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

Holiday Rentals in Monroe County

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Top Cities in Monroe County

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

Key West

Key West

Our top choices for Monroe County holiday rentals

Outdoor pool, pool loungers

1. Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,282 reviews)
"I will stay here again"
United States
Peter
The price is €184
includes taxes & fees
16 Aug - 17 Aug
Skipjack Resort & Marina
Premium bedding, soundproofing, iron/ironing board, free WiFi

2. Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,218 reviews)
"The rooms are always clean, no bugs, and walking distance to Sunset Grill."
United States
Cristina
The price is €104
includes taxes & fees
18 Aug - 19 Aug
Knight's Key Suites
Lobby

3. Anchorage Resort & Yacht Club

Anchorage Resort & Yacht Club
3.0 star property
Key Largo
8.8 out of 10, Excellent, (340 reviews)
"Great place "
United States
Jay
The price is €206
includes taxes & fees
2 Aug - 3 Aug
Anchorage Resort & Yacht Club
Private beach, sun-loungers, beach umbrellas, beach towels

4. Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (174 reviews)
"The place is beautiful"
United States
Adriana
The price is €251
includes taxes & fees
2 Aug - 3 Aug
Island Bay Resort
Exterior

5. Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.8 out of 10, Exceptional, (347 reviews)
"Incredible stay , very unique and cozy . Friendly staff ,we will most definitely stay here again. My son had a blast at this place oh and pet friendly even better ."
United States
Christian
The price is €233
includes taxes & fees
21 Aug - 22 Aug
Yacht Haven Marina
Exterior

6. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (713 reviews)
"my 2nd time staying here and i will be back for a 3rd"
United States
Tristan
The price is €114
includes taxes & fees
24 Aug - 25 Aug
Breezy Palms Resort
House | Exterior

7. Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
Key West
The price is €310
includes taxes & fees
25 Aug - 26 Aug
Ocean Front One Bedroom Residence
25-inch flat-screen TV with digital channels, TV

8. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (166 reviews)
"The houseboat were a great experience not only for the kid's but the adults also. Seeing the manatees swim around the cove was awesome! It was a great place to meet your neighbors as the porches are very close. The swimming pool is a great addition to the property! If going back to the area, I would definitely go there again! We really enjoyed our visit there!"
United States
Kelly
The price is €245
includes taxes & fees
3 Aug - 4 Aug
Treasure Harbor
Private beach, sun-loungers

9. Kings Kamp

Kings Kamp
2.5 star property
Key Largo
8.6 out of 10, Excellent, (41 reviews)
"Everything was good but the parking, they should reserve the parking before the guess arrive"
United States
Roberto
The price is €196
includes taxes & fees
2 Aug - 3 Aug
Kings Kamp
Outdoor pool, pool umbrellas, pool loungers

10. Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
2.5 star property
Marathon
9.0 out of 10, Wonderful, (141 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 €182
includes taxes & fees
26 Aug - 27 Aug
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
1 Bedroom Aqualodge # 6 Tarpon | Living area

11. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (359 reviews)
"We stayed in the 2 bedroom condo. It was spacious and clean. We enjoyed our time there."
United States
Kathy
The price is €218
includes taxes & fees
2 Aug - 3 Aug
Old Wooden Bridge Resort and Marina
BBQ/picnic Area

12. Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (229 reviews)
"I never give 5 stars but it was as advertised and good pricing and fun little spot. Keep it up folks.."
Canada
Wesley
The price is €264
includes taxes & fees
30 Aug - 31 Aug
Aqua Lodge Rentals At Coconut Cay
Exterior

13. Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (989 reviews)
"Very well kept-nice cottage! Would book again!"
United States
Susan
The price is €107
includes taxes & fees
23 Aug - 24 Aug
Tropical Cottages
Luxury House, 2 Bedrooms, Pool View, Poolside

14. Lighthouse Suites Collection

Lighthouse Suites Collection
4.0 star property
Old Town Key West
The price is €955
includes taxes & fees
5 Aug - 6 Aug
Lighthouse Suites Collection
Front of property

15. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (193 reviews)
"The bathroom smelled a bit, but we loved the loft and the vibes of the houseboat. It’s hard to find 3 bedrooms at that reasonable price and we have 3 kids that do not want to sleep together so this was perfect. We ate at the bar and really enjoyed watching the jellyfish. It was a cool!"
United States
Emily
The price is €256
includes taxes & fees
31 Jul - 1 Aug
Aqua Lodges at Hurricane Hole Marina
Boating

16. Key Largo Cottages

Key Largo Cottages
2.5 star property
Key Largo
9.2 out of 10, Wonderful, (29 reviews)
"Beautiful and peaceful place "
United States
Jacqueline
The price is €382
includes taxes & fees
31 Jul - 1 Aug
Key Largo Cottages
House | Exterior

17. Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (3 reviews)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
The price is €295
includes taxes & fees
17 Aug - 18 Aug
Island View 1BR Residence With Balcony
2 outdoor pools, open 8:00 AM to 6:00 PM, pool loungers

18. The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (78 reviews)
"Love this property! Our family had the most amazing time in the villas. The location is great and the property is really well kept with amazing staff. We enjoyed the pool, the kids game area, pickle ball and relaxing in the home. Highly recommend!!"
United States
Christian
The price is €558
includes taxes & fees
5 Aug - 6 Aug
The Islands of Islamorada
Condo | Living area

19. Coconut Mallory Marina and Resort Condo

Coconut Mallory Marina and Resort Condo
3.0 star property
Key West
2.0 out of 10, (1 review)
"They did not have a room for me when i arrived. Said there was nothing they could do. I was left stranded and ended up paying twice the price for a worst room which was all I could find."
United States
Paris
The price is €1,144
includes taxes & fees
31 Jul - 1 Aug
Coconut Mallory Marina and Resort Condo
House (1 Bedroom) | Interior

20. Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
3.0 star property
Old Town Key West
9.8 out of 10, Exceptional, (7 reviews)
"Property was clean and quiet nice amenities "
United States
Bradley
The price is €563
includes taxes & fees
12 Aug - 13 Aug
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
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

Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

10/10 Excellent
"The room was clean and the five pools were wonderful!"
Roxy 1-night trip
Posted 1 hour ago
Isla Bella Beach Resort & Spa

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Holiday Homes in Monroe County

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