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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 June
In two months
27 June - 29 June

Featured Condo Rentals in Cudjoe Key

Coconut Mallory Resort And Marina By Kees Vacations
2 outdoor pools

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (808)
"Very tropical, on the water. Everything u need in amenities. Pools were great!"
Coconut Mallory Resort And Marina By Kees Vacations
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval
A heated pool

Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval

9.2 out of 10, Wonderful, (130)
"Overall we enjoyed our stay. Positive highlights: the pool including southern exposure, large dining table, and comfortable beds. Not shown in pictures is a larger TV (50" ?), a new glasstop range, and coffee maker which can both make a pot and accepts KCups. The unit was nicely furnished with kitchen supplies (cups, plates, pans, measuring cups etc).Negatives insights: a LOT of no see ums, pool area could use more umbrellas (get there by mid-morning), a broken living room chair (wobbles; needs...
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval
Spectacular Morning Sunrises, Smathers Beach convenience La Brisa 3 Bedroom.
Beach/ocean view

Spectacular Morning Sunrises, Smathers Beach convenience La Brisa 3 Bedroom.

9.8 out of 10, Exceptional, (7)
"The place was great - had most everything we needed. Location was ideal across the street from the beach. Pool and tennis court were both great. "
Spectacular Morning Sunrises, Smathers Beach convenience La Brisa 3 Bedroom.
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Outdoor pool, a heated pool

Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

9.8 out of 10, Exceptional, (286)
"Excellent accommodations, gorgeous condon"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Key West Beachfront Luxury 2/2 Condo A212
Outdoor pool, a heated pool

Key West Beachfront Luxury 2/2 Condo A212

10.0 out of 10, Exceptional, (146)
"Third time at this address. Never disappoints"
Key West Beachfront Luxury 2/2 Condo A212
Sundial Luxurious 2 Bedroom Ocean View Condominium- Quality at its Best.
A heated pool

Sundial Luxurious 2 Bedroom Ocean View Condominium- Quality at its Best.

9.8 out of 10, Exceptional, (15)
"We really enjoyed our stay. Perfect location for everything. Will consider coming back "
Sundial Luxurious 2 Bedroom Ocean View Condominium- Quality at its Best.
**ATLANTIC REFLECTIONS @ THE BEACH** Ocean Penthouse / Pool + LAST KEY SERVICES.
Pool

**ATLANTIC REFLECTIONS @ THE BEACH** Ocean Penthouse / Pool + LAST KEY SERVICES.

10.0 out of 10, Exceptional, (113)
"Perfect "
**ATLANTIC REFLECTIONS @ THE BEACH** Ocean Penthouse / Pool + LAST KEY SERVICES.
Direct Ocean View from Your Condo-No Contact Check-In
Outdoor dining

Direct Ocean View from Your Condo-No Contact Check-In

9.4 out of 10, Exceptional, (152)
"I chose this property as it was ocean view, which it was. Easy access to the beach. Easy for deliveries and Uber pick ups. The only complaint was that the elevator was down due to a power surge the week before, but that was due to a storm and nothing could help that. We had to go up and down 4 flights of stairs, not a big deal for my sister and I, but difficult for our 73 year old mother. The property manager was great - quick responses to questions/concerns. If you have someone that...
Direct Ocean View from Your Condo-No Contact Check-In
**NATURES EDGE @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES...
Pool

**NATURES EDGE @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES...

10.0 out of 10, Exceptional, (149)
"This property was awesome! We loved the homey feel to the place, but we also felt the beach vacation vibe. Great location and even better pool with an incredible view. Amazing hosts as well, so helpful and the place was fully stocked. Amazing place. "
**NATURES EDGE @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES...
ATLANTIC BREEZE ~ 2B/2BA Renovated Retreat w/ Pool, Fitness Area & Beach!
Pool

ATLANTIC BREEZE ~ 2B/2BA Renovated Retreat w/ Pool, Fitness Area & Beach!

9.8 out of 10, Exceptional, (200)
"great property"
ATLANTIC BREEZE ~ 2B/2BA Renovated Retreat w/ Pool, Fitness Area & Beach!
Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West
Beach nearby

Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West

9.0 out of 10, Wonderful, (107)
"The property was very well furnished, clean and comfortable. Secure and quiet. Updated kitchen, baths and floors. Beautiful plantation shutters and sliders. Giant east facing balcony which gave us views of the ocean and morning sunshine. Large, shimmering oceanfront pool with plenty of lounge chairs. Very nice biking, walking lane along the ocean. Needed a taxi/Uber to go to town but they are plentiful. It was a bit noisy with jets and road traffic during the day. Highly recommend if you don’t...
Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West
Beautiful Stock Island Rental ~10 Min from Downtown Key West
Fridge, microwave, oven, stovetop

Beautiful Stock Island Rental ~10 Min from Downtown Key West

9.6 out of 10, Exceptional, (37)
"The condominium was great, and the host was really responsive to our needs. The property lists a sleeper sofa, but apparently they just replaced that sofa, so there is no fold out bed. But, the host sent an air mattress to make up for this. The vertical blinds in the master bath keep falling off. This was just a nuisance and didn’t really detract from our stay, but these likely need to be replaced. Overall, it was a good place to stay with our 4 kids. The view was outstanding and the pool was...
Beautiful Stock Island Rental ~10 Min from Downtown Key West
**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo / Pool + LAST KEY SERVICES
Pool

**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo / Pool + LAST KEY SERVICES

9.8 out of 10, Exceptional, (167)
"the property was not like it appeared on the advertisement. The property showed just how old it really was. Up keep had a lot to be desired."
**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo / Pool + LAST KEY SERVICES
**SET SAIL @ COCONUT MALLORY** Condo + LAST KEY SERVICES…
Beach

**SET SAIL @ COCONUT MALLORY** Condo + LAST KEY SERVICES…

9.8 out of 10, Exceptional, (84)
"Clean and comfortable. A calm place to retreat to after a fun day!"
**SET SAIL @ COCONUT MALLORY** Condo + LAST KEY SERVICES…
Pool View 3BR Residence | Beachside Resort
Pool

Pool View 3BR Residence | Beachside Resort

9.6 out of 10, Exceptional, (4)
"Good room. Good location. Fun pool and beach."
The price is AU$1,525
includes taxes & fees
6 May - 7 May
Pool View 3BR Residence | Beachside Resort
Oceanfront Marina Condo With All Luxuries
Sun-loungers, beach towels

Oceanfront Marina Condo With All Luxuries

9.8 out of 10, Exceptional, (142)
"There were 6 of us here for my beach wedding. Others stayed in other locations but were jealous they didn’t have our set up. The fishing trips we booked were walking distance and a phenomenal experience. We were close enough to have all the Duvall experiences needed and far enough away to relax and enjoy relaxing! All in all, we absolutely will be returning!"
Oceanfront Marina Condo With All Luxuries
**NEPTUNE'S PENTHOUSE @ THE BEACH** Oceanfront Condo / Pool + LAST KEY SERVICE.
Pool

**NEPTUNE'S PENTHOUSE @ THE BEACH** Oceanfront Condo / Pool + LAST KEY SERVICE.

9.8 out of 10, Exceptional, (111)
"Worked really well for our family. It was clean and quiet, a lovely setting to unwind and relax. Thanks a bunch!"
**NEPTUNE'S PENTHOUSE @ THE BEACH** Oceanfront Condo / Pool + LAST KEY SERVICE.
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
A heated pool

Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing

9.8 out of 10, Exceptional, (123)
"Great property and host. Everything you need for a family especially with small children to be comfortable. The community is quiet and friendly and the space is well maintained. We will be coming back next year. "
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
Penthouse Beach Ocean Views- Live the Dream
On the beach, beach towels

Penthouse Beach Ocean Views- Live the Dream

9.6 out of 10, Exceptional, (236)
"This was the best place, all the amenities, great location and great communication with the owners.Thank you very much!"
Penthouse Beach Ocean Views- Live the Dream
Two Bedroom Residence
Pool

Two Bedroom Residence

10.0 out of 10, Exceptional, (5)
"Nice property and loved the space in the condo"
The price is AU$976
includes taxes & fees
6 May - 7 May
Two Bedroom Residence
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

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, (135)
"2nd time and it's a nice relaxing stay.Catch a few fish off the dock or to one of the bridges.And my dogs love it!!"
Cottage with Pool and Boat Dockage just minutes to Key West!
Cottage with swimming pool and dockage, just minutes to Key West!
Miscellaneous

Cottage with swimming pool and dockage, just minutes to Key West!

9.0 out of 10, Wonderful, (145)
"Wonderful stay with great property and pool. Very well maintained!"
The price is AU$452
includes taxes & fees
30 May - 31 May
Cottage with swimming pool and dockage, 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, (140)
"Good Fishing, Good local eateries. "
The price is AU$552
includes taxes & fees
1 May - 2 May
Cottage with Pool and 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.

Frequently asked questions

What is there to do in Cudjoe Key near my condo?
You’ll find plenty of impressive things to put on your itinerary in Cudjoe Key. Head for major attractions like Florida Keys Beaches, Sugarloaf Beach and Big Pine Key Flea Market. Blue Hole, Cook Island and Upper Sugarloaf Sound are other must-do’s.