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Compare 827 Vacation Homes in Key West with updated reviews, rates, and availability.

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

9.0 out of 10, Wonderful, (32)
"We spent Thanksgiving week with family at this cute little house. Many of the reviews comment about the neighborhood, but we felt safe and even met some neighbors. The houses are on top of one another but with the privacy fence, it doesn't feel like it.The house feels like new construction but the pictures no longer match what is inside (now has a bigger TV, window furnishings are different, etc.). It was fun riding the bike around the island but I would have really appreciated the kayaks...
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

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

9.6 out of 10, Exceptional, (30)
"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!

Spec. Jan 26-31 --219. lodg + w. 3 night stay close beach

9.0 out of 10, Wonderful, (155)
"This spot is a good spot for a couple looking for a place that’s quiet but close. The place has everything you need for a stay with a full size stove and fridge, comfortable bed and roomy enough considering you’re out way more than you’d be in. There’s WiFi, AC if hot, a private outside patio area , beach chairs available, and the basic needs to prepare food if you don’t want to go out. It’s close enough to walk to Duval St or the beach. The owner is easy to work with and very communicative....
Spec. Jan 26-31 --219. lodg + w. 3 night stay close beach

Poolside Cottage #411

10.0 out of 10, Exceptional, (35)
"Great little condo - perfect for our family to visit Key West! "
The price is SAR 912
SAR 1,516 total
includes taxes & fees
16 Jan - 17 Jan
Poolside Cottage #411

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

9.8 out of 10, Exceptional, (76)
"We very much enjoyed our stay. Very nice condo and beautiful pool close to Key West and Botanical Gardens which we enjoyed!"
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!

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

9.6 out of 10, Exceptional, (175)
"We really love this place. The pool is excellent and well heated! We swam even on the one cold day we had. Really great customer service and response from the management. Everything was clean and well maintained and worked! Definitely a Key West dream house with the old timey historic feel that we all love about the island…and a great pool."
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

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

9.4 out of 10, Exceptional, (54)
"Amazing time and experience! "
Villa Déjà vu Key West - Steps Off Duval w Private Pool

Coastal Comfort; Waterfront Luxury Home with private pool!

9.4 out of 10, Exceptional, (63)
"This property was awsome! The area is quiet and close to grocery stores. And a.short drive to down townlpve it, love it, love it. Definitely coming back!!"
Coastal Comfort; Waterfront Luxury Home with private pool!

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

10.0 out of 10, Exceptional, (2)
"I am glad I was able to find this location to stay for myself and my family. It turned out to be very convenient. We had a blast seeing all of the sites in Key West. We do hope to be back soon with more family. "
The price is SAR 1,243
SAR 2,672 total
includes taxes & fees
14 Jan - 15 Jan
Duval Street Retreat | Dog-Friendly Home w/ Hot Tub, Patio, & Parking

SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!

9.8 out of 10, Exceptional, (172)
"The house was so cute and charming. Barely a block from Duval St., the location couldn't be beat. Walking distance to everything! Kitchen is very small with mini appliances so don't recommend if you want to do lots of cooking for more than 2 people. Front porch was perfect for morning coffee and people watching. Really enjoyed it!"
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!

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

9.8 out of 10, Exceptional, (88)
"Beautiful property. Great communication. Very clean. Literally right next to duval street. Highly recommend "
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!

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

9.6 out of 10, Exceptional, (199)
"Delighted with the location & size. Quiet but close to activities. Enjoyed the outdoor space- well appointed."
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!

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

9.6 out of 10, Exceptional, (23)
"Clean, cozy and cute "
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!

The Flower Power House - Boho Beautiful

2.5 star property
8.8 out of 10, Excellent, (24)
"Wonderful home, great for groups or extended family. Very authentic Key West home. Beautiful property. Favors creativity and history over logic and pristine conditions. Exactly as described. "
The Flower Power House - Boho Beautiful

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

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is SAR 1,502
SAR 2,261 total
includes taxes & fees
14 Jan - 15 Jan
Luxurious 3-Bedroom Key West Home with WiFi, EV charging, AC & Tropical Vibes!

Duval Hideaway | Dog-Friendly Home w/ Shared Hot Tub, Patio & Prime Location

The price is SAR 1,243
SAR 2,672 total
includes taxes & fees
14 Jan - 15 Jan
Duval Hideaway | Dog-Friendly Home w/ Shared Hot Tub, Patio & Prime Location

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

10.0 out of 10, Exceptional, (2)
"Everything was top notch at Helen’s Hideaway! Great spot to enjoy everything Key West. Nice location. Comfy place with room for 3 adult friends with king sized beds and ample bathrooms. Just what we needed to attend a conference. Rick was a gracious host with responsive and helpful communications. "
The price is SAR 2,899
SAR 5,900 total
includes taxes & fees
14 Jan - 15 Jan
Conch Cove - 3br/3ba with private heated pool and private parking

Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!

9.8 out of 10, Exceptional, (215)
"Great stay in this historic property. We had lots of room for 10. Everyone enjoyed the heated pool - which is really more of a hot tub. It was especially enjoyed by the youngest in our group. Great location to enjoy Duval Street and the rest of Key West. The parking is very narrow but will fit two cars. You just have to move the first one to get the second one out."
The price is SAR 2,624
SAR 5,705 total
includes taxes & fees
26 Jan - 27 Jan
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!

Poolside Cottage #412

9.8 out of 10, Exceptional, (16)
"We really enjoyed this property as a mid vacation stop. We did 2 nights in Key Largo, 4 nights here, and 3 nights in Miami. We were thrilled to have the full kitchen, included parking space, and the laundry was free (I was almost expecting it to be coin operated). This unit is one I would 100% stay at again. My only complaints were we found the bed in bedroom to be warm (mattress cover was thick so we actually utilized Murphy bed in living room more). The ceiling fan in bedroom is also very...
The price is SAR 912
SAR 1,516 total
includes taxes & fees
16 Jan - 17 Jan
Poolside Cottage #412

LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool

10.0 out of 10, Exceptional, (188)
"The location of this house is perfect. Two (2) blocks from Duval St and four (4) blocks from Key West harbor and all the great restaurants. We will definitely rent again "
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' 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 Key West

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (109)
"Family had a great time "
The price is SAR 774
SAR 1,398 total
includes taxes & fees
20 Jan - 21 Jan
Aqua Lodges at Hurricane Hole Marina

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (361)
"Fun little place with a great pool. Ken was very helpful in all aspects. Highly recommended. Be aware its a small place but very comfortable."
Steps from Duval, Pool on Site & Bikes Included!

34’ Catamaran Sailboat

9.4 out of 10, Exceptional, (30)
"We had a wonderful time. It is an older, smaller boat but we enjoyed it. There is a port a pot in the cabin but there is a huge shower and bathroom under the carport. We were able to fish right off the boat. Frank will answer texts pretty quickly. "
34’ Catamaran Sailboat
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.