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

Skipjack Resort & Marina
Outdoor pool, pool loungers

Skipjack Resort & Marina

3.0 star property
8.6 out of 10, Excellent, (1141)
"We love staying at this property because it’s just like an apartment with all the comforts of home."
The price is €357
includes taxes & fees
5 Jan - 6 Jan 2025
Skipjack Resort & Marina
Breezy Palms Resort
Exterior

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (380)
"Spacious studio on the water. Highly recommend."
The price is €180
includes taxes & fees
6 Jan - 7 Jan 2025
Breezy Palms Resort
Aqua Lodge Rentals At Coconut Cay
Front of property

Aqua Lodge Rentals At Coconut Cay

3.5 star property
9.6 out of 10, Exceptional, (126)
"Unique floating accommodations were so nice. Highly recommend this stay."
The price is €653
includes taxes & fees
27 Dec - 28 Dec
Aqua Lodge Rentals At Coconut Cay
Tropical Cottages
Superior Bungalow, Ensuite (Cottage 04) | Exterior

Tropical Cottages

3.0 star property
8.4 out of 10, Very good, (757)
"The Cottage made a wonderful stay for a quick getaway. I shared the main cottage with another family and my only complaint is that because the walls are thin, we were awakened by their incessant argument and the constant slamming of their suite and main doors. "
The price is €150
includes taxes & fees
5 Jan - 6 Jan 2025
Tropical Cottages
Old Wooden Bridge Resort and Marina
2 Bedroom Aqua Lodge # 13 Barracuda | Living area

Old Wooden Bridge Resort and Marina

2.5 star property
8.4 out of 10, Very good, (171)
"Nice area"
The price is €235
includes taxes & fees
5 Jan - 6 Jan 2025
Old Wooden Bridge Resort and Marina
Aqua Lodges at Hurricane Hole Marina
Restaurant

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (106)
"Nice for affordable price "
The price is €346
includes taxes & fees
7 Jan - 8 Jan 2025
Aqua Lodges at Hurricane Hole Marina
Yacht Haven Marina
Standard Bungalow | Living area

Yacht Haven Marina

3.5 star property
9.8 out of 10, Exceptional, (99)
"Excellent value for money."
Yacht Haven Marina
Knight's Key Suites
Outdoor pool, pool loungers

Knight's Key Suites

3.0 star property
9.0 out of 10, Wonderful, (1069)
"Sits right by the ocean!"
The price is €181
includes taxes & fees
9 Jan - 10 Jan 2025
Knight's Key Suites
Steps from Duval, Pool on Site & Bikes Included!
Beach towels

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (358)
"very clean, was able to park the car and walk to where we wanted to go. I would stay again."
The price is €311
includes taxes & fees
9 Jan - 10 Jan 2025
Steps from Duval, Pool on Site & Bikes Included!
Poolside Cottage #411
Outdoor dining

Poolside Cottage #411

10.0 out of 10, Exceptional, (33)
"Really nice place to stay. We had a pleasant stay and the property was great "
The price is €515
includes taxes & fees
8 Jan - 9 Jan 2025
Poolside Cottage #411
34’ Catamaran Sailboat
Interior

34’ Catamaran Sailboat

9.6 out of 10, Exceptional, (28)
"The property was great and the host was very responsive to communication. "
34’ Catamaran Sailboat
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
Property grounds

SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!

9.8 out of 10, Exceptional, (16)
"Staying on the Grand Admiral was really awesome for my wife and I. The location at Perry Marina was exceptional. The whole process was very easy, working with Kathy for booking, Stephanie for check-in and Captain John for our charter, everything went smooth. "
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
The Islands of Islamorada
2 outdoor pools, open 8:00 AM to 6:00 PM, pool loungers

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (39)
"We loved the entire experiences; especially the amenities on site (kayaks, paddle boards, swimming-pool & ocean, food & bar) and Emmanuel (person responsible kayaks and paddle boards)."
The price is €527
includes taxes & fees
22 Jan - 23 Jan 2025
The Islands of Islamorada
VOTED BEST KEY LARGO VACATION RENTAL
Terrace/patio

VOTED BEST KEY LARGO VACATION RENTAL

10.0 out of 10, Exceptional, (69)
"The townhome was large and I liked the layout so everyone had their own space. There are multiple balconies which was one of our favorite places to hang out while there. The sunrise/sunsets at the beach were beautiful! We were busy so didn’t spend much time in the lagoon or pools but the grounds were well-kept. "
VOTED BEST KEY LARGO VACATION RENTAL
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC
Fridge, microwave, oven, stovetop

Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC

8.8 out of 10, Excellent, (203)
"I recently stayed at this property and had a generally pleasant experience. The property itself is nice and well-maintained, with a great location that adds to its appeal. The surrounding area is excellent, making it convenient and enjoyable. However, there were a few downsides to my stay. The internet was not working, which was quite inconvenient. Additionally, while the property is good overall, it could benefit from having a few more amenities. The bathroom, in particular, could use some...
The price is €449
includes taxes & fees
12 Jan - 13 Jan 2025
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC
FONTANA ~ Adults Only, Pool Access King Suite at Azul Mansion!
Miscellaneous

FONTANA ~ Adults Only, Pool Access King Suite at Azul Mansion!

9.4 out of 10, Exceptional, (108)
"Easy location and overall peaceful neighborhood. Surprisingly peaceful for how close it is to main roads"
The price is €444
includes taxes & fees
4 Jan - 5 Jan 2025
FONTANA ~ Adults Only, Pool Access King Suite at Azul Mansion!
Anchorage Resort & Yacht Club
Dock

Anchorage Resort & Yacht Club

3.0 star property
8.6 out of 10, Excellent, (266)
"Have stayed here many times and will continue to do so. Near my daughter and lots of other things to do. It is a two room suite overlooking Florida Bay. Got a boat? Dock it here. Rooms are big, spotless, comfortable and a kitchenette included. Five stars."
The price is €264
includes taxes & fees
5 Jan - 6 Jan 2025
Anchorage Resort & Yacht Club
Cabins at Bonefish Bay
Exclusive Cabin | Living area

Cabins at Bonefish Bay

3.0 star property
10.0 out of 10, Exceptional, (23)
"Nice place to stay. "
Cabins at Bonefish Bay
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!
Beach

RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!

9.6 out of 10, Exceptional, (172)
"We stayed at Riptides this last week. Centrally located, this efficient unit is nestled right into the neighborhood just a few streets off of Duvall. It is still very quiet while close to action. Check in and communication with our host Whitney was great! Comfy bed, little kitchen and easy stay. It lived up to the positive ratings!"
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!
HAVANA VIEJA ~ Adults Only, Poolside Queen Suite w/ Shared Pool!
Beach nearby

HAVANA VIEJA ~ Adults Only, Poolside Queen Suite w/ Shared Pool!

9.4 out of 10, Exceptional, (115)
"The property was great and as advertised. Overall location was very good in terms of proximity to Duval St, museums etc. Truman st can get very busy but ended up not being an issue. Would recommend the Inn to friends. "
The price is €286
includes taxes & fees
25 Dec - 26 Dec
HAVANA VIEJA ~ Adults Only, Poolside Queen Suite w/ Shared Pool!
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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