Search Florida Keys Villa Rentals from CA $398

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Florida Keys villas

Balcony view

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (75 reviews)
"What a wonderful venue for our last 2 nights in the Keys. This place is a hidden gem. The entire staff, especially Edith, the bartender, were fantastic."
United States
Michael
The price is CA $792
CA $966 total
includes taxes & fees
May 17 - May 18
The Islands of Islamorada
Outdoor dining

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

Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.4 out of 10, Exceptional, (21 reviews)
"Awesome place to stay"
United States
Takuma F.
The price is CA $382
CA $876 total
includes taxes & fees
May 18 - May 19
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA
Exterior

Seas the Keys Getaway with plunge pool/spa

Seas the Keys Getaway with plunge pool/spa
Marathon
9.6 out of 10, Exceptional, (14 reviews)
"Great location, great accomodation, hot tub and patio in the back area was great for relaxing in the evenings."
United States
Justus
The price is CA $252
CA $693 total
includes taxes & fees
May 21 - May 22
Seas the Keys Getaway with plunge pool/spa
Exterior

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, (6 reviews)
"Everything about the stay was nice. "
United States
Mario S.
The price is CA $382
CA $875 total
includes taxes & fees
May 21 - May 22
Villa 5034 on Duck Key Boat Slip Available - 2BD 2.5BA
Exterior

Poolside Queen Room Steps from Duval!

Poolside Queen Room Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (2 reviews)
"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 CA $314
CA $398 total
includes taxes & fees
May 18 - May 19
Poolside Queen Room Steps from Duval!
Outdoor dining

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, (32 reviews)
"Wonderful experience, great views, clean rooms, great amount of space. Great price"
United States
Race
The price is CA $382
CA $876 total
includes taxes & fees
May 18 - May 19
Villa 7075 on Duck Key Boat Slip Available - 2BD 2.5BA
Exterior

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (2 reviews)
"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 CA $771
CA $1,407 total
includes taxes & fees
May 21 - May 22
Atlantic View Luxury Villa with Pool
Exterior

Poolside Studio Villa Steps from Duval!

Poolside Studio Villa Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (24 reviews)
"Host were incredibly warm and welcoming. The daily happy hour was a great way to connect with other guests and the host. Highly recommend to stay here for all the amenities, convenient location, 5 star services and comfort."
United States
Linda C.
The price is CA $341
CA $433 total
includes taxes & fees
May 19 - May 20
Poolside Studio Villa Steps from Duval!
Exterior

Loft Villa Steps from Duval!

Loft Villa Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (19 reviews)
"This was an exceptional place to stay, it was updated and clean. The owners were very nice and you could tell that they wanted their rental to be homey and warm. I highly recommend this place!"
United States
Carole C.
The price is CA $410
CA $520 total
includes taxes & fees
May 20 - May 21
Loft Villa Steps from Duval!
Outdoor dining

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 review)
"The location was perfect, house was very clean, and the view was breathtaking. We will 100% return."
United States
Gina A.
The price is CA $382
CA $876 total
includes taxes & fees
May 18 - May 19
Villa 5008 on Duck Key Boat Slip Available - 2BD 1.5BA
Exterior

One Bedroom Deck Villa Steps from Duval!

One Bedroom Deck Villa Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (10 reviews)
"This place was great one of the best host I’ve ever had!!"
United States
Donnie S.
The price is CA $410
CA $520 total
includes taxes & fees
May 18 - May 19
One Bedroom Deck Villa Steps from Duval!
Exterior

Beautiful Oceanside Mariner`s 3 Bedroom Townhome

Beautiful Oceanside Mariner`s 3 Bedroom Townhome
Rock Harbor
10.0 out of 10, Exceptional, (98 reviews)
"The amenities were more than adequate. Home is well appointed, clean and in great condition. "
United States
Kevin P.
The price is CA $684
CA $1,246 total
includes taxes & fees
May 17 - May 18
Beautiful Oceanside Mariner`s 3 Bedroom Townhome
Outdoor pool

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

Villa 7218 on Duck Key - 3 BR & 3 BA - Boat Slip Available
Duck Key
10.0 out of 10, Exceptional, (2 reviews)
"House was fantastic. Back deck and pool area were so nice !!!"
United States
Ryan M.
The price is CA $684
CA $1,519 total
includes taxes & fees
May 26 - May 27
Villa 7218 on Duck Key - 3 BR & 3 BA - Boat Slip Available
Exterior

Two Bedroom Two Bath Poolside Villa Steps from Duval!

Two Bedroom Two Bath Poolside Villa Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (57 reviews)
"Key West Villa's is an awesome place!"
United States
Andrew B.
The price is CA $684
CA $867 total
includes taxes & fees
May 25 - May 26
Two Bedroom Two Bath Poolside Villa Steps from Duval!
Exterior

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, (45 reviews)
"Location was great. Facility and rooms were clean. Great amenities - we will book again"
United States
William P.
The price is CA $684
CA $867 total
includes taxes & fees
May 25 - May 26
Two Bedroom Two Bath Balcony Villa Steps from Duval!
Outdoor pool

Luxe Beachfront Villa

Luxe Beachfront Villa
3.0 star property
Matecumbe
The price is CA $1,853
CA $3,009 total
includes taxes & fees
May 21 - May 22
Luxe Beachfront Villa
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
Duck Key
9.8 out of 10, Exceptional, (14 reviews)
"We enjoyed our stay here! It was perfect for a family of 4!"
United States
Amy S.
The price is CA $516
CA $1,054 total
includes taxes & fees
May 15 - May 16
Waterfront Villa in Paradise. Dipping pool. Middle Keys. Soak in the sun
Outdoor dining

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, (61 reviews)
"Nice place"
United States
Orlando P.
The price is CA $382
CA $876 total
includes taxes & fees
May 18 - May 19
Villa 5027 on Duck Key Boat Slip Available - 2BD 2.5BA
Outdoor dining

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, (29 reviews)
"Great location! We enjoyed our time there."
United States
Erin T.
The price is CA $369
CA $859 total
includes taxes & fees
May 18 - May 19
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
Duck Key
8.8 out of 10, Excellent, (9 reviews)
"Property was clean and comfortable with an excellent sunset view each evening."
United States
william d.
The price is CA $423
CA $927 total
includes taxes & fees
May 21 - May 22
Villa 5028 on Duck Key Boat Slip Available - 2BD 2.5BA
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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Top Florida Keys Hotel Reviews

Bayside Inn Key Largo

Bayside Inn Key Largo

10/10 Excellent
"Area was very nice. Staff was wonderful and friendly. Has a nice little outside restaurant/ bar with music on property. Pets were welcome everywhere. Pool was very relaxing.We definitely mark this on our map to stay again when visiting."
Susan e 1-night trip
Posted 3 hours ago
Bayside Inn Key Largo

Find out more about Florida Keys

Florida Keys Villas information

Number of reviews
462
Accommodation
99 Villas
Lowest Price
CA $398
Highest Price
CA $3,009

Frequently asked questions

How much do villas in Florida Keys cost?
Prepare to pay between CA $398 and CA $3,009 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 vacation mode in one of Florida Keys's multiple villas. With a total average guest review rating of 9.8, 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 cozy 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 Harbor Marina too.