A tropical island with clear blue waters, palm trees, and a thatched-roof hut.

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Our top choices for Cudjoe Key ski hotels

1. Canalfront Coastal Retreat w/Open Water Views & Fishing Dock

Canalfront Coastal Retreat w/Open Water Views & Fishing Dock
Cudjoe Key
9.8 out of 10, Exceptional, (6 reviews)
"The property was perfect for a family. Boat launch and marina on site. Kids loved the pool. The amenities were perfect. Such a relaxing stay in the lower keys. To have off street parking and a place to keep your boat and trailer is huge. Wonderful place"
United States
Duvall's M.
The price is ¥29,841
¥74,881 total
includes taxes & fees
Nov 10 - Nov 11
Canalfront Coastal Retreat w/Open Water Views & Fishing Dock

2. Post Card Point #319 - Ocean Views!

Post Card Point #319 - Ocean Views!
Cudjoe Key
10.0 out of 10, Exceptional, (56 reviews)
"We loved our stay! Prime location"
United States
Lacey C.
The price is ¥58,190
¥118,338 total
includes taxes & fees
Nov 8 - Nov 9
Post Card Point #319 - Ocean Views!

3. Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views

Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views
Cudjoe Key
9.8 out of 10, Exceptional, (25 reviews)
"We had a nice stay."
United States
Kandie B.
The price is ¥71,287
¥134,020 total
includes taxes & fees
Nov 14 - Nov 15
Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views

4. Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Cudjoe Key
9.6 out of 10, Exceptional, (5 reviews)
"Stayed with family and good location for family vacations. "
United States
Phani U.
The price is ¥29,841
¥75,354 total
includes taxes & fees
Nov 8 - Nov 9
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

5. Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Cudjoe Key
8.8 out of 10, Excellent, (11 reviews)
"We loved our stayed and booked again for next year. Its in our price range, plenty of space and we were all so comfortable. Its our favorite house we have rented in the area and hope to be able to continue to enjoy it years to come. "
United States
Alisa M.
The price is ¥29,841
¥74,881 total
includes taxes & fees
Nov 5 - Nov 6
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

6. 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)
"Heated pool was very nice, and location of rental."
United States
Angela C.
The price is ¥39,078
¥77,436 total
includes taxes & fees
Nov 5 - Nov 6
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

7. Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape

Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape
Cudjoe Key
8.8 out of 10, Excellent, (3 reviews)
"It was a short trip but we enjoyed our stay! "
United States
Jennifer S.
The price is ¥29,841
¥74,881 total
includes taxes & fees
Nov 9 - Nov 10
Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape

8. Open Water Views | 32' Boat, King Beds, Fish Cleaning Station, Waterfront Escape

Open Water Views | 32' Boat, King Beds, Fish Cleaning Station, Waterfront Escape
Cudjoe Key
8.8 out of 10, Excellent, (3 reviews)
"Great location and accommodations "
United States
Brandie Lane c.
The price is ¥44,762
¥92,772 total
includes taxes & fees
Nov 5 - Nov 6
Open Water Views | 32' Boat, King Beds, Fish Cleaning Station, Waterfront Escape

9. 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 Friendly
Cudjoe Key
8.0 out of 10, Very good, (1 review)
The price is ¥29,841
¥74,881 total
includes taxes & fees
Nov 10 - Nov 11
Ground Level Waterfront 2BR in Venture Out - 23' Seawall, Pool, Marina & Pet Friendly

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 ¥33,571
¥79,234 total
includes taxes & fees
Nov 8 - Nov 9
2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.

11. Florida Keys Waterfront Escape - 2BR with 44' Seawall

Florida Keys Waterfront Escape - 2BR with 44' Seawall
Cudjoe Key
The price is ¥29,841
¥73,302 total
includes taxes & fees
Nov 10 - Nov 11
Florida Keys Waterfront Escape - 2BR with 44' Seawall

12. Florida Keys Waterfront Escape w/35' Seawall & Seconds to Open Water

Florida Keys Waterfront Escape w/35' Seawall & Seconds to Open Water
Cudjoe Key
9.4 out of 10, Exceptional, (3 reviews)
"Good location to stay with family. "
United States
Phani U.
The price is ¥28,349
¥73,518 total
includes taxes & fees
Nov 8 - Nov 9
Florida Keys Waterfront Escape w/35' Seawall & Seconds to Open Water

13. Waterfront Venture Out Retreat w/ 35' Dock, Kayaks & Pool Access

Waterfront Venture Out Retreat w/ 35' Dock, Kayaks & Pool Access
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"We really loved the location of this home ! Right on a canal and could see the most beautiful sunsets right outside! They provided and thought of everything we needed to make our stay comfortable ! We loved being about to ride the bikes provided around the venture out. The pool felt amazing and loved visiting the cute snack market ! We had the best time and will definitely be back! Thank you !!"
United States
Miles H.
The price is ¥28,349
¥73,045 total
includes taxes & fees
Nov 10 - Nov 11
Waterfront Venture Out Retreat w/ 35' Dock, Kayaks & Pool Access

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 Key
Cudjoe Key
10.0 out of 10, Exceptional, (5 reviews)
"Pool area was nice but only visited it once as so much to see and do!"
United States
Karen
The price is ¥32,079
¥77,556 total
includes taxes & fees
Nov 9 - Nov 10
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

15. Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
Cudjoe Key
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful views from the deck. The resort was quiet and peaceful. "
United States
G G.
The price is ¥78,748
¥133,533 total
includes taxes & fees
Nov 17 - Nov 18
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

16. Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Cudjoe Key
9.8 out of 10, Exceptional, (148 reviews)
"Everything was exactly as described and we could not be happier. The community that this house is in is very pleasant as well"
United States
Jaret R.
The price is ¥59,682
¥110,662 total
includes taxes & fees
Nov 13 - Nov 14
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

17. Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise

Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise
Cudjoe Key
9.6 out of 10, Exceptional, (53 reviews)
"Our stay was wonderful. Accommodations were as described and very comfortable. Location was great and the best views for the sunrise. "
United States
Kathy A.
The price is ¥58,936
¥109,822 total
includes taxes & fees
Nov 10 - Nov 11
Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise

18. Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Cudjoe Key
9.4 out of 10, Exceptional, (18 reviews)
"Perfect location, great price."
United States
Suzanne T.
The price is ¥28,349
¥73,045 total
includes taxes & fees
Nov 8 - Nov 9
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

19. Canal-Front Retreat with Dock, Pool & Open Ocean Views

Canal-Front Retreat with Dock, Pool & Open Ocean Views
Cudjoe Key
9.0 out of 10, Wonderful, (13 reviews)
"This property is convenient to food and fun. It was very clean, comfortable and we felt safe to walk around the resort. We had a wonderful stay here."
United States
Catherine C.
The price is ¥32,328
¥77,521 total
includes taxes & fees
Nov 15 - Nov 16
Canal-Front Retreat with Dock, Pool & Open Ocean Views

20. 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 West
Cudjoe Key
8.6 out of 10, Excellent, (4 reviews)
" Great 2 bedroom home in a lovely vacation community . We enjoyed the 2 recliners to relax after a full day of exploring as well as in the morning with our coffee. The screened in patio was a nice perk as well . At check in , a calendar of events was provided and the staff were friendly and helpful. FYI : We enjoyed a gorgeous sunrise right by the beach near the pool ."
United States
jim b.
The price is ¥24,618
¥68,530 total
includes taxes & fees
Nov 11 - Nov 12
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
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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