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
$580 nightly
The price is $653
Oct 15 - Oct 16
Total with taxes and fees
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
$222 nightly
The price is $250
Oct 18 - Oct 19
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.

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, (200 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
$259 nightly
The price is $292
Oct 15 - Oct 16
Total with taxes and fees
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
$925 nightly
The price is $1,041
Oct 15 - Oct 16
Total with taxes and fees
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
$285 nightly
The price is $321
Oct 29 - Oct 30
Total with taxes and fees
Resort View 1BR Suite
A modern building with a concrete facade, a large window, and a metal gate.

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
$1,063 nightly
The price is $1,195
Oct 19 - Oct 20
Total with taxes and fees
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
$313 nightly
The price is $352
Oct 15 - Oct 16
Total with taxes and fees
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
$509 nightly
The price is $572
Oct 28 - Oct 29
Total with taxes and fees
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
$466 nightly
The price is $524
Oct 15 - Oct 16
Total with taxes and fees
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
$315 nightly
The price is $354
Oct 15 - Oct 16
Total with taxes and fees
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
$287 nightly
The price is $323
Oct 15 - Oct 16
Total with taxes and fees
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
$494 nightly
The price is $556
Oct 29 - Oct 30
Total with taxes and fees
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
$562 nightly
The price is $632
Oct 18 - Oct 19
Total with taxes and fees
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
$350 nightly
The price is $393
Oct 29 - Oct 30
Total with taxes and fees
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
$1,306 nightly
The price is $1,469
Oct 19 - Oct 20
Total with taxes and fees
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
$481 nightly
The price is $542
Oct 15 - Oct 16
Total with taxes and fees
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
$1,640 nightly
The price is $1,845
Oct 19 - Oct 20
Total with taxes and fees
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
$1,306 nightly
The price is $1,469
Nov 9 - Nov 10
Total with taxes and fees
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
$492 nightly
The price is $553
Nov 9 - Nov 10
Total with taxes and fees
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
$1,306 nightly
The price is $1,469
Nov 2 - Nov 3
Total with taxes and fees
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

Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

8/10 Good
"Waterfront Parking cost"
Richard 2-night trip
Posted 2 hours ago
Opal Key Resort & Marina, 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 $208 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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