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Our top choices for Summerland Key holiday homes

1. 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 £316
includes taxes & fees
11 Nov - 12 Nov

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 £373
includes taxes & fees
21 Nov - 22 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 £343
includes taxes & fees
20 Nov - 21 Nov

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 £313
includes taxes & fees
11 Nov - 12 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 £376
includes taxes & fees
14 Nov - 15 Nov

6. 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 £350
includes taxes & fees
11 Nov - 12 Nov

7. 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 £367
includes taxes & fees
13 Nov - 14 Nov

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 £351
includes taxes & fees
14 Nov - 15 Nov

9. 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 £309
includes taxes & fees
10 Nov - 11 Nov

10. 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 £336
includes taxes & fees
8 Nov - 9 Nov

11. 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 £360
includes taxes & fees
9 Nov - 10 Nov

12. 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 £350
includes taxes & fees
6 Nov - 7 Nov

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 £336
includes taxes & fees
11 Nov - 12 Nov

14. Florida Keys Waterfront Escape - 2BR with 44' Seawall
Florida Keys Waterfront Escape - 2BR with 44' SeawallCudjoe Key
The price is £351
includes taxes & fees
11 Nov - 12 Nov

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 £350
includes taxes & fees
9 Nov - 10 Nov

16. 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 £360
includes taxes & fees
9 Nov - 10 Nov

17. 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 £379
includes taxes & fees
19 Nov - 20 Nov

18. 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 £360
includes taxes & fees
9 Nov - 10 Nov

19. 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 £356
includes taxes & fees
9 Nov - 10 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 £503
includes taxes & fees
12 Nov - 13 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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Top Summerland Key Hotel Reviews

Sugarloaf Key RV Resort & Cottages
10/10 Excellent
Find out more about Summerland Key
Summerland Key Holiday Homes information
Number of reviews | 438 |
|---|---|
Accommodation | 385 Holiday Homes |
Lowest Price | £309 |
Highest Price | £503 |



































































