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Check prices for these dates

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15 Aug - 17 Aug
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22 Aug - 24 Aug
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5 Sept - 7 Sept
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3 Oct - 5 Oct

Featured Villas in Florida Keys

The Islands of Islamorada
Relax by the pool surrounded by palm trees and enjoy stunning ocean views.

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 AU$1,041
includes taxes & fees
9 Aug - 10 Aug
The Islands of Islamorada
Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer
Traditional home with a charming front porch and garden, surrounded by a picket fence.

Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer

8.6 out of 10, Excellent, (54)
"This was a great place to stay away from the business but close enough to Marathon to go to dinner or activities. The condo was cozy and had a great sunset view. Will definitely look at this place again if we return to the Keys."
Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer
Villa 5027 on Duck Key BOAT SLIP available
Enjoy a tranquil moment on the deck overlooking the serene water.

Villa 5027 on Duck Key BOAT SLIP available

9.6 out of 10, Exceptional, (54)
"Very clean. "
The price is AU$916
includes taxes & fees
7 Aug - 8 Aug
Villa 5027 on Duck Key BOAT SLIP available
Life in Paradise at #1 Rated Resort in Marathon - Coral Lagoon - Boat Slip Avail
Relax on the covered porch with comfortable seating and enjoy the surrounding greenery.

Life in Paradise at #1 Rated Resort in Marathon - Coral Lagoon - Boat Slip Avail

10.0 out of 10, Exceptional, (212)
"Very nice place in a great location."
Life in Paradise at #1 Rated Resort in Marathon - Coral Lagoon - Boat Slip Avail
iykyk WTF! ELEVATOR~TIKI BAR~BOAT SLIP on site! MOON DECK/POOL~GULF FRONT BABY!!
Relax by the ocean at this beachfront resort, where a pool and dock await.

iykyk WTF! ELEVATOR~TIKI BAR~BOAT SLIP on site! MOON DECK/POOL~GULF FRONT BABY!!

10.0 out of 10, Exceptional, (140)
"Nice place, can walk to restaurants.loved the top floor patio."
iykyk WTF! ELEVATOR~TIKI BAR~BOAT SLIP on site! MOON DECK/POOL~GULF FRONT BABY!!
Oceanfront Villa overlooking the Atlantic and Molasses Reef Marina
Boats docked in a serene marina surrounded by lush greenery and palm trees.

Oceanfront Villa overlooking the Atlantic and Molasses Reef Marina

9.8 out of 10, Exceptional, (51)
"Great location Vivian was very responsive to any questions we had"
Oceanfront Villa overlooking the Atlantic and Molasses Reef Marina
DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage INCL
Relax by the pool or enjoy a drink at the adjacent bar amidst lush palm trees and serene surroundings.

DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage INCL

9.8 out of 10, Exceptional, (168)
"Enjoy the stay in good location "
DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage INCL
Isla Marlin 28: Palm lined luxury villa w/dockage and sunset views
Property grounds

Isla Marlin 28: Palm lined luxury villa w/dockage and sunset views

9.8 out of 10, Exceptional, (10)
"From the location to the views to the villa itself, everything was just so special and beautiful! This was our third time to Marathon but first time staying here and we are already working on our next trip! Thank you for the sweetest memories! "
Isla Marlin 28: Palm lined luxury villa w/dockage and sunset views
Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views!
Stunning two-story residence with a central entrance, double doors, and beautifully manicured gardens.

Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views!

9.6 out of 10, Exceptional, (69)
"Perfect place to relax "
Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views!
PLUNGE POOL VILLA ON BLUE WATER LAGOON DUCK Key/MARATHON, FL
Relax by the serene pool surrounded by lush tropical plants and palm trees.

PLUNGE POOL VILLA ON BLUE WATER LAGOON DUCK Key/MARATHON, FL

9.6 out of 10, Exceptional, (73)
"We enjoyed our stay!"
PLUNGE POOL VILLA ON BLUE WATER LAGOON DUCK Key/MARATHON, FL
Crystal Waters - 2/2.5 Villa
Relax on the deck overlooking the pool, surrounded by lush tropical vegetation and a serene body of water.

Crystal Waters - 2/2.5 Villa

10.0 out of 10, Exceptional, (2)
"We had a wonderful expérience in Duck Key.Thank you Ana for your kind hospitality!See you next time !"
Crystal Waters - 2/2.5 Villa
2bd/2ba Ocean Retreat in Kawama Yacht Club
Enjoy al fresco dining and relaxation in this shaded patio area, complete with a barbecue grill and comfortable seating.

2bd/2ba Ocean Retreat in Kawama Yacht Club

10.0 out of 10, Exceptional, (41)
"We enjoy the property and great Key Largo location. Owner was very quick to respond to questions. Some repairs are needed that he is aware of and he said they would be fixed soon. "
2bd/2ba Ocean Retreat in Kawama Yacht Club
Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC
Relax by the serene pool surrounded by lush greenery and palm trees.

Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC

8.6 out of 10, Excellent, (233)
"The property has potential but needs A lot of maintenance and upgrades. Also wasn’t very clean. In addition since they do not participate of hawks cay resort program you can’t enjoy the area. I stayed in this area and other owners are part of the program so you can enjoy the amenities around "
Duck Key waterfront villa with private pool, kayak, SUP, washer/dryer & AC
DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage
Relax by the serene pool surrounded by palm trees and lounge chairs.

DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage

9.8 out of 10, Exceptional, (156)
"We stayed for 4 nights, 2 adults and 2 kids. It was a pleasant stay. "
DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage
✦Unwind on your Oceanedge villa on Seapalm island✦
Relax by the ocean with a serene pool and lounge area, offering a tranquil escape.

✦Unwind on your Oceanedge villa on Seapalm island✦

9.8 out of 10, Exceptional, (32)
"Great house. Nice amenities- peaceful and secluded. However no beach access from house. Nearest beach is Sombrero beach which is very nice."
✦Unwind on your Oceanedge villa on Seapalm island✦
Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc
Relax by the serene pool surrounded by palm trees and a well-maintained hedge.

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

10.0 out of 10, Exceptional, (44)
"Property was amazing. House was extreamly well stocked which made flying a breeze. Beds were super comfortable and clean. Would definitely stay again."
Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc
Waterfront Villa in Paradise. Dipping pool. Middle Keys. Soak in the sun
Situated on a rocky shoreline, this coastal property offers access to the sea via a wooden dock.

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 AU$1,084
includes taxes & fees
7 Aug - 8 Aug
Waterfront Villa in Paradise. Dipping pool. Middle Keys. Soak in the sun
Villa 5028 on Duck Key BOAT SLIP available
Enjoy a serene view of the water from this deck with a round table and four chairs.

Villa 5028 on Duck Key BOAT SLIP available

9.6 out of 10, Exceptional, (7)
"Great location on the water with beautiful sunset views. Plenty of room for our group. "
The price is AU$933
includes taxes & fees
26 Aug - 27 Aug
Villa 5028 on Duck Key BOAT SLIP available
5% Off Any Booking through Jan 31, 2026! Canal Front/Private Pool/Hot Tub/Dock!
Relax by the pool with a view of the surrounding buildings, surrounded by wicker furniture and a comfortable sofa.

5% Off Any Booking through Jan 31, 2026! Canal Front/Private Pool/Hot Tub/Dock!

10.0 out of 10, Exceptional, (94)
"We had a great two week stay. We especially enjoyed the private pool area encircled by Palm trees and foliage. "
5% Off Any Booking through Jan 31, 2026! Canal Front/Private Pool/Hot Tub/Dock!
Marlin House 52: Gated Luxury Villa w/ Dockage, Sunset Views and Pool
Relax in a serene outdoor space with a pergola, wicker chair, and lounge chair, overlooking a tranquil body of water and lush palm trees.

Marlin House 52: Gated Luxury Villa w/ Dockage, Sunset Views and Pool

10.0 out of 10, Exceptional, (51)
"Our family really enjoyed our stay at this property. It has amazing water views and the villa provided everything we needed for a great stay. Highly recommend, we would stay here again."
Marlin House 52: Gated Luxury Villa w/ Dockage, Sunset Views and 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.
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Frequently asked questions

How much do villas in Florida Keys cost?
Expect to pay between AU$916 and AU$1,084 per night for villas in Florida Keys. Whatever your budget, a terrific stay is just a click or two away on Expedia. This price was 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.
How many villas are there in Florida Keys?
Select from 105 villas in Florida Keys. Whether you're getting away with the kids or a group of pals, and wherever you want to go, Expedia makes it simple to find the perfect digs.
What is there to do near my villa in Florida Keys?
Whether you're into arts, culture, shopping or dining, Florida Keys offers the lot, and then some! The terrific city of Key West boasts plenty of things to do, including Smathers Beach, South Beach and Fort Zachary Taylor Historic State Park. If you're escaping to Marathon, Sombrero Beach, The Turtle Hospital and Crane Point Museum and Nature Centre will fill up your itinerary.