condo rentals

A beach with lounge chairs, palm trees, and a water body.

1. Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.6 out of 10, Exceptional, (33 reviews)
"Pool was great! Just far enough from Duval street to get away and relax if needed or jump in the car and head down for live music! "
United States
Brent H.
$563 nightly
The price is $626
Oct 1 - Oct 2
Total with taxes and fees
Grand Marina Suite - Poolside & Waterfront Condo
A wooden pathway leading to a beach with palm trees and a clear blue sky.

2. Island Time | Luxury Beach Condo w/ Pool & Hot Tub

Island Time | Luxury Beach Condo w/ Pool & Hot Tub
Key West
10.0 out of 10, Exceptional, (9 reviews)
"Neat and clean, spacious, easy walking access to the beach, nice amenities on the property with pool and hot tub."
United States
Stacey P.
$592 nightly
The price is $658
Oct 6 - Oct 7
Total with taxes and fees
Island Time | Luxury Beach Condo w/ Pool & Hot Tub
A bedroom with a bed, a chair, a wardrobe, and a bathroom visible through an open door.

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
$453 nightly
The price is $503
Oct 12 - Oct 13
Total with taxes and fees
The Tahiti Suite | Updated Key West Condo w/ Pool, Hot Tub, & Balcony!
A swimming pool with lounge chairs, palm trees, and a view of the sunset over the water.

4. Pool View Suite | Beachside Resort

Pool View Suite | Beachside Resort
Key West
8.0 out of 10, Very good, (3 reviews)
"It was a holiday weekend. Key West in general all lodging was expensive. The room was very comfortable and clean. More than enough room. I was on the water which was amazing. The pool area was very awesome. Love that they have a bar and restaurant available. All the available excursions. I took advantage of the Sunset Tour. Property manager was available for any questions. Beachside staff was also very helpful. Would definitely visit again. Great Experience!! Thank you."
United States
Christie Y.
$237 nightly
The price is $263
Oct 1 - Oct 2
Total with taxes and fees
Pool View Suite | Beachside Resort
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
9.8 out of 10, Exceptional, (9 reviews)
"Absolutely beautiful property as well as room I loved it everything about it was beautiful "
United States
Misty C.
$666 nightly
The price is $740
Oct 1 - Oct 2
Total with taxes and fees
Atlantic Parrot | Oceanfront Condo w/ Pool
A wooden boardwalk leading to a hotel with a green roof, surrounded by palm trees and a water feature.

6. 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.
$446 nightly
The price is $496
Oct 1 - Oct 2
Total with taxes and fees
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.

7. The Butterfly Nest | Newly Updated w/ Shared Pool

The Butterfly Nest | Newly Updated w/ Shared Pool
Key West
9.8 out of 10, Exceptional, (48 reviews)
"Had a great time place is lovely "
United States
Sarah P.
$446 nightly
The price is $496
Oct 1 - Oct 2
Total with taxes and fees
The Butterfly Nest | Newly Updated w/ Shared Pool
A tropical garden pathway leading to a building with a yellow facade and green shutters.

8. 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, (137 reviews)
"Great place to stay"
United States
walter l.
$284 nightly
The price is $315
Oct 1 - Oct 2
Total with taxes and fees
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
A covered balcony with wicker chairs, a view of palm trees, and multiple flags.

9. NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!

NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!
Old Town Key West
10.0 out of 10, Exceptional, (14 reviews)
"Wonderful stay, location was great!"
United States
Taffy M.
$254 nightly
The price is $282
Oct 6 - Oct 7
Total with taxes and fees
NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!
A modern kitchen with a white island, bar stools, and a view into the dining area.

10. 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.
$411 nightly
The price is $456
Oct 5 - Oct 6
Total with taxes and fees
Waterfront Dock Pool Condo Near Duval St Pet OK
A tropical garden pathway leading to a building with a yellow facade and green shutters.

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, (112 reviews)
"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: The studio and surroundings matched photos posted and provided a Key West atmosphere and experience. Walking to Key West activities and sites was feasible. Very happy with and positive addition to our Key West visit."
United States
Ken L.
$312 nightly
The price is $346
Oct 8 - Oct 9
Total with taxes and fees
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
A wooden boardwalk leading to a building with a green roof, surrounded by lush greenery and palm trees.

12. 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.
$450 nightly
The price is $500
Oct 26 - Oct 27
Total with taxes and fees
The Cat Island Suite | Charmingly Renovated w/ Pool
A wide sandy beach with palm trees and a clear sky.

13. Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Key West
9.0 out of 10, Wonderful, (49 reviews)
"Great place for our 1 night in key west "
United States
Thadd W.
$422 nightly
The price is $469
Oct 1 - Oct 2
Total with taxes and fees
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
An outdoor tennis court with a blue surface, surrounded by a fence, palm trees, and buildings in the background.

14. 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.
$467 nightly
The price is $519
Oct 1 - Oct 2
Total with taxes and fees
The Grenada at Sunrise Suites - Shared Pool
A wide sandy beach with palm trees and a clear sky.

15. 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.
$422 nightly
The price is $469
Oct 1 - Oct 2
Total with taxes and fees
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
A swimming pool with lounge chairs and palm trees, surrounded by a fence.

16. Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.2 out of 10, Wonderful, (14 reviews)
"Beautiful location and really nice layout "
United States
Janey
$570 nightly
The price is $633
Oct 1 - Oct 2
Total with taxes and fees
Grand Marina Suite - Poolside & Waterfront Condo
A swimming pool with lounge chairs and palm trees, surrounded by a fence.

17. 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.
$563 nightly
The price is $626
Oct 1 - Oct 2
Total with taxes and fees
Grand Marina Suite - Poolside & Waterfront Condo
A tranquil pond with a fountain in a park setting.

18. 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.
$446 nightly
The price is $495
Oct 4 - Oct 5
Total with taxes and fees
The Tortuga at Sunrise Suites - Balcony & Pool
A white colonial-style building with balconies, palm trees, and a street view.

19. LA CASA CUBANA @ Cuban Club Suites

LA CASA CUBANA @ Cuban Club Suites
Old Town Key West
9.6 out of 10, Exceptional, (75 reviews)
"Everything was terrific and as advertised! Thank you and would 100 stay here again! "
United States
Edmund
$522 nightly
The price is $580
Oct 15 - Oct 16
Total with taxes and fees
LA CASA CUBANA @ Cuban Club Suites
A two-story building with a balcony, storefronts, and a sign for 'Frangipani Gallery'.

20. Escape to the wonderful Cuban Paradise!

Escape to the wonderful Cuban Paradise!
Old Town Key West
9.6 out of 10, Exceptional, (145 reviews)
"clean, great location"
United States
jessica l.
$573 nightly
The price is $637
Oct 1 - Oct 2
Total with taxes and fees
Escape to the wonderful Cuban Paradise!
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

Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

10/10 Excellent
"This property is nicer than anything we found closer to Duval Street. This property is 5 stars! Roomy, worth every penny. I loved my king size bed. I loved the properties gardens and the pools. It was quiet, private, and luxurious. I have one critique, valet parking is not needed. $30 for Valet is not needed."
Krystal 1-night trip
Posted less than an hour ago
Parrot Key Hotel & Villas

Find out more about Sugarloaf Key

Sugarloaf Key Condo Rentals information

Number of reviews
465
Accommodation
321 Condo Rentals
Lowest Price
$263
Highest Price
$740

Frequently asked questions

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