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

Exterior

1. Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.8 out of 10, Exceptional, (360 reviews)
"Fantastic place! It was super clean and looked just like the photos. We would stay here again!"
United States
Clara
The price is €211
includes taxes & fees
20 Sept - 21 Sept
Yacht Haven Marina
1 Bedroom Aqualodge # 6 Tarpon | Living area

2. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (371 reviews)
"Nice place"
United States
abhimanyu
The price is €211
includes taxes & fees
27 Sept - 28 Sept
Old Wooden Bridge Resort and Marina
25-inch flat-screen TV with digital channels, TV

3. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (175 reviews)
"We loved sitting in the deck in the evening and again in the morning."
Canada
Molly
The price is €236
includes taxes & fees
16 Oct - 17 Oct
Treasure Harbor
Front of property

4. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (196 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is €251
includes taxes & fees
23 Sept - 24 Sept
Aqua Lodges at Hurricane Hole Marina
BBQ/picnic Area

5. Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (235 reviews)
"Never stayed in a houseboat before. It was a novel experience!"
United States
Susan
The price is €221
includes taxes & fees
22 Sept - 23 Sept
Aqua Lodge Rentals At Coconut Cay
Exterior

6. Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (999 reviews)
"A/c was amazing, clean and beautiful cabins."
Canada
Natasha
The price is €77
includes taxes & fees
21 Sept - 22 Sept
Tropical Cottages
Exterior

7. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (748 reviews)
"Great resorts - will return again. Highly recommend"
United States
Lourdes
The price is €88
includes taxes & fees
30 Sept - 1 Oct
Breezy Palms Resort
Premium bedding, soundproofing, iron/ironing board, free WiFi

8. Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,235 reviews)
"Clean room with exceptional hospitality"
United States
chantal
The price is €86
includes taxes & fees
27 Sept - 28 Sept
Knight's Key Suites
Beach towels

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

Steps from Duval, Pool on Site & Bikes Included!
Old Town Key West
9.6 out of 10, Exceptional, (456 reviews)
"Clean comfortable and close too many attractions."
United States
Mark A.
The price is €212
includes taxes & fees
20 Sept - 21 Sept
Steps from Duval, Pool on Site & Bikes Included!
Lobby

10. Anchorage Resort & Yacht Club

Anchorage Resort & Yacht Club
3.0 star property
Key Largo
8.8 out of 10, Excellent, (343 reviews)
"Great place "
United States
Jay
The price is €156
includes taxes & fees
23 Sept - 24 Sept
Anchorage Resort & Yacht Club
Exterior detail

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

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Old Town Key West
9.8 out of 10, Exceptional, (137 reviews)
"Great place to stay"
United States
walter l.
The price is €263
includes taxes & fees
29 Sept - 30 Sept
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Outdoor pool, pool loungers

12. Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,290 reviews)
"Great spot"
Canada
Justin
The price is €176
includes taxes & fees
20 Sept - 21 Sept
Skipjack Resort & Marina
Exterior detail

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

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (111 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The studio and surroundings matched photos posted and provided a Key West atmosphere and experience. Walking to Key West activities and sites was feasible. Very happy with and positive addition to our Key West visit."
United States
Ken L.
The price is €269
includes taxes & fees
27 Sept - 28 Sept
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Exterior

14. Aqua Lodges at 47th Street Gulfside

Aqua Lodges at 47th Street Gulfside
3.0 star property
Marathon
8.8 out of 10, Excellent, (58 reviews)
"Loved our stay at the aqua lodges 10/10 would do it again"
United States
Lauren
The price is €237
includes taxes & fees
1 Oct - 2 Oct
Aqua Lodges at 47th Street Gulfside
Private beach, sun-loungers, beach umbrellas, beach towels

15. Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
9.8 out of 10, Exceptional, (183 reviews)
"Amazing vacation spot!!"
United States
Katie Lyn
The price is €196
includes taxes & fees
29 Sept - 30 Sept
Island Bay Resort
1 bedroom, free WiFi, bed sheets

16. Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Old Town Key West
9.6 out of 10, Exceptional, (54 reviews)
"Great property. Walking Blocks away from the downtown action, yet far away to be quiet. Parking is very tough. If you don’t need to rent a car because you’re going to be hanging out in town the whole time, don’t bother. Uber and transportation are plentiful but again, the parking is very difficult to find free parking."
United States
Timothy
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
A heated pool

17. VanGogh Studio | Updated, Old Town, Heated Pool

VanGogh Studio | Updated, Old Town, Heated Pool
Old Town Key West
8.8 out of 10, Excellent, (57 reviews)
"Nice clean apartment and good walking distance to Old Town restaurants and neighborhood."
United States
Justin R.
The price is €315
includes taxes & fees
19 Sept - 20 Sept
VanGogh Studio | Updated, Old Town, Heated Pool
Outdoor pool, pool umbrellas, pool loungers

18. 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, (145 reviews)
"It is an excellent place."
United States
Arianna
The price is €152
includes taxes & fees
24 Sept - 25 Sept
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
Exterior

19. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (38 reviews)
"Great place to stay down on the keys."
United States
GJ W.
Florida Keys Getaway - Slps 4 - Ocean View
Terrace/patio

20. Duval Delight | Recently Remodeled Condo on Duval!

Duval Delight | Recently Remodeled Condo on Duval!
Old Town Key West
9.8 out of 10, Exceptional, (75 reviews)
"Fantastic location"
United States
Jennifer
Duval Delight | Recently Remodeled Condo on 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

Beachside Resort & Residences

Beachside Resort & Residences

8/10 Good
"The staff was very helpful. I had absolutely no problem with my suite. It was a very well furnished, one bedroom apartment. The the problem I guess, would be that the outside hot tub at the pool had not been working for months. The elevators were being repaired on the side where I was at the restaurant there. To me was overpriced, and not a lot to choose from. The outside bar, the staff really didn't either know how to make certain drinks, or they didn't have the ingredients to make certain drinks. And the food was so so they only had one Van. That brought you to and from downtown. And they stated that they had 2 more vans, but they've been broke for a very long time, because they can't get parts. Well, how about management getting involved? And going as high up as it takes to get the type of vans that you need and to get the place maintained and staffed properly. There was no pool person, and you had to go inside to get your towels, and it got a little messy at the pool area...And then I heard that there's some people that did have some issues with a room, but those problems were fixed within a day. So, I had wished that the Van would have offered rides to the airport, which was just a 12 minute ride down the street. If that.... the extra excursions they offered did not work out because they didn't have enough people to go on the boat they had. So you had to seek out other sailboats or boats in the area to do things. And if they were no"
Maria 4-night trip
Posted 9 hours ago
Beachside Resort & Residences

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Holiday Homes in Monroe County

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