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

Sugarloaf Key Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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 ￥47,127
￥107,800 total
includes taxes & fees
Oct 27 - Oct 28
Starlight Serenity - Hideaway w Stunning Views
A wooden deck with a hanging hammock and a view of a green landscape.

2. Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"This place was everything we needed. The location was the perfect combination of secluded but with accessibility to Marathon and Key West. The house had everything we needed. We loved the appliances, the bed, the shower and the wrap-around porch with the swing. And the people managing the property made our visit the best experience from booking to departure. Will book again!"
United States
Tom H.
The price is ￥36,521
￥100,751 total
includes taxes & fees
Oct 27 - Oct 28
Starlight Serenity - Hideaway with Stunning Views
A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.

3. SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (98 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is ￥23,557
￥68,616 total
includes taxes & fees
Oct 21 - Oct 22
SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A two-story house with a balcony, a staircase, and a view of the beach.

4. Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (104 reviews)
"short drive to downtown of course as long as traffic allows it...quiet stay beautiful views...bring mosquito repellent. "
United States
Lismary D.
The price is ￥51,357
￥115,178 total
includes taxes & fees
Oct 29 - Oct 30
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
A covered outdoor seating area with white chairs and tables, overlooking turquoise waters and distant islands.

5. Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Cudjoe Key
9.8 out of 10, Exceptional, (148 reviews)
"Everything was exactly as described and we could not be happier. The community that this house is in is very pleasant as well"
United States
Jaret R.
The price is ￥62,220
￥118,609 total
includes taxes & fees
Oct 18 - Oct 19
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

6. Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Cudjoe Key
9.4 out of 10, Exceptional, (18 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is ￥31,525
￥80,601 total
includes taxes & fees
Oct 21 - Oct 22
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Pool

7. Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Cudjoe Key
8.8 out of 10, Excellent, (11 reviews)
"We loved our stayed and booked again for next year. Its in our price range, plenty of space and we were all so comfortable. Its our favorite house we have rented in the area and hope to be able to continue to enjoy it years to come. "
United States
Alisa M.
The price is ￥33,184
￥82,151 total
includes taxes & fees
Oct 18 - Oct 19
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
A view from a balcony overlooking a beach with a clear sky and calm sea.

8. Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
Cudjoe Key
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful views from the deck. The resort was quiet and peaceful. "
United States
G G.
The price is ￥74,664
￥134,190 total
includes taxes & fees
Oct 18 - Oct 19
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
A waterfront property with a covered porch, a boat dock, and a clear sky.

9. SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (113 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
The price is ￥25,138
￥70,236 total
includes taxes & fees
Oct 19 - Oct 20
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

10. Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views

Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views
Cudjoe Key
9.6 out of 10, Exceptional, (17 reviews)
"Great water view and comfortable for four adults "
United States
Kyle F.
The price is ￥35,691
￥85,943 total
includes taxes & fees
Oct 26 - Oct 27
Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

11. Post Card Point #319 - Ocean Views!

Post Card Point #319 - Ocean Views!
Cudjoe Key
10.0 out of 10, Exceptional, (56 reviews)
"We loved our stay! Prime location"
United States
Lacey C.
The price is ￥64,709
￥131,563 total
includes taxes & fees
Oct 18 - Oct 19
Post Card Point #319 - Ocean Views!
An aerial view of a resort with a large pool, palm trees, and a pier.

12. Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (26 reviews)
"Really nice unit, well equipped, and quiet.Would stay again for sure."
United States
Tom A.
The price is ￥55,307
￥109,626 total
includes taxes & fees
Oct 26 - Oct 27
Spanish Queen @Venture Out, Cudjoe Key
A swimming pool with a tiled edge, surrounded by lounge chairs and umbrellas, under a cloudy sky.

13. Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Cudjoe Key
8.0 out of 10, Very good, (21 reviews)
"Heated pool was very nice, and location of rental."
United States
Angela C.
The price is ￥39,110
￥80,660 total
includes taxes & fees
Oct 18 - Oct 19
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
A pier with a palm tree, clear turquoise water, and a distant shoreline.

14. 2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Cudjoe Key
9.8 out of 10, Exceptional, (33 reviews)
"This place was great! As advertised. It is located within a resort community, so it is safe with lots of amenities. "
United States
BRIAN S.
The price is ￥57,936
￥96,637 total
includes taxes & fees
Nov 8 - Nov 9
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
A covered outdoor area with a grill, wicker furniture, and a table with drinks, overlooking the sea.

15. Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views

Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views
Cudjoe Key
9.8 out of 10, Exceptional, (24 reviews)
"We had a nice stay."
United States
Kandie B.
The price is ￥62,220
￥128,446 total
includes taxes & fees
Oct 18 - Oct 19
Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views
A coastal property with a dock, white buildings, and a clear view of the ocean.

16. Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise

Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise
Cudjoe Key
9.6 out of 10, Exceptional, (53 reviews)
"Our stay was wonderful. Accommodations were as described and very comfortable. Location was great and the best views for the sunrise. "
United States
Kathy A.
The price is ￥65,539
￥122,660 total
includes taxes & fees
Oct 29 - Oct 30
Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise
A modern kitchen with granite countertops, stainless steel appliances, and light-colored cabinetry.

17. Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (129 reviews)
"Great location and Host was very helpful and responsive."
United States
Dennis G.
The price is ￥31,288
￥79,860 total
includes taxes & fees
Oct 18 - Oct 19
Kelly's Kabin - Adorable Private Summerland Key Cottage
A cozy room with a brown leather sofa, a white table, and a ceiling fan.

18. 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 ￥13,235
￥37,111 total
includes taxes & fees
Oct 26 - Oct 27
Old Wooden Bridge Resort and Marina
A beachside resort with a wooden deck, palm trees, and a sunset view.

19. 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 ￥51,308
￥96,139 total
includes taxes & fees
Oct 26 - Oct 27
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.

20. 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 ￥23,930
￥54,217 total
includes taxes & fees
Oct 31 - Nov 1
Aqua Lodges at Hurricane Hole Marina
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sugarloaf Key Hotel Reviews

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

8/10 Good
"👍"
Peter 1-night trip
Posted 1 hour ago
Southernmost Beach Resort and Guesthouses

Find out more about Sugarloaf Key

Search for holiday rentals in Sugarloaf Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Sugarloaf Key using one of the methods below:

  • View our selection of featured holiday rentals in Sugarloaf Key
  • Use the map to find apartments and other holiday homes in the Sugarloaf Key neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sugarloaf Key while they last

Look no further and take a look at our great range of rental properties in Sugarloaf Key!

Explore a world of travel with Expedia