Villas in Monroe County

Compare and save
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Top Cities in Monroe County

Our top choices for Monroe County villas

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.8 out of 10, Exceptional, (70 reviews)
"Amazing stay, can’t wait to stay there again!"
United States
Anonymous traveler
The price is AED 3,302
AED 3,917 total
includes taxes & fees
4 Feb - 5 Feb
The Islands of Islamorada

TF Pool Beach Kitchen Sleep 6, Hot Tub W&D Marina WiFi Parking

TF Pool Beach Kitchen Sleep 6, Hot Tub W&D Marina WiFi Parking
Marathon
9.4 out of 10, Exceptional, (128 reviews)
"Quiet and friendly "
United States
Damon J.
TF Pool Beach Kitchen Sleep 6, Hot Tub W&D Marina WiFi Parking

Villa del Sol - Sunset Views, Kayaks, 2/2.5 - Slip Available/Ramp/Free Pkg

Villa del Sol - Sunset Views, Kayaks, 2/2.5 - Slip Available/Ramp/Free Pkg
Duck Key
10.0 out of 10, Exceptional, (2 reviews)
"What a great place to stay in the Key. W had a great time, my wife and two boys who are 20 and 23 lived the Villa. The boys lived the kayaks and we took advantage of walking to our deep sea fishing charter just across the road as well as swimming with the the dolphins at Dolphin a discovery both on Duck Key. Very clean. Beautiful views, great amenitis in the home, just wonderful. Also great to be in the middle of the keys to explore the whole area."
United States
Matt B.
Villa del Sol - Sunset Views, Kayaks, 2/2.5 - Slip Available/Ramp/Free Pkg

Stunning Panoramic rooftop views from this gulf side Tuscan style Villa!

Stunning Panoramic rooftop views from this gulf side Tuscan style Villa!
Marathon
9.0 out of 10, Wonderful, (52 reviews)
"Great location "
United States
Jason K.
Stunning Panoramic rooftop views from this gulf side Tuscan style Villa!

Seas the Keys Getaway with plunge pool/spa

Seas the Keys Getaway with plunge pool/spa
Marathon
9.6 out of 10, Exceptional, (12 reviews)
"Great location, great accomodation, hot tub and patio in the back area was great for relaxing in the evenings."
United States
Justus
Seas the Keys Getaway with plunge pool/spa

Charming 3-bedroom villa with WiFi, AC in welcoming Marathon

Charming 3-bedroom villa with WiFi, AC in welcoming Marathon
Marathon
10.0 out of 10, Exceptional, (1 review)
"This property is like no other for the price. The home is older but well kept and clean. Very nostalgic and charming this has the ultimate view. The breeze is constant and wonderful! The house is fun.. odd shaped with 3 balconies and one is screened in. The pool is small but so clear and refreshing.. even has a seated jet pool to relax in before dipping into the hot tub… all with a spectacular ocean view but secluded and private. There are Kayak s on the property and are so much fun! ...
United States
Shawn B.
Charming 3-bedroom villa with WiFi, AC in welcoming Marathon

Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere

Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
Old Town Key West
9.8 out of 10, Exceptional, (168 reviews)
"Family trip for 30th bday. Great location and yes its loud however we had no issues with that. Pool was fantastic. House was clean and well equiped. Communication is hit or miss but dont let that deter you. "
United States
Amy S.
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere

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, (20 reviews)
"Property was very nice, everything as expected based on listing. Very good place for families."
United States
Nicholas H.
The price is AED 1,539
AED 2,970 total
includes taxes & fees
10 Feb - 11 Feb
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA

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, (51 reviews)
"Owners were amazing and so helpful! Great communication from the start and hospitality during the stay was unmatched. Made everyone feel welcome. We rented the suite right off the pool and it had two private bedrooms and bathrooms. Such a great experience!"
United States
Bobbiejean J.
The price is AED 3,118
AED 3,953 total
includes taxes & fees
18 Feb - 19 Feb
Two Bedroom Two Bath Poolside Villa Steps from Duval!

DUPLEX IN DUCK KEY 3/2 W/90' Private Dock, Trailer Storage included

DUPLEX IN DUCK KEY 3/2 W/90' Private Dock, Trailer Storage included
Marathon
9.8 out of 10, Exceptional, (206 reviews)
"Amazing stay"
United States
Jeff C.
DUPLEX IN DUCK KEY 3/2 W/90' Private Dock, Trailer Storage included

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 review)
"The host was extremely communicative and welcoming. What ever we needed he provided"
United States
Amy G.
The price is AED 1,172
AED 2,505 total
includes taxes & fees
4 Feb - 5 Feb
Villa 5021 on Duck Key Boat Slip Available - 2BD 2.5BA

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 reviews)
"Location was great. Facility and rooms were clean. Great amenities - we will book again"
United States
William P.
The price is AED 3,302
AED 4,170 total
includes taxes & fees
2 Mar - 3 Mar
Two Bedroom Two Bath Balcony Villa Steps from Duval!

Luxury Villa-Infinity Pool-Jacuzzi-Endless Amenities-

Luxury Villa-Infinity Pool-Jacuzzi-Endless Amenities-
Marathon
10.0 out of 10, Exceptional, (16 reviews)
"Awesome house! All 3 floors are beautifully appointed and each bedroom had more than the needed amenities. AC units kept the place super cool, and we received great service while at the house. Ice machine made it great for fishing, dock was perfect for our boats and jet ski. Outdoor amenities were perfect. Highly recommended! You will not be disappointed."
United States
Gary G.
Luxury Villa-Infinity Pool-Jacuzzi-Endless Amenities-

Location In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking

Location In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking
Old Town Key West
9.8 out of 10, Exceptional, (78 reviews)
"Nice and clean homes with great space for family."
United States
Lynn F.
Location In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking

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

Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer
Duck Key
8.6 out of 10, Excellent, (58 reviews)
"We loved our stay. Very nice and peaceful."
United States
Dawn M.
Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer

KG Arrive any day, pool on beach, full Kitchen, W/D, Parking, Docks, balcony,

KG Arrive any day, pool on beach, full Kitchen, W/D, Parking, Docks, balcony,
Marathon
9.2 out of 10, Wonderful, (306 reviews)
"Nice stay"
United States
Henry C.
KG Arrive any day, pool on beach, full Kitchen, W/D, Parking, Docks, balcony,

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 review)
"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 AED 2,066
AED 3,771 total
includes taxes & fees
4 Feb - 5 Feb
Atlantic View Luxury Villa with Pool

Waterfront House with Boat Dock

Waterfront House with Boat Dock
5.0 star property
Hammer Point
7.0 out of 10, Good, (2 reviews)
"Everything was fine except half way through the stay the water department came and shut off the water at the street. It came back on a few hours later, so it all worked out. The house was fine"
United States
Philip J
Waterfront House with Boat Dock

Discount Available! Private Pool, Canal Front, Dock, Bikes, Paddleboards & More!

Discount Available! Private Pool, Canal Front, Dock, Bikes, Paddleboards & More!
Marathon
9.8 out of 10, Exceptional, (59 reviews)
"Great property and location for our family. We enjoyed our time here."
United States
Ashley G.
Discount Available! Private Pool, Canal Front, Dock, Bikes, Paddleboards & More!

Stunning Waterfront Two-Story Villa in Duck Key!

Stunning Waterfront Two-Story Villa in Duck Key!
Duck Key
9.6 out of 10, Exceptional, (4 reviews)
"Optimal for a week stay, close proximity to fishing charts, marinas and restaurants."
United States
Michael S.
Stunning Waterfront Two-Story Villa in Duck Key!
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

Top Monroe County Hotel Reviews