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

Monroe County Holiday Rentals

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Our top choices for Monroe County holiday rentals

A marina with several docked boats and a row of small, white cabins with blue roofs.

1. Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.8 out of 10, Exceptional, (354 reviews)
"Fantastic place! It was super clean and looked just like the photos. We would stay here again!"
United States
Clara
The price is HK$691
HK$1,880 total
includes taxes & fees
1 Sept - 2 Sept
Yacht Haven Marina
An outdoor seating area with wicker furniture and cushions, a thatched-roof structure, and lush greenery.

2. Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (997 reviews)
"A/c was amazing, clean and beautiful cabins."
Canada
Natasha
The price is HK$745
HK$838 total
includes taxes & fees
1 Sept - 2 Sept
Tropical Cottages
A hotel room with two beds, each with a wooden headboard, white bedding, and a bedside table with a lamp.

3. Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,227 reviews)
"It was absolutely amazing.We'll definitely stay there again"
United States
Jessica
The price is HK$540
HK$776 total
includes taxes & fees
1 Sept - 2 Sept
Knight's Key Suites
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

4. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (172 reviews)
"We loved sitting in the deck in the evening and again in the morning."
Canada
Molly
The price is HK$1,051
HK$2,285 total
includes taxes & fees
1 Sept - 2 Sept
Treasure Harbor
A cozy room with a brown leather sofa, a white table, and a ceiling fan.

5. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (367 reviews)
"Love being on the water in the houseboat. The dark skies were nice for stargazing"
United States
Lisa
The price is HK$706
HK$1,896 total
includes taxes & fees
1 Sept - 2 Sept
Old Wooden Bridge Resort and Marina
A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

6. 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 HK$699
HK$2,100 total
includes taxes & fees
1 Sept - 2 Sept
Aqua Lodges at Hurricane Hole Marina
A beach with palm trees, a sandy path, and beach chairs.

7. Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (232 reviews)
"Cleanness relaxing location, nice views, good air conditioning"
United States
Hakan
The price is HK$887
HK$2,201 total
includes taxes & fees
13 Sept - 14 Sept
Aqua Lodge Rentals At Coconut Cay
A nighttime pool area with a clear view of the pool, surrounding palm trees, and a building with a sign.

8. Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,289 reviews)
"Great spot"
Canada
Justin
The price is HK$1,122
HK$1,580 total
includes taxes & fees
1 Sept - 2 Sept
Skipjack Resort & Marina
A beach with palm trees, thatched-roof huts, and lounge chairs.

9. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (735 reviews)
"Good location"
United States
Orlando
The price is HK$726
HK$1,223 total
includes taxes & fees
6 Sept - 7 Sept
Breezy Palms Resort
A wooden signpost with city names and distances in miles.

10. 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, (451 reviews)
"Clean comfortable and close too many attractions."
United States
Mark A.
The price is HK$699
HK$1,784 total
includes taxes & fees
7 Sept - 8 Sept
Steps from Duval, Pool on Site & Bikes Included!
A kitchen with a refrigerator, stove, and two bar stools.

11. Sept Special@119.lodging + With 5 night stay 5th night FREE lodging!

Sept Special@119.lodging + With 5 night stay 5th night FREE lodging!
Old Town Key West
9.0 out of 10, Wonderful, (198 reviews)
"Fantastic location! Close enough to walk to all the things, but very quiet and relaxing to hang out. Loved the back deck. Owner was very responsive and helpful. Neighbors were nice as well."
United States
Jeanine
Sept Special@119.lodging + With 5 night stay 5th night FREE lodging!
A tropical garden pathway leading to a building with a yellow facade and green shutters.

12. 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, (136 reviews)
"Great place to stay"
United States
walter l.
The price is HK$815
HK$2,218 total
includes taxes & fees
1 Sept - 2 Sept
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
A spacious living room with a large window, a white sofa, a coffee table, and a painting of a tropical scene.

13. Anchorage Resort & Yacht Club

Anchorage Resort & Yacht Club
3.0 star property
Key Largo
8.8 out of 10, Excellent, (342 reviews)
"Great place "
United States
Jay
The price is HK$1,646
HK$1,852 total
includes taxes & fees
1 Sept - 2 Sept
Anchorage Resort & Yacht Club
A tropical garden pathway leading to a building with a yellow facade and green shutters.

14. 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, (110 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 property was just as listed. Very clean, quiet, the pool was very refreshing! Great location, walkable to almost anything. Would highly recommend!"
United States
Chris & Sarah F.
The price is HK$815
HK$2,218 total
includes taxes & fees
1 Sept - 2 Sept
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
A beachfront hotel with two palm trees, a flag, and a pool area with lounge chairs.

15. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (38 reviews)
"A comfortable little condo, conveniently located for exploring the Keys. There’s a nice pool and small beach area with a bar/restaurant that are well maintained."
United States
Stephen
The price is HK$656
HK$2,423 total
includes taxes & fees
8 Sept - 9 Sept
Florida Keys Getaway - Slps 4 - Ocean View
A compact bedroom with a bed, a small kitchenette, and a door leading to a bathroom.

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, (53 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
The price is HK$803
HK$3,111 total
includes taxes & fees
1 Sept - 2 Sept
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
A resort with a pool, lounge chairs, and a view of the ocean.

17. 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, (143 reviews)
"Amazing stay "
United States
Anthony
The price is HK$1,090
HK$1,447 total
includes taxes & fees
2 Sept - 3 Sept
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
A marina with boats docked, a clear sky, and a rainbow.

18. Waterfront Condo Dock Pool Near Duval St

Waterfront Condo Dock Pool Near Duval St
Meadows
9.8 out of 10, Exceptional, (29 reviews)
"Great stay! Beautiful view. No complaints. Easy check in and great communication with owner. Thanks for a great trip!"
United States
Haley P.
The price is HK$966
HK$3,064 total
includes taxes & fees
2 Sept - 3 Sept
Waterfront Condo Dock Pool Near Duval St
A wooden boardwalk leading to a building with a green roof, surrounded by lush greenery and palm trees.

19. The Cat Island Suite | Charmingly Renovated w/ Pool

The Cat Island Suite | Charmingly Renovated w/ Pool
Key West
9.8 out of 10, Exceptional, (47 reviews)
"I liked that it was pretty centrally located to everything very nice Thank you we had a great time "
United States
Patti E.
The price is HK$1,213
HK$3,732 total
includes taxes & fees
13 Sept - 14 Sept
The Cat Island Suite | Charmingly Renovated w/ Pool
A beach with clear shallow waters, a row of blue lounge chairs, and palm trees.

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

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Tavernier
10.0 out of 10, Exceptional, (169 reviews)
"Beautifully appointed, clean and comfortable. This place is worth it! We had a great stay. Location is also excellent. Would definitely stay here again. "
United States
Erica C.
The price is HK$1,686
HK$3,707 total
includes taxes & fees
4 Sept - 5 Sept
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
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
"2nd time here and was just beautiful"
Jill 5-night trip
Posted 1 hour ago
Isla Bella Beach Resort & Spa