Key West Vacation Rentals from ￥34,727: Search Short-Term Rentals

Q: What are some of the best vacation rentals in Key West?

3-bedroom house boat in tranquil Key West with AC : This Key West vacation home rental offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Some other homes for rent in Key West include ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking and Hemingway Caribbean Townhome/Private Pool by Beach,Key West charm,free parking .

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Key West vacation rentals

A wooden signpost with city names and distances in miles.

1. Steps from Duval, Pool on Site & Bikes Included!

Old Town Key West

Laura D.

￥37,707 total

includes taxes & fees

Oct 19 - Oct 20

A narrow brick pathway flanked by white buildings with potted plants and a bench.

2. Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West

Old Town Key West

Jay M.

￥58,785 total

includes taxes & fees

Oct 25 - Oct 26

A courtyard with a gravel path, palm trees, and a building with a white facade.

3. Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval

Old Town Key West

Stephanie

￥66,114 total

includes taxes & fees

Oct 18 - Oct 19

A poolside area with a wooden deck, lounge chairs, and a staircase leading to a balcony.

4. VanGogh Studio | Updated, Old Town, Heated Pool

Old Town Key West

Jesse M.

￥54,540 total

includes taxes & fees

Oct 25 - Oct 26

A covered balcony with wicker chairs, a view of palm trees, and multiple flags.

5. NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!

Old Town Key West

Taffy M.

￥44,582 total

includes taxes & fees

Oct 19 - Oct 20

A small, private entrance to a house with a brick pathway leading to a door.

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

Old Town Key West

Jamie F.

￥61,252 total

includes taxes & fees

Oct 20 - Oct 21

A pool area with a wooden deck, a two-story building with balconies, and palm trees.

7. Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool

Old Town Key West

Shawn

￥54,856 total

includes taxes & fees

Oct 28 - Oct 29

A tropical garden pathway leading to a building with a yellow facade and green shutters.

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

Old Town Key West

Laura T.

￥47,031 total

includes taxes & fees

Oct 20 - Oct 21

View all properties

Find vacation rentals that suit your style

Private vacation homes

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Key West Hotel Reviews

Southernmost Beach Resort and Guesthouses

10/10 Excellent

"."

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent

"The property was well maintained and clean. The tropical plants and trees were beautiful and made it feel like a little oasis. Our room was clean and we had what we needed. The staff we interacted with were very friendly and welcoming. Breakfast was good and was just enough to get the day started. We enjoyed the bar and the pools and the welcome drink was a nice treat! Overall we had a great experience and we would recommend this place for the amenities and the location."

Parrot Key Hotel & Villas

10/10 Excellent

"The staff is amazing. Super welcoming and they gave me a great layout of what the hotel had to offer. The wallet John was a class act I really appreciated his help particularly. I only went to 2 of the 4 pools but they were clean and relaxing. The food truck had some surprisingly good food, and the bar was good too. You can walk the little beach they have here, layout and relax in the hammocks, and if you want to hang in the room there is plenty in there as well. Location wise there is a Walgreens within walking distance and there are two large shopping plazas within a quarter of a mile so you have plenty of options for food or items for the room. The shuttle service to the beach and to Duval Street came in clutch as well. If you are looking for a place that is a little quieter to sleep at than Duval but close to the action this is the place. I will certainly stay here again when in the area."

The Perry Hotel & Marina Key West

10/10 Excellent

"This is a great place just minutes away from Key West proper. The rooms are nice (at least, ours was), the staff was very pleasant and helpful, and the property is well-maintained. Parking is in a gravel lot adjacent to the buildings and very close to the lobby, elevators, and restaurants. We did not use any of their resort amenities, so I will not opine on their quality. I will note that you need to add the daily resort fee to your room charge and tax to estimate the daily rate for staying there."

Beachside Resort & Residences

10/10 Excellent

"We were very happy with how nice, clean and comfortable our 1 bedroom was. The staff was very helpful via text messages for anything we needed like coffee. The pool was clean and well kept. The shuttle bus to Duval street was a very pleasant surprise and the drivers were really prompt."

Find out more about Key West

Search for holiday rentals in Key West on Expedia! You can easily find your home rentals, villas, holiday apartments in Key West using one of the methods below:

View our selection of featured holiday rentals in Key West
Use the map to find apartments and other holiday homes in the Key West neighbourhood you prefer
Enter your travel dates to view the best deals on holiday rentals in Key West while they last

Look no further and take a look at our great range of rental properties in Key West!

Explore a world of travel with Expedia

Key West Vacations

Big Pine Key Vacation Rentals

Frequently asked questions

Can I find vacation rentals in Key West?

Yes, there are vacation rentals in Key West close to Mel Fisher Maritime Museum, or you can select a more secluded option if you want a relaxing stay. Travelers 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 vacation rentals in Key West?

3-bedroom house boat in tranquil Key West with AC: This Key West vacation home rental offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Some other homes for rent in Key West include ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking and Hemingway Caribbean Townhome/Private Pool by Beach,Key West charm,free parking.

How many vacation rentals will I find in Key West?

With 1025 Expedia vacation rentals, you're sure to find just the right place for your Key West stay.

What can I see and do in Key West?

Mel Fisher Maritime Museum and Florida Keys Eco - Discovery Center are a couple of 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 vacation rentals like in Key West?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Key West. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for family gatherings.

Key West Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Key West vacation rentals

1. Steps from Duval, Pool on Site & Bikes Included!

2. Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West

3. Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval

4. VanGogh Studio | Updated, Old Town, Heated Pool

5. NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!

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

7. Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool

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

9. Aqua Lodges at Hurricane Hole Marina

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

11. Duval Delight | Recently Remodeled Condo on Duval!

12. Underwater Cabana at Custom House Inn | On Duval!

13. Poolside Cottage #412

14. Kingfish Keep | Lively Escape on Duval! Balcony!

15. Resort View 1BR Suite

16. Holly's Hideaway - Truman @ Duval | Charming Hideaway Near Duval!

17. Poolside Cottage #411

18. The Saint Kitts Suite | Breathtaking View, Heated Pool

19. OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST

20. The Cat Island Suite | Charmingly Renovated w/ Pool

Find vacation rentals that suit your style

Top Key West Hotel Reviews

Southernmost Beach Resort and Guesthouses

Find out more about Key West

Explore a world of travel with Expedia

Frequently asked questions

Expedia's Latest Trends

Go further with the Expedia app