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
9.4 out of 10, Exceptional, (3)
"The Blue Lobster is a gem. Clean, cute, enough room to spread out and every extra provided to make your stay comfortable. Community is friendly and has a nice pool, hot tubs and pickle ball courts. Loved it here. "
The price is NZ$1,003
includes taxes & fees
25 June - 26 June
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

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

9.6 out of 10, Exceptional, (93)
"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 NZ$820
includes taxes & fees
29 June - 30 June
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

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 NZ$834
includes taxes & fees
1 July - 2 July
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

Island Time #110 Ocean Views - Cudjoe Key

2.5 star property
9.4 out of 10, Exceptional, (3)
"The house was lovely and the view outstanding. We had fun fishing, swimming, and talking to neighbors. Thank you for your hospitality. "
The price is NZ$1,038
includes taxes & fees
8 July - 9 July
Island Time #110 Ocean Views - Cudjoe Key

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

The price is NZ$613
includes taxes & fees
29 June - 30 June
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

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

2.0 star property
9.4 out of 10, Exceptional, (3)
"Place was perfect for our trip. Staff was super nice and helpful as well. "
The price is NZ$1,171
includes taxes & fees
25 June - 26 June
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

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 NZ$852
includes taxes & fees
25 June - 26 June
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

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

9.2 out of 10, Wonderful, (5)
"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 NZ$1,064
includes taxes & fees
27 June - 28 June
Reel Island Retreat #273 at Venture Out in the Florida Keys

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

The price is NZ$986
includes taxes & fees
7 July - 8 July
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

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

The price is NZ$1,085
includes taxes & fees
7 July - 8 July
Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key

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

8.8 out of 10, Excellent, (83)
"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 NZ$1,244
includes taxes & fees
25 June - 26 June
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

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."
Post Card Point #319 - Ocean Views!

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

8.8 out of 10, Excellent, (148)
"The place was spacious, very clean and beautiful!"
The price is NZ$1,169
includes taxes & fees
29 June - 30 June
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

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 NZ$1,355
includes taxes & fees
25 June - 26 June
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

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 NZ$1,370
includes taxes & fees
1 July - 2 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 NZ$1,705
includes taxes & fees
28 June - 29 June
Keys to Paradise #95 - 56' Dock & Ocean Views!

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

The price is NZ$1,235
includes taxes & fees
8 July - 9 July
Charming 3-bedroom house in Big Pine Key near Beach and Key West

Keys 3 Bedroom Corner Home near Beach & Key West

9.8 out of 10, Exceptional, (6)
"We stayed for four nights. They have ample beds, a nice tv, a large kitchen, and many parking spots. There are not many walkable beaches but there is a couple of good restaurants nearby. We had a great time, everything was nice, and everything was as listed. I would rent again. "
The price is NZ$985
includes taxes & fees
25 June - 26 June
Keys 3 Bedroom Corner Home near Beach & Key West

Ocean View Suite Barnacle Resort

The price is NZ$1,114
includes taxes & fees
26 June - 27 June
Ocean View Suite Barnacle Resort
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.