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

Holiday Homes in Monroe County

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Our top choices for Monroe County holiday homes

Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages
3.0 star property
Summerland Key
9.4 out of 10, Exceptional, (18 reviews)
"First time staying here it won’t be our last!"
United States
Thomas
Sugarloaf Key RV Resort & Cottages

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
2.5 star property
Marathon
9.2 out of 10, Wonderful, (140 reviews)
"This was the perfect place, right on the ocean and a full kitchen so you can cook your own meals. The room was very clean, I loved that they had a laundry basket and laundry detergent in the room for you, came in handy seeing as we stayed for 7 days. Amazing place to watch the sunset from a hammock and we got lucky enough to see some nurse sharks at the docks right outside of our hotel."
United States
Andrew Jackson
The price is 7.305.409 ₫
8.957.532 ₫ total
includes taxes & fees
26 Jul - 27 Jul
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House
2.0 star property
Raccoon Key
The price is 49.258.578 ₫
82.367.895 ₫ total
includes taxes & fees
26 Jul - 27 Jul
Waterfront Luxury Home - Tidelands House

Contra House Key West

Contra House Key West
3.0 star property
Old Town Key West
8.0 out of 10, Very good, (1 review)
"Pool and outside was undesirable"
United States
Rosalie
The price is 24.771.667 ₫
38.375.726 ₫ total
includes taxes & fees
10 Aug - 11 Aug
Contra House Key West

Angler's Reef Resort by KeysCaribbean

Angler's Reef Resort by KeysCaribbean
3.5 star property
Islamorada
9.0 out of 10, Wonderful, (14 reviews)
"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

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food."
United States
max
The price is 10.615.245 ₫
21.206.900 ₫ total
includes taxes & fees
12 Aug - 13 Aug
Starlight Serenity - Hideaway w Stunning Views

Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (1 review)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
The price is 28.018.305 ₫
50.050.090 ₫ total
includes taxes & fees
20 Jul - 21 Jul
Capmar House by Brightwild Huge Home Pool

Mirador House by Brightwild Pool Dock

Mirador House by Brightwild Pool Dock
2.0 star property
Raccoon Key
The price is 38.760.201 ₫
66.682.871 ₫ total
includes taxes & fees
12 Aug - 13 Aug
Mirador House by Brightwild Pool Dock

New Waterfront Home - Sunray House

New Waterfront Home - Sunray House
2.0 star property
Raccoon Key
New Waterfront Home - Sunray House

New Waterfront Home - Dreamside House

New Waterfront Home - Dreamside House
2.0 star property
Raccoon Key
The price is 46.713.521 ₫
79.504.705 ₫ total
includes taxes & fees
19 Jul - 20 Jul
New Waterfront Home - Dreamside House

New Altair House by Brightwild Pool Pets

New Altair House by Brightwild Pool Pets
2.0 star property
Raccoon Key
The price is 28.924.061 ₫
57.807.063 ₫ total
includes taxes & fees
20 Jul - 21 Jul
New Altair House by Brightwild Pool Pets

Southern Palms by Brightwild Pool Parking

Southern Palms by Brightwild Pool Parking
2.0 star property
Old Town Key West
The price is 51.654.311 ₫
78.325.096 ₫ total
includes taxes & fees
29 Jul - 30 Jul
Southern Palms by Brightwild Pool Parking

Poolside Paradise by Brightwild Heated Pool

Poolside Paradise by Brightwild Heated Pool
2.0 star property
Old Town Key West
The price is 19.996.897 ₫
35.130.257 ₫ total
includes taxes & fees
14 Jul - 15 Jul
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 24.950.716 ₫
41.377.103 ₫ total
includes taxes & fees
13 Aug - 14 Aug
Keys Please by Brightwild Pool Steps to Duval

Palmgale House in Key West

Palmgale House in Key West
2.0 star property
Raccoon Key
The price is 28.018.305 ₫
56.788.089 ₫ total
includes taxes & fees
15 Jul - 16 Jul
Palmgale House in Key West

Spindrift House by Brightwild Huge Pool Dock

Spindrift House by Brightwild Huge Pool Dock
2.0 star property
Raccoon Key
The price is 31.131.450 ₫
53.552.378 ₫ total
includes taxes & fees
14 Jul - 15 Jul
Spindrift House by Brightwild Huge Pool Dock

New Rose Retreat - Pool Parking

New Rose Retreat - Pool Parking
2.0 star property
Key West Historic District
The price is 14.812.564 ₫
29.297.883 ₫ total
includes taxes & fees
15 Jul - 16 Jul
New Rose Retreat - Pool Parking

Waterlane House by Brightwild Pool Boat Dock

Waterlane House by Brightwild Pool Boat Dock
2.0 star property
Raccoon Key
The price is 31.131.450 ₫
53.552.378 ₫ total
includes taxes & fees
16 Jul - 17 Jul
Waterlane House by Brightwild Pool Boat 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
6.0 out of 10, (1 review)
"The pool was very dirty with lots of leaves & the pool spa did not work upon arrival. Contacted mgt company several times about the spa. They sent someone out but he was not able to fix it. The worst issues were the showers as the settings were too hot & the temperature could not be adjusted. "
United States
Marlene
The price is 28.018.305 ₫
46.681.091 ₫ total
includes taxes & fees
10 Aug - 11 Aug
Contra House by Brightwild Luxury Home w Pool

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 26.878.861 ₫
46.915.265 ₫ total
includes taxes & fees
11 Aug - 12 Aug
The Mesa House by Brightwild Close to Duval
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

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Monroe County Holiday Homes information

Number of reviews
176
Accommodation
161 Holiday Homes
Lowest Price
8.957.532 ₫
Highest Price
82.367.895 ₫