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

Sugarloaf Key Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Sugarloaf Key vacation rentals

A wooden deck with a railing, wicker chairs, and a view of greenery.

1. Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food."
United States
max
The price is NT$9,690
NT$22,045 total
includes taxes & fees
Oct 15 - Oct 16
Starlight Serenity - Hideaway w Stunning Views
A cozy room with a brown leather sofa, a white table, and a ceiling fan.

2. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (374 reviews)
"Best stop over before going to Key west. We enjoyed here a lot, parking our trailer was never a problem."
United States
Daisybel
The price is NT$2,866
NT$7,746 total
includes taxes & fees
Oct 15 - Oct 16
Old Wooden Bridge Resort and Marina
A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

3. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (199 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is NT$3,444
NT$9,382 total
includes taxes & fees
Oct 15 - Oct 16
Aqua Lodges at Hurricane Hole Marina
A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

4. Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
7.4 out of 10, Good, (3 reviews)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
The price is NT$16,643
NT$31,387 total
includes taxes & fees
Oct 18 - Oct 19
Atlantic View Luxury Villa with Pool
Room

5. Resort View 1BR Suite

Resort View 1BR Suite
2.0 star property
Key West
9.0 out of 10, Wonderful, (4 reviews)
"Open sewage behind pool bar rude front desk grumpy bartender Nice condo good restaurant "
United States
Michael
The price is NT$6,515
NT$10,145 total
includes taxes & fees
Oct 15 - Oct 16
Resort View 1BR Suite
A modern house with a swimming pool, a balcony, and a well-maintained garden.

6. Contra House Key West

Contra House Key West
3.0 star property
Old Town Key West
8.0 out of 10, Very good, (1 review)
"Pool and outside was undesirable"
United States
Rosalie
The price is NT$22,738
NT$38,444 total
includes taxes & fees
Oct 19 - Oct 20
Contra House Key West
Exterior

7. Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (3 reviews)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
The price is NT$6,975
NT$10,684 total
includes taxes & fees
Oct 27 - Oct 28
Island View 1BR Residence With Balcony
A beachside resort with a wooden deck, palm trees, and a sunset view.

8. Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
2.0 star property
Stock Island
10.0 out of 10, Exceptional, (3 reviews)
"Nice place "
United States
Pawel
The price is NT$10,360
NT$19,413 total
includes taxes & fees
Oct 15 - Oct 16
Grand Marina Suite by Brightwild Waterfront
A wooden boardwalk leading to a building with a green roof, surrounded by palm trees and a body of water.

9. The Grenada Suite Pool View Private Balcony

The Grenada Suite Pool View Private Balcony
2.0 star property
Key West
9.0 out of 10, Wonderful, (2 reviews)
"A little dated, but clean and well located."
United States
Luis
The price is NT$7,742
NT$17,761 total
includes taxes & fees
Oct 27 - Oct 28
The Grenada Suite Pool View Private Balcony
A room with a bed, two armchairs, a small table, and a window with a view of palm trees and the sea.

10. Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
Key West
The price is NT$6,865
NT$10,509 total
includes taxes & fees
Oct 15 - Oct 16
Ocean Front One Bedroom Residence
Exterior

11. Resort View 1BR Suite With Direct Pool Access

Resort View 1BR Suite With Direct Pool Access
2.0 star property
Key West
The price is NT$6,515
NT$10,145 total
includes taxes & fees
Oct 15 - Oct 16
Resort View 1BR Suite With Direct Pool Access
A view through white blinds of a swimming pool area with a hot tub, surrounded by palm trees and a white fence.

12. Poolside Retreat by Brightwild Cottage w Pool

Poolside Retreat by Brightwild Cottage w Pool
3.0 star property
Old Town Key West
2.0 out of 10, (2 reviews)
"My boyfriend and I booked this for our first anniversary together and I cannot stress enough to not book this listing. There was trash from people before us, back door was broken to get to the pool, air conditioning didn’t work (it was so hot inside that the glass was all fogged up it was like a sauna), and the blow dryer in the bathroom SHOCKED ME when I tried to plug it in, my boyfriend heard the sound of the shock loudly from two rooms away. Horrifying to say the least and when I reached out...
United States
Julia
The price is NT$9,453
NT$16,713 total
includes taxes & fees
Oct 27 - Oct 28
Poolside Retreat by Brightwild Cottage w Pool
A swimming pool with a green-roofed building nearby, surrounded by palm trees.

13. Tortuga Suite Sparkling Pool Hot Tub

Tortuga Suite Sparkling Pool Hot Tub
2.0 star property
Key West
The price is NT$8,697
NT$18,835 total
includes taxes & fees
Oct 27 - Oct 28
Tortuga Suite Sparkling Pool Hot Tub
A beach view with palm trees, a wooden pier, and a sunset over the water.

14. Ocean Front 1BR Suite With Direct Beach Access

Ocean Front 1BR Suite With Direct Beach Access
2.0 star property
Key West
10.0 out of 10, Exceptional, (3 reviews)
"Clean and spacious. Great view from room!"
United States
Jacqueline
The price is NT$8,257
NT$12,075 total
includes taxes & fees
Oct 15 - Oct 16
Ocean Front 1BR Suite With Direct Beach Access
A two-story house with a swimming pool, surrounded by greenery and palm trees.

15. Seagate House by Brightwild Waterfront w Dock

Seagate House by Brightwild Waterfront w Dock
2.0 star property
Raccoon Key
The price is NT$24,523
NT$49,712 total
includes taxes & fees
Oct 22 - Oct 23
Seagate House by Brightwild Waterfront w Dock
Exterior

16. Two Bedroom Residence With Balcony

Two Bedroom Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (1 review)
"The roosters crowing early morning was irritating "
United States
Catherine
The price is NT$8,504
NT$16,333 total
includes taxes & fees
Oct 15 - Oct 16
Two Bedroom Residence With Balcony
A spacious living area with a blue sofa, a grey armchair, and a wooden coffee table. Large sliding glass doors lead to a pool and outdoor furniture.

17. Suncoast House by Brightwild Pool Boat Dock

Suncoast House by Brightwild Pool Boat Dock
2.0 star property
Raccoon Key
The price is NT$24,523
NT$55,142 total
includes taxes & fees
Oct 26 - Oct 27
Suncoast House by Brightwild Pool Boat Dock
A white two-story house with a balcony and a swimming pool.

18. Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (1 review)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
The price is NT$24,705
NT$50,081 total
includes taxes & fees
Oct 15 - Oct 16
Capmar House by Brightwild Huge Home Pool
A covered porch with a table and chairs, overlooking a street with houses and cars.

19. Banana Split by Brightwild Pool Grill

Banana Split by Brightwild Pool Grill
2.0 star property
Key West Historic District
The price is NT$10,995
NT$19,056 total
includes taxes & fees
Nov 9 - Nov 10
Banana Split by Brightwild Pool Grill
A spacious living area with a large sofa, a coffee table, and a view of a balcony with a railing.

20. Mastway House by Brightwild Pool Dock

Mastway House by Brightwild Pool Dock
2.0 star property
Raccoon Key
The price is NT$24,705
NT$50,081 total
includes taxes & fees
Oct 18 - Oct 19
Mastway House by Brightwild Pool Dock
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

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"Great location. Friendly staff"
Elizabeth 8-night trip
Posted less than an hour ago
Southernmost Beach Resort and Guesthouses

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