Vacation Homes in Monroe County

Compare and save

    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

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Top Cities in Monroe County

Key Largo showing outdoor eating and cafe lifestyle
Vacation HomesVacation Homes

Key Largo

Key Largo
Islamorada featuring a beach and tropical scenes
Vacation HomesVacation Homes

Islamorada

Islamorada

Vacation Homes in Monroe County

Our top choices for Monroe County vacation homes

The Hammocks at Marathon
Outdoor pool, pool umbrellas, sun loungers

The Hammocks at Marathon

2.5 star property
9.0 out of 10, Wonderful, (98)
"Very nice and clean nice pool area nice tity bar an restant easy to get in and out good gym area"
The Hammocks at Marathon
Waterfront Luxury Home - Tidelands House
House | 8 bedrooms, Internet

Waterfront Luxury Home - Tidelands House

2.0 star property
The price is NT$64,210
NT$101,952 total
includes taxes & fees
Sep 7 - Sep 8
Waterfront Luxury Home - Tidelands House
New Waterfront Home - Sunray House
House | 8 bedrooms, Internet

New Waterfront Home - Sunray House

2.0 star property
The price is NT$64,210
NT$101,952 total
includes taxes & fees
Sep 7 - Sep 8
New Waterfront Home - Sunray House
Angler's Reef Resort by KeysCaribbean
Private beach, sun loungers

Angler's Reef Resort by KeysCaribbean

3.5 star property
9.0 out of 10, Wonderful, (14)
"House is situated right off the main road and very noisy at all times day and night. Also no blinds in the Master room which is located at back of home off the road. Had to buy a set of frying pans because the pans there were in terrible condition for Teflon coated."
Angler's Reef Resort by KeysCaribbean
Keys Please by Brightwild Pool Steps to Duval
House | 3 bedrooms, Internet

Keys Please by Brightwild Pool Steps to Duval

2.0 star property
Keys Please by Brightwild Pool Steps to Duval
Poolside Paradise by Brightwild Heated Pool
House | 3 bedrooms, Internet

Poolside Paradise by Brightwild Heated Pool

2.0 star property
The price is NT$21,833
NT$38,491 total
includes taxes & fees
Aug 25 - Aug 26
Poolside Paradise by Brightwild Heated Pool
Mariner's Club Key Largo by KeysCaribbean
2 outdoor pools, open 10:00 AM to 6:00 PM, sun loungers

Mariner's Club Key Largo by KeysCaribbean

3.5 star property
7.4 out of 10, Good, (263)
"Great property "
Mariner's Club Key Largo by KeysCaribbean
Mirador House by Brightwild Pool Dock
House | 5 bedrooms, Internet

Mirador House by Brightwild Pool Dock

2.0 star property
The price is NT$40,946
NT$71,508 total
includes taxes & fees
Aug 25 - Aug 26
Mirador House by Brightwild Pool Dock
Palm Tree Cove Resort
Exterior

Palm Tree Cove Resort

2.5 star property
Palm Tree Cove Resort
New Rose Retreat - Pool Parking
House | 2 bedrooms

New Rose Retreat - Pool Parking

2.0 star property
The price is NT$29,099
NT$46,665 total
includes taxes & fees
Sep 7 - Sep 8
New Rose Retreat - Pool Parking
Palmgale House in Key West
House | 6 bedrooms, Internet

Palmgale House in Key West

2.0 star property
The price is NT$47,030
NT$80,768 total
includes taxes & fees
Sep 7 - Sep 8
Palmgale House in Key West
Luxury Seaside Escape Pool Dock Scenic Views
House, Accessible | 5 bedrooms, desk, Internet

Luxury Seaside Escape Pool Dock Scenic Views

2.5 star property
Luxury Seaside Escape Pool Dock Scenic Views
The Mesa House by Brightwild Close to Duval
House | 3 bedrooms, Internet

The Mesa House by Brightwild Close to Duval

2.0 star property
The price is NT$22,441
NT$39,176 total
includes taxes & fees
Sep 16 - Sep 17
The Mesa House by Brightwild Close to Duval
Contra House by Brightwild Luxury Home w Pool
House | 4 bedrooms, Internet

Contra House by Brightwild Luxury Home w Pool

2.0 star property
The price is NT$38,619
NT$60,162 total
includes taxes & fees
Aug 26 - Aug 27
Contra House by Brightwild Luxury Home w Pool
Coastline Marine Extremes Chilln
Luxury House, Private Bathroom, Ocean View | Shared kitchen

Coastline Marine Extremes Chilln

2.5 star property
Coastline Marine Extremes Chilln
Parrot Perch by Avantstay Old Town Key West w/ Shared Pool Week Long Stays Only
House (2 Bedrooms) | Interior

Parrot Perch by Avantstay Old Town Key West w/ Shared Pool Week Long Stays Only

3.5 star property
10.0 out of 10, Exceptional, (4)
"Perfect for our needs. Within walking distance to everything, yet quiet and peaceful. "
Parrot Perch by Avantstay Old Town Key West w/ Shared Pool Week Long Stays Only
Family Couples Getaway Sleeps 6 Guests
House, 2 Bedrooms, Patio | Living area

Family Couples Getaway Sleeps 6 Guests

2.0 star property
Family Couples Getaway Sleeps 6 Guests
1 Beautiful 4 Bed 3 Bath Pool Home w Free Dock
House | 4 bedrooms

1 Beautiful 4 Bed 3 Bath Pool Home w Free Dock

2.0 star property
1 Beautiful 4 Bed 3 Bath Pool Home w Free Dock
Waterfront Oasis W Boat Dock Heated Pool
House | 4 bedrooms

Waterfront Oasis W Boat Dock Heated Pool

2.0 star property
Waterfront Oasis W Boat Dock Heated Pool
Coastal Comfort
House, Multiple Beds (Coastal Comfort) | Pool | Outdoor pool, a heated pool

Coastal Comfort

2.0 star property
Coastal Comfort
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 Monroe County Hotel Reviews

Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"The property was excellent, located in the heart of everything!! 😍"
Bonita 4-night trip
Posted 12 hours ago
Beachside Resort & Residences