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

Lower 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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Lower Sugarloaf Key vacation rentals

1. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (366 reviews)
"Love being on the water in the houseboat. The dark skies were nice for stargazing"
United States
Lisa
The price is CA $124
CA $334 total
includes taxes & fees
Sep 7 - Sep 8
Old Wooden Bridge Resort and Marina

2. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (194 reviews)
"The bathroom smelled a bit, but we loved the loft and the vibes of the houseboat. It’s hard to find 3 bedrooms at that reasonable price and we have 3 kids that do not want to sleep together so this was perfect. We ate at the bar and really enjoyed watching the jellyfish. It was a cool!"
United States
Emily
The price is CA $129
CA $378 total
includes taxes & fees
Aug 21 - Aug 22
Aqua Lodges at Hurricane Hole Marina

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

SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (95 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is CA $304
CA $727 total
includes taxes & fees
Aug 26 - Aug 27
SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

4. SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (110 reviews)
"Stay was great. We met the hosts and they were wonderful people."
United States
James B.
The price is CA $275
CA $685 total
includes taxes & fees
Aug 29 - Aug 30
SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

5. Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (5 reviews)
"Property was perfectly located and very clean and comfortable."
United States
Kiara
The price is CA $266
CA $816 total
includes taxes & fees
Aug 25 - Aug 26
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

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, (17 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is CA $275
CA $836 total
includes taxes & fees
Aug 25 - Aug 26
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

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 CA $290
CA $855 total
includes taxes & fees
Aug 25 - Aug 26
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

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

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (128 reviews)
"Very nice place. Centrally located near good restaurants, markets, etc.. Pet friendly which worked for us. Nice long walking trail behind cottage."
United States
John B.
The price is CA $267
CA $695 total
includes taxes & fees
Sep 7 - Sep 8
Kelly's Kabin - Adorable Private Summerland Key Cottage

9. 47ft Viking Yacht · 2 Pools · Perry Marina · Key West

47ft Viking Yacht · 2 Pools · Perry Marina · Key West
Stock Island
7.6 out of 10, Good, (41 reviews)
"Great set up!!!"
United States
Benjamin
The price is CA $230
CA $552 total
includes taxes & fees
Sep 7 - Sep 8
47ft Viking Yacht · 2 Pools · Perry Marina · Key West

10. 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
8.8 out of 10, Excellent, (101 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 CA $486
CA $1,058 total
includes taxes & fees
Aug 21 - Aug 22
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

11. 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 CA $483
CA $945 total
includes taxes & fees
Sep 2 - Sep 3
Spanish Queen @Venture Out, Cudjoe Key

12. 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)
"Nice property in a beautiful location. Great place to sit and enjoy the scenery and activities. "
United States
Andy D.
The price is CA $544
CA $1,179 total
includes taxes & fees
Sep 2 - Sep 3
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

13. 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 CA $569
CA $1,214 total
includes taxes & fees
Sep 1 - Sep 2
Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise

14. 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, (23 reviews)
"Great location, beautiful rental very clean with access to the complex pool and also has a golf cart!"
United States
Michael C.
The price is CA $544
CA $1,260 total
includes taxes & fees
Sep 20 - Sep 21
Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views

15. 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 CA $602
CA $1,253 total
includes taxes & fees
Sep 7 - Sep 8
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

16. 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 CA $378
CA $763 total
includes taxes & fees
Aug 31 - Sep 1
Grand Marina Suite by Brightwild Waterfront

17. Steps from Duval, Pool on Site & Bikes Included!

Steps from Duval, Pool on Site & Bikes Included!
Old Town Key West
9.6 out of 10, Exceptional, (450 reviews)
"Great location! Close to everything! We biked everywhere and accommodations had everything we needed. "
United States
Richard A.
The price is CA $123
CA $309 total
includes taxes & fees
Sep 7 - Sep 8
Steps from Duval, Pool on Site & Bikes Included!

18. SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Old Town Key West
9.8 out of 10, Exceptional, (136 reviews)
"Great place to stay"
United States
walter l.
The price is CA $157
CA $405 total
includes taxes & fees
Aug 25 - Aug 26
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

19. 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 CA $565
CA $1,295 total
includes taxes & fees
Aug 25 - Aug 26
Post Card Point #319 - Ocean Views!

20. Waterfront Condo Dock Pool Near Duval St

Waterfront Condo Dock Pool Near Duval St
Meadows
9.8 out of 10, Exceptional, (29 reviews)
"Great stay! Beautiful view. No complaints. Easy check in and great communication with owner. Thanks for a great trip!"
United States
Haley P.
The price is CA $170
CA $538 total
includes taxes & fees
Aug 25 - Aug 26
Waterfront Condo Dock Pool Near Duval St
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Lower Sugarloaf Key Hotel Reviews

Find out more about Lower Sugarloaf Key

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Lower Sugarloaf Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia