Holiday Rentals in Monroe County

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Top Cities in Monroe County

Holiday RentalsHoliday Rentals

Key West

Key West

Featured Holiday Rentals in Monroe County

Yacht Haven Marina
Relax in this spacious room with a comfortable sofa, dining area, and kitchen.

Yacht Haven Marina

3.5 star property
9.8 out of 10, Exceptional, (185)
"We loved our weekend stay here. "
Yacht Haven Marina
Hyatt Vacation Club at Sunset Harbor, Key West
Surrounded by lush tropical vegetation and a serene waterfall, this tranquil oasis offers a peaceful escape with a mountain view.

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very good, (307)
"We had a nice stay. The property was in a great location."
The price is €254
includes taxes & fees
24 Aug - 25 Aug
Hyatt Vacation Club at Sunset Harbor, Key West
Breezy Palms Resort
Relax on the beachfront lawn with lounge chairs, enjoy the tranquil atmosphere, and take in the views of the calm sea.

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (497)
"Great Property, easy check in and "
The price is €123
includes taxes & fees
17 Aug - 18 Aug
Breezy Palms Resort
Skipjack Resort & Marina
Enjoy waterfront views and serene surroundings from the marina and adjacent building with its balconies.

Skipjack Resort & Marina

3.0 star property
8.6 out of 10, Excellent, (1197)
"Great stay"
Skipjack Resort & Marina
Old Wooden Bridge Resort and Marina
Relax in a cozy seating area with a sofa and small table, and enjoy a fully equipped kitchenette with microwave, coffee maker, and refrigerator.

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (252)
"I love ❤️ this place "
Old Wooden Bridge Resort and Marina
Tropical Cottages
Relax in a serene outdoor space surrounded by lush greenery, featuring a thatched-roof structure and comfortable wicker seating.

Tropical Cottages

3.0 star property
8.4 out of 10, Very good, (836)
"Super cute little cottage with a great location, would definitely stay again!"
The price is €97
includes taxes & fees
17 Aug - 18 Aug
Tropical Cottages
Cabins at Bonefish Bay
Deluxe Bungalow | Terrace/patio

Cabins at Bonefish Bay

3.0 star property
10.0 out of 10, Exceptional, (53)
"Awesome cabins!"
Cabins at Bonefish Bay
The Islands of Islamorada
Relax by the pool surrounded by palm trees and enjoy stunning ocean views.

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (65)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is €581
includes taxes & fees
3 Aug - 4 Aug
The Islands of Islamorada
Treasure Harbor
Relax in this open-plan living space with a high ceiling and large windows leading to a patio.

Treasure Harbor

3.0 star property
9.0 out of 10, Wonderful, (91)
"Unique House boat experience, friendly staff. "
The price is €234
includes taxes & fees
17 Aug - 18 Aug
Treasure Harbor
Aqua Lodges at Hurricane Hole Marina
Relax by the marina with a casual meal or snack at this tranquil waterfront spot.

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (160)
"It was a great place to stay! There were a few bugs in the aqua Lodge in the kitchen area, but other than that awesome place!"
The price is €222
includes taxes & fees
10 Aug - 11 Aug
Aqua Lodges at Hurricane Hole Marina
Aqua Lodges at 47th Street Gulfside
Relax in this stylish space with a comfortable sofa and dining area leading out to an outdoor space.

Aqua Lodges at 47th Street Gulfside

3.0 star property
8.6 out of 10, Excellent, (47)
"Great place to stay. A small area but otherwise a nice place. I would suggest a plunger for the "
The price is €234
includes taxes & fees
10 Aug - 11 Aug
Aqua Lodges at 47th Street Gulfside
Knight's Key Suites
Two single beds with white bedding and pillows, a nightstand with a lamp and remote control, and a window with blue curtains.

Knight's Key Suites

3.0 star property
9.0 out of 10, Wonderful, (1130)
"It was an amazing place with a nice pool, close to Key West. The kitchen and the needs were good ! The employees are really nice ! I highly recommend this place !"
The price is €91
includes taxes & fees
3 Aug - 4 Aug
Knight's Key Suites
Coconut Mallory Resort And Marina By Kees Vacations
Relax in a serene outdoor oasis surrounded by lush greenery and a wooden pergola.

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (818)
"Great place really nice rooms"
Coconut Mallory Resort And Marina By Kees Vacations
Steps from Duval, Pool on Site & Bikes Included!
Bicycles line the quiet street, surrounded by lush greenery and a charming white building with green shutters.

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (393)
"this was exactly as advertised and close to all the action"
The price is €195
includes taxes & fees
3 Aug - 4 Aug
Steps from Duval, Pool on Site & Bikes Included!
Key Largo Cottages
Sailboats glide effortlessly across the calm waters.

Key Largo Cottages

2.5 star property
9.4 out of 10, Exceptional, (22)
"Beautiful and peaceful place "
Key Largo Cottages
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!
Escape to a secluded beach paradise with tall palm trees and soft sandy shores.

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 €215
includes taxes & fees
3 Aug - 4 Aug
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Guests can enjoy stunning marina views from the hotel's elevated balconies.

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

7.4 out of 10, Good, (10)
"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 €657
includes taxes & fees
11 Aug - 12 Aug
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Heart of Downtown Key West Cottage With Off-Street Parking
Cozy home with a front porch and garden, perfect for relaxation.

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (133)
"We very much enjoyed our stay at the cottage. Everything you need for a comfortable stay and a location that can't be beat. Also, the off-street parking was a time, money, and sanity saver. Thanks to Marcela and family!"
Heart of Downtown Key West Cottage With Off-Street Parking
Old Florida Style, wrap around porch, boat basin for dockage, open water
Relax on the waterfront with Adirondack chairs and a small dining table.

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

9.6 out of 10, Exceptional, (77)
"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
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Comfortable bedroom with two beds, a wall-mounted TV, and a ceiling fan.

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (18)
"We had a wonderful stay here with our kids. Can’t beat the location."
The price is €285
includes taxes & fees
12 Aug - 13 Aug
Pelican Suite | Cozy Cottage, Hot Tubs, Close to 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

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

10/10 Excellent
"I really loved the whole experience from beginning to end! The receptionist are awesome and very pleasant to speak to all the staff are very pleasant and we really really enjoyed our stay"
Jodi C 5-night trip
Posted 10 hours ago
Oceans Edge Key West Resort, Hotel & Marina