Cudjoe Key Holiday Rentals

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Holiday Rentals in Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

2.5 star property
9.6 out of 10, Exceptional, (5)
"A cozy, clean, and great stay in Cudjoe! Only 30 mins from Key West."
The price is AU$958
includes taxes & fees
9 July - 10 July
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

9.8 out of 10, Exceptional, (80)
"Great atmosphere, right on a canal. A perfect and comfortable home!"
The price is AU$770
includes taxes & fees
11 July - 12 July
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes, Boat Dock

9.8 out of 10, Exceptional, (235)
"We (family of 5) really enjoyed our stay. All the equipment was as listed and in great condition. The location was perfect if you're looking for a less hectic Florida Keys experience."
The price is AU$1,348
includes taxes & fees
25 July - 26 July
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes, Boat Dock

WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

9.6 out of 10, Exceptional, (95)
"Really great, friendly community with lots of activities and a great view of the beach. Would definitely be on my list for another visit soon."
The price is AU$825
includes taxes & fees
28 July - 29 July
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

Island Time #110 Ocean Views - Cudjoe Key

2.5 star property
9.6 out of 10, Exceptional, (5)
"We loved the property so much that we barely left it. The view from the porch was the most peaceful serene view. "
The price is AU$958
includes taxes & fees
13 July - 14 July
Island Time #110 Ocean Views - Cudjoe Key

Reel Island Retreat #273 at Venture Out in the Florida Keys

9.4 out of 10, Exceptional, (6)
"The staff at Venture one was absolutely amazing. The home we stayed in was also a great location. Dated but clean. Definitely will stay at Venture again !"
The price is AU$989
includes taxes & fees
9 July - 10 July
Reel Island Retreat #273 at Venture Out in the Florida Keys

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

2.0 star property
9.0 out of 10, Wonderful, (4)
"Place was perfect for our trip. Staff was super nice and helpful as well. "
The price is AU$1,317
includes taxes & fees
12 July - 13 July
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

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

The price is AU$917
includes taxes & fees
9 July - 10 July
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Sailfish Haven #390 - Ocean Views, 35' seawall

8.8 out of 10, Excellent, (6)
"Liked the location! Easy to get to Key West & great restaurants close!I felt the money we paid for 2 nights was high for the cleanliness of the place. Kitchen could use an update & the front cover over furnace was filthy! Beds were not comfortable. We enjoyed the lanai & the scenery "
The price is AU$1,008
includes taxes & fees
15 July - 16 July
Sailfish Haven #390 - Ocean Views, 35' seawall

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

8.8 out of 10, Excellent, (84)
"Property was adequate but could use a few updates. The location was great. Easy to get to Key West near good local restaurants and beaches. Would stay again. "
The price is AU$1,149
includes taxes & fees
15 July - 16 July
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

7.8 out of 10, Good, (12)
"Good experience. The property is well place and the Venture is really nice and quiet."
The price is AU$797
includes taxes & fees
9 July - 10 July
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key

The price is AU$958
includes taxes & fees
9 July - 10 July
Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key

Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

9.8 out of 10, Exceptional, (8)
"Venture Out is a gated community in Cudjoe Key. The house was very clean and had everything you need to make yourself comfortable. We visited Key West which is about 30 minutes by car. Great place to stay"
The price is AU$1,419
includes taxes & fees
9 July - 10 July
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

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

10.0 out of 10, Exceptional, (1)
"We just needed a place to sleep for a few days while visiting friends on Big Pine. The house had what we needed. The home and furnishings were quite dated with some rust stains on the air vents and in the bath but if you're not picky about that, then this is a great place. The main areas were clean, although there was dirt and dust behind the night stands (needed to access the outlet so had to look there). We didn't use any of the amenities but still had to pay 130 extra when we checked in at...
The price is AU$665
includes taxes & fees
5 Aug - 6 Aug
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Mahi House #440 - 35' seawall

10.0 out of 10, Exceptional, (1)
"The house was just right. Nice community. Quiet and peaceful. Just what we needed. The host was kind and responsive. "
The price is AU$1,265
includes taxes & fees
9 July - 10 July
Mahi House #440 - 35' seawall

Keys to Paradise #95 - 56' Dock & Ocean Views!

9.8 out of 10, Exceptional, (141)
"Very clean cottage right on the corner of the harbor and the canal. Wonderful views!"
The price is AU$1,574
includes taxes & fees
13 July - 14 July
Keys to Paradise #95 - 56' Dock & Ocean Views!

Post Card Point #319 - Ocean Views!

10.0 out of 10, Exceptional, (47)
"Really nice super clean & modern house with a great view. Lots of space. The community it’s in was very nice and quiet."
The price is AU$1,284
includes taxes & fees
19 July - 20 July
Post Card Point #319 - Ocean Views!

Oceanfront 2BR in Venture Out | 35' Dock, Sunrise Views, Coastal Charm

The price is AU$1,780
includes taxes & fees
9 July - 10 July
Oceanfront 2BR in Venture Out | 35' Dock, Sunrise Views, Coastal Charm

Charming 3-bedroom house in Big Pine Key near Beach and Key West

The price is AU$1,150
includes taxes & fees
14 July - 15 July
Charming 3-bedroom house in Big Pine Key near Beach and 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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Frequently asked questions

Can I find holiday rentals in Cudjoe Key?

Yes, there are holiday rentals close to the most popular sights in Cudjoe Key, or you can select a more secluded option if you're looking for a relaxing stay. Cudjoe Key is known for its seafood restaurants and seaside.

What are some of the best holiday rentals that Cudjoe Key has to offer?

3 night minimum! Spectacular Ocean Views!: This highly rated holiday home rental in Cudjoe Key offers a balcony, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Our travellers also rate Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West as a favourite home for rent in Cudjoe Key.

How many holiday rentals are there in Cudjoe Key?

With 205 Expedia holiday rentals, you're guaranteed to find just the right place for your Cudjoe Key stay.

What can I see and do in Cudjoe Key?

While exploring the area, visit family-friendly sights like Key West Visitors Center, or get outside and enjoy nature at Florida Keys Beaches. Boca Chica Beach and Calusa Beach are a couple of places you'll find in the wider area.

What are holiday rentals like in Cudjoe Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cudjoe Key. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for family trips or small group gatherings.