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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Sugarloaf Key holiday 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 RM1,191
RM2,754 total
includes taxes & fees
27 Oct - 28 Oct
Starlight Serenity - Hideaway w Stunning Views
A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

2. 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 RM2,113
RM3,984 total
includes taxes & fees
26 Oct - 27 Oct
Atlantic View Luxury Villa with Pool
A cozy room with a brown leather sofa, a white table, and a ceiling fan.

3. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (376 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 RM364
RM983 total
includes taxes & fees
25 Oct - 26 Oct
Old Wooden Bridge Resort and Marina
A beachside resort with a wooden deck, palm trees, and a sunset view.

4. 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 RM1,324
RM2,481 total
includes taxes & fees
27 Oct - 28 Oct
Grand Marina Suite by Brightwild Waterfront
A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

5. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (200 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is RM474
RM1,234 total
includes taxes & fees
26 Oct - 27 Oct
Aqua Lodges at Hurricane Hole Marina
A modern home with a glass door leading to a bedroom and a pool area.

6. Lighthouse Suites Collection

Lighthouse Suites Collection
4.0 star property
Old Town Key West
10.0 out of 10, Exceptional, (1 review)
"My favorite place now. Won’t stay anywhere else. Lost track of the amount of my Key West stays, but this place has been the the most memorable."
United States
Melissa
The price is RM2,094
RM3,050 total
includes taxes & fees
9 Nov - 10 Nov
Lighthouse Suites Collection
A modern house with a swimming pool, a balcony, and a well-maintained garden.

7. 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 RM3,848
RM5,961 total
includes taxes & fees
5 Nov - 6 Nov
Contra House Key West
A room with a bed, two armchairs, a small table, and a window with a view of palm trees and the sea.

8. Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
Key West
Ocean Front One Bedroom Residence
Exterior

9. 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 RM885
RM1,356 total
includes taxes & fees
25 Oct - 26 Oct
Island View 1BR Residence With Balcony
A poolside area with lounge chairs, a wooden table, and palm trees.

10. The Fairhaven House at Solaire Lunara Bay

The Fairhaven House at Solaire Lunara Bay
2.0 star property
Raccoon Key
The price is RM5,230
RM9,999 total
includes taxes & fees
1 Nov - 2 Nov
The Fairhaven House at Solaire Lunara Bay
A modern kitchen with a central island, pendant lighting, and large windows offering a view of the outdoors.

11. Parking Pool Dock - Shellstone House

Parking Pool Dock - Shellstone House
2.0 star property
Raccoon Key
The price is RM5,227
RM9,994 total
includes taxes & fees
5 Nov - 6 Nov
Parking Pool Dock - Shellstone House
A modern kitchen with a large island, bar stools, and a view of the outdoors.

12. New Waterfront Home - Sunray House

New Waterfront Home - Sunray House
2.0 star property
Raccoon Key
The price is RM5,230
RM9,999 total
includes taxes & fees
25 Oct - 26 Oct
New Waterfront Home - Sunray House
A spacious living room with a large dining table, comfortable seating, and large windows offering a view of the outdoors.

13. Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House
2.0 star property
Raccoon Key
The price is RM5,227
RM9,994 total
includes taxes & fees
25 Oct - 26 Oct
Waterfront Luxury Home - Tidelands House
A modern kitchen with a large island, bar stools, and pendant lighting.

14. The Joyrise House at Solaire Lunara Bay

The Joyrise House at Solaire Lunara Bay
2.0 star property
Raccoon Key
The price is RM6,277
RM11,176 total
includes taxes & fees
29 Oct - 30 Oct
The Joyrise House at Solaire Lunara Bay
A white two-story house with a balcony and a swimming pool.

15. 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 RM3,136
RM6,357 total
includes taxes & fees
29 Oct - 30 Oct
Capmar House by Brightwild Huge Home Pool
A spacious living area with a large sofa, a coffee table, and a view of a balcony with a railing.

16. Mastway House by Brightwild Pool Dock

Mastway House by Brightwild Pool Dock
2.0 star property
Raccoon Key
The price is RM3,136
RM6,357 total
includes taxes & fees
25 Oct - 26 Oct
Mastway House by Brightwild Pool Dock
A modern house with a swimming pool, outdoor seating, and palm trees.

17. Floralee House in Key West

Floralee House in Key West
2.0 star property
Raccoon Key
The price is RM4,183
RM8,564 total
includes taxes & fees
27 Oct - 28 Oct
Floralee House in Key West
A spacious foyer with a wooden staircase, a console table with decorative items, and a view of the outdoors through a glass door.

18. Evershore House Pool Parking Dock

Evershore House Pool Parking Dock
2.0 star property
Raccoon Key
The price is RM3,135
RM6,355 total
includes taxes & fees
5 Nov - 6 Nov
Evershore House Pool Parking Dock
A modern kitchen with a central island, bar stools, and a large window.

19. Brand New Catchlight House With Private Pool

Brand New Catchlight House With Private Pool
3.0 star property
Raccoon Key
The price is RM4,300
RM8,696 total
includes taxes & fees
19 Nov - 20 Nov
Brand New Catchlight House With Private Pool
A spacious kitchen with modern appliances, a dining area with a wooden table and chairs, and a view of a lake through large windows.

20. Springtide House by Brightwild Waterfront Pool

Springtide House by Brightwild Waterfront Pool
2.0 star property
Raccoon Key
The price is RM3,136
RM6,357 total
includes taxes & fees
1 Nov - 2 Nov
Springtide House by Brightwild Waterfront 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.
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Top Sugarloaf Key Hotel Reviews

Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages

10/10 Excellent
"Great"
Lori 7-night trip
Posted 3 hours ago
Sugarloaf Key RV Resort & Cottages

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