Search Florida Keys Villa Rentals from CA $308

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 19 - Sep 21
In one month
Oct 3 - Oct 5
In two months
Oct 31 - Nov 2
In three months
Nov 28 - Nov 30

Browse Select Florida Keys Villas

Our top choices for Florida Keys villas

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

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (66)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is CA $756
CA $926 total
includes taxes & fees
Sep 4 - Sep 5
The Islands of Islamorada
Villa 5028 on Duck Key BOAT SLIP available
Outdoor dining

Villa 5028 on Duck Key BOAT SLIP available

9.0 out of 10, Wonderful, (8)
"Great location on the water with beautiful sunset views. Plenty of room for our group. "
The price is CA $308
CA $779 total
includes taxes & fees
Sep 7 - Sep 8
Villa 5028 on Duck Key BOAT SLIP available
Villa 5087 on Duck Key BOAT SLIP available
Outdoor dining

Villa 5087 on Duck Key BOAT SLIP available

9.2 out of 10, Wonderful, (18)
"The place was very clean and very comfortable. The location was great and we had a wonderful stay. The kitchen had all the utensils needed to cook a meal or two."
The price is CA $335
CA $802 total
includes taxes & fees
Sep 2 - Sep 3
Villa 5087 on Duck Key BOAT SLIP available
Atlantic View Luxury Villa with Pool
Deluxe Villa, Ocean View | Beach/ocean view

Atlantic View Luxury Villa with Pool

3.5 star property
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. "
The price is CA $696
CA $1,264 total
includes taxes & fees
Sep 13 - Sep 14
Atlantic View Luxury Villa with Pool
Villa 5086 on Duck Key
Exterior

Villa 5086 on Duck Key

8.6 out of 10, Excellent, (25)
"Great location! We enjoyed our time there."
The price is CA $295
CA $762 total
includes taxes & fees
Sep 7 - Sep 8
Villa 5086 on Duck Key
Villa 7075 on Duck Key BOAT SLIP available
Property grounds

Villa 7075 on Duck Key BOAT SLIP available

9.2 out of 10, Wonderful, (29)
"Great location, incredible view just as advertised. Definitely would stay there again."
The price is CA $335
CA $812 total
includes taxes & fees
Sep 7 - Sep 8
Villa 7075 on Duck Key BOAT SLIP available
Waterfront Villa in Paradise. Dipping pool. Middle Keys. Soak in the sun
Exterior

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

10.0 out of 10, Exceptional, (13)
"We enjoyed our stay."
The price is CA $425
CA $931 total
includes taxes & fees
Sep 2 - Sep 3
Waterfront Villa in Paradise. Dipping pool. Middle Keys. Soak in the sun
Villa 7218 on Duck Key - 3 BR & 2.5 BA - Boat Slip Available
Terrace/patio

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

The price is CA $739
CA $1,534 total
includes taxes & fees
Sep 2 - Sep 3
Villa 7218 on Duck Key - 3 BR & 2.5 BA - Boat Slip Available
One Bedroom Deck Villa Steps from Duval!
Exterior

One Bedroom Deck Villa Steps from Duval!

10.0 out of 10, Exceptional, (6)
"Beautiful property, clean and comfortable suite, friendly staff, fantastic hospitality, ideal central location! We'll be back!"
The price is CA $548
CA $695 total
includes taxes & fees
Sep 29 - Sep 30
One Bedroom Deck Villa Steps from Duval!
Loft Villa Steps from Duval!
Exterior

Loft Villa Steps from Duval!

10.0 out of 10, Exceptional, (16)
"Can’t say enough great things about this place. From the hosts to the property itself, top notch!"
The price is CA $548
CA $695 total
includes taxes & fees
Sep 29 - Sep 30
Loft Villa Steps from Duval!
Two Bedroom Two Bath Balcony Villa Steps from Duval!
Exterior

Two Bedroom Two Bath Balcony Villa Steps from Duval!

10.0 out of 10, Exceptional, (41)
"Great place to stay and great owners!"
The price is CA $823
CA $1,033 total
includes taxes & fees
Sep 29 - Sep 30
Two Bedroom Two Bath Balcony Villa Steps from Duval!
Two Bedroom Two Bath Poolside Villa Steps from Duval!
Exterior

Two Bedroom Two Bath Poolside Villa Steps from Duval!

10.0 out of 10, Exceptional, (44)
"Staff, accommodations and location were excellent. Would definitely stay there again."
The price is CA $892
CA $1,126 total
includes taxes & fees
Sep 26 - Sep 27
Two Bedroom Two Bath Poolside Villa Steps from Duval!
Waterfront Luxe Pool, Hot Tub, Theater, Games and More!
A heated pool

Waterfront Luxe Pool, Hot Tub, Theater, Games and More!

The price is CA $2,102
CA $3,588 total
includes taxes & fees
Sep 2 - Sep 3
Waterfront Luxe Pool, Hot Tub, Theater, Games and More!
Villa 5034 on Duck Key Boat Slip available
Exterior

Villa 5034 on Duck Key Boat Slip available

10.0 out of 10, Exceptional, (4)
"Everything about the stay was nice. "
The price is CA $322
CA $779 total
includes taxes & fees
Sep 2 - Sep 3
Villa 5034 on Duck Key Boat Slip available
Villa 5027 on Duck Key BOAT SLIP available
Exterior

Villa 5027 on Duck Key BOAT SLIP available

9.6 out of 10, Exceptional, (54)
"Very clean. "
The price is CA $308
CA $768 total
includes taxes & fees
Sep 2 - Sep 3
Villa 5027 on Duck Key BOAT SLIP available
Cozy Remodeled Private Guest House
Property grounds

Cozy Remodeled Private Guest House

The price is CA $137
CA $297 total
includes taxes & fees
Sep 2 - Sep 3
Cozy Remodeled Private Guest House
Villa Paradise ~ Miami Lux Gem ~ Heated Pool ~ Game Room
Exterior

Villa Paradise ~ Miami Lux Gem ~ Heated Pool ~ Game Room

9.6 out of 10, Exceptional, (4)
"Amazing stay for me and my family . Thank you for having us over . "
The price is CA $419
CA $947 total
includes taxes & fees
Sep 2 - Sep 3
Villa Paradise ~ Miami Lux Gem ~ Heated Pool ~ Game Room
6BR | Heated Pool | Jacuzzi | Sauna | Beach area
Exterior

6BR | Heated Pool | Jacuzzi | Sauna | Beach area

10.0 out of 10, Exceptional, (5)
"As homebodies this property was perfect. Super clean, nice pool & hot tub. And Pup friendly. "
The price is CA $600
CA $1,378 total
includes taxes & fees
Sep 3 - Sep 4
6BR | Heated Pool | Jacuzzi | Sauna | Beach area
LUXURY VILLA
Outdoor pool, a heated pool

LUXURY VILLA

The price is CA $742
CA $1,589 total
includes taxes & fees
Sep 2 - Sep 3
LUXURY VILLA
Modern Luxury in Massive Mansion w/ Heated Pool!
Pool

Modern Luxury in Massive Mansion w/ Heated Pool!

10.0 out of 10, Exceptional, (3)
"The property manager made the entire stay so pleasant and responded to all requests timely. The house accommodated 8 couples."
The price is CA $2,686
CA $5,159 total
includes taxes & fees
Sep 2 - Sep 3
Modern Luxury in Massive Mansion w/ Heated Pool!
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
Sign in
Sign up, it's free

Top Florida Keys Hotel Reviews

Find out more about Florida Keys

Find out more about Florida Keys

Florida Keys Villas information

Number of reviews
Accommodation
105 Villas
Lowest Price
CA $308
Highest Price
CA $756

Explore a world of travel with Expedia

Explore a world of travel with Expedia