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

Lower Sugarloaf Key Vacation Rentals

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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, (385 reviews)
"Very clean for Florida keys room - no complaints easy check in and out"
United States
Anthony
The price is CA $100
CA $313 total
includes taxes & fees
Dec 4 - Dec 5
Old Wooden Bridge Resort and Marina

2. Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"Excellent location - clean, quiet, well-kept community. Boat launch was key for us. Pool and beach looked very nice, but we didn't use. The unit is as described and has a nice patio out back that we used every day."
United States
Cheryl V.
The price is CA $202
CA $599 total
includes taxes & fees
Nov 20 - Nov 21
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

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, (202 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is CA $180
CA $448 total
includes taxes & fees
Nov 15 - Nov 16
Aqua Lodges at Hurricane Hole Marina

4. Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Cudjoe Key
8.6 out of 10, Excellent, (4 reviews)
" Great 2 bedroom home in a lovely vacation community . We enjoyed the 2 recliners to relax after a full day of exploring as well as in the morning with our coffee. The screened in patio was a nice perk as well . At check in , a calendar of events was provided and the staff were friendly and helpful. FYI : We enjoyed a gorgeous sunrise right by the beach near the pool ."
United States
jim b.
The price is CA $222
CA $623 total
includes taxes & fees
Nov 19 - Nov 20
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

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

SAVE BIG $$$ NOV./DEC. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (113 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
The price is CA $255
CA $677 total
includes taxes & fees
Nov 19 - Nov 20
SAVE BIG $$$ NOV./DEC. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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)
"Perfect location, great price."
United States
Suzanne T.
The price is CA $256
CA $664 total
includes taxes & fees
Nov 19 - Nov 20
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 $270
CA $681 total
includes taxes & fees
Nov 19 - Nov 20
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

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

SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (99 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

9. 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 CA $276
CA $688 total
includes taxes & fees
Nov 15 - Nov 16
Kelly's Kabin - Adorable Private Summerland Key Cottage

10. 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 CA $353
CA $704 total
includes taxes & fees
Nov 19 - Nov 20
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

11. Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Cudjoe Key
8.8 out of 10, Excellent, (240 reviews)
"A wonderful place overlooking the water. Morning sunrises on the patio couldn't have been better. A safe, friendly community."
United States
Iva B.
The price is CA $357
CA $696 total
includes taxes & fees
Nov 20 - Nov 21
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

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 CA $499
CA $950 total
includes taxes & fees
Nov 16 - Nov 17
Spanish Queen @Venture Out, Cudjoe Key

13. 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, (149 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 CA $539
CA $1,007 total
includes taxes & fees
Nov 16 - Nov 17
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

14. 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 $640
CA $1,129 total
includes taxes & fees
Nov 19 - Nov 20
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

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, (25 reviews)
"We had a nice stay."
United States
Kandie B.
The price is CA $580
CA $1,143 total
includes taxes & fees
Nov 19 - Nov 20
Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views

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 CA $532
CA $999 total
includes taxes & fees
Nov 19 - Nov 20
Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise

17. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (38 reviews)
"Wonderful stay. Thank you."
United States
shannon b.
The price is CA $264
CA $450 total
includes taxes & fees
Dec 1 - Dec 2
Poolside Cottage #412

18. 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, (464 reviews)
"We liked sitting by the pool and visiting with other guests. The air conditioner struggled to keep the room cool; it ran all night long to maintain 72 degrees."
United States
Karen
The price is CA $179
CA $390 total
includes taxes & fees
Dec 2 - Dec 3
Steps from Duval, Pool on Site & Bikes Included!

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 $526
CA $1,078 total
includes taxes & fees
Nov 19 - Nov 20
Post Card Point #319 - Ocean Views!

20. 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, (43 reviews)
"Great set up!!!"
United States
Benjamin
The price is CA $357
CA $692 total
includes taxes & fees
Nov 19 - Nov 20
47ft Viking Yacht · 2 Pools · Perry Marina · Key West
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 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.

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