Search Villas in Florida Keys

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan
In one month
23 Jan - 25 Jan
In two months
20 Feb - 22 Feb

Our top choices for Florida Keys villas

2 outdoor pools, open 8:00 AM to 6:00 PM, pool loungers
The Islands of Islamorada

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.8 out of 10, Exceptional, (69)
"Great for family vacation with kids. love it"
United States
Dixania
The price is €632
includes taxes & fees
5 Jan - 6 Jan 2026
The Islands of Islamorada
10 outdoor pools, pool umbrellas, pool loungers
Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (1)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
The price is €877
includes taxes & fees
16 Jan - 17 Jan 2026
Atlantic View Luxury Villa with Pool
Beach
Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
10.0 out of 10, Exceptional, (4)
"Everything about the stay was nice. "
United States
Mario S.
The price is €564
includes taxes & fees
8 Jan - 9 Jan 2026
Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA
Outdoor dining
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.2 out of 10, Wonderful, (18)
"Property was very nice, everything as expected based on listing. Very good place for families."
United States
Nicholas H.
The price is €566
includes taxes & fees
11 Jan - 12 Jan 2026
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA
Property grounds
Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA
Marathon
9.2 out of 10, Wonderful, (30)
"Wonderful experience, great views, clean rooms, great amount of space. Great price"
United States
Race
The price is €561
includes taxes & fees
13 Jan - 14 Jan 2026
Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA
Exterior
Poolside Queen Room Steps from Duval!

Poolside Queen Room Steps from Duval!

Poolside Queen Room Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (1)
"Perfect location, awesome hosts, and the Key West Villas were wonderful. The pool area provided a tranquil area to relax."
United States
Travis P.
The price is €420
includes taxes & fees
8 Jan - 9 Jan 2026
Poolside Queen Room Steps from Duval!
Exterior
Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA
Duck Key
10.0 out of 10, Exceptional, (1)
"The location was perfect, house was very clean, and the view was breathtaking. We will 100% return."
United States
Gina A.
The price is €630
includes taxes & fees
5 Jan - 6 Jan 2026
Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA
Exterior
Poolside Studio Villa Steps from Duval!

Poolside Studio Villa Steps from Duval!

Poolside Studio Villa Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (22)
"Great place to stay"
United States
Benjamin K.
The price is €440
includes taxes & fees
7 Jan - 8 Jan 2026
Poolside Studio Villa Steps from Duval!
Exterior
Poolside King Room Steps from Duval!

Poolside King Room Steps from Duval!

Poolside King Room Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (1)
"If you’re looking to stay in Old Town this is the perfect location. Pool right outside the room, FREE Happy Hour from 4-5 and very accommodating hosts. Good for families or couples alike. Awesome!"
United States
Michael L R.
The price is €443
includes taxes & fees
5 Jan - 6 Jan 2026
Poolside King Room Steps from Duval!
Exterior
Waterfront Villa in Paradise. Dipping pool. Middle Keys. Soak in the sun

Waterfront Villa in Paradise. Dipping pool. Middle Keys. Soak in the sun

Waterfront Villa in Paradise. Dipping pool. Middle Keys. Soak in the sun
Duck Key
10.0 out of 10, Exceptional, (13)
"We enjoyed our stay here! It was perfect for a family of 4!"
United States
Amy S.
Waterfront Villa in Paradise. Dipping pool. Middle Keys. Soak in the sun
Exterior
One Bedroom Deck Villa Steps from Duval!

One Bedroom Deck Villa Steps from Duval!

One Bedroom Deck Villa Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (8)
"Beautiful property, clean and comfortable suite, friendly staff, fantastic hospitality, ideal central location! We'll be back!"
United States
Tim P.
The price is €553
includes taxes & fees
5 Jan - 6 Jan 2026
One Bedroom Deck Villa Steps from Duval!
Exterior
Loft Villa Steps from Duval!

Loft Villa Steps from Duval!

Loft Villa Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (17)
"Can’t say enough great things about this place. From the hosts to the property itself, top notch!"
United States
Dave N.
The price is €554
includes taxes & fees
5 Jan - 6 Jan 2026
Loft Villa Steps from Duval!
Exterior
Two Bedroom Two Bath Balcony Villa Steps from Duval!

Two Bedroom Two Bath Balcony Villa Steps from Duval!

Two Bedroom Two Bath Balcony Villa Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (43)
"The hosts were the best we have ever encountered. Their attention to detail surpassed all expectations. We will stay here again without hesitation. "
United States
Barb B.
The price is €885
includes taxes & fees
6 Jan - 7 Jan 2026
Two Bedroom Two Bath Balcony Villa Steps from Duval!
Terrace/patio
Villa 7218 on Duck Key - 3 BR & 2.5 BA - Boat Slip Available

Villa 7218 on Duck Key - 3 BR & 2.5 BA - Boat Slip Available

Villa 7218 on Duck Key - 3 BR & 2.5 BA - Boat Slip Available
Duck Key
The price is €1,276
includes taxes & fees
5 Jan - 6 Jan 2026
Villa 7218 on Duck Key - 3 BR & 2.5 BA - Boat Slip Available
Exterior
Villa 5027 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5027 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5027 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.6 out of 10, Exceptional, (57)
"Very clean. "
United States
Oksana K.
The price is €564
includes taxes & fees
5 Jan - 6 Jan 2026
Villa 5027 on Duck Key Boat Slip Available - 2BD 2.5BA
Exterior
Villa 5086 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa 5086 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa 5086 on Duck Key Boat Slip Available - 2BD 1.5BA
Duck Key
8.6 out of 10, Excellent, (25)
"Great location! We enjoyed our time there."
United States
Erin T.
The price is €525
includes taxes & fees
4 Jan - 5 Jan 2026
Villa 5086 on Duck Key Boat Slip Available - 2BD 1.5BA
Outdoor dining
Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.0 out of 10, Wonderful, (8)
"Property was clean and comfortable with an excellent sunset view each evening."
United States
william d.
The price is €562
includes taxes & fees
15 Jan - 16 Jan 2026
Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA
Exterior
Villa 5021 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5021 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5021 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
10.0 out of 10, Exceptional, (1)
"The host was extremely communicative and welcoming. What ever we needed he provided"
United States
Amy G.
The price is €560
includes taxes & fees
4 Jan - 5 Jan 2026
Villa 5021 on Duck Key Boat Slip Available - 2BD 2.5BA
Exterior
Villa 7071 on Duck Key Boat Slip Available - 3BD 3BA

Villa 7071 on Duck Key Boat Slip Available - 3BD 3BA

Villa 7071 on Duck Key Boat Slip Available - 3BD 3BA
Marathon
The price is €913
includes taxes & fees
6 Jan - 7 Jan 2026
Villa 7071 on Duck Key Boat Slip Available - 3BD 3BA
Exterior
Palm Wave Retreat

Palm Wave Retreat

Palm Wave Retreat
2.0 star property
South Miami Heights
Palm Wave Retreat
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Florida Keys Hotel Reviews

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

10/10 Excellent
"Enjoyed the duplex, instead of a standard hotel room. Full kitchen, nice bathroom, and bedroom. "
Alejandra 3-night trip
Posted 16 hours ago
Old Wooden Bridge Resort and Marina

Find out more about Florida Keys

Florida Keys Villas information

Number of reviews
301
Accommodation
99 Villas
Lowest Price
€420
Highest Price
€1,276

Frequently asked questions

How much do villas in Florida Keys cost?
Prepare to pay between €420 and €1,276 per night for villas in Florida Keys. Whatever your budget, an ideal getaway is just a click or two away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best villas in Florida Keys?
Jump straight into holiday mode in one of Florida Keys's multiple villas. With a total average guest review rating of 9.6, there's something for everyone's budget and style. Many visitors to Key West highly recommend a stay at Old Town Garden Villas, a 3.5-star option with a garden and WiFi. Another unbeatable choice in this popular destination is 6 Bedroom Duval Compound - Old Town Key West. This 4-star escape includes amenities like a jetted bathtub and a swimming pool.
How many villas are there in Florida Keys?
Florida Keys has 99 villas on offer. Enter your travel dates and destination and get a head start on planning your perfect stay today.
Are there any family-friendly villas in Florida Keys?
You'll find some comfortable family-friendly villas in Florida Keys. If you're on your way to Key West, look up 6 Bedroom Duval Compound - Old Town Key West. With amenities such as a picnic area and laundry facilities, your crew will feel relaxed and comfy at this 4-star property. Duval Penthouse is another great pick for families in Key West. This 4-star option includes conveniences like WiFi and a cafe. After you've unpacked your bags, get out and discover Key West. Look forward to memorable days out at family-friendly attractions such as Smathers Beach and South Beach.
Are there any 5-star villas in Florida Keys?
In Florida Keys, 5-star villas are tough to come by. However, there are some 4-star options worth considering. If you're on your way to Key West, get cosy at 6 Bedroom Duval Compound - Old Town Key West. It comes with handy amenities including a rooftop terrace and a swimming pool. Or, make yourself at home at Duval Penthouse, also in Key West. Make the most of its conveniences such as a jetted bathtub and a rooftop terrace.
Why book your villa in Florida Keys with Expedia?
Booking a villa in Florida Keys is as easy as entering your travel dates and choosing a place that suits your style. On the lookout for something low cost or luxurious, or a property that also comes with a kitchenette? Use Expedia's search filters to narrow your results and find your ideal pad.
How can I find cheap villas in Florida Keys?
Expedia can help you track down cheap villas in Florida Keys. Use our convenient filter tool to choose amenities, star rating and budget to refine your search and find an amazing place to stay in a couple of quick clicks.
What is there to do near my villa in Florida Keys?
The most important travel accessory for your Florida Keys escape is an exciting itinerary! Duval Street, Clarence S. Higgs Memorial Beach Park and Nancy Forrester's Secret Garden are some of the top things to do if you're visiting Key West. Key Largo is also home to excellent attractions, such as Jimmy Johnson's Big Chill. In the mood to explore more? Visit Baker's Cay Resort Beach and Bluefin Rock Harbour Marina too.