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Our top choices for Sugarloaf Key holiday rentals

1. Private and Exclusive Florida Keys Getaway
Private and Exclusive Florida Keys GetawayUpper Sugarloaf Key
10.0 out of 10, Exceptional, (15 reviews)

2. Starlight Serenity - Hideaway w Stunning Views
Starlight Serenity - Hideaway w Stunning ViewsSummerland Key
10.0 out of 10, Exceptional, (1 review)
The price is €638
includes taxes & fees
19 Nov - 20 Nov

3. Starlight Serenity - Hideaway with Stunning Views
Starlight Serenity - Hideaway with Stunning ViewsSummerland Key
10.0 out of 10, Exceptional, (1 review)
The price is €591
includes taxes & fees
19 Nov - 20 Nov

4. 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)
The price is €429
includes taxes & fees
16 Nov - 17 Nov

5. 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)
The price is €640
includes taxes & fees
16 Nov - 17 Nov

6. 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)
The price is €411
includes taxes & fees
16 Nov - 17 Nov

7. 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)

8. 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)
The price is €386
includes taxes & fees
16 Nov - 17 Nov

9. 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)
The price is €722
includes taxes & fees
19 Nov - 20 Nov

10. 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)
The price is €731
includes taxes & fees
16 Nov - 17 Nov

11. Post Card Point #319 - Ocean Views!
Post Card Point #319 - Ocean Views!Cudjoe Key
10.0 out of 10, Exceptional, (56 reviews)
The price is €689
includes taxes & fees
16 Nov - 17 Nov

12. Spanish Queen @Venture Out, Cudjoe Key
Spanish Queen @Venture Out, Cudjoe KeyCudjoe Key
9.4 out of 10, Exceptional, (26 reviews)
The price is €604
includes taxes & fees
16 Nov - 17 Nov

13. 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)
The price is €440
includes taxes & fees
16 Nov - 17 Nov

14. 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)
The price is €412
includes taxes & fees
19 Nov - 20 Nov

15. Canal front, dockage, 2 bedroom, 2 bath
Canal front, dockage, 2 bedroom, 2 bathCudjoe Key
8.8 out of 10, Excellent, (110 reviews)
The price is €354
includes taxes & fees
16 Dec - 17 Dec

16. 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)
The price is €642
includes taxes & fees
16 Nov - 17 Nov

17. 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)
The price is €424
includes taxes & fees
20 Nov - 21 Nov

18. Old Wooden Bridge Resort and Marina
Old Wooden Bridge Resort and MarinaPunta Brisa
8.6 out of 10, Excellent, (386 reviews)
The price is €217
includes taxes & fees
29 Nov - 30 Nov

19. 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)
The price is €440
includes taxes & fees
16 Nov - 17 Nov

20. Aqua Lodges at Hurricane Hole Marina
Aqua Lodges at Hurricane Hole MarinaStock Island
8.8 out of 10, Excellent, (202 reviews)
The price is €293
includes taxes & fees
16 Nov - 17 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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