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. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (198 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
$243 nightly
The price is $274
Oct 7 - Oct 8
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina

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

SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (98 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
$379 nightly
The price is $421
Oct 6 - Oct 7
Total with taxes and fees
SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (112 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
$399 nightly
The price is $443
Oct 13 - Oct 14
Total with taxes and fees
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

4. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (373 reviews)
"Best stop over before going to Key west. We enjoyed here a lot, parking our trailer was never a problem."
United States
Daisybel
$225 nightly
The price is $253
Oct 6 - Oct 7
Total with taxes and fees
Old Wooden Bridge Resort and Marina

5. 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)
"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.
$441 nightly
The price is $491
Oct 11 - Oct 12
Total with taxes and fees
Kelly's Kabin - Adorable Private Summerland Key Cottage

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

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
9.8 out of 10, Exceptional, (6 reviews)
"Property was perfectly located and very clean and comfortable."
United States
Kiara
$521 nightly
The price is $578
Oct 6 - Oct 7
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

7. 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.
$460 nightly
The price is $510
Oct 6 - Oct 7
Total with taxes and fees
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

8. 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
9.4 out of 10, Exceptional, (16 reviews)
"Great water view and comfortable for four adults "
United States
Kyle F.
$489 nightly
The price is $543
Oct 6 - Oct 7
Total with taxes and fees
Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views

9. 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.
$471 nightly
The price is $523
Oct 6 - Oct 7
Total with taxes and fees
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

10. Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views

Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views
Cudjoe Key
9.0 out of 10, Wonderful, (12 reviews)
"This property is convenient to food and fun. It was very clean, comfortable and we felt safe to walk around the resort. We had a wonderful stay here."
United States
Catherine C.
$481 nightly
The price is $534
Oct 7 - Oct 8
Total with taxes and fees
Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views

11. 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
$260 nightly
The price is $292
Oct 7 - Oct 8
Total with taxes and fees
Island View 1BR Residence With Balcony

12. ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (113 reviews)
"Not really close to much but a comfortable bed and clean room. The pool and grounds are lovely. Will stay again but rent a golf cart. "
United States
Laura T.
$284 nightly
The price is $315
Oct 8 - Oct 9
Total with taxes and fees
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

13. 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, (457 reviews)
"This studio is in a wonderful location and comes with bikes and a pool spa. It is a fabulous place to stay for a relaxing get-away island-style."
United States
Laura D.
$215 nightly
The price is $239
Oct 19 - Oct 20
Total with taxes and fees
Steps from Duval, Pool on Site & Bikes Included!

14. 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.
$609 nightly
The price is $677
Oct 12 - Oct 13
Total with taxes and fees
Spanish Queen @Venture Out, Cudjoe Key

15. 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.
$652 nightly
The price is $724
Oct 19 - Oct 20
Total with taxes and fees
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

16. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Definitely would stay here again. Very smooth process. Property was perfect for our family of 5. We loved having access to the pool right at our doorstep. Very accurate photos and description. Excellent value for the money."
United States
Danielle D.
$272 nightly
The price is $302
Oct 18 - Oct 19
Total with taxes and fees
Poolside Cottage #412

17. Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool

Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool
Old Town Key West
8.8 out of 10, Excellent, (56 reviews)
"The room was exactly what we expected, clean, cozy and a good place to chill after a day of adventuring in Key West. The pool/hot tub was wonderful and I wish I had one at home we didn’t want to leave and can’t wait to be back!"
United States
Cody S.
$309 nightly
The price is $343
Oct 6 - Oct 7
Total with taxes and fees
Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool

18. COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!

COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (121 reviews)
"Excellent stay, great location! "
United States
Dr. Christopher S.
$272 nightly
The price is $302
Oct 6 - Oct 7
Total with taxes and fees
COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!

19. The Andros | Incredible Views w/ Shared Pool

The Andros | Incredible Views w/ Shared Pool
Key West
9.0 out of 10, Wonderful, (45 reviews)
"Stayed 3,nights- would have stayed forever! Rick and staff could not have been more accommodating and friendly- the property was immaculate and maybe the most comfortable bed I’ve ever slept in! Rick was so knowledgeable about the island - had the answers for everything- such a lovely, relaxing stay, we will definitely be back!"
United States
Cynthia R.
$446 nightly
The price is $496
Oct 6 - Oct 7
Total with taxes and fees
The Andros | Incredible Views w/ Shared Pool

20. Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Old Town Key West
9.6 out of 10, Exceptional, (55 reviews)
"Great property. Walking Blocks away from the downtown action, yet far away to be quiet. Parking is very tough. If you don’t need to rent a car because you’re going to be hanging out in town the whole time, don’t bother. Uber and transportation are plentiful but again, the parking is very difficult to find free parking."
United States
Timothy
$373 nightly
The price is $414
Oct 6 - Oct 7
Total with taxes and fees
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
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

Everything you need to know about Lower 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 Lower 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 Lower Sugarloaf Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Lower Sugarloaf Key vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Lower 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 Lower 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 $206 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 Lower Sugarloaf Key rentals

At Expedia, we put the best Lower 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 Lower 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 Lower 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 Lower 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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