Holiday Homes in Monroe County

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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, (116)
"It was my first time staying there but it won’t be my last."
United States
Dennis
The Hammocks at Marathon

Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House
2.0 star property
Raccoon Key
The price is Rp35.236.621
Rp55.948.442 total
includes taxes & fees
11 Jan - 12 Jan 2026
Waterfront Luxury Home - Tidelands House

Contra House Key West

Contra House Key West
3.0 star property
Old Town Key West
The price is Rp19.276.773
Rp28.397.169 total
includes taxes & fees
12 Jan - 13 Jan 2026
Contra House Key West

New Waterfront Home - Sunray House

New Waterfront Home - Sunray House
2.0 star property
Raccoon Key
The price is Rp28.218.464
Rp48.026.772 total
includes taxes & fees
4 Jan - 5 Jan 2026
New Waterfront Home - Sunray House

Mirador House by Brightwild Pool Dock

Mirador House by Brightwild Pool Dock
2.0 star property
Raccoon Key
The price is Rp23.512.087
Rp40.391.705 total
includes taxes & fees
5 Jan - 6 Jan 2026
Mirador House by Brightwild Pool Dock

Contra House by Brightwild Luxury Home w Pool

Contra House by Brightwild Luxury Home w Pool
2.0 star property
Old Town Key West
The price is Rp45.116.261
Rp59.928.617 total
includes taxes & fees
20 Jan - 21 Jan 2026
Contra House by Brightwild Luxury Home w Pool

Poolside Paradise by Brightwild Heated Pool

Poolside Paradise by Brightwild Heated Pool
2.0 star property
Old Town Key West
Poolside Paradise by Brightwild Heated Pool

Keys Please by Brightwild Pool Steps to Duval

Keys Please by Brightwild Pool Steps to Duval
2.0 star property
Old Town Key West
The price is Rp24.884.842
Rp36.034.191 total
includes taxes & fees
24 Dec - 25 Dec
Keys Please by Brightwild Pool Steps to Duval

New Rose Retreat - Pool Parking

New Rose Retreat - Pool Parking
2.0 star property
Key West Historic District
The price is Rp24.158.880
Rp34.822.760 total
includes taxes & fees
11 Jan - 12 Jan 2026
New Rose Retreat - Pool Parking

The Mesa House by Brightwild Close to Duval

The Mesa House by Brightwild Close to Duval
2.0 star property
Key West Historic District
The price is Rp26.201.648
Rp37.120.874 total
includes taxes & fees
11 Jan - 12 Jan 2026
The Mesa House by Brightwild Close to Duval

Azul Paradise - Waterfront - Heated Pool - Dock

Azul Paradise - Waterfront - Heated Pool - Dock
2.0 star property
Marathon
Azul Paradise - Waterfront - Heated Pool - Dock

Angler's Reef Resort by KeysCaribbean

Angler's Reef Resort by KeysCaribbean
3.5 star property
Islamorada
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."
United States
Timothy
Angler's Reef Resort by KeysCaribbean

Palm Tree Cove Resort

Palm Tree Cove Resort
2.5 star property
Marathon
Palm Tree Cove Resort

Coastline Marine Extremes Chilln

Coastline Marine Extremes Chilln
2.5 star property
Marathon
Coastline Marine Extremes Chilln

Palmgale House in Key West

Palmgale House in Key West
2.0 star property
Raccoon Key
The price is Rp24.590.638
Rp42.927.906 total
includes taxes & fees
11 Jan - 12 Jan 2026
Palmgale House in Key West

Southern Palms by Brightwild Pool Parking

Southern Palms by Brightwild Pool Parking
2.0 star property
Old Town Key West
Southern Palms by Brightwild Pool Parking

Luxury Seaside Escape Pool Dock Scenic Views

Luxury Seaside Escape Pool Dock Scenic Views
2.5 star property
Marathon
Luxury Seaside Escape Pool Dock Scenic Views

1 Beautiful 4 Bed 3 Bath Pool Home w Free Dock

1 Beautiful 4 Bed 3 Bath Pool Home w Free Dock
2.0 star property
Marathon
1 Beautiful 4 Bed 3 Bath Pool Home w Free Dock

Waterfront Oasis W Boat Dock Heated Pool

Waterfront Oasis W Boat Dock Heated Pool
2.0 star property
Coury
Waterfront Oasis W Boat Dock Heated Pool

3 4 Tim e

3 4 Tim e
2.0 star property
Northside Resort
3 4 Tim e
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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Top Monroe County Hotel Reviews

Find out more about Monroe County

Monroe County Holiday Homes information

Number of reviews
116
Accommodation
235 Holiday Homes
Lowest Price
Rp28.397.169
Highest Price
Rp59.928.617