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
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Sugarloaf Key vacation rentals

A wooden deck with a hanging hammock and a view of a green landscape.

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
$650 nightly
The price is $731
Nov 19 - Nov 20
Total with taxes and fees
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
$925 nightly
The price is $1,041
Nov 15 - Nov 16
Total with taxes and fees
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, (380 reviews)
"Great view , clean room and excellent staff ( Mr. shaggy )"
United States
Jordan
$201 nightly
The price is $226
Dec 4 - Dec 5
Total with taxes and fees
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.

4. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (202 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
$259 nightly
The price is $291
Nov 12 - Nov 13
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
A beachside resort with a wooden deck, palm trees, and a sunset view.

5. 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
$650 nightly
The price is $731
Nov 30 - Dec 1
Total with taxes and fees
Grand Marina Suite by Brightwild Waterfront
A pool area with a wooden deck, lounge chairs, and a waterfall feature.

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
$688 nightly
The price is $753
Nov 13 - Nov 14
Total with taxes and fees
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
$1,063 nightly
The price is $1,195
Nov 9 - Nov 10
Total with taxes and fees
Contra House Key West
A modern kitchen with a long island counter, bar stools, pendant lighting, and large windows.

8. Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House
2.0 star property
Raccoon Key
$2,162 nightly
The price is $2,433
Nov 8 - Nov 9
Total with taxes and fees
Waterfront Luxury Home - Tidelands House
A poolside area with lounge chairs, a wooden table, and palm trees.

9. The Fairhaven House at Solaire Lunara Bay

The Fairhaven House at Solaire Lunara Bay
2.0 star property
Raccoon Key
$2,206 nightly
The price is $2,482
Nov 10 - Nov 11
Total with taxes and fees
The Fairhaven House at Solaire Lunara Bay
A white two-story house with a balcony and a swimming pool.

10. 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
$1,347 nightly
The price is $1,515
Nov 12 - Nov 13
Total with taxes and fees
Capmar House by Brightwild Huge Home Pool
A modern kitchen with a large island, bar stools, and pendant lighting.

11. The Joyrise House at Solaire Lunara Bay

The Joyrise House at Solaire Lunara Bay
2.5 star property
Raccoon Key
$2,433 nightly
The price is $2,738
Nov 11 - Nov 12
Total with taxes and fees
The Joyrise House at Solaire Lunara Bay
A white two-story house with a central archway and a paved driveway.

12. Palmgale House in Key West

Palmgale House in Key West
2.5 star property
Raccoon Key
$1,773 nightly
The price is $1,994
Nov 9 - Nov 10
Total with taxes and fees
Palmgale House in Key West
A modern kitchen with a central island, wooden cabinets, a built-in oven, and a large window providing natural light.

13. Brand New The Greenmoor House With Pool

Brand New The Greenmoor House With Pool
2.0 star property
Raccoon Key
$2,192 nightly
The price is $2,466
Nov 19 - Nov 20
Total with taxes and fees
Brand New The Greenmoor House With Pool
A spacious living area with a large sofa, a coffee table, and a view of a balcony with a railing.

14. Mastway House by Brightwild Pool Dock

Mastway House by Brightwild Pool Dock
2.0 star property
Raccoon Key
$1,384 nightly
The price is $1,557
Nov 11 - Nov 12
Total with taxes and fees
Mastway House by Brightwild Pool Dock
A modern kitchen with a central island, pendant lighting, and large windows offering a view of the outdoors.

15. Parking Pool Dock - Shellstone House

Parking Pool Dock - Shellstone House
2.0 star property
Raccoon Key
$2,177 nightly
The price is $2,449
Nov 26 - Nov 27
Total with taxes and fees
Parking Pool Dock - Shellstone House
A modern kitchen with a large island, bar stools, and a view of the outdoors.

16. New Waterfront Home - Sunray House

New Waterfront Home - Sunray House
2.0 star property
Raccoon Key
$2,177 nightly
The price is $2,449
Nov 15 - Nov 16
Total with taxes and fees
New Waterfront Home - Sunray House
A poolside area with lounge chairs and umbrellas, a pool, and a view of the ocean.

17. New Waterfront Home - Dreamside House

New Waterfront Home - Dreamside House
2.0 star property
Raccoon Key
$2,177 nightly
The price is $2,449
Nov 10 - Nov 11
Total with taxes and fees
New Waterfront Home - Dreamside House
A spacious kitchen with a large island, white cabinetry, and pendant lighting.

18. Aquaria House by Brightwild Pool Boat Dock

Aquaria House by Brightwild Pool Boat Dock
2.0 star property
Raccoon Key
$1,489 nightly
The price is $1,675
Nov 8 - Nov 9
Total with taxes and fees
Aquaria House by Brightwild Pool Boat 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
$1,876 nightly
The price is $2,111
Nov 9 - Nov 10
Total with taxes and fees
Brand New Catchlight House With Private Pool
A two-story house with a swimming pool, surrounded by greenery and palm trees.

20. Seagate House by Brightwild Waterfront w Dock

Seagate House by Brightwild Waterfront w Dock
2.0 star property
Raccoon Key
$1,641 nightly
The price is $1,846
Nov 16 - Nov 17
Total with taxes and fees
Seagate House by Brightwild Waterfront w 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

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"Everything clean and politely"
Marvelis 1-night trip
Posted 1 hour ago
DoubleTree Resort by Hilton Grand Key - Key West

Find out more about Sugarloaf Key

Everything you need to know about Sugarloaf Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sugarloaf Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sugarloaf Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sugarloaf Key vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sugarloaf Key. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Sugarloaf Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $226 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sugarloaf Key rentals

At Expedia, we put the best Sugarloaf Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Sugarloaf Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sugarloaf Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sugarloaf Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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