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Our top choices for Sugarloaf Key vacation homes

1. Starlight Serenity - Hideaway with Stunning Views
Starlight Serenity - Hideaway with Stunning ViewsSummerland Key
10.0 out of 10, Exceptional, (1 review)
The price is ¥37,851
¥102,535 total
includes taxes & fees
Nov 19 - Nov 20

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 ¥48,547
¥109,955 total
includes taxes & fees
Nov 19 - Nov 20

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

4. Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated AccessCudjoe Key
10.0 out of 10, Exceptional, (1 review)
The price is ¥22,639
¥66,455 total
includes taxes & fees
Nov 20 - Nov 21

5. Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal ViewsCudjoe Key
9.0 out of 10, Wonderful, (2 reviews)
The price is ¥26,411
¥71,018 total
includes taxes & fees
Nov 20 - Nov 21

6. 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 ¥24,902
¥69,321 total
includes taxes & fees
Nov 16 - Nov 17

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)
The price is ¥28,676
¥73,887 total
includes taxes & fees
Nov 16 - Nov 17

8. 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 ¥20,603
¥64,923 total
includes taxes & fees
Nov 16 - Nov 17

9. 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 ¥30,185
¥75,744 total
includes taxes & fees
Nov 16 - Nov 17

10. Canal-Front Retreat with Dock, Pool & Open Ocean Views
Canal-Front Retreat with Dock, Pool & Open Ocean ViewsCudjoe Key
9.0 out of 10, Wonderful, (13 reviews)
The price is ¥29,430
¥74,733 total
includes taxes & fees
Nov 20 - Nov 21

11. 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)

12. Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape
Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys EscapeCudjoe Key
8.8 out of 10, Excellent, (3 reviews)
The price is ¥30,185
¥75,744 total
includes taxes & fees
Nov 16 - Nov 17

13. Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart
Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf CartCudjoe Key
9.6 out of 10, Exceptional, (7 reviews)
The price is ¥28,676
¥73,887 total
includes taxes & fees
Nov 21 - Nov 22

14. 2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.Cudjoe Key
The price is ¥33,958
¥80,148 total
includes taxes & fees
Nov 16 - Nov 17

15. Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious ComfortCudjoe Key
9.6 out of 10, Exceptional, (5 reviews)
The price is ¥30,185
¥76,223 total
includes taxes & fees
Nov 16 - Nov 17

16. Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views
Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys ViewsCudjoe Key
9.6 out of 10, Exceptional, (18 reviews)
The price is ¥33,958
¥80,148 total
includes taxes & fees
Nov 20 - Nov 21

17. 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 ¥30,904
¥76,393 total
includes taxes & fees
Nov 16 - Nov 17

18. Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe KeyCudjoe Key
10.0 out of 10, Exceptional, (6 reviews)
The price is ¥32,448
¥78,449 total
includes taxes & fees
Nov 16 - Nov 17

19. Sailfish Haven #390 - Ocean Views, 35' seawall
Sailfish Haven #390 - Ocean Views, 35' seawallCudjoe Key
9.0 out of 10, Wonderful, (9 reviews)
The price is ¥36,055
¥82,507 total
includes taxes & fees
Nov 29 - Nov 30

20. 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 ¥39,928
¥77,001 total
includes taxes & fees
Nov 20 - Nov 21
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.
Learn more about Sugarloaf Key
Kayak through mangrove tunnels and spot colorful fish in the crystal-clear waters surrounding this laid-back island. Unwind on Sugarloaf Beach's white sands or explore Upper Sugarloaf Sound, where local boaters know the best snorkeling spots.

































































