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Our top choices for Sugarloaf Key holiday rentals
1. Starlight Serenity - Hideaway with Stunning Views
Starlight Serenity - Hideaway with Stunning ViewsSummerland 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!"
Tom H.
The price is HK$2,000
HK$5,084 total
includes taxes & fees
19 Nov - 20 Nov
2. Starlight Serenity - Hideaway w Stunning Views
Starlight Serenity - Hideaway w Stunning ViewsSummerland 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."
max
The price is HK$2,613
HK$5,657 total
includes taxes & fees
19 Nov - 20 Nov
3. Old Wooden Bridge Resort and Marina
Old Wooden Bridge Resort and MarinaPunta Brisa
8.6 out of 10, Excellent, (380 reviews)
"Great view , clean room and excellent staff ( Mr. shaggy )"
Jordan
The price is HK$548
HK$1,719 total
includes taxes & fees
4 Dec - 5 Dec
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 WestCudjoe 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 ."
jim b.
The price is HK$1,222
HK$3,403 total
includes taxes & fees
11 Nov - 12 Nov
5. 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 BEDSCudjoe Key
9.6 out of 10, Exceptional, (99 reviews)
"Great location, wonderful hosts!"
Blue Mountain Footwear F.
The price is HK$1,560
HK$3,859 total
includes taxes & fees
21 Nov - 22 Nov
6. 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 BEDSCudjoe 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!"
Mckayla S.
The price is HK$1,168
HK$3,379 total
includes taxes & fees
11 Nov - 12 Nov
7. Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart OptionCudjoe Key
9.4 out of 10, Exceptional, (18 reviews)
"Perfect location, great price."
Suzanne T.
The price is HK$1,408
HK$3,627 total
includes taxes & fees
11 Nov - 12 Nov
8. Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key WestCudjoe 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. "
Alisa M.
The price is HK$1,482
HK$3,718 total
includes taxes & fees
11 Nov - 12 Nov
9. Canal Front home with easy Ocean access
Canal Front home with easy Ocean accessCudjoe Key
8.8 out of 10, Excellent, (191 reviews)
"Porsche Berry Duty"
Rafael G.
The price is HK$1,294
HK$2,827 total
includes taxes & fees
26 Nov - 27 Nov
10. Kelly's Kabin - Adorable Private Summerland Key Cottage
Kelly's Kabin - Adorable Private Summerland Key CottageSummerland Key
9.8 out of 10, Exceptional, (129 reviews)
"Great location and Host was very helpful and responsive."
Dennis G.
The price is HK$1,517
HK$3,758 total
includes taxes & fees
14 Nov - 15 Nov
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 WestCudjoe 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."
Iva B.
The price is HK$1,960
HK$3,764 total
includes taxes & fees
22 Nov - 23 Nov
12. 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."
Angela C.
The price is HK$1,940
HK$3,845 total
includes taxes & fees
11 Nov - 12 Nov
13. Aqua Lodges at Hurricane Hole Marina
Aqua Lodges at Hurricane Hole MarinaStock Island
8.8 out of 10, Excellent, (202 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
Kagni
The price is HK$840
HK$2,287 total
includes taxes & fees
11 Nov - 12 Nov
14. Canal front, dockage, 2 bedroom, 2 bath
Canal front, dockage, 2 bedroom, 2 bathCudjoe Key
8.8 out of 10, Excellent, (110 reviews)
"Exactly as shown in the pictures and as described. Appreciated the extra location for the boat trailer."
Laurie C.
The price is HK$2,235
HK$4,129 total
includes taxes & fees
14 Nov - 15 Nov
15. Spanish Queen @Venture Out, Cudjoe Key
Spanish Queen @Venture Out, Cudjoe KeyCudjoe Key
9.4 out of 10, Exceptional, (26 reviews)
"Really nice unit, well equipped, and quiet.Would stay again for sure."
Tom A.
The price is HK$2,744
HK$5,180 total
includes taxes & fees
18 Nov - 19 Nov
16. Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & PoolCudjoe 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"
Jaret R.
The price is HK$2,963
HK$5,495 total
includes taxes & fees
13 Nov - 14 Nov
17. Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-FriendlyCudjoe Key
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful views from the deck. The resort was quiet and peaceful. "
G G.
The price is HK$3,520
HK$6,161 total
includes taxes & fees
14 Nov - 15 Nov
18. Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views
Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning ViewsCudjoe Key
9.8 out of 10, Exceptional, (25 reviews)
"We had a nice stay."
Kandie B.
The price is HK$3,186
HK$6,233 total
includes taxes & fees
14 Nov - 15 Nov
19. Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise
Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's ParadiseCudjoe 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. "
Kathy A.
The price is HK$2,927
HK$5,455 total
includes taxes & fees
11 Nov - 12 Nov
20. 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"
Lacey C.
The price is HK$2,889
HK$5,876 total
includes taxes & fees
11 Nov - 12 Nov
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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