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

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Sugarloaf Key condo rentals

Coffee/tea maker, fridge, microwave, oven

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.
The price is ￥39,070
￥88,025 total
includes taxes & fees
Sep 19 - Sep 20
Grand Marina Suite - Poolside & Waterfront Condo
Property grounds

2. 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, (13 reviews)
"Wonderful stay, location was great!"
United States
Taffy M.
The price is ￥18,128
￥44,091 total
includes taxes & fees
Sep 27 - Sep 28
NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!
Property grounds

3. 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
Property grounds

4. 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 price is ￥25,389
￥75,026 total
includes taxes & fees
Sep 22 - Sep 23
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
Property grounds

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

The Salt Cay | Updated! Stunning Sunset View, Pool
Key West
9.6 out of 10, Exceptional, (59 reviews)
"Everything was amazing! My family and I enjoyed every part of our stay; 10 out of 10 would recommend :)"
United States
Rebecca H.
The price is ￥25,442
￥75,184 total
includes taxes & fees
Oct 1 - Oct 2
The Salt Cay | Updated! Stunning Sunset View, Pool
Exterior detail

6. 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.
The price is ￥20,118
￥47,099 total
includes taxes & fees
Sep 29 - Sep 30
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Beach

7. 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.
The price is ￥30,162
￥89,745 total
includes taxes & fees
Sep 28 - Sep 29
Island Time | Luxury Beach Condo w/ Pool & Hot Tub
Pool

8. 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.
The price is ￥23,723
￥115,645 total
includes taxes & fees
Sep 27 - Sep 28
Atlantic Parrot | Oceanfront Condo w/ Pool
Exterior detail

9. 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, (111 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.
The price is ￥18,558
￥46,592 total
includes taxes & fees
Sep 28 - Sep 29
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Pool

10. 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.
The price is ￥23,286
￥43,193 total
includes taxes & fees
Sep 20 - Sep 21
Pool View Suite | Beachside Resort
TV

11. 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.
The price is ￥15,409
￥53,769 total
includes taxes & fees
Sep 22 - Sep 23
Waterfront Dock Pool Condo Near Duval St Pet OK
Property grounds

12. 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
The price is ￥23,895
￥73,272 total
includes taxes & fees
Sep 26 - Sep 27
The Tahiti Suite | Updated Key West Condo w/ Pool, Hot Tub, & Balcony!
Marina

13. Waterfront Condo Dock Pool Near Duval St

Waterfront Condo Dock Pool Near Duval St
Meadows
9.8 out of 10, Exceptional, (29 reviews)
"Great stay! Beautiful view. No complaints. Easy check in and great communication with owner. Thanks for a great trip!"
United States
Haley P.
The price is ￥20,988
￥62,546 total
includes taxes & fees
Sep 21 - Sep 22
Waterfront Condo Dock Pool Near Duval St
Beach nearby, beach towels

14. 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 ￥38,988
￥61,543 total
includes taxes & fees
Sep 20 - Sep 21
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
Fitness facility

15. Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.2 out of 10, Wonderful, (24 reviews)
"Great stay"
United States
Dustin H.
The price is ￥39,070
￥88,025 total
includes taxes & fees
Sep 19 - Sep 20
Grand Marina Suite - Poolside & Waterfront Condo
Beach nearby

16. 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
9.2 out of 10, Wonderful, (47 reviews)
"Great place for our 1 night in key west "
United States
Thadd W.
The price is ￥39,070
￥64,017 total
includes taxes & fees
Sep 20 - Sep 21
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
2 bedrooms, iron/ironing board, WiFi, bed sheets

17. 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 price is ￥26,568
￥75,074 total
includes taxes & fees
Sep 23 - Sep 24
The Tortuga at Sunrise Suites - Balcony & Pool
Exterior detail

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

Hidden Key West Cottage - Walk to Duval !!!
Old Town Key West
10.0 out of 10, Exceptional, (3 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 ￥12,476
￥33,256 total
includes taxes & fees
Sep 23 - Sep 24
Hidden Key West Cottage - Walk to Duval !!!
Property grounds

19. 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 ￥29,537
￥80,447 total
includes taxes & fees
Sep 20 - Sep 21
The Grenada at Sunrise Suites - Shared Pool
Smart TV

20. Turtle Nest Condo + Pool / 2nd Floor

Turtle Nest Condo + Pool / 2nd Floor
Key West Historic District
The price is ￥12,659
￥39,716 total
includes taxes & fees
Sep 20 - Sep 21
Turtle Nest Condo + Pool / 2nd Floor
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

Beachside Resort & Residences

Beachside Resort & Residences

8/10 Good
"The staff was very helpful. I had absolutely no problem with my suite. It was a very well furnished, one bedroom apartment. The the problem I guess, would be that the outside hot tub at the pool had not been working for months. The elevators were being repaired on the side where I was at the restaurant there. To me was overpriced, and not a lot to choose from. The outside bar, the staff really didn't either know how to make certain drinks, or they didn't have the ingredients to make certain drinks. And the food was so so they only had one Van. That brought you to and from downtown. And they stated that they had 2 more vans, but they've been broke for a very long time, because they can't get parts. Well, how about management getting involved? And going as high up as it takes to get the type of vans that you need and to get the place maintained and staffed properly. There was no pool person, and you had to go inside to get your towels, and it got a little messy at the pool area...And then I heard that there's some people that did have some issues with a room, but those problems were fixed within a day. So, I had wished that the Van would have offered rides to the airport, which was just a 12 minute ride down the street. If that.... the extra excursions they offered did not work out because they didn't have enough people to go on the boat they had. So you had to seek out other sailboats or boats in the area to do things. And if they were no"
Maria 4-night trip
Posted 6 hours ago
Beachside Resort & Residences

Find out more about Sugarloaf Key

Sugarloaf Key Condo Rentals information

Number of reviews
315
Accommodation
326 Condo Rentals
Lowest Price
￥33,256
Highest Price
￥115,645

Frequently asked questions

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