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Our top choices for Summerland Key vacation rentals

1. Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Affordable Dog Friendly Keys Retreat in Venture Out Near Key WestCudjoe Key
10.0 out of 10, Exceptional, (1 review)
The price is CA $175
CA $561 total
includes taxes & fees
Nov 22 - Nov 23

2. 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 $281
CA $705 total
includes taxes & fees
Nov 21 - Nov 22

3. 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 $220
CA $617 total
includes taxes & fees
Nov 11 - Nov 12

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 CA $199
CA $589 total
includes taxes & fees
Nov 14 - Nov 15

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 CA $258
CA $661 total
includes taxes & fees
Nov 22 - Nov 23

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)
The price is CA $209
CA $597 total
includes taxes & fees
Nov 10 - Nov 11

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 CA $265
CA $652 total
includes taxes & fees
Nov 10 - Nov 11

8. 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 $273
CA $681 total
includes taxes & fees
Nov 14 - Nov 15

9. Canal Front home with easy Ocean access
Canal Front home with easy Ocean accessCudjoe Key
8.8 out of 10, Excellent, (190 reviews)
The price is CA $231
CA $510 total
includes taxes & fees
Nov 27 - Nov 28

10. 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 $300
CA $715 total
includes taxes & fees
Nov 13 - Nov 14

11. 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 $265
CA $652 total
includes taxes & fees
Nov 10 - Nov 11

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 $254
CA $658 total
includes taxes & fees
Nov 11 - Nov 12

13. 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 $252
CA $653 total
includes taxes & fees
Nov 10 - Nov 11

14. Florida Keys Waterfront Escape w/35' Seawall & Seconds to Open Water
Florida Keys Waterfront Escape w/35' Seawall & Seconds to Open WaterCudjoe Key
9.4 out of 10, Exceptional, (3 reviews)
The price is CA $252
CA $653 total
includes taxes & fees
Nov 10 - Nov 11

15. Waterfront RV lot in Venture Out Cudjoe Key, FL minutes to Blue Water & Key West
Waterfront RV lot in Venture Out Cudjoe Key, FL minutes to Blue Water & Key WestCudjoe Key
The price is CA $158
CA $194 total
includes taxes & fees
Nov 10 - Nov 11

16. 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 $260
CA $667 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, (8 reviews)
The price is CA $285
CA $693 total
includes taxes & fees
Nov 10 - Nov 11

18. 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 $265
CA $669 total
includes taxes & fees
Nov 10 - Nov 11

19. Florida Keys Waterfront Escape - 2BR with 44' Seawall
Florida Keys Waterfront Escape - 2BR with 44' SeawallCudjoe Key
The price is CA $265
CA $654 total
includes taxes & fees
Nov 11 - Nov 12

20. 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, (5 reviews)
The price is CA $287
CA $698 total
includes taxes & fees
Nov 9 - Nov 10
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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