Key West Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Key West holiday rentals

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
9.0 out of 10, Wonderful, (187 reviews)
"Beautiful location, quick reply when you contact them. The bar and restaurant were so nice!! We would definitely stay again. "
United States
Stacy
The price is AU$415
includes taxes & fees
1 June - 2 June
Aqua Lodges at Hurricane Hole Marina

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Old Town Key West
9.8 out of 10, Exceptional, (132 reviews)
"Amazing place to stay, excellent experience!!!"
United States
Brad
The price is AU$439
includes taxes & fees
1 June - 2 June
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

Steps from Duval, Pool on Site & Bikes Included!

Steps from Duval, Pool on Site & Bikes Included!
Old Town Key West
9.6 out of 10, Exceptional, (433 reviews)
"Great location within walking distance to both ends of Duval. The bikes were nice as well and the unit was very clean. Enjoyed our stay."
United States
Jeff T.
The price is AU$378
includes taxes & fees
20 June - 21 June
Steps from Duval, Pool on Site & Bikes Included!

Osprey Suite | Charming Hideaway, Hot Tubs!

Osprey Suite | Charming Hideaway, Hot Tubs!
Old Town Key West
9.8 out of 10, Exceptional, (47 reviews)
"Host was responsive to all of our inquiries and needs"
United States
Ron O.
The price is AU$574
includes taxes & fees
14 June - 15 June
Osprey Suite | Charming Hideaway, Hot Tubs!

Leo's Lodge | Newly Updated!

Leo's Lodge | Newly Updated!
Old Town Key West
8.8 out of 10, Excellent, (33 reviews)
"Very nice place to stay, great pool area and great room. "
United States
Blake
The price is AU$504
includes taxes & fees
4 June - 5 June
Leo's Lodge | Newly Updated!

Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!

Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!
Old Town Key West
9.8 out of 10, Exceptional, (34 reviews)
"The property was cozy and a great location for walking."
United States
Elizabeth E.
The price is AU$580
includes taxes & fees
1 June - 2 June
Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!

STEPS TO DUVAL! OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!

STEPS TO DUVAL! OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!
Old Town Key West
9.8 out of 10, Exceptional, (44 reviews)
"Great location, one block from Duval Street but still quiet, clean and comfortable. "
United States
Jackie H.
STEPS TO DUVAL! OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!

Claude Monet Suite | Cozy Studio with Pool & Patio

Claude Monet Suite | Cozy Studio with Pool & Patio
Old Town Key West
9.6 out of 10, Exceptional, (34 reviews)
"Room was clean and within easy walk to most attractions. Check in and check out was easy. "
United States
Sharon
The price is AU$526
includes taxes & fees
6 June - 7 June
Claude Monet Suite | Cozy Studio with Pool & Patio

Kingfish Keep | Lively Escape on Duval! Balcony!

Kingfish Keep | Lively Escape on Duval! Balcony!
Old Town Key West
9.8 out of 10, Exceptional, (35 reviews)
"Great place to stay!"
United States
Andrew M.
The price is AU$736
includes taxes & fees
1 June - 2 June
Kingfish Keep | Lively Escape on Duval! Balcony!

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (104 reviews)
"Nice property, great location, comfortable bed, lovely pool. "
United States
Candice B.
The price is AU$437
includes taxes & fees
2 June - 3 June
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

Chagall's Corner | Newly Remodeled!

Chagall's Corner | Newly Remodeled!
Old Town Key West
9.0 out of 10, Wonderful, (42 reviews)
"Very nice place to stay, close to many attractions. "
United States
Maria B.
The price is AU$496
includes taxes & fees
21 June - 22 June
Chagall's Corner | Newly Remodeled!

VanGogh Studio | Updated, Old Town, Heated Pool

VanGogh Studio | Updated, Old Town, Heated Pool
Old Town Key West
8.6 out of 10, Excellent, (49 reviews)
"Room had everything we needed!Owners and staff were very responsive and offered free shuttle to/from the airport!"
United States
Timothy P.
The price is AU$504
includes taxes & fees
2 June - 3 June
VanGogh Studio | Updated, Old Town, Heated Pool

Ricky's Retreat - Truman @ Duval | Ideal Getaway!

Ricky's Retreat - Truman @ Duval | Ideal Getaway!
Old Town Key West
9.8 out of 10, Exceptional, (36 reviews)
"Great location!!"
United States
Julie
The price is AU$580
includes taxes & fees
2 June - 3 June
Ricky's Retreat - Truman @ Duval | Ideal Getaway!

The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
Key West
10.0 out of 10, Exceptional, (31 reviews)
"Pleasant stay - had a couple issues that we needed to be fixed that were resolved as quickly as possible. "
United States
Christina M.
The price is AU$724
includes taxes & fees
1 June - 2 June
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

47ft Viking Yacht · 2 Pools · Perry Marina · Key West

47ft Viking Yacht · 2 Pools · Perry Marina · Key West
Stock Island
7.6 out of 10, Good, (37 reviews)
"The location was fabulous, due to the hotel’s amenities. Ie the hourly transport to downtown.pools and restaurants. The accommodations were a bit dated but adequate. The host responded immediately to our request! "
United States
Leigh P.
The price is AU$611
includes taxes & fees
1 June - 2 June
47ft Viking Yacht · 2 Pools · Perry Marina · Key West

The Barbados | Private Balcony, Pool View!

The Barbados | Private Balcony, Pool View!
Key West
9.6 out of 10, Exceptional, (5 reviews)
"Great trip"
United States
Doug P.
The price is AU$691
includes taxes & fees
2 June - 3 June
The Barbados | Private Balcony, Pool View!

The Cat Island Suite | Charmingly Renovated w/ Pool

The Cat Island Suite | Charmingly Renovated w/ Pool
Key West
9.8 out of 10, Exceptional, (45 reviews)
"A good value for the travel dollar."
United States
sandra j.
The price is AU$724
includes taxes & fees
3 June - 4 June
The Cat Island Suite | Charmingly Renovated w/ Pool

Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (60 reviews)
"Friendly host and unique location"
United States
Scott
The price is AU$559
includes taxes & fees
1 June - 2 June
Living the Dream Key West Style

Waterfront Condo Dock Pool Near Duval St

Waterfront Condo Dock Pool Near Duval St
Meadows
9.8 out of 10, Exceptional, (26 reviews)
"Really enjoyed the accommodations. "
United States
Timothy
The price is AU$873
includes taxes & fees
14 June - 15 June
Waterfront Condo Dock Pool Near Duval St

Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!

Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
Old Town Key West
10.0 out of 10, Exceptional, (120 reviews)
"Very communicative, property was as pictured and bikes were perfect for getting around. We didn’t need a car but had no trouble parking right next to the front door. Sandy’s had the best coffee and food was delicious! Will definitely come again!"
United States
Emily F.
The price is AU$527
includes taxes & fees
8 June - 9 June
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Key West Hotel Reviews

Find out more about Key West

Everything you need to know about Key West holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Key West holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Key West holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Key West holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Key West. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Key West holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Key West holiday rentals we have selected for you start as low as AU$378 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Key West rentals

At Expedia, we put the best Key West holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Key West rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Key West holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Key West. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Key West?

Yes, there are holiday rentals in Key West close to Florida Keys Eco - Discovery Center, or you can select a more secluded option if you're looking for a relaxing stay. Travellers who like culture and the arts give Key West high marks for its great live music and entertainment choices. While you're in the area, you can also enjoy the scenic seaside and lively festivals.

What are some of the best holiday rentals that Key West has to offer?

CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!: This highly rated holiday home rental in Key West is located in the city centre, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and an oven, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind. Some other homes for rent in Key West include Atlantic Paradise by AvantStay | Great Location w/ & Shared Pool and hot tub! and EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!.

How many holiday rentals will I find in Key West?

With 1008 Expedia holiday rentals, you're guaranteed to find just the right place for your Key West stay.

What can I see and do in Key West?

Florida Keys Eco - Discovery Center and Florida Keys National Marine Sanctuary are a couple of the family-friendly sights, whereas cultural attractions include Ernest Hemingway Home and Museum and Key West Lighthouse and Keeper's Quarters Museum. You can also visit some other popular places in town, such as Duval Street and Florida Keys Beaches.

What are holiday rentals like in Key West?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Key West. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for family trips.