Holiday Homes in Key West

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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

Featured Holiday Homes in Key West and around

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, (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
Terrace/patio

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
Outdoor dining

Poolside Cottage #411

9.8 out of 10, Exceptional, (38)
"Quiet area close to everything we were looking for. "
The price is €509
includes taxes & fees
3 Mar - 4 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!
Feb 3-10 $245 off the rates close beach full kitchen & patio
Exterior detail

Feb 3-10 $245 off the rates close beach 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 3-10 $245 off the rates close beach full kitchen & patio
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
A heated pool

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
A heated pool

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

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 €841
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
Terrace/patio

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 €904
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!
A heated pool

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!
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!
The Flower Power House - Boho Beautiful
A heated pool

The Flower Power House - Boho Beautiful

2.5 star property
8.8 out of 10, Excellent, (25)
"We truly enjoyed our stay at the Flower Power House! The house was awesome, in a great neighborhood and had everything we needed! The property manager was very pleasant, responsive and accommodating! We will definitely return the next time we are in Key West! Thank you! "
The Flower Power House - Boho Beautiful
Conch Cove - 3br/3ba with private heated pool and private parking
A heated pool

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 €1,693
includes taxes & fees
23 Feb - 24 Feb
Conch Cove - 3br/3ba with private heated pool and private parking
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)
Luxurious 3-Bedroom Key West Home with WiFi, EV charging, AC & Tropical Vibes!
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
Fridge, microwave, oven, stovetop

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 Bedroom, 2 Bath w/ Private Pool!
A heated pool

BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w/ Private 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 Bedroom, 2 Bath w/ Private Pool!
Duval Hideaway | Dog-Friendly Home w/ Shared Hot Tub, Patio & Prime Location
Terrace/patio

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

9.4 out of 10, Exceptional, (3)
"Great location- private, quiet and you can walk to everything in downtown KW- restaurants, bars, shopping, etc. or take free Duval Loop bus system- terrific!The first floor location was great- easy to get to with luggage. Designated parking was a huge plus- we parked on Friday and didn't move car until we left on Sunday. Comfortable for a small group, kitchen was outfitted well, used the hot tub at night and enjoyed the music from LaTeDa with a glass of wine!Only negative- We hope that the owner...
The price is €841
includes taxes & fees
2 Mar - 3 Mar
Duval Hideaway | Dog-Friendly Home w/ Shared Hot Tub, Patio & Prime Location
BLUE BUNGALOW ~ 2 Bedroom Townhome in Truman Annex Community with Pool!
Fridge, microwave, oven, stovetop

BLUE BUNGALOW ~ 2 Bedroom Townhome in Truman Annex Community with Pool!

9.8 out of 10, Exceptional, (64)
"Key West is very walkable and the Blue Bungalow is a great place to start - Truman Waterfront Park and Zachary Taylor State Park in one direction, The Green Parrot and Duval Street in the other. Whitney was a great host - very responsive. Well furnished property. Cleanliness was outstanding. Just a wonderful place to experience paradise!"
BLUE BUNGALOW ~ 2 Bedroom Townhome in Truman Annex Community with Pool!
Gone Coastal
Outdoor pool

Gone Coastal

9.8 out of 10, Exceptional, (10)
"The property was clean and we enjoyed our stay. We especially enjoyed the balcony by our bedroom. "
Gone Coastal
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
Restaurant

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 €384
includes taxes & fees
25 Feb - 26 Feb
Aqua Lodges at Hurricane Hole Marina
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, (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!
Beach towels

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"
The price is €271
includes taxes & fees
6 Mar - 7 Mar
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.