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

Cudjoe Key Vacation Rentals

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Our top choices for Cudjoe Key vacation rentals

1. SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (110 reviews)
"Stay was great. We met the hosts and they were wonderful people."
United States
James B.
The price is CA $207
CA $604 total
includes taxes & fees
Aug 16 - Aug 17
SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

2. Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (101 reviews)
"short drive to downtown of course as long as traffic allows it...quiet stay beautiful views...bring mosquito repellent. "
United States
Lismary D.
The price is CA $486
CA $1,056 total
includes taxes & fees
Aug 29 - Aug 30
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

3. 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 CA $291
CA $859 total
includes taxes & fees
Aug 16 - Aug 17
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

4. Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"Excellent location - clean, quiet, well-kept community. Boat launch was key for us. Pool and beach looked very nice, but we didn't use. The unit is as described and has a nice patio out back that we used every day."
United States
Cheryl V.
The price is CA $233
CA $785 total
includes taxes & fees
Aug 16 - Aug 17
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

5. SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (95 reviews)
"Great location, very clean, and a responsive host. We enjoyed our stay and highly recommended this spot!"
United States
David T.
The price is CA $208
CA $606 total
includes taxes & fees
Aug 20 - Aug 21
SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

6. Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (5 reviews)
"Property was perfectly located and very clean and comfortable."
United States
Kiara
The price is CA $273
CA $827 total
includes taxes & fees
Aug 26 - Aug 27
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

7. 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, (4 reviews)
"Stayed with family and good location for family vacations. "
United States
Phani U.
The price is CA $291
CA $859 total
includes taxes & fees
Aug 19 - Aug 20
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

8. 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, (17 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is CA $277
CA $840 total
includes taxes & fees
Aug 17 - Aug 18
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

9. 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
7.8 out of 10, Good, (20 reviews)
"Heated pool was very nice, and location of rental."
United States
Angela C.
The price is CA $325
CA $690 total
includes taxes & fees
Aug 17 - Aug 18
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

10. Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West

Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West
Cudjoe Key
The price is CA $313
CA $889 total
includes taxes & fees
Aug 16 - Aug 17
Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West

11. 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 CA $568
CA $1,300 total
includes taxes & fees
Aug 24 - Aug 25
Post Card Point #319 - Ocean Views!

12. 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 CA $291
CA $836 total
includes taxes & fees
Sep 9 - Sep 10
Waterfront Venture Out Retreat w/ 35' Dock, Kayaks & Pool Access

13. 105 - Newly renovated house Oceanside and Pool

105 - Newly renovated house Oceanside and Pool
Cudjoe Key
The price is CA $549
CA $1,212 total
includes taxes & fees
Aug 16 - Aug 17
105 - Newly renovated house Oceanside and Pool

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, (4 reviews)
"Pool area was nice but only visited it once as so much to see and do!"
United States
Karen
The price is CA $313
CA $881 total
includes taxes & fees
Sep 9 - Sep 10
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

15. 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)
"Nice property in a beautiful location. Great place to sit and enjoy the scenery and activities. "
United States
Andy D.
The price is CA $546
CA $1,168 total
includes taxes & fees
Sep 2 - Sep 3
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

16. Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views

Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views
Cudjoe Key
8.8 out of 10, Excellent, (10 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 CA $306
CA $871 total
includes taxes & fees
Sep 9 - Sep 10
Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views

17. Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
Cudjoe Key
8.0 out of 10, Very good, (1 review)
"The unit was very old and tired. As such, several windows did not open, the cook top light was not working, the shower surround was cracked and the joint caulking was bad to name some examples. However, the place was spotless when we arrived and with (needed) working AC. The kitchen is WELL appointed with cooking items, some spices, and baking supplies. The washer/dryer was a treat as we travel light. The waterfront deck/patio area was great for morning coffee and evening cocktails. Venture out...
United States
Pauline Y.
The price is CA $240
CA $795 total
includes taxes & fees
Aug 16 - Aug 17
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

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

Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape
Cudjoe Key
8.0 out of 10, Very good, (2 reviews)
"It was a short trip but we enjoyed our stay! "
United States
Jennifer S.
The price is CA $291
CA $859 total
includes taxes & fees
Aug 16 - Aug 17
Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape

19. 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)
"Beautiful home with an amazing view friendly community my family and I will definitely be back highly recommend Elma’s escape "
United States
Mary T.
The price is CA $291
CA $854 total
includes taxes & fees
Sep 9 - Sep 10
Canalfront Coastal Retreat w/Open Water Views & Fishing Dock

20. 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 CA $605
CA $1,241 total
includes taxes & fees
Sep 9 - Sep 10
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
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 Cudjoe Key Hotel Reviews

Find out more about Cudjoe Key

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Cudjoe Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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