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

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Our top choices for Sugarloaf Key holiday rentals

1. 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 £460
includes taxes & fees
17 Aug - 18 Aug
Starlight Serenity - Hideaway with Stunning Views

2. 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 £487
includes taxes & fees
17 Aug - 18 Aug
Starlight Serenity - Hideaway w Stunning Views

3. The Hemingway - Beach Houses Key West

The Hemingway - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (8 reviews)
"Great place for our family of 5 A little off the beaten path which is exactly what we wanted Great host who answered all our questions promptly Sunrise and sunsets here were magnificent Great fishing off the dock as well"
United States
Brian K.
The price is £1,028
includes taxes & fees
3 Aug - 4 Aug
The Hemingway - Beach Houses Key West

4. Private and Exclusive Beach Getaway

Private and Exclusive Beach Getaway
Sugarloaf Key
10.0 out of 10, Exceptional, (11 reviews)
"Location was amazing. Lots of great local restaurants and food markets nearby. Property was gorgeous, very private, and spacious interiors. Beds were so comfortable! Friendly staff and the pool was a 10 out of 10!! I will be back. "
United States
Joanna G.
Private and Exclusive Beach Getaway

5. Private and Exclusive Beach Getaway

Private and Exclusive Beach Getaway
Sugarloaf Key
8.0 out of 10, Very good, (2 reviews)
"If you're looking for a peaceful and picturesque getaway, the Bungalows at Sugarloaf Beach is the perfect choice!Thank you, Cadmier, for your hospitality. See again. Respectfully, Samat Sakebaev "
United States
Samat S.
The price is £1,757
includes taxes & fees
3 Aug - 4 Aug
Private and Exclusive Beach Getaway

6. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (193 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 £219
includes taxes & fees
3 Aug - 4 Aug
Aqua Lodges at Hurricane Hole Marina

7. 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)
"Great stay and an excellent host! "
United States
Mike T.
The price is £300
includes taxes & fees
1 Sept - 2 Sept
47ft Viking Yacht · 2 Pools · Perry Marina · Key West

8. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (360 reviews)
"We stayed in the 2 bedroom condo. It was spacious and clean. We enjoyed our time there."
United States
Kathy
The price is £179
includes taxes & fees
1 Sept - 2 Sept
Old Wooden Bridge Resort and Marina

9. 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 £445
includes taxes & fees
1 Sept - 2 Sept
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

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

SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (95 reviews)
"Great location, very clean, and a responsive host. We enjoyed our stay and highly recommended this spot!"
United States
David T.
The price is £365
includes taxes & fees
20 Aug - 21 Aug
SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

11. 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 £388
includes taxes & fees
1 Sept - 2 Sept
Kelly's Kabin - Adorable Private Summerland Key Cottage

12. Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
8.8 out of 10, Excellent, (102 reviews)
"The bedrooms and bathrooms were a little small but everything else was fantastic. We loved the outdoor spaces."
United States
Carla R.
Canal front, dockage, 2 bedroom, 2 bath

13. 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, (32 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 £383
includes taxes & fees
20 Aug - 21 Aug
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

14. 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 £507
includes taxes & fees
4 Aug - 5 Aug
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
8.8 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 £559
includes taxes & fees
8 Aug - 9 Aug
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

16. 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, (8 reviews)
"Beautiful views from the deck. The resort was quiet and peaceful. "
United States
G G.
The price is £738
includes taxes & fees
15 Aug - 16 Aug
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

17. One of the very few beach houses with a daily, rental license in the Keys.

One of the very few beach houses with a daily, rental license in the Keys.
Summerland Key
8.8 out of 10, Excellent, (72 reviews)
"Such a beautiful home, the view is to die for. It could definitely use some upgrades like the washer and dryer, but can’t beat the location and the fact that its beachfront. "
United States
LIZ
The price is £955
includes taxes & fees
3 Aug - 4 Aug
One of the very few beach houses with a daily, rental license in the Keys.

18. 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 £653
includes taxes & fees
3 Aug - 4 Aug
Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise

19. 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 £629
includes taxes & fees
1 Sept - 2 Sept
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
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 Sugarloaf Key Hotel Reviews

Find out more about Sugarloaf Key

Everything you need to know about 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 Sugarloaf Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Sugarloaf Key holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Sugarloaf Key holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A 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 Sugarloaf Key holiday rentals we have selected for you start as low as £179 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Sugarloaf Key rentals

At Expedia, we put the best 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 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 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 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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