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

Holiday Homes in Monroe County

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Monroe County holiday homes

Two people sitting by a pool with palm trees in the background.

1. Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages
3.0 star property
Summerland Key
9.2 out of 10, Wonderful, (33 reviews)
"Nice for a chill weekend in the lower keys and for people with family accompanying them"
United States
Janey
Sugarloaf Key RV Resort & Cottages
A resort with a pool, lounge chairs, and a view of the ocean.

2. 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, (147 reviews)
"It is an excellent place."
United States
Arianna
The price is 4.411.033 ₫
5.691.879 ₫ total
includes taxes & fees
14 Oct - 15 Oct
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
A spacious living room with a large dining table, comfortable seating, and large windows offering a view of the outdoors.

3. Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House
2.0 star property
Raccoon Key
The price is 33.219.256 ₫
63.511.119 ₫ total
includes taxes & fees
22 Oct - 23 Oct
Waterfront Luxury Home - Tidelands House
A wooden deck with a railing, wicker chairs, and a view of greenery.

4. 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 6.649.288 ₫
16.465.887 ₫ total
includes taxes & fees
14 Oct - 15 Oct
Starlight Serenity - Hideaway w Stunning Views
A paved pathway leading to a beach with clear blue skies and greenery on both sides.

5. 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
A white two-story house with a balcony and a swimming pool.

6. 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)
The price is 19.920.478 ₫
40.381.416 ₫ total
includes taxes & fees
14 Oct - 15 Oct
Capmar House by Brightwild Huge Home Pool
A two-story house with a pool, surrounded by palm trees and a clear sky.

7. Mirador House by Brightwild Pool Dock

Mirador House by Brightwild Pool Dock
2.0 star property
Raccoon Key
The price is 19.920.478 ₫
44.792.448 ₫ total
includes taxes & fees
14 Oct - 15 Oct
Mirador House by Brightwild Pool Dock
A modern kitchen with a large island, bar stools, and a view of the outdoors.

8. New Waterfront Home - Sunray House

New Waterfront Home - Sunray House
2.0 star property
Raccoon Key
The price is 33.219.256 ₫
63.511.119 ₫ total
includes taxes & fees
27 Oct - 28 Oct
New Waterfront Home - Sunray House
A modern kitchen with white cabinetry, a marble countertop, and a central island with bar stools.

9. New Altair House by Brightwild Pool Pets

New Altair House by Brightwild Pool Pets
2.0 star property
Raccoon Key
The price is 26.569.766 ₫
54.396.727 ₫ total
includes taxes & fees
14 Oct - 15 Oct
New Altair House by Brightwild Pool Pets
A covered outdoor patio with a pool, seating area, and lush greenery.

10. Southern Palms by Brightwild Pool Parking

Southern Palms by Brightwild Pool Parking
2.0 star property
Old Town Key West
The price is 37.042.698 ₫
61.277.628 ₫ total
includes taxes & fees
27 Oct - 28 Oct
Southern Palms by Brightwild Pool Parking
A pool area with a waterfall feature, surrounded by palm trees and a white fence.

11. Poolside Paradise by Brightwild Heated Pool

Poolside Paradise by Brightwild Heated Pool
2.0 star property
Old Town Key West
The price is 21.361.090 ₫
37.100.955 ₫ total
includes taxes & fees
27 Oct - 28 Oct
Poolside Paradise by Brightwild Heated Pool
A modern house with a swimming pool, a balcony, and a well-maintained garden.

12. 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 18.333.924 ₫
30.998.464 ₫ total
includes taxes & fees
14 Oct - 15 Oct
Contra House Key West
A spacious living area with a wooden dining table, comfortable seating, a flat-screen TV, and large windows offering a view of the outdoors.

13. Spindrift House by Brightwild Huge Pool Dock

Spindrift House by Brightwild Huge Pool Dock
2.0 star property
Raccoon Key
The price is 19.920.478 ₫
40.381.416 ₫ total
includes taxes & fees
14 Oct - 15 Oct
Spindrift House by Brightwild Huge Pool Dock
A spacious living area with a sofa, glass coffee table, and a kitchen with sliding doors leading to a balcony.

14. 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 23.245.122 ₫
40.854.206 ₫ total
includes taxes & fees
27 Oct - 28 Oct
Contra House by Brightwild Luxury Home w Pool
A covered porch with two black chairs and a table, white building with a door and windows, and palm trees in the background.

15. 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 19.449.471 ₫
38.054.444 ₫ total
includes taxes & fees
14 Oct - 15 Oct
The Mesa House by Brightwild Close to Duval
A poolside area with lounge chairs and umbrellas, a pool, and a view of the ocean.

16. New Waterfront Home - Dreamside House

New Waterfront Home - Dreamside House
2.0 star property
Raccoon Key
The price is 34.998.823 ₫
66.913.458 ₫ total
includes taxes & fees
19 Oct - 20 Oct
New Waterfront Home - Dreamside House
Exterior

17. 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 20.225.153 ₫
35.659.654 ₫ total
includes taxes & fees
14 Oct - 15 Oct
Keys Please by Brightwild Pool Steps to Duval
A spacious room with a wooden floor, wicker chairs, a dining table, and a staircase with a wooden railing.

18. New Rose Retreat - Pool Parking

New Rose Retreat - Pool Parking
2.0 star property
Key West Historic District
New Rose Retreat - Pool Parking
A pool area with a circular pool, surrounded by lush greenery and a white fence. There are wicker chairs and a table near the pool.

19. Seafarer's Refuge

Seafarer's Refuge
3.0 star property
Meadows
Seafarer's Refuge
A waterfront property with a pool, multiple balconies, and a dock with boats.

20. Azul Paradise - Waterfront - Heated Pool - Dock

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

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"Loved complimentary transportation!"
Robert 2-night trip
Posted less than an hour ago
DoubleTree Resort by Hilton Grand Key - Key West

Find out more about Monroe County

Monroe County Holiday Homes information

Number of reviews
51
Accommodation
148 Holiday Homes
Lowest Price
5.691.879 ₫
Highest Price
66.913.458 ₫