Cudjoe Key Vacation Rentals
Bundle & SaveGet more, spend less whenever you see Bundle & Save deals
OneKeyCashEarn OneKeyCash on all your eligible bookings
Upfront pricingWe are not like the others - we include taxes and fees
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Cudjoe 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)
"This property was meticulously clean and perfect for us. The property was decorated well-very home-like feel. The communication with the host was prompt and they answered all questions asked. In addition, we loved that we could bring our fur-babies (dogs) to the property with us. We highly recommend this property!"
Elena S.
$342 nightly
The price is $382
Nov 5 - Nov 6
Total with taxes and fees
2. 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)
" 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 ."
jim b.
$389 nightly
The price is $434
Nov 11 - Nov 12
Total with taxes and fees
3. 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)
"Great location, wonderful hosts!"
Blue Mountain Footwear F.
$443 nightly
The price is $492
Nov 21 - Nov 22
Total with taxes and fees
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)
"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."
Cheryl V.
$374 nightly
The price is $417
Nov 10 - Nov 11
Total with taxes and fees
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)
"This was a sweet little modular home that gave us a clean and comfortable place to stay… away from the tourist scene."
Nora Kay F.
$399 nightly
The price is $446
Nov 5 - Nov 6
Total with taxes and fees
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)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
Mckayla S.
$388 nightly
The price is $431
Nov 9 - Nov 10
Total with taxes and fees
7. Canal Front home with easy Ocean access
Canal Front home with easy Ocean accessCudjoe Key
8.8 out of 10, Excellent, (190 reviews)
"Porsche Berry Duty"
Rafael G.
$323 nightly
The price is $361
Nov 26 - Nov 27
Total with taxes and fees
8. 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)
"It was a short trip but we enjoyed our stay! "
Jennifer S.
$425 nightly
The price is $474
Nov 9 - Nov 10
Total with taxes and fees
9. 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)
"Perfect location, great price."
Suzanne T.
$415 nightly
The price is $463
Nov 8 - Nov 9
Total with taxes and fees
10. 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)
"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."
Catherine C.
$440 nightly
The price is $491
Nov 14 - Nov 15
Total with taxes and fees
11. 2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.Cudjoe Key
$449 nightly
The price is $501
Nov 13 - Nov 14
Total with taxes and fees
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)
"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. "
Alisa M.
$425 nightly
The price is $474
Nov 8 - Nov 9
Total with taxes and fees
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)
"Clean and excellent water access"
Chris P.
$415 nightly
The price is $463
Nov 11 - Nov 12
Total with taxes and fees
14. Sailfish Haven #390 - Ocean Views, 35' seawall
Sailfish Haven #390 - Ocean Views, 35' seawallCudjoe Key
9.0 out of 10, Wonderful, (8 reviews)
"great House , and if you are a boater , venture out is great in cudjoe key FL"
freddy c.
$440 nightly
The price is $491
Nov 7 - Nov 8
Total with taxes and fees
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)
"Stayed with family and good location for family vacations. "
Phani U.
$428 nightly
The price is $477
Nov 8 - Nov 9
Total with taxes and fees
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)
"Pool area was nice but only visited it once as so much to see and do!"
Karen
$440 nightly
The price is $491
Nov 9 - Nov 10
Total with taxes and fees
17. 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
$125 nightly
The price is $139
Nov 5 - Nov 6
Total with taxes and fees
18. 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)
"Good location to stay with family. "
Phani U.
$418 nightly
The price is $466
Nov 8 - Nov 9
Total with taxes and fees
19. Canalfront Coastal Retreat w/Open Water Views & Fishing Dock
Canalfront Coastal Retreat w/Open Water Views & Fishing DockCudjoe 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"
Duvall's M.
$425 nightly
The price is $474
Nov 8 - Nov 9
Total with taxes and fees
20. 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)
"It was great!"
Jennifer B.
$464 nightly
The price is $518
Nov 19 - Nov 20
Total with taxes and fees
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.
Find vacation rentals that suit your style
Aparthotels
Private vacation homes
Save an average of 15% on thousands of hotels when you're signed in
Top Cudjoe Key Hotel Reviews
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
10/10 Excellent
Price trends for vacation rentals in Cudjoe Key
Less expensive | More expensive | This month | Next month |
|---|---|---|---|
April | December | $349 | $428 |
Month | Price |
|---|---|
January | $400 |
February | $301 |
March | $311 |
April | $299 |
May | $300 |
June | $340 |
July | $355 |
August | $337 |
September | $350 |
October | $331 |
November | $349 |
December | $428 |
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Cudjoe Key. Select dates and complete search for nightly totals inclusive of taxes and fees.
Find out more about Cudjoe Key
Everything you need to know about Cudjoe Key vacation rentals
Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cudjoe Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.
There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cudjoe Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
Cudjoe Key vacation rentals: An excellent choice for every season
Whenever you want to travel, a warm welcome awaits you in Cudjoe Key. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Cudjoe Key in high season.
Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $286 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!
How to find incredible deals on Cudjoe Key rentals
At Expedia, we put the best Cudjoe Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.
To find some top Cudjoe Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cudjoe Key vacation.
If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cudjoe Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.
Explore a world of travel with Expedia
- Privatevacationhomes in Cudjoe Key
- Motels in Big Pine Key
- Hotels in Big Pine Key
- 4 Star Hotels in Cudjoe Key
- Residences in Bahia Honda Key
- Hilton Hotels in Summerland Key
- Resorts in Cudjoe Key
- Inns in Key West
- Condominiumresort in Sugarloaf Key
- Agritourism in Summerland Key
- Condos in Summerland Key
- Guesthouses in Sugarloaf Key
- Chalets in Sugarloaf Key
- Ocean View in Cudjoe Key
- Independent Hotels in Ramrod Key
- Holidayparks in Big Pine Key
- 5 Star Hotels in Summerland Key
- Treehouses in Big Pine Key
- Hotels in Summerland Key
- Caravanparks in Cudjoe Key
- Lodges in Big Pine Key
- Villas in Sugarloaf Key
- Castles in Little Torch Key
- Bedandbreakfast in Cudjoe Key
- Houseboats in Sugarloaf Key
- Cabins in Sugarloaf Key
- Hostels in Sugarloaf Key
- Beach in Lower Keys
- Apartments in Cudjoe Key
- Cottages in Cudjoe Key
- Ryokans in Big Pine Key
- Townhouses in Big Pine Key
- Ranches in Big Pine Key
- Aparthotels in Lower Florida Keys
- Countryhouse in Big Pine Key
- Flights to Sugarloaf Key
- Flights from Tampa (TPA) to Key West (EYW)
- Flights to Lower Keys
- Flights to Little Torch Key
- JetBlue Airways Boston (BOS) to Key West (EYW) flights
- Flights to Summerland Key
- Flights to Cudjoe Key
- Delta Air Lines Atlanta (ATL) to Key West (EYW) flights
- Flights to Big Pine Key
- Flights from Orlando (MCO) to Key West (EYW)
- Grassy Key Vacation Rentals
- Cow Key Vacation Rentals
- Big Pine Key Vacation Rentals
- Raccoon Key Vacation Rentals
- Ramrod Key Vacation Rentals
- Lower Sugarloaf Key Vacation Rentals
- Big Torch Key Vacation Rentals
- Tingler Island Vacation Rentals
- Lower Keys Vacation Rentals
- Long Key Vacation Rentals
- Key Colony Beach Vacation Rentals
- Dredgers Key Vacation Rentals
- Key Haven Vacation Rentals
- Little Torch Key Vacation Rentals
- Melody Key Vacation Rentals
- Marathon Vacation Rentals
- Key West Vacation Rentals
- Sugarloaf Key Vacation Rentals
- Stock Island Vacation Rentals
- Duck Key Vacation Rentals
- Boca Chica Key Vacation Rentals
- Lower Florida Keys Vacation Rentals
- No Name Key Vacation Rentals
- Bahia Honda Key Vacation Rentals
- Summerland Key Vacation Rentals
- No Name Key Vacation Rentals
- Conch Key Vacation Rentals
- Layton Vacation Rentals
