Vacation rentals in Monroe County

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Top cities to explore in Monroe County

South Beach featuring tropical scenes, general coastal views and a beach

Key West

Vacation Rentals
Key West

Top vacation rentals in Monroe County

Yacht Haven Marina

Yacht Haven Marina

3.5 out of 5
5 Sombrero Blvd, Marathon, FL
44.89 mi from city center
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This houseboat doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area and barbecue grills are also provided.
Kitchen
Parking included
Skipjack Resort & Marina

Skipjack Resort & Marina

3 out of 5
19 Sombrero Blvd, Marathon, FL
Free Cancellation
Reserve now, pay when you stay
44.63 mi from city center
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A marina and an outdoor pool are featured at this aparthotel. Business travelers can take advantage of the business center. Enjoy the gym and perks like free self parking.
Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

2.5 out of 5
1791 Bogie Drive, Big Pine Key, FL
28.21 mi from city center
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A marina and an outdoor pool are featured at this cottage. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a picnic area, and express check-in are also on offer.
Pool
Pet friendly
Tropical Cottages

Tropical Cottages

3 out of 5
243 61st Street Gulf, Marathon, FL
45.33 mi from city center
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A restaurant and a bar/lounge are featured at this cottage. Free self parking, a garden, and a snack bar/deli are also offered.
Parking included
Restaurant
Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina

2 out of 5
5130 Overseas Hwy, Key West, FL
1.7 mi from city center
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This houseboat features a marina and free WiFi in public areas. Take advantage of the free self parking.
Parking included
Free WiFi
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
73.87 mi from city center
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A marina and an outdoor pool are featured at this aparthotel. WiFi in public areas is free. Self parking, a terrace, and a picnic area are also offered.
Treasure Harbor

Treasure Harbor

3 out of 5
200 Treasure Harbor Dr, Islamorada, FL
80.05 mi from city center
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Free WiFi in public areas is available at this hotel. Take advantage of the free self parking.
Parking included
Free WiFi
Knight's Key Suites

Knight's Key Suites

3 out of 5
40 Kyle Way W, Marathon, FL
41.94 mi from city center
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An outdoor pool, free self parking, and barbecue grills are featured at this aparthotel. WiFi in public areas is free. A picnic area and a virtual front desk are also provided.
Pool
Parking included
Cabins at Bonefish Bay

Cabins at Bonefish Bay

3 out of 5
12565 Overseas Hwy, Marathon, FL
48.54 mi from city center
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An outdoor pool, free self parking, and laundry facilities are featured at this cabin. WiFi in public areas is free. A picnic area and barbecue grills are also provided.
Pool
Kitchen
The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy, Islamorada, FL
Free Cancellation
Reserve now, pay when you stay
76.4 mi from city center
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2 outdoor pools, a 24-hour gym, and a hot tub are all featured at this smoke-free villa. Spend a day at the beach kayaking, or relax with sun loungers and beach umbrellas. Families will appreciate the playground and barbecue grills.
Pool
Hot Tub
Aqua Lodges at 47th Street Gulfside

Aqua Lodges at 47th Street Gulfside

3 out of 5
1 47th Street Gulf, Marathon, FL
44.61 mi from city center
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This houseboat doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area and barbecue grills are also provided.
Parking included
Free WiFi
VanGogh Studio | Updated, Old Town, Heated Pool

VanGogh Studio | Updated, Old Town, Heated Pool

2.06 mi from city center
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This apartment features laundry facilities.
Pool
Washer
Coconut Mallory Resort And Marina By Kees Vacations

Coconut Mallory Resort And Marina By Kees Vacations

3 out of 5
1445 S Roosevelt Blvd, Key West, FL
1.37 mi from city center
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This condo's 2 outdoor pools and hot tub are among the featured amenities. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area and barbecue grills are also provided.
Heart of Downtown Key West Cottage With Off-Street Parking

Heart of Downtown Key West Cottage With Off-Street Parking

2.07 mi from city center
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This cottage includes free WiFi in public areas and laundry facilities.
Kitchen
Washer
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

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

2.1 mi from city center
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A gym is featured at this houseboat, along with laundry facilities and barbecue grills.
Pool
Kitchen
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

1.59 mi from city center
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Stay at this houseboat in Key West. Popular attractions Duval Street and Smathers Beach are located nearby.
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

1.79 mi from city center
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This condo featured laundry facilities and concierge services.
Kitchen
Washer
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

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

1.48 mi from city center
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This condo features concierge services.
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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.

The Best Way to Find Vacation Rentals in Monroe County 

How cheap is a vacation rental in Monroe County?


You can find Monroe County vacation rentals from just per night. 


How do you look for the best vacation rental deals in Monroe County with Travelocity?


Simply enter your travel dates and filter by price, property type, bedrooms, amenities, and more. We put all the best deals in one place, so it’s easy to find your perfect stay. You’ll always find incredible deals on Monroe County vacation rentals with Travelocity. 


Are cancellations free on vacation rentals with Travelocity?


You may be able to cancel your Monroe County vacation rental for free. Cancellation policies differ between properties so check the terms of your stay before you book. Travelocity offers many flexible cancellation options as well as book now, pay later deals for peace of mind.


What types of vacation rentals are available in Monroe County?


Whether you’re in search of adventure, planning a romantic getaway, or booking a trip for the whole family, you’re sure to find the perfect Monroe County vacation rental. Check out our tempting selection of resorts, apartments, vacation homes, condos and more and start building a trip to really look forward to, whatever your budget and your wish list.


What are the benefits of booking a short-term rental in Monroe County?


Whether you’re a winter wanderer or planning a summer sojourn, Monroe County vacation rentals make for a great trip—find one at Travelocity for a fantastic price. With a range of amenities on offer, like swimming-pools, free WiFi, breakfast included, pet-friendly options and many more, it’s easy to book a vacation rental that checks all the boxes. And with Travelocity’s easy filtering system, you’ll find yours in no time. 


Where can I find vacation rentals in Monroe County?


Take your pick from the excitement of the big Monroe County cities. Or escape to nature in the miles of greenery that are waiting for you. Browse a selection of the best deals with Travelocity, enter your travel dates, or check out the map view to find a hidden gem. 


How do I find a family-friendly vacation rental in Monroe County?


Simply enter your travel dates and hit search. From here, you can filter to find your family-friendly stay, as well as a range of other amenities, such as hot tubs, pools, and even waterparks. 


Why is Travelocity the best site to find your Monroe County rentals?


Travelocity takes care of everything, bringing incredible deals on an impressive selection of accommodation into one simple-to-use portal. And because we always source incredible deals, you can make a saving on many bookings. Travelocity makes it easy.


How do I cancel my vacation rental with Travelocity?


It’s simple. Just contact the property manager. You’ll find their contact information in the itinerary section of your Travelocity account. In many cases, you may be able to get a full refund if you cancel before the cancellation deadline. Deadlines differ between properties, so it’s always best to check before you book. To find out more, visit the Customer Service PortalOpens in a new window.