Holiday Homes in Cudjoe Key

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Holiday Homes in Cudjoe Key

🌴 TROPICAL RETREAT 🌴 RV in the Keys
Outdoor dining

🌴 TROPICAL RETREAT 🌴 RV in the Keys

10.0 out of 10, Exceptional, (1)
"Its clean and plenty of room.Outdoor seating is wonderful. Could use a gas grill. But definitely a great place."
The price is AU$515
includes taxes & fees
22 Aug - 23 Aug
🌴 TROPICAL RETREAT 🌴 RV in the Keys
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
A heated pool

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

2.5 star property
9.2 out of 10, Wonderful, (7)
"A cozy, clean, and great stay in Cudjoe! Only 30 mins from Key West."
The price is AU$932
includes taxes & fees
22 Aug - 23 Aug
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!
Outdoor pool, a heated pool

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

9.8 out of 10, Exceptional, (81)
"Great location near Key West. Awesome property, will book again."
The price is AU$744
includes taxes & fees
25 Aug - 26 Aug
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
Outdoor dining

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

9.6 out of 10, Exceptional, (96)
"Good location, short drive to lots of activities. Had to leave a day early due to family crises, but had a great two nights there. Thanks!!"
The price is AU$675
includes taxes & fees
29 Aug - 30 Aug
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes
On the beach, beach towels

Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes

9.8 out of 10, Exceptional, (236)
"Clean and inviting property, great location, attentive host. Highly recommend."
The price is AU$1,281
includes taxes & fees
22 Aug - 23 Aug
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes
Island Time #110 Ocean Views - Cudjoe Key
A heated pool

Island Time #110 Ocean Views - Cudjoe Key

2.5 star property
9.8 out of 10, Exceptional, (7)
"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$973
includes taxes & fees
25 Aug - 26 Aug
Island Time #110 Ocean Views - Cudjoe Key
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Beach nearby

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

8.8 out of 10, Excellent, (86)
"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$1,079
includes taxes & fees
26 Aug - 27 Aug
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Galleon Getaway #533- Oceanfront Community
A heated pool

Galleon Getaway #533- Oceanfront Community

The price is AU$848
includes taxes & fees
22 Aug - 23 Aug
Galleon Getaway #533- Oceanfront Community
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Exterior detail

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$695
includes taxes & fees
1 Sept - 2 Sept
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key
A heated pool

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

The price is AU$921
includes taxes & fees
25 Aug - 26 Aug
Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key
Docked in Paradise
Terrace/patio

Docked in Paradise

The price is AU$683
includes taxes & fees
29 Aug - 30 Aug
Docked in Paradise
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community
A heated pool

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

9.8 out of 10, Exceptional, (8)
"Beautiful place!"
The price is AU$1,285
includes taxes & fees
22 Aug - 23 Aug
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community
Sailfish Haven #390 - Ocean Views, 35' seawall
A heated pool

Sailfish Haven #390 - Ocean Views, 35' seawall

8.8 out of 10, Excellent, (6)
"We really enjoyed our stay. The home was exactly as advertised which we definitely appreciated. It was nice to have the kitchen with a wine opener and decent dishes. Being on the water was a plus for our cousin specifically but enjoyed by all. We sat on the back deck morning and night. It was fun to watch the pelicans and boats. Definitely highly recommend. "
The price is AU$921
includes taxes & fees
9 Sept - 10 Sept
Sailfish Haven #390 - Ocean Views, 35' seawall
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key
A heated pool

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

2.0 star property
9.0 out of 10, Wonderful, (7)
"Loved the location! Very nice park. Our place had an amazing view to watch the sunrise and to enjoy a nice home cooked meal before heading up to the pool."
The price is AU$972
includes taxes & fees
5 Sept - 6 Sept
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key
Reel Island Retreat #273 at Venture Out in the Florida Keys
A heated pool

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

9.6 out of 10, Exceptional, (7)
"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$972
includes taxes & fees
5 Sept - 6 Sept
Reel Island Retreat #273 at Venture Out in the Florida Keys
Charming 1-Bedroom, 1-Beth Sailboat in wonderful Key West
Outdoor pool

Charming 1-Bedroom, 1-Beth Sailboat in wonderful Key West

The price is AU$713
includes taxes & fees
1 Sept - 2 Sept
Charming 1-Bedroom, 1-Beth Sailboat in wonderful Key West
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
A heated pool

Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

9.4 out of 10, Exceptional, (26)
"Close to Key West and lots of great boating"
The price is AU$976
includes taxes & fees
3 Sept - 4 Sept
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A heated pool

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

The price is AU$899
includes taxes & fees
5 Sept - 6 Sept
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Mahi House #440 - 35' seawall
A heated pool

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$961
includes taxes & fees
5 Sept - 6 Sept
Mahi House #440 - 35' seawall
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
Dining

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

10.0 out of 10, Exceptional, (1)
"Beautiful "
The price is AU$1,499
includes taxes & fees
3 Sept - 4 Sept
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

Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"I decided to go with this property despite some negative reviews and I am so glad i did. The entire stay was perfect. Staff was so nice and helpful. Special shout out to Ro for making sure we were taken care of. Definitely book again!"
Karen 3-night trip
Posted 10 hours ago
Beachside Resort & Residences