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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 1058 Vacation Homes in Cow Key with updated reviews, rates, and availability.

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Grill up your fresh catch (Kayaks not included)

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

9.0 out of 10, Wonderful, (35)
"Stay was fun and place was clean. Could use a little improvement. Couch was u comfortable and coffeetable broken. The bikes def need some attending to. The table outside is very nice but a little too high; needs adjusting. Hot tub was wonderful and it was quiet for sleeping. "
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Spec.Feb.24-Mar 1 @229+ w. 3 night stay close beach
Dining Area

Spec.Feb.24-Mar 1 @229+ w. 3 night stay close beach

9.0 out of 10, Wonderful, (157)
"The good: convenient location, quiet, bed was comfortable, the little patio in the back is nice. The bad: there is no “on site’ parking but we always found parking on the street about a block away, The communication with property manager was a bit strange, she accused us of still being inside the unit a full day after we had check out on time, despite texting her to tell her we had left (an hour before check out)"
Spec.Feb.24-Mar 1 @229+ w. 3 night stay close beach
Poolside Cottage #411
Pool

Poolside Cottage #411

9.8 out of 10, Exceptional, (38)
"Quiet area close to everything we were looking for. "
The price is AED 1,241
AED 1,916 total
includes taxes & fees
3 Mar - 4 Mar
Poolside Cottage #411
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
Sunny days ahead

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!
Feb 2-5 spec 279.lodg. + extras Close to beach w full kitchen. & patio
Varela St. downstairs front porch

Feb 2-5 spec 279.lodg. + extras Close to beach w full kitchen. & patio

9.6 out of 10, Exceptional, (209)
"Had enjoyable three day visit in Key West. Stayed in comfortable little VRBO house apartment in southern part of Old Town. "
Feb 2-5 spec 279.lodg. + extras Close to beach w full kitchen. & patio
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
Private home with Old Town Charm

CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

9.6 out of 10, Exceptional, (177)
"This property was perfect. The house itself is lovely and has a great set up. 4 bedrooms (one is in a little attached cottage outside). The pool is a very nice addition. The home is located a little bit off the beaten track, so it is quiet. It is in walking distance of everything. We would definitely stay here again!walkingof "
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
Villa Déjà vu Key West - Steps Off Duval w Private Pool
living room

Villa Déjà vu Key West - Steps Off Duval w Private Pool

9.4 out of 10, Exceptional, (55)
"This house was exactly what our group was looking for. Loved the location and proximity to Duval Street. Also loved the outdoor pool area for hanging out. Would def recommend. "
Villa Déjà vu Key West - Steps Off Duval w Private Pool
Coastal Comfort; Waterfront Luxury Home with private pool!

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!
Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location

Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location

10.0 out of 10, Exceptional, (5)
"The property was so beautiful and clean! It was close proximity to everything you want to do in Key West. We did notice a small leak on the first floor balcony and it was a little slippery.But overall loved!!!"
The price is AED 1,283
AED 3,161 total
includes taxes & fees
26 Feb - 27 Feb
Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location
Duval Street Retreat | Dog-Friendly Home w/ Hot Tub, Patio, & Parking

Duval Street Retreat | Dog-Friendly Home w/ Hot Tub, Patio, & Parking

10.0 out of 10, Exceptional, (5)
"We loved our hideaway location! Unit was clean and well stocked with everything we needed. Easy access, great directions and a parking space too.We will return again! "
The price is AED 1,792
AED 3,399 total
includes taxes & fees
24 Mar - 25 Mar
Duval Street Retreat | Dog-Friendly Home w/ Hot Tub, Patio, & Parking
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
Welcome to the HEART of DUVAL!

EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!

9.8 out of 10, Exceptional, (90)
"Clean, roomy, comfortable. Adequate seating and dishes for 6 adults. Great mattresses and pillows. "
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
Plush linen

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!
Exterior

3 night minimum! Spectacular Ocean Views!

8.4 out of 10, Very Good, (19)
"Venture out is a great location for being on the water. This rental was reasonable, spacious and clean! We had an amazing stay with no issues!"
3 night minimum! Spectacular Ocean Views!
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Front / Side View of home

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
The Flower Power House - Boho Beautiful

The Flower Power House - Boho Beautiful

2.5 star property
8.8 out of 10, Excellent, (25)
The Flower Power House - Boho Beautiful
Conch Cove - 3br/3ba with private heated pool and private parking

Conch Cove - 3br/3ba with private heated pool and private parking

10.0 out of 10, Exceptional, (4)
"Rick and team were awesome and exceptional throughout the whole stay! Nice house!! "
The price is AED 3,629
AED 6,858 total
includes taxes & fees
18 Mar - 19 Mar
Conch Cove - 3br/3ba with private heated pool and private parking
Luxurious 3-Bedroom Key West Home with WiFi, EV charging, AC & Tropical Vibes!
Interior

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!
Cozy decor

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!
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
Welcome to Mango Margarita!

MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!

9.6 out of 10, Exceptional, (201)
"Loved the location. House was really comfortable and well stocked with everything we needed. Pool area very tropical and private and although our weather was unusually a bit cool, we enjoyed the outside area. The property manager was very responsive to any communication and we even got to check in early as soon as we landed which was an excellent perk. Definitely would stay here again on our next trip. "
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
Welcome to island time!

BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!

9.6 out of 10, Exceptional, (65)
"Overall the best things about the home was location to Duval St and historic sites. The pool was relaxing and the large covered porch with big table was an ideal place to eat and hang outdoors."
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
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 Cow Key

Aqua Lodges at Hurricane Hole Marina
Exterior

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (117)
"Awesome place, with a cool location right near the mangroves. Has a little restaurant and bar and gift shop, as well as kayak tours and rentals. Paddle boards too. We liked the visits from the manatees and nurse sharks near the fish cleaning station. Only negatives I have are that the ceiling fan chains were broken and harder to reach, some of the pillows were a bit yellowish and have seen better days and multiple devices like the Air conditioner and TV remotes batteries were dead, but they...
The price is AED 988
AED 1,628 total
includes taxes & fees
3 Mar - 4 Mar
Aqua Lodges at Hurricane Hole Marina
Coconut Mallory Resort And Marina By Kees Vacations
Exterior

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very Good, (803)
"Great location, clean, and good customer service. wish they had fishing rods and more to do around the property, and the AC didn't keep the upstairs cool, very hot up there at night. overall, happy about the stay."
Coconut Mallory Resort And Marina By Kees Vacations
Steps from Duval, Pool on Site & Bikes Included!
Pool

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (371)
"2nd time staying here. Clean and close to everything. Great stay"
Steps from Duval, Pool on Site & Bikes Included!
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.