Monroe County Holiday Rentals

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Top Cities in Monroe County

Top Holiday Rentals Destinations in Monroe County

Our top choices for Monroe County holiday rentals

Oceans Edge Key West Resort, Hotel & Marina

4.0 star property
9.0 out of 10, Wonderful, (1724)
"Amazing place to stay! "
The price is NZ$431
includes taxes & fees
21 Sept - 22 Sept
Oceans Edge Key West Resort, Hotel & Marina

Margaritaville Beach House Key West

4.0 star property
8.8 out of 10, Excellent, (1783)
"Great place to stay"
The price is NZ$441
includes taxes & fees
2 Oct - 3 Oct
Margaritaville Beach House Key West

Parrot Key Hotel & Villas

4.0 star property
9.0 out of 10, Wonderful, (1096)
"Great location, very cute resort, huge rooms, would stay again. "
The price is NZ$299
includes taxes & fees
28 Sept - 29 Sept
Parrot Key Hotel & Villas

Beachside Resort & Residences

3.5 star property
8.6 out of 10, Excellent, (1537)
"Beautiful place, convenient and friendly staff"
The price is NZ$301
includes taxes & fees
24 Sept - 25 Sept
Beachside Resort & Residences

Hyatt Vacation Club at Windward Pointe, Key West

3.5 star property
9.6 out of 10, Exceptional, (1016)
"Love this place "
The price is NZ$652
includes taxes & fees
20 Sept - 21 Sept
Hyatt Vacation Club at Windward Pointe, Key West

Havana Cabana at Key West

4.0 star property
8.8 out of 10, Excellent, (1761)
"Place was great we had the absolute best time"
The price is NZ$357
includes taxes & fees
14 Oct - 15 Oct
Havana Cabana at Key West

Casa Marina Key West, Curio Collection by Hilton

4.0 star property
8.4 out of 10, Very good, (351)
"Resort is beautiful very clean staff is excellent 👍👍"
The price is NZ$455
includes taxes & fees
25 Sept - 26 Sept
Casa Marina Key West, Curio Collection by Hilton

Southernmost Beach Resort and Guesthouses

4.0 star property
8.6 out of 10, Excellent, (2756)
"Definitely a great place to stay, reasonably priced, friendliness staff i have seen in a long time"
The price is NZ$415
includes taxes & fees
21 Sept - 22 Sept
Southernmost Beach Resort and Guesthouses

The Reach Key West, Curio Collection by Hilton

4.0 star property
8.4 out of 10, Very good, (1005)
"Overall a great place to stay with family "
The price is NZ$470
includes taxes & fees
25 Sept - 26 Sept
The Reach Key West, Curio Collection by Hilton

Hilton Garden Inn Key West / The Keys Collection

3.5 star property
7.8 out of 10, Good, (1082)
"Great property and excellent staff. Very clean and enjoyable stay."
The price is NZ$253
includes taxes & fees
28 Sept - 29 Sept
Hilton Garden Inn Key West / The Keys Collection

DoubleTree Resort by Hilton Grand Key - Key West

4.0 star property
8.0 out of 10, Very good, (1008)
"Beautiful hotel great pool with plenty of seating "
The price is NZ$258
includes taxes & fees
28 Sept - 29 Sept
DoubleTree Resort by Hilton Grand Key - Key West

Hampton Inn Key West FL

2.5 star property
9.0 out of 10, Wonderful, (1225)
"Was an amazing stay"
The price is NZ$246
includes taxes & fees
24 Sept - 25 Sept
Hampton Inn Key West FL

Blue Flamingo Resort Key West

4.0 star property
7.8 out of 10, Good, (1589)
"Great resort. "
The price is NZ$300
includes taxes & fees
21 Sept - 22 Sept
Blue Flamingo Resort Key West

Chesapeake Beach Resort

3.5 star property
9.2 out of 10, Wonderful, (1531)
"Great location, clean rooms, great amenities and the staff is very friendly. "
The price is NZ$313
includes taxes & fees
21 Sept - 22 Sept
Chesapeake Beach Resort

Pier House Resort & Spa

4.0 star property
9.0 out of 10, Wonderful, (1005)
"Convenient to Duvall street, shopping, eating, and very clean and on the water"
Pier House Resort & Spa

Cheeca Lodge & Spa

5.0 star property
9.2 out of 10, Wonderful, (1204)
"Great place to stay and the staff was great. "
The price is NZ$336
includes taxes & fees
21 Sept - 22 Sept
Cheeca Lodge & Spa

Delightful Aqualodge! Cabana Club Access!

9.6 out of 10, Exceptional, (27)
"Clean and convenient place to sleep. Good for a couple. For a family a larger place would be better. Cabana club access as always is great and a must when staying in KCB."
Delightful Aqualodge! Cabana Club Access!

The Perry Hotel & Marina Key West

4.0 star property
9.4 out of 10, Exceptional, (1095)
"Great rooms awesome service beautiful pool!"
The price is NZ$305
includes taxes & fees
2 Oct - 3 Oct
The Perry Hotel & Marina Key West

Isla Bella Beach Resort & Spa

5.0 star property
9.2 out of 10, Wonderful, (1056)
"Sea view, amazing staff , beautiful rooms "
The price is NZ$541
includes taxes & fees
29 Sept - 30 Sept
Isla Bella Beach Resort & Spa

Fairfield Inn and Suites by Marriott Key West

3.0 star property
7.8 out of 10, Good, (1159)
"Hotel was ok"
The price is NZ$238
includes taxes & fees
28 Sept - 29 Sept
Fairfield Inn and Suites by Marriott 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.
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Top Monroe County Hotel Reviews

Find out more about Monroe County

Find out more about Monroe County

Everything you need to know about Monroe County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Monroe County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Monroe County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Monroe County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Monroe County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Monroe County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Monroe County holiday rentals we have selected for you start as low as NZ$160 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Monroe County rentals

At Expedia, we put the best Monroe County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Monroe County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Monroe County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Monroe County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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