Monroe County Holiday Rentals from NZ$220: Search Short-Term Rentals

Top Cities in Monroe County

A beach with palm trees, people sunbathing, and a resort in the background.

A beach with palm trees and white lounge chairs under a clear blue sky.

Our top choices for Monroe County holiday rentals

A beach with palm trees, thatched-roof huts, and lounge chairs.

1. Breezy Palms Resort

Matecumbe

Gavin

includes taxes & fees

11 Nov - 12 Nov

A motel with a blue exterior, multiple balconies, and a parking lot.

2. Knight's Key Suites

Marathon

Brandy

includes taxes & fees

29 Nov - 30 Nov

A marina with several boats docked, a thatched-roof structure, and a row of mobile homes.

3. Aqua Lodges at Hurricane Hole Marina

Stock Island

Kagni

includes taxes & fees

11 Nov - 12 Nov

An outdoor seating area with wicker furniture and cushions, a thatched-roof structure, and lush greenery.

4. Tropical Cottages

Marathon

Douglas

includes taxes & fees

10 Nov - 11 Nov

A spacious living room with a large window, a white sofa, a coffee table, and a painting of a tropical scene.

5. Anchorage Resort & Yacht Club

Key Largo

Doris

includes taxes & fees

8 Nov - 9 Nov

A floating houseboat with a covered deck and seating area, docked at a marina.

6. Aqua Lodge Rentals At Coconut Cay

Marathon

Susan

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

7. Treasure Harbor

Islamorada

Diane

includes taxes & fees

9 Nov - 10 Nov

A cozy room with a brown leather sofa, a white table, and a ceiling fan.

8. Old Wooden Bridge Resort and Marina

Punta Brisa

Jordan

includes taxes & fees

12 Nov - 13 Nov

A hotel with a pool, palm trees, and red umbrellas.

9. Skipjack Resort & Marina

Marathon

Justin

includes taxes & fees

8 Nov - 9 Nov

A waterfront marina with a row of white buildings, each with a dock extending into the water. A signboard above reads "Yacht Haven 305-393-5073".

10. Yacht Haven Marina

Marathon

Lauren

includes taxes & fees

8 Nov - 9 Nov

A beachfront hotel with two palm trees, a flag, and a pool area with lounge chairs.

11. Florida Keys Getaway - Slps 4 - Ocean View

Tavernier

Nick

includes taxes & fees

16 Nov - 17 Nov

A swimming pool with a wooden deck and a white fence.

12. Steps from Duval, Pool on Site & Bikes Included!

Old Town Key West

Laura D.

includes taxes & fees

18 Nov - 19 Nov

A resort with a swimming pool, lounge chairs, and a view of the ocean.

13. Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Marathon

Arianna

includes taxes & fees

2 Dec - 3 Dec

14. Piece of Paradise

Key largo

includes taxes & fees

1 Dec - 2 Dec

A wooden deck with a large tree, outdoor seating, and a marina in the background.

15. Poolside Cottage #412

Key West

shannon b.

includes taxes & fees

29 Nov - 30 Nov

A small, private entrance to a house with a brick pathway leading to a door.

16. Ricky's Retreat - Truman @ Duval | Ideal Getaway!

Old Town Key West

Brian R.

includes taxes & fees

16 Nov - 17 Nov

A sign reading "Sugar Palm Studio" on a wooden door.

17. SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

Old Town Key West

walter l.

includes taxes & fees

10 Nov - 11 Nov

A small, single-story building with a blue roof, surrounded by trees and a gravel ground.

18. Aqua Lodges at 47th Street Gulfside

Marathon

Lauren

includes taxes & fees

10 Nov - 11 Nov

A bedroom with a bed, nightstand, dresser, and a ceiling fan.

19. ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

Old Town Key West

Justin D.

includes taxes & fees

1 Dec - 2 Dec

A room with a wooden desk, two chairs, a window with a view of the ocean, a sign above the window, and a plant on the desk.

20. Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Tavernier

Les

includes taxes & fees

19 Nov - 20 Nov

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Top Monroe County Hotel Reviews

Isla Bella Beach Resort & Spa

10/10 Excellent

"Amazing hotel"

Parrot Key Hotel & Villas

8/10 Good

"We had a fantastic stay at Parrot Key Resort in Key West. The property is beautiful and very well kept, the pools were nice, and our room was clean and spacious. I do wish they’d made better use of all that space. A little more storage, seating, and somewhere to set our stuff down would’ve made a difference. I would’ve liked the option to park my own car instead of paying over $30 a night for valet, and I didn’t feel like we got much out of the resort fee. The minibar prices were insane. A full liter of vodka costs less than the 375 mL bottle in the room. At that price, it feels like they’re taking advantage of people coming back after a night out. Overall, we really enjoyed our stay. I’d stay here again, reluctantly pay for valet, and happily spend another afternoon by the pool."

Hilton Key West Resort & Marina

8/10 Good

"The property is beautiful - we enjoyed the room, the pool. The bed was comfortable. We enjoyed the robes they offered to the guests. The room was quite spacious as well and our room had a balcony and overlooked the pool (building 3). We participated in some of the activities that the resort had (the yoga was the best!) There were just a few things that happened which is why I gave it 4 stars. We had arrived early and they said our room was being cleaned and they would call us. We waited 3 hours, They never called so we just went back and they forgot they said. When we got our room - the toilet didn't work. Things happen - no big deal. The next day tho - housekeeping never cleaned our room - I had to call twice. After that tho - they did clean our room daily. We hung out at the pool one day and someone came by with menus and said they would be back to take orders. They didn't come for over an hour - I had to actually call the restaurant and ask if they could have them come take our poolside order (as they offer this). If they are going to offer poolside - then they should have someone checking back with guests. Management did offer free breakfast for the issue with housekeeping and they did credit us the resort fee on the day of our arrival. The grounds were nice, the views were nice - I would go back, I'm just not sure if this would be my first option. I might check out another place first."

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

10/10 Excellent

"Super Wonderful & Beautiful Place. Breathtaking Views And Felt Like We Are In A Tropical Island. In our Personal Experience We Had A Kinda Loud Neighbour But They Simply Became Quite After 10 PM. Other Than That, Everything Was Amazing. Helpful Staff, Beautiful Scenery, And A Shuttle Service To Old Town Back And Forth. Keep Up The Good Work Fairfield 👍👍👍."

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$220 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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Top Cities in Monroe County

Key West

Islamorada

Our top choices for Monroe County holiday rentals

1. Breezy Palms Resort

2. Knight's Key Suites

3. Aqua Lodges at Hurricane Hole Marina

4. Tropical Cottages

5. Anchorage Resort & Yacht Club

6. Aqua Lodge Rentals At Coconut Cay

7. Treasure Harbor

8. Old Wooden Bridge Resort and Marina

9. Skipjack Resort & Marina

10. Yacht Haven Marina

11. Florida Keys Getaway - Slps 4 - Ocean View

12. Steps from Duval, Pool on Site & Bikes Included!

13. Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

14. Piece of Paradise

15. Poolside Cottage #412

16. Ricky's Retreat - Truman @ Duval | Ideal Getaway!

17. SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

18. Aqua Lodges at 47th Street Gulfside

19. ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

20. Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ

Find holiday rentals that suit your style

Top Monroe County Hotel Reviews

Isla Bella Beach Resort & Spa

Lime Tree Bay Resort

Parrot Key Hotel & Villas

Hilton Key West Resort & Marina

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Chesapeake Beach Resort

DoubleTree Resort by Hilton Grand Key - Key West

Blue Flamingo Resort Key West

Southernmost Beach Resort and Guesthouses

Find out more about Monroe County