Vacation Homes in Monroe County

  • 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 holiday homes

The Hammocks at Marathon

The Hammocks at Marathon
2.5 star property
Marathon
9.0 out of 10, Wonderful, (134 reviews)
"Amazing stay "
United States
Anthony
The Hammocks at Marathon

Oceanview 3BR/3BA Cottage 5009: Village at Hawks Cay Villas

Oceanview 3BR/3BA Cottage 5009: Village at Hawks Cay Villas
Duck Key
Oceanview 3BR/3BA Cottage 5009: Village at Hawks Cay Villas

Dog-Friendly, Water Front Home with Tiki Hut and 40 Ft Dock and Launch

Dog-Friendly, Water Front Home with Tiki Hut and 40 Ft Dock and Launch
Key Largo
9.0 out of 10, Wonderful, (2 reviews)
"Joseph was a great host! This place is a gem. "
United States
Faye F.
Dog-Friendly, Water Front Home with Tiki Hut and 40 Ft Dock and Launch

Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball

Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball
Key Largo
9.8 out of 10, Exceptional, (112 reviews)
"Excellent accommodations. Well worth the stay especially if you are bringing your boat. "
United States
Dianna B.
Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball

Charming 3-bedroom house featuring a heated private pool.

Charming 3-bedroom house featuring a heated private pool.
Duck Key
10.0 out of 10, Exceptional, (19 reviews)
"GORGEOUS HOUSE! Host was super sweet and communicative. Check in/out was easy and she made us feel very welcome while we were there."
United States
Regan C.
The price is HK$3,524
HK$6,934 total
includes taxes & fees
13 Apr - 14 Apr
Charming 3-bedroom house featuring a heated private pool.

BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!

BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
Old Town Key West
9.8 out of 10, Exceptional, (104 reviews)
"Amazing stay!!"
United States
Zac C.
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!

Refined. Safe. Clean. Waterfront. Golf cart , courtesy to our guests

Refined. Safe. Clean. Waterfront. Golf cart , courtesy to our guests
Key Largo
9.8 out of 10, Exceptional, (118 reviews)
"Love it, will be definitely stay here again!"
United States
Amy N.
Refined. Safe. Clean. Waterfront. Golf cart , courtesy to our guests

Key West Dreamin` - Private Pool Steps Off Duval

Key West Dreamin` - Private Pool Steps Off Duval
Old Town Key West
9.8 out of 10, Exceptional, (56 reviews)
"Great location! Clear communication and house was clean and cozy. Would rexommendz"
United States
Anonymous traveller
Key West Dreamin` - Private Pool Steps Off Duval

Perfect Location, Private Heated Pool, Pristine Luxury Home!

Perfect Location, Private Heated Pool, Pristine Luxury Home!
Old Town Key West
10.0 out of 10, Exceptional, (205 reviews)
"Great location."
United States
Bruce L.
The price is HK$11,746
HK$20,107 total
includes taxes & fees
21 Apr - 22 Apr
Perfect Location, Private Heated Pool, Pristine Luxury Home!

★Remodeled tropical delight townhome★private plunge pool close to fun activities

★Remodeled tropical delight townhome★private plunge pool close to fun activities
Duck Key
10.0 out of 10, Exceptional, (53 reviews)
"My family of four had an excellent stay at this property. The townhome was very modern, extremely clean, and had everything we needed. The outside area was relaxing, and the kids especially enjoyed the plunge pool. Miguel was communicative, and everything went smoothly. We liked the residential and private feel of Duck Key. "
United States
Daniel
★Remodeled tropical delight townhome★private plunge pool close to fun activities

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (96 reviews)
"We had a great time and will be back. "
United States
Michelle K.
The price is HK$2,819
HK$6,055 total
includes taxes & fees
27 Apr - 28 Apr
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Oceanfront, Pool, Tiki, Amazing Views, Near Vaca, Great Dockage, Kayaks, Bikes

Oceanfront, Pool, Tiki, Amazing Views, Near Vaca, Great Dockage, Kayaks, Bikes
Marathon Shores
10.0 out of 10, Exceptional, (103 reviews)
"Will be staying again next year for a longer stay…Thanks "
United States
Scott M.
Oceanfront, Pool, Tiki, Amazing Views, Near Vaca, Great Dockage, Kayaks, Bikes

**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...

**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
Old Town Key West
10.0 out of 10, Exceptional, (88 reviews)
"We had a fantastic stay at the Contented Crane. Beds were comfortable and room layout was ideal for our group of 6 adults traveling together. Allowed for adequate space and privacy while also having plenty of comfortable communal space. Location is excellent, easy walk to Duval Street and either southern most point or mallory square. We look forward to returning!"
United States
Katie B.
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
Key Largo
10.0 out of 10, Exceptional, (51 reviews)
"super nice and modern house, really lovely host, the kitchen is equipped with all you need for cookingall decoration is so nice fits to the beach feelingall rooms are modern and nice decoratedwe could just recommend ! if we will come back to Florida this will be again our choice!"
United States
Anonymous traveller
The price is HK$2,763
HK$5,489 total
includes taxes & fees
14 Apr - 15 Apr
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Key Largo
9.6 out of 10, Exceptional, (82 reviews)
"Great location with respect to attractions (snorkeling, etc), restaurants and groceries; great sunrise and sunset views; property is very quiet/serene; straightforward logistics for checking in and checking out."
United States
Jeffrey W.
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Luxurious 3-bedroom house perfect for relaxing in the heart of Key Largo.

Luxurious 3-bedroom house perfect for relaxing in the heart of Key Largo.
Sunrise Point
10.0 out of 10, Exceptional, (10 reviews)
Luxurious 3-bedroom house perfect for relaxing in the heart of Key Largo.

HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!

HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
Stock Island
9.6 out of 10, Exceptional, (56 reviews)
"Beautiful property with lots of spots for lounging and enjoying the view. A nice respite from the busier areas of Key West. Highly recommend!"
United States
Jennifer
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
Stock Island
9.4 out of 10, Exceptional, (75 reviews)
"Very clean and well decorated. We loved everything about our stay!"
United States
Lindsey
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
Matecumbe
9.8 out of 10, Exceptional, (45 reviews)
"Very clean Extremely well stocked Perfect for 2 couples!"
United States
Carol
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Private Secluded Ocean View & Pool Near Key West

Private Secluded Ocean View & Pool Near Key West
Summerland Key
8.0 out of 10, Very good, (103 reviews)
"Great house far enough away from Key West to be quiet and peaceful, and close enough to enjoy the nightlife! "
United States
Paul K.
Private Secluded Ocean View & Pool Near Key West
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

Find out more about Monroe County

Monroe County Vacation Homes information

Number of reviews
1,512
Accommodation
3519 Vacation Homes
Lowest Price
HK$5,489
Highest Price
HK$20,107

Explore a world of travel with Expedia