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Check prices for these dates

Next weekend
14 Rab. I - 16 Rab. I
In two weeks
21 Rab. I - 23 Rab. I
In one month
4 Rab. II - 6 Rab. II
In two months
2 Jum. I - 4 Jum. I

Compare Vacation Homes in Cudjoe Key with updated reviews, rates, and availability.

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Terrace/patio

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

9.0 out of 10, Wonderful, (37)
"As a mom I liked the cleanliness of kitchen, basic supplies, clean sponge, dish soap etc. it was very cute place. Perfect for three people! Location was good to get to Key West. Stock Island has several good restaurants we didn’t get to try them.all. Had fun using bikes to bike to Starbucks! Beds are comfortable. "
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Old Florida Style, wrap around porch, boat basin for dockage, open water
Property grounds

Old Florida Style, wrap around porch, boat basin for dockage, open water

9.6 out of 10, Exceptional, (68)
"Cannot beat location! Need to declutter house inside and out. Could have been cleaner. Loved view from house and private location. Beds comfortable. Communication with host very responsive."
The price is SAR 1,688
SAR 3,321 total
includes taxes & fees
10 Mar - 11 Mar
Old Florida Style, wrap around porch, boat basin for dockage, open water
Poolside Cottage #411
Outdoor dining

Poolside Cottage #411

9.8 out of 10, Exceptional, (38)
"Quiet area close to everything we were looking for. "
The price is SAR 1,268
SAR 1,956 total
includes taxes & fees
20 Mar - 21 Mar
Poolside Cottage #411
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
Property grounds

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

9.4 out of 10, Exceptional, (33)
"This was a very smooth, perfect 5 night visit. The property offered us everything that we could need. It was a short drive to Duval St and all of the activities in Key West yet the property was very peaceful with a wonderful waterfront patio that we sat out on and enjoyed. The hot tub was a nice treat as well. I have to mention the incredible responsiveness of the property manager. Every question that I had they responded to within minutes which was very much appreciated. "
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
Beachside @ Torchview Waterfront Retreat
On the beach, beach towels

Beachside @ Torchview Waterfront Retreat

9.8 out of 10, Exceptional, (40)
"Saw deer and raccoons in the yard, almost daily, one large iguana on the pier, great views"
Beachside @ Torchview Waterfront Retreat
Coastal Comfort; Waterfront Luxury Home with private pool!
Property grounds

Coastal Comfort; Waterfront Luxury Home with private pool!

9.4 out of 10, Exceptional, (64)
"excellent location, quiet from the town noise, but close proximity, and access to all the Key West points. great rental house amenities for up to 8 people , and great ocean view "
Coastal Comfort; Waterfront Luxury Home with private pool!
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
Terrace/patio

HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!

9.6 out of 10, Exceptional, (26)
"Very comfortable unit to stay near Key West.Beautiful water view.Just 15-20 min from downtown .Will stay again . "
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
3 night minimum! Spectacular Ocean Views!
A heated pool

3 night minimum! Spectacular Ocean Views!

8.2 out of 10, Very Good, (20)
"We loved the Venture Out property the home was located on. There was ample bedding and towels of good quality and a well stocked kitchen. The house could’ve been 5 star with a little more effort put into cleaning. It appeared that floors hadn’t been mopped, surfaces hadn’t been dusted, and appliances weren’t wiped down. However, the two most important items were clean - the beds and showers! Overall, we enjoyed our stay!"
3 night minimum! Spectacular Ocean Views!
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Exterior

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

9.8 out of 10, Exceptional, (234)
"Clean, easy access, friendly complex/neighborhood. "
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Luxurious 3-Bedroom Key West Home with WiFi, EV charging, AC & Tropical Vibes!
Miscellaneous

Luxurious 3-Bedroom Key West Home with WiFi, EV charging, AC & Tropical Vibes!

2.0 star property
6.0 out of 10, (2)
"Plenty of room indoors and outdoors to live in. Comfortable beds. Clean and tidy"
Luxurious 3-Bedroom Key West Home with WiFi, EV charging, AC & Tropical Vibes!
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Outdoor dining

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

9.4 out of 10, Exceptional, (29)
"Excellent views, very quiet, pool was outstanding "
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
Marina

Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5

10.0 out of 10, Exceptional, (217)
"Everything was great! Thanks!"
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
Gone Coastal
Outdoor pool

Gone Coastal

10.0 out of 10, Exceptional, (12)
"I am so happy we opted to stay at Chris’ Stock Island townhome instead of in the heart of Key West!! We would absolutely stay there on a future visit. The accommodations were spacious and comfortable, exactly as described. The two upstairs bedrooms both have balconies and full baths. Downstairs has another bedroom and powder room.and another balcony. Full kitchen and large dining table. It’s super close to a CVS and Roostica for amazing pizza. We also ate at Hogfish a few times for great casual...
Gone Coastal
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
On the beach, sun loungers, beach towels

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

9.8 out of 10, Exceptional, (223)
"Great week in the Florida Keys. Home was extremely clean, very well equipped, had everything you needed to make you feel at home. Each bedroom had it's own ensuite bath and it was perfect for two couples. Location was excellent and would not hesitate to book here again.Thanks Melanie!"
The price is SAR 1,500
SAR 3,245 total
includes taxes & fees
22 Mar - 23 Mar
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Poolside Cottage #412
Outdoor dining

Poolside Cottage #412

9.6 out of 10, Exceptional, (20)
"The cottage was clean and comfortable. We only stayed one night for a wedding, but we would definitely return to use the pool and chill on the cottage's patio. The kitchen had plenty of pots and pans for my next visit! We ubered easily downtown for the wedding and a few drinks afterward. The property manager responded quickly to any questions before arrival."
The price is SAR 1,268
SAR 1,964 total
includes taxes & fees
11 Mar - 12 Mar
Poolside Cottage #412
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
A heated pool

OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!

9.8 out of 10, Exceptional, (77)
"Would return"
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
Havana Daydream; Spacious Waterfront 4 Bedroom Home With Private Heated Pool
Exterior

Havana Daydream; Spacious Waterfront 4 Bedroom Home With Private Heated Pool

9.6 out of 10, Exceptional, (78)
"We had a wonderful time! The place was beautiful-very clean and a convenient location "
Havana Daydream; Spacious Waterfront 4 Bedroom Home With Private Heated Pool
Eisenhower Retreat: Conch style home in Oldtown with private pool AND dock!
Marina

Eisenhower Retreat: Conch style home in Oldtown with private pool AND dock!

9.8 out of 10, Exceptional, (106)
"Overall we really enjoyed this home, it was very clean and set up nicely. The pool heater was not working and the decor in the living room was a bit aged. Otherwise everything was great. Be prepared to be woken up by the roosters and the daily musical series at the Naval Base. "
Eisenhower Retreat: Conch style home in Oldtown with private pool AND dock!
Seafarer's Refuge: 3 Story spacious conch style home w/ private pool & dock!
Marina

Seafarer's Refuge: 3 Story spacious conch style home w/ private pool & dock!

9.8 out of 10, Exceptional, (120)
"This is a beautiful, large home. Excellent cleanliness!! BUT, need to have simple directions for microwave & jacuzzi. Never did figure out how to work the jacuzzi. Walking distance to restaurants & Ferry. We thoroughly enjoyed our stay here.."
Seafarer's Refuge: 3 Story spacious conch style home w/ private pool & dock!
Seaside Retreat: Waterfront Home with private heated pool & lush landscaping
Terrace/patio

Seaside Retreat: Waterfront Home with private heated pool & lush landscaping

9.8 out of 10, Exceptional, (61)
"This was a nice location with a great pool. The amenities were lovely and the neighborhood was quiet and convenient. It was great for a family get-together. "
Seaside Retreat: Waterfront Home with private heated pool & lush landscaping
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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Other property types in Cudjoe Key

Charming cottages, dockage, pool, just minutes to Key West
Fridge, microwave, oven, stovetop

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

8.6 out of 10, Excellent, (107)
"Drove From CLE to The Keys with my dog and enjoyed the quietness of the property. 30 an hour from Key West. Great rate. Would recommend. "
The price is SAR 844
SAR 1,548 total
includes taxes & fees
14 Mar - 15 Mar
Charming cottages, dockage, pool, just minutes to Key West
Cottage with Pool and Dockage, just minutes to Key West
Pool

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (133)
"We enjoyed our stay, would stay again. Communication was excellent. Property is just as pictured. Great location, great value for the price. Could use a little freshening up, light bulb in laundry room, etc."
The price is SAR 1,031
SAR 1,785 total
includes taxes & fees
15 Mar - 16 Mar
Cottage with Pool and Dockage, just minutes to Key West
Cottage with Pool and Boat Dockage just minutes to Key West!
Exterior

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

8.6 out of 10, Excellent, (132)
"Perfect location for us 23 miles to key west. Restaurants near by, pool, fishing pier. Can't wait to come back and do it all over again!"
Cottage with Pool and Boat Dockage just minutes to 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.