Monroe County Holiday Rentals

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Top Cities in Monroe County

Top Holiday Rentals Destinations in Monroe County

Yacht Haven Marina

3.5 star property
9.8 out of 10, Exceptional, (174)
"We loved our weekend stay here. "
Yacht Haven Marina

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very good, (305)
"We had a nice stay. The property was in a great location."
The price is AU$440
includes taxes & fees
12 Aug - 13 Aug
Hyatt Vacation Club at Sunset Harbor, Key West

Skipjack Resort & Marina

3.0 star property
8.6 out of 10, Excellent, (1192)
"Great stay"
Skipjack Resort & Marina

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (488)
"Laid back atmosphere with renovated rooms."
The price is AU$179
includes taxes & fees
15 July - 16 July
Breezy Palms Resort

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (245)
"Old Wooden Bridge was one of the coolest and most relaxing spots my family and I have ever stayed at! House Boat was clean and wonderful view of the beautiful waters in Big Pine Key! Also we were greeted by Key Deer every night which was an Amazing experience! "
Old Wooden Bridge Resort and Marina

Tropical Cottages

3.0 star property
8.4 out of 10, Very good, (825)
"Cute place, convenient location"
The price is AU$188
includes taxes & fees
13 July - 14 July
Tropical Cottages

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (61)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is AU$1,022
includes taxes & fees
22 July - 23 July
The Islands of Islamorada

Treasure Harbor

3.0 star property
9.0 out of 10, Wonderful, (85)
"Very clean and great atmosphere "
The price is AU$407
includes taxes & fees
5 Aug - 6 Aug
Treasure Harbor

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (157)
"Such a unique stay and affordable!"
The price is AU$359
includes taxes & fees
14 July - 15 July
Aqua Lodges at Hurricane Hole Marina

Cabins at Bonefish Bay

3.0 star property
10.0 out of 10, Exceptional, (49)
"I loved the little cabins it was a great trip for my son’s graduation. "
Cabins at Bonefish Bay

Aqua Lodges at 47th Street Gulfside

3.0 star property
8.6 out of 10, Excellent, (42)
"Great place to stay. A small area but otherwise a nice place. I would suggest a plunger for the "
The price is AU$434
includes taxes & fees
14 July - 15 July
Aqua Lodges at 47th Street Gulfside

Knight's Key Suites

3.0 star property
9.0 out of 10, Wonderful, (1125)
"Nice pool area with view of the 7 mile bridge "
The price is AU$176
includes taxes & fees
4 Aug - 5 Aug
Knight's Key Suites

Key Largo Cottages

2.5 star property
9.4 out of 10, Exceptional, (20)
"The stay was great and the property manager Jenn was amazing. Would stay again"
Key Largo Cottages

Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

8.0 out of 10, Very good, (9)
"We were here celebrating 55th birthdays and had a blast. Great location and communication with Capt. We will return for sure, hoping to make it an annual get together."
The price is AU$771
includes taxes & fees
1 Aug - 2 Aug
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (816)
"Great place really nice rooms"
Coconut Mallory Resort And Marina By Kees Vacations

COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

9.6 out of 10, Exceptional, (136)
"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: Great getaway, far enough away from noise, but close enough to enjoy all Key West has to offer. Place was just what we were looking for."
The price is AU$385
includes taxes & fees
13 July - 14 July
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (131)
"Perfect spot for small group or couple to stay one block over from Duval St. Highly recommend staying here!"
Heart of Downtown Key West Cottage With Off-Street Parking

Old Florida Style, wrap around porch, boat basin for dockage, open water

9.6 out of 10, Exceptional, (76)
"Very nice place to stay. Quick and efficient communication with host! Seemless check in and check out process. "
Old Florida Style, wrap around porch, boat basin for dockage, open water

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (178)
"We would definitely stay here again! Great location, exactly as described, overall great place."
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

Living the Dream Key West Style

10.0 out of 10, Exceptional, (19)
"Wonderful spot, great hosts. Spectacular sunset cruise aboard Serenity. "
The price is AU$522
includes taxes & fees
13 July - 14 July
Living the Dream Key West Style
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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