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

Sugarloaf Key Vacation Rentals

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Our top choices for Sugarloaf Key vacation rentals

1. 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 ¥33,172
¥92,686 total
includes taxes & fees
Sep 30 - Oct 1
Starlight Serenity - Hideaway w Stunning Views

2. 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 ¥27,963
¥91,122 total
includes taxes & fees
Sep 30 - Oct 1
Starlight Serenity - Hideaway with Stunning Views

3. The Lighthouse - Beach Houses Key West

The Lighthouse - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (11 reviews)
"Thank you for our wonderful stay at this beautiful property - everything was perfect - Peter"
United States
Peter Q.
The price is ¥101,067
¥216,375 total
includes taxes & fees
Sep 20 - Sep 21
The Lighthouse - Beach Houses Key West

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, (367 reviews)
"Love being on the water in the houseboat. The dark skies were nice for stargazing"
United States
Lisa
The price is ¥14,379
¥38,648 total
includes taxes & fees
Sep 7 - Sep 8
Old Wooden Bridge Resort and Marina

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

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (111 reviews)
"$125.00 extra charge when arriving. Almost all the remotes needed batteries. Furniture was all shoved up against walls, everything needed to be set back up. Kayaks were under house buried under a massive amount of junk and covered with sand and debris. A/C worked on and off. A/c window unit drain poured water on steps down to sea wall making them very slippery all the time. May have been a very nice place years ago but really shows its age and poor maintenance. Did not feel like calling the...
United States
Ken
The price is ¥20,613
¥65,115 total
includes taxes & fees
Sep 3 - Sep 4
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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

SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (95 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is ¥23,809
¥69,189 total
includes taxes & fees
Sep 3 - Sep 4
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

7. Canal Front home with easy Ocean access

Canal Front home with easy Ocean access
Cudjoe Key
8.6 out of 10, Excellent, (188 reviews)
"Very nice property, as advertised. Great location for boating and fishing. "
United States
Lawrence L.
The price is ¥26,365
¥60,800 total
includes taxes & fees
Sep 9 - Sep 10
Canal Front home with easy Ocean access

8. 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
The price is ¥29,913
¥92,834 total
includes taxes & fees
Sep 8 - Sep 9
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

9. 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 ¥31,878
¥96,425 total
includes taxes & fees
Sep 3 - Sep 4
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

10. 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 ¥31,638
¥81,553 total
includes taxes & fees
Sep 8 - Sep 9
Kelly's Kabin - Adorable Private Summerland Key Cottage

11. 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 ¥33,556
¥98,472 total
includes taxes & fees
Sep 3 - Sep 4
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

12. 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 ¥55,927
¥121,601 total
includes taxes & fees
Sep 23 - Sep 24
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

13. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (196 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is ¥13,810
¥42,321 total
includes taxes & fees
Sep 3 - Sep 4
Aqua Lodges at Hurricane Hole Marina

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.
The price is ¥55,927
¥109,377 total
includes taxes & fees
Sep 7 - Sep 8
Spanish Queen @Venture Out, Cudjoe Key

15. 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 ¥62,917
¥136,297 total
includes taxes & fees
Sep 3 - Sep 4
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

16. 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)
"This was a beautiful property with amazing views."
United States
Rebecca G.
The price is ¥62,917
¥146,564 total
includes taxes & fees
Sep 8 - Sep 9
Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views

17. 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 ¥65,434
¥149,875 total
includes taxes & fees
Sep 3 - Sep 4
Post Card Point #319 - Ocean Views!

18. 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 ¥69,628
¥144,966 total
includes taxes & fees
Sep 7 - Sep 8
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

19. 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 ¥66,273
¥140,713 total
includes taxes & fees
Sep 3 - Sep 4
Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise

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, (41 reviews)
"Great set up!!!"
United States
Benjamin
The price is ¥27,963
¥65,774 total
includes taxes & fees
Sep 7 - Sep 8
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 Sugarloaf Key Hotel Reviews

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