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

Lower Sugarloaf Key Holiday Rentals

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Our top choices for Lower Sugarloaf Key holiday rentals

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (354 reviews)
"We had a great time! It was family, friendly, and we saw a ton of key deer. Pool was perfect as well!"
United States
Maya
The price is AU$388
includes taxes & fees
7 Aug - 8 Aug
Old Wooden Bridge Resort and Marina

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

SAVE BIG $$$ JULY/AUG. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (93 reviews)
"Great location, very clean, and a responsive host. We enjoyed our stay and highly recommended this spot!"
United States
David T.
The price is AU$613
includes taxes & fees
20 July - 21 July
SAVE BIG $$$ JULY/AUG. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (98 reviews)
"Perfect location. Privacy and comfort."
United States
Anthony
The price is AU$564
includes taxes & fees
2 Aug - 3 Aug
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (192 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 AU$426
includes taxes & fees
19 July - 20 July
Aqua Lodges at Hurricane Hole Marina

Canal-view 2BR/2BA home with pool, hot tub, and dock access.

Canal-view 2BR/2BA home with pool, hot tub, and dock access.
Cudjoe Key
9.2 out of 10, Wonderful, (30 reviews)
"Close to Key West and lots of great boating"
United States
Simon S.
The price is AU$879
includes taxes & fees
26 July - 27 July
Canal-view 2BR/2BA home with pool, hot tub, and dock access.

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)
"Very clean, charming home. Host was fast with responses."
United States
April W.
The price is AU$911
includes taxes & fees
17 Aug - 18 Aug
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (161 reviews)
"This was our second stay here and just as we remembered. It was clean and we had everything we needed. Would recommend it for visiting Key West as its only a 30 minute drive in."
United States
John S.
The price is AU$843
includes taxes & fees
24 July - 25 July
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (125 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 AU$705
includes taxes & fees
11 Aug - 12 Aug
Kelly's Kabin - Adorable Private Summerland Key Cottage

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Cudjoe Key
9.6 out of 10, Exceptional, (14 reviews)
"All was excellent "
United States
Bryan M.
The price is AU$853
includes taxes & fees
24 July - 25 July
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

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 AU$1,001
includes taxes & fees
24 July - 25 July
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

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, (39 reviews)
"Perfect location! Had options of 2 pools to enjoy on property. The marina serves complimentary coffee. "
United States
Crystal A.
The price is AU$573
includes taxes & fees
17 Aug - 18 Aug
47ft Viking Yacht · 2 Pools · Perry Marina · Key West

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, (132 reviews)
"Great place to stay"
United States
walter l.
The price is AU$447
includes taxes & fees
17 Aug - 18 Aug
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
8.8 out of 10, Excellent, (102 reviews)
"We stayed one night, everything was as described"
United States
Anonymous traveller
The price is AU$870
includes taxes & fees
3 Aug - 4 Aug
Canal front, dockage, 2 bedroom, 2 bath

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (26 reviews)
"Everything about our stay was simply wonderful. It was very Clean and quiet. It is in a very nice neighborhood and pet friendly. We loved the pool and the privacy. I will be back!"
United States
Marie
The price is AU$959
includes taxes & fees
4 Aug - 5 Aug
Spanish Queen @Venture Out, Cudjoe Key

Pelican Suite | Cozy Cottage, Hot Tubs, Close to D

Pelican Suite | Cozy Cottage, Hot Tubs, Close to D
Old Town Key West
9.8 out of 10, Exceptional, (41 reviews)
"Great location"
United States
Glen V.
The price is AU$558
includes taxes & fees
18 July - 19 July
Pelican Suite | Cozy Cottage, Hot Tubs, Close to D

House of the Rising Sun - VO479

House of the Rising Sun - VO479
Cudjoe Key
8.8 out of 10, Excellent, (14 reviews)
"Located in a great community and location in the Keys. Wonderful trip, we will be back. Great communication from the host."
United States
Emily H.
House of the Rising Sun - VO479

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

SAVE BIG $$$ JULY/AUG. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (109 reviews)
"Enjoyed our stay at Venture Out. Loved having the water view. We used the pool, bikes and kayaks. Owners were very responsive. House was clean. Would definitely stay again."
United States
Lindsey S.
The price is AU$997
includes taxes & fees
17 Aug - 18 Aug
SAVE BIG $$$ JULY/AUG. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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 AU$1,223
includes taxes & fees
4 Aug - 5 Aug
Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise

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, (444 reviews)
"Great location! Close to everything! We biked everywhere and accommodations had everything we needed. "
United States
Richard A.
The price is AU$345
includes taxes & fees
20 July - 21 July
Steps from Duval, Pool on Site & Bikes Included!

Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (37 reviews)
"Great to stay. Good places to eat close by."
United States
Robert B.
The price is AU$897
includes taxes & fees
21 July - 22 July
Paradise found
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Lower Sugarloaf Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Lower Sugarloaf Key holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Lower Sugarloaf Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Lower Sugarloaf Key holiday rentals we have selected for you start as low as AU$345 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Lower Sugarloaf Key rentals

At Expedia, we put the best Lower Sugarloaf Key holiday 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 holiday.

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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