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Cottages
Our top choices for Summerland Key vacation 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 CA $202
CA $599 total
includes taxes & fees
Nov 14 - Nov 15

2. 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 CA $255
CA $677 total
includes taxes & fees
Nov 19 - Nov 20

3. 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 CA $276
CA $688 total
includes taxes & fees
Nov 14 - Nov 15

4. 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)
The price is CA $327
CA $767 total
includes taxes & fees
Nov 29 - Nov 30

5. 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 CA $222
CA $623 total
includes taxes & fees
Nov 14 - Nov 15

6. 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 CA $270
CA $681 total
includes taxes & fees
Nov 14 - Nov 15

7. 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 CA $236
CA $640 total
includes taxes & fees
Nov 20 - Nov 21

8. 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 CA $263
CA $673 total
includes taxes & fees
Nov 14 - Nov 15

9. 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 CA $303
CA $722 total
includes taxes & fees
Nov 14 - Nov 15

10. 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 CA $270
CA $681 total
includes taxes & fees
Nov 14 - Nov 15

11. 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 CA $256
CA $664 total
includes taxes & fees
Nov 14 - Nov 15

12. 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 CA $256
CA $664 total
includes taxes & fees
Nov 14 - Nov 15

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 CA $270
CA $681 total
includes taxes & fees
Nov 14 - Nov 15

14. 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 CA $290
CA $705 total
includes taxes & fees
Nov 16 - Nov 17

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 CA $303
CA $722 total
includes taxes & fees
Nov 20 - Nov 21

16. Florida Keys Waterfront Escape - 2BR with 44' Seawall
Florida Keys Waterfront Escape - 2BR with 44' SeawallCudjoe Key
The price is CA $270
CA $665 total
includes taxes & fees
Nov 14 - Nov 15

17. 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 CA $290
CA $705 total
includes taxes & fees
Nov 14 - Nov 15

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 CA $270
CA $681 total
includes taxes & fees
Nov 14 - Nov 15

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 CA $353
CA $704 total
includes taxes & fees
Nov 14 - Nov 15

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 CA $342
CA $932 total
includes taxes & fees
Nov 19 - Nov 20
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.


































































