Venture Out in Cudjoe Key, Florida Keys.

Holiday Rentals in Cudjoe Key

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Our top choices for Cudjoe Key holiday rentals

Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Boat Dockage just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (166 reviews)
"Quite location, nice amenities and directions for check in/out were clear."
United States
Kasey M.
The price is €236
includes taxes & fees
21 Jun - 22 Jun
Cottage with Pool and Boat Dockage just minutes to Key West!

Charming cottages, dockage, pool, just minutes to Key West

Charming cottages, dockage, pool, just minutes to Key West
Cudjoe Key
8.6 out of 10, Excellent, (129 reviews)
"Value for money: Fair This is a unit in a 3-unit divided house, not a cottage as described. It was clean, comfortable, quiet, and a good size, located a convenient drive to Key West. We enjoyed our stay."
United States
Laura
Charming cottages, dockage, pool, just minutes to Key West

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 €491
includes taxes & fees
18 Jul - 19 Jul
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Waterfront Home

Waterfront Home
Cudjoe Key
8.8 out of 10, Excellent, (187 reviews)
"Clean, great view, wonderful porch, comfortable bed"
United States
Karen H.
The price is €344
includes taxes & fees
23 Jun - 24 Jun
Waterfront Home

SAVE BIG $$ JUNE/JULY. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$ JUNE/JULY. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (108 reviews)
"Enjoyed our stay at Venture Out. Loved having the water view. We used the pool, bikes and kayaks. Owners were very responsive. House was clean. Would definitely stay again."
United States
Lindsey S.
The price is €476
includes taxes & fees
28 Jun - 29 Jun
SAVE BIG $$ JUNE/JULY. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (91 reviews)
"Great location, very clean, and a responsive host. We enjoyed our stay and highly recommended this spot!"
United States
David T.
The price is €455
includes taxes & fees
29 Jun - 30 Jun
SAVE BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Cudjoe Key
The price is €433
includes taxes & fees
18 Jun - 19 Jun
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

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
8.0 out of 10, Very good, (3 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 €508
includes taxes & fees
29 Jun - 30 Jun
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Canalfront Keys Home - Dock for 35' Boat, Large Porch, Big Yard & Quick Access to Open Water

Canalfront Keys Home - Dock for 35' Boat, Large Porch, Big Yard & Quick Access to Open Water
Cudjoe Key
The price is €571
includes taxes & fees
1 Jul - 2 Jul
Canalfront Keys Home - Dock for 35' Boat, Large Porch, Big Yard & Quick Access to Open Water

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 €317
includes taxes & fees
18 Jul - 19 Jul
Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West

Seabreeze Escape WF RV Lot 489

Seabreeze Escape WF RV Lot 489
Cudjoe Key
8.0 out of 10, Very good, (1 review)
The price is €259
includes taxes & fees
18 Jun - 19 Jun
Seabreeze Escape WF RV Lot 489

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, (4 reviews)
"Very clean, charming home. Host was fast with responses."
United States
April W.
The price is €530
includes taxes & fees
23 Jun - 24 Jun
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

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, (3 reviews)
"Pool area was nice but only visited it once as so much to see and do!"
United States
Karen
The price is €564
includes taxes & fees
23 Jun - 24 Jun
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

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)
"Everything was perfect location house amenities Really enjoyed our time there"
United States
Matt S.
The price is €398
includes taxes & fees
1 Jul - 2 Jul
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

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 €505
includes taxes & fees
22 Jun - 23 Jun
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

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
9.4 out of 10, Exceptional, (3 reviews)
"Stayed with family and good location for family vacations. "
United States
Phani U.
The price is €537
includes taxes & fees
30 Jun - 1 Jul
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

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

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Cudjoe Key
9.2 out of 10, Wonderful, (15 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is €526
includes taxes & fees
29 Jun - 30 Jun
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key
Cudjoe Key
8.8 out of 10, Excellent, (10 reviews)
"Great place! Perfect location"
United States
Troy B.
The price is €566
includes taxes & fees
29 Jun - 30 Jun
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (158 reviews)
"This was our second stay here and just as we remembered. It was clean and we had everything we needed. Would recommend it for visiting Key West as its only a 30 minute drive in."
United States
John S.
The price is €513
includes taxes & fees
29 Jun - 30 Jun
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Endless Ocean Views - RV589

Endless Ocean Views - RV589
Cudjoe Key
The price is €280
includes taxes & fees
18 Jun - 19 Jun
Endless Ocean Views - RV589
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

Everything you need to know about Cudjoe Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cudjoe Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Cudjoe Key holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cudjoe Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cudjoe Key holiday rentals we have selected for you start as low as €213 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cudjoe Key rentals

At Expedia, we put the best Cudjoe Key holiday 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 holiday.

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. 

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