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Our top choices for Summerland Key holiday homes

1. 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 HK$1,112
HK$3,265 total
includes taxes & fees
20 Nov - 21 Nov

2. 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 HK$1,223
HK$3,405 total
includes taxes & fees
16 Nov - 17 Nov

3. 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 HK$1,297
HK$3,489 total
includes taxes & fees
20 Nov - 21 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 HK$1,483
HK$3,721 total
includes taxes & fees
16 Nov - 17 Nov

5. 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 HK$1,518
HK$3,753 total
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 HK$1,409
HK$3,630 total
includes taxes & fees
16 Nov - 17 Nov

7. 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 HK$1,483
HK$3,721 total
includes taxes & fees
16 Nov - 17 Nov

8. 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 HK$1,668
HK$3,937 total
includes taxes & fees
16 Nov - 17 Nov

9. 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)

10. 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 HK$1,404
HK$3,678 total
includes taxes & fees
19 Nov - 20 Nov

11. 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 HK$1,409
HK$3,630 total
includes taxes & fees
21 Nov - 22 Nov

12. 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 HK$1,446
HK$3,671 total
includes taxes & fees
20 Nov - 21 Nov

13. 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 HK$1,483
HK$3,744 total
includes taxes & fees
16 Nov - 17 Nov

14. Florida Keys Waterfront Escape - 2BR with 44' Seawall
Florida Keys Waterfront Escape - 2BR with 44' SeawallCudjoe Key
The price is HK$1,483
HK$3,619 total
includes taxes & fees
16 Nov - 17 Nov

15. 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 HK$1,668
HK$3,937 total
includes taxes & fees
20 Nov - 21 Nov

16. 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 HK$1,771
HK$4,053 total
includes taxes & fees
29 Nov - 30 Nov

17. 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 HK$1,594
HK$3,854 total
includes taxes & fees
16 Nov - 17 Nov

18. Ground Level Waterfront 2BR in Venture Out - 23' Seawall, Pool, Marina & Pet Friendly
Ground Level Waterfront 2BR in Venture Out - 23' Seawall, Pool, Marina & Pet FriendlyCudjoe Key
8.0 out of 10, Very good, (1 review)
The price is HK$1,483
HK$3,713 total
includes taxes & fees
18 Nov - 19 Nov

19. 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 HK$1,942
HK$3,848 total
includes taxes & fees
16 Nov - 17 Nov

20. Starlight Serenity - Hideaway with Stunning Views
Starlight Serenity - Hideaway with Stunning ViewsSummerland Key
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,883
HK$5,063 total
includes taxes & fees
19 Nov - 20 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.
Learn more about Summerland Key
Snorkel the vibrant coral reefs at Looe Key, where rangers can direct you to spots with fewer boats. Rent kayaks to explore the mangrove trails, then ask locals about their favourite seafood shacks serving fresh-caught Keys lobster.


































































