A waterfront promenade with multi-story buildings, palm trees, and a clear blue sky.

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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Top Cities in Monroe County

A sunset over a beach with a wooden pier and a small structure on it.
VillasVillas

Tavernier

Tavernier

Our top choices for Monroe County villas

Aerial view

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
9.2 out of 10, Wonderful, (175 reviews)
"One of the few resorts right on a beach! And being in Marathon, it’s a quick drive up to Islamorada or to Key West!"
United States
James S.
TF Pool Beach Kitchen Sleep 6, Hot Tub W&D Marina WiFi Parking
Balcony view

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (76 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 AED 2,347
AED 2,843 total
includes taxes & fees
6 Jul - 7 Jul
The Islands of Islamorada
Terrace/patio

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, (182 reviews)
"Great place to stay!"
United States
Andrew M.
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
Exterior

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, (324 reviews)
"Great place to stay"
United States
Lisa B.
KG Arrive any day, pool on beach, full Kitchen, W/D, Parking, Docks, balcony,
Exterior

Free Golf Cart Free Kayaks Steps to Pool Pickleball

Free Golf Cart Free Kayaks Steps to Pool Pickleball
Key Largo
9.6 out of 10, Exceptional, (89 reviews)
"Description was accurate. Excellent location and resort."
United States
Ben C.
Free Golf Cart Free Kayaks Steps to Pool Pickleball
Terrace/patio

UPDATED Villa- Coral Lagoon 3bed 2.5 bath Luxury Home

UPDATED Villa- Coral Lagoon 3bed 2.5 bath Luxury Home
Coral Lagoon
10.0 out of 10, Exceptional, (12 reviews)
"It was spectacular. Loved the place and the location."
United States
Donna H.
UPDATED Villa- Coral Lagoon 3bed 2.5 bath Luxury Home
Property grounds

Tropical bayfront villa with sandy beach

Tropical bayfront villa with sandy beach
Key Largo
10.0 out of 10, Exceptional, (13 reviews)
"Would stay again"
United States
Ryan K.
Tropical bayfront villa with sandy beach
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, (59 reviews)
"Key West Villa's is an awesome place!"
United States
Andrew B.
The price is AED 1,649
AED 2,090 total
includes taxes & fees
5 Jul - 6 Jul
Two Bedroom Two Bath Poolside Villa Steps from Duval!
Property grounds

Duck Key waterfront villa with private pool, kayak, SUP

Duck Key waterfront villa with private pool, kayak, SUP
Duck Key
8.6 out of 10, Excellent, (239 reviews)
"Laundry was convenient. Pool looked nice but we did not use it."
United States
Scott B.
Duck Key waterfront villa with private pool, kayak, SUP
Exterior

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, (217 reviews)
"enjoyed the tiki hut"
United States
marjorie s.
DUPLEX IN DUCK KEY 3/2 W/90' Private Dock, Trailer Storage included
Outdoor dining

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

DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage INCL
Marathon
9.8 out of 10, Exceptional, (188 reviews)
"Very clean, beautiful location set up for relaxation and quality family time!"
United States
Edward Lee W.
DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage INCL
Terrace/patio

DUPLEX IN DUCK KEY, 2 Bedroom /2 Bath w/40' Dock, Trailer Storage Incl.

DUPLEX IN DUCK KEY, 2 Bedroom /2 Bath w/40' Dock, Trailer Storage Incl.
Marathon
10.0 out of 10, Exceptional, (178 reviews)
"Always love our vacations in the Keys!"
United States
Edith T.
DUPLEX IN DUCK KEY, 2 Bedroom /2 Bath w/40' Dock, Trailer Storage Incl.
A heated pool

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

PLUNGE POOL VILLA ON BLUE WATER LAGOON DUCK Key/MARATHON, FL
Marathon
9.6 out of 10, Exceptional, (82 reviews)
"Very quiet and relaxing with a beautiful view of the channel right in your back yard. "
United States
Kevin D.
PLUNGE POOL VILLA ON BLUE WATER LAGOON DUCK Key/MARATHON, FL
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, (23 reviews)
"Awesome place to stay"
United States
Takuma F.
The price is AED 1,078
AED 2,396 total
includes taxes & fees
29 Jun - 30 Jun
Villa 5087 on Duck Key Boat Slip Available - 2BD 2.5BA
Exterior

Secret Villa II @ Old Town: with Private Pool, close to Duval!

Secret Villa II @ Old Town: with Private Pool, close to Duval!
Old Town Key West
10.0 out of 10, Exceptional, (163 reviews)
"Host was very welcoming! Its a beutiful place, very comfortable, great pool patio area… we lacked for nothing…can’t wait to go back!"
United States
Kim N.
Secret Villa II @ Old Town: with Private Pool, close to Duval!
Property grounds

Stunning & Welcoming Pool Home on Canal

Stunning & Welcoming Pool Home on Canal
Marathon
8.6 out of 10, Excellent, (108 reviews)
"The house was perfect. Lots of room for all of us and it’s beautifully decorated. The manager was extremely responsive whenever we needed anything. "
United States
Deana D.
Stunning & Welcoming Pool Home on Canal
Terrace/patio

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

Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer
Duck Key
Waterfront retreat with balcony views, kayak, SUP, central AC & washer/dryer
Outdoor dining

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

DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage
Duck Key
9.8 out of 10, Exceptional, (174 reviews)
"Have stayed here on numerous occasions and always love it!!"
United States
Kim B.
DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage
Exterior

Isla Key Lime: Boutique Resort, FREE Boat Dockage Sept-Oct Only!

Isla Key Lime: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Matecumbe
10.0 out of 10, Exceptional, (5 reviews)
"Very nice accommodations."
United States
Jeff B.
Isla Key Lime: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Property grounds

Newly upgraded Key Largo Villa W/Boat Slip

Newly upgraded Key Largo Villa W/Boat Slip
Key Largo
10.0 out of 10, Exceptional, (84 reviews)
" Beautiful place with great views. Thanks for a great stay!"
United States
Jenn W.
Newly upgraded Key Largo Villa W/Boat Slip
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 Monroe County Hotel Reviews

Reefhouse Resort & Marina

Reefhouse Resort & Marina

10/10 Excellent
"Todo en un solo lugar acogedor y con variedad de actividad para la familia"
Idyelin 1-night trip
Posted less than an hour ago
Reefhouse Resort & Marina