Vacation Homes in Monroe County, FL
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Top cities with Vacation Homes to explore in Monroe County

Key West
Top Vacation Homes in Monroe County

Sugarloaf Key RV Resort & Cottages

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking

Hemingway Caribbean Townhome/Private Pool by Beach,Key West charm,free parking

Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball

Pagitt House – Historic Charm Meets Modern Luxury in the Heart of Key West

Ocean Dream, Family friendly, Direct Ocean, Pool/spa, Kayaks, Giant chess, bocci

Luxury Waterfront Home with Private Pool and Dock!

Views ~ Pool~Private Hot Tub~FREE Boat Slip~Heaven!!!

Waterfront Keys Retreat Private Heated Pool + Dock Near Sombrero Beach Sleeps 10
Top Vacation Homes in Monroe County

Sugarloaf Key RV Resort & Cottages

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking

Hemingway Caribbean Townhome/Private Pool by Beach,Key West charm,free parking

Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball

Pagitt House – Historic Charm Meets Modern Luxury in the Heart of Key West

Ocean Dream, Family friendly, Direct Ocean, Pool/spa, Kayaks, Giant chess, bocci

Luxury Waterfront Home with Private Pool and Dock!

Views ~ Pool~Private Hot Tub~FREE Boat Slip~Heaven!!!

Waterfront Keys Retreat Private Heated Pool + Dock Near Sombrero Beach Sleeps 10
Top hotels in Monroe County

Cheeca Lodge & Spa
Find the Best Vacation Homes in Monroe County
Why book a vacation home in Monroe County?
Vacation homes in Monroe County make for a different travel experience. Your holiday home will allow you to feel at home during your visit. You’ll usually have more space, more privacy, and extra amenities not typically included with hotel stays.
How much is a vacation home in Monroe County?
Private Monroe County rental homes range between $147 - $2,669 per night. Prices change based on seasonal demand, travel dates, property location, capacity, amenities, etc.
What are the cancellation and flexibility options on Travelocity?
To cancel your vacation home, you must reach out to the individual property manager. Their contact details are available in your itinerary. For more information, head over to our customer service portal. Use the ‘free cancellation’ or ‘reserve now, pay later’ filters to find the most flexible options for your bookings.
What amenities should I look out for in a vacation home?
There are some exciting amenities available in Monroe County vacation home rentals. You might look for Monroe County rental houses with a private pool or free Wi-Fi. Some popular amenities also include a private hot tub, air-conditioning, laundry facilities, and a games room.
Vacation rentals in Monroe County offer other accommodations that may interest you. Some have resort-like amenities such as a fitness center, bar/lounge, or swimming pool.
When is the best time to rent a vacation home in Monroe County?
You’ll typically get cheaper rates when staying during the off-season, . Prices are usually at their lowest for stays in . are the most popular months to visit.
Why book a vacation home with Travelocity?
Travel smart with Travelocity. Search over 1 million properties worldwide and access an incredible selection of holiday homes in Monroe County. Our members save 10% or more on select hotels, and if you find a lower price, we’ll match it with our Price Match Guarantee. Get started finding Monroe County hotels and vacation homes that best suit your stay. We also have deals for flights, and Monroe County car rentals. You’ll save even more when you bundle your items into a Monroe County vacation package!
How many vacation homes are available to book in Monroe County?
There are 3489 rental homes in Monroe County. Enter your travel dates to check availability.
How do I find the best price for a vacation home in Monroe County?
Private vacation homes vary in price, and we’ll help you get the best deal possible. Use the map feature to compare rental house prices in different neighborhoods. Also, try adjusting your dates to compare nightly rates within a similar timeframe.
Monroe County Vacation Homes essential information
Accommodation | 3489 Vacation Homes |
|---|---|
Lowest Price | $147 |
Highest Price | $2,669 |
Popular accommodation | Sugarloaf Key RV Resort & Cottages, Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort, ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking, Hemingway Caribbean Townhome/Private Pool by Beach,Key West charm,free parking, Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball, Pagitt House – Historic Charm Meets Modern Luxury in the Heart of Key West, Ocean Dream, Family friendly, Direct Ocean, Pool/spa, Kayaks, Giant chess, bocci, Luxury Waterfront Home with Private Pool and Dock!, Views ~ Pool~Private Hot Tub~FREE Boat Slip~Heaven!!!, Waterfront Keys Retreat Private Heated Pool + Dock Near Sombrero Beach Sleeps 10, SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!, Spacious 3-bedroom townhome on Stock Island with resort style pool. |
Monroe County Vacation Homes essential information
Accommodation | 3489 Vacation Homes |
|---|---|
Lowest Price | $147 |
Highest Price | $2,669 |
Popular accommodation | Sugarloaf Key RV Resort & Cottages, Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort, ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking, Hemingway Caribbean Townhome/Private Pool by Beach,Key West charm,free parking, Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball, Pagitt House – Historic Charm Meets Modern Luxury in the Heart of Key West, Ocean Dream, Family friendly, Direct Ocean, Pool/spa, Kayaks, Giant chess, bocci, Luxury Waterfront Home with Private Pool and Dock!, Views ~ Pool~Private Hot Tub~FREE Boat Slip~Heaven!!!, Waterfront Keys Retreat Private Heated Pool + Dock Near Sombrero Beach Sleeps 10, SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!, Spacious 3-bedroom townhome on Stock Island with resort style pool. |
More ways to wander Monroe County
Explore More Ways to Travel with Travelocity
- Hotels near Mallory Square
- Isla Bella Beach Resort & Spa
- Hotels in Marathon
- Condos in Monroe County
- Cottages in Monroe County
- Houseboats in Monroe County
- Old Town Key West Hotels
- Hotels near Southernmost Point
- Condos in Stock Island
- Houseboats in Stock Island
- Privatevacationhomes in Stock Island
- Sugar Loaf Lodge
- Sunset Key Hotels
- Duval House
- Family Friendly in Key West
- H2O Suites - Adults Only
- Havana Cabana at Key West
- Heron House - Adult Only
- Hotels in Big Pine Key
- Casa Marina Hotels
- Cottages in Cow Key
- Houseboats in Cow Key
- Resorts in Cow Key
- Caravanparks in Cow Key
- Privatevacationhomes in Dredgers Key
- Hotels near Duval Street
- Condos in Fleming Key
- Aparthotels in Fleming Key
- Privatevacationhomes in Fleming Key
- Hotels near Fort Zachary Taylor Historic State Park
- Apartments in Key West
- Bedandbreakfast in Key West
- Cabins in Key West
- Capsulehotels in Key West
- Condominiumresort in Key West
- Condos in Key West
- Cottages in Key West
- Aparthotels in Key West
- Guesthouses in Key West
- Key West Historic District Hotels
- Hostels in Key West
- The Independent Inn - Formerly Heron House Court
- Adults Only in Key West
- All-Inclusive in Key West
- Amsterdam's Curry Mansion Inn
- Beach in Key West
- Casa Marina Key West Curio Collection by Hilton
- Budget in Key West
- Suites in Key West
- Island City House Hotel
- Beachside Resort & Residences
- Ella's Cottages - Key West Historic Inns
- Lighthouse Hotel - Key West Historic Inns
- Winslow's Bungalows - Key West Historic Inns
- LA TE DA Hotel - Adults Only
- New Orleans House - Gay Men Adult Resort
- NYAH Key West - Adults Only
- Ocean Key Resort - A Noble House Resort
- Hilton Key West Resort & Marina
- Opal Key Resort & Marina Key West
- Orchid Key Inn - Adults Only
- Parrot Key Hotel & Villas
- Pier House Resort & Spa
- Seashell Motel
- Silver Palms Inn & Historic Homes
- Simonton Court Historic Inn & Cottages
- Southernmost Beach Resort and Guesthouses
- Southwinds Motel
- The Cabana Inn Key West - Adults Only
- The Gardens Hotel
- The Laureate Key West
- The Marker Key West Harbor Resort
- The Marquesa Hotel
- The Perry Hotel & Marina Key West
- Southernmost House - Adult Exclusive
- The Southernmost Inn - Adults Only
- Wicker Guesthouse
- Hotels in Key West
- Houseboats in Key West
- Inns in Key West
- Motels in Key West
- Privatevacationhomes in Key West
- Coconut Beach Resort
- Resorts in Key West
- Villas in Key West
- Hotels near Mallory Square
- Isla Bella Beach Resort & Spa
- Hotels in Marathon
- Condos in Monroe County
- Cottages in Monroe County
- Houseboats in Monroe County
- Old Town Key West Hotels
- Hotels near Southernmost Point
- Condos in Stock Island
- Houseboats in Stock Island
- Privatevacationhomes in Stock Island
- Sugar Loaf Lodge
- Sunset Key Hotels
- Duval House
- Family Friendly in Key West
- H2O Suites - Adults Only
- Havana Cabana at Key West
- Heron House - Adult Only
- Hotels in Big Pine Key
- Casa Marina Hotels
- Cottages in Cow Key
- Houseboats in Cow Key
- Resorts in Cow Key
- Caravanparks in Cow Key
- Privatevacationhomes in Dredgers Key
- Hotels near Duval Street
- Condos in Fleming Key
- Aparthotels in Fleming Key
- Privatevacationhomes in Fleming Key
- Hotels near Fort Zachary Taylor Historic State Park
- Apartments in Key West
- Bedandbreakfast in Key West
- Cabins in Key West
- Capsulehotels in Key West
- Condominiumresort in Key West
- Condos in Key West
- Cottages in Key West
- Aparthotels in Key West
- Guesthouses in Key West
- Key West Historic District Hotels
- Hostels in Key West
- The Independent Inn - Formerly Heron House Court
- Adults Only in Key West
- All-Inclusive in Key West
- Amsterdam's Curry Mansion Inn
- Beach in Key West
- Casa Marina Key West Curio Collection by Hilton
- Budget in Key West
- Suites in Key West
- Island City House Hotel
- Beachside Resort & Residences
- Ella's Cottages - Key West Historic Inns
- Lighthouse Hotel - Key West Historic Inns
- Winslow's Bungalows - Key West Historic Inns
- LA TE DA Hotel - Adults Only
- New Orleans House - Gay Men Adult Resort
- NYAH Key West - Adults Only
- Ocean Key Resort - A Noble House Resort
- Hilton Key West Resort & Marina
- Opal Key Resort & Marina Key West
- Orchid Key Inn - Adults Only
- Parrot Key Hotel & Villas
- Pier House Resort & Spa
- Seashell Motel
- Silver Palms Inn & Historic Homes
- Simonton Court Historic Inn & Cottages
- Southernmost Beach Resort and Guesthouses
- Southwinds Motel
- The Cabana Inn Key West - Adults Only
- The Gardens Hotel
- The Laureate Key West
- The Marker Key West Harbor Resort
- The Marquesa Hotel
- The Perry Hotel & Marina Key West
- Southernmost House - Adult Exclusive
- The Southernmost Inn - Adults Only
- Wicker Guesthouse
- Hotels in Key West
- Houseboats in Key West
- Inns in Key West
- Motels in Key West
- Privatevacationhomes in Key West
- Coconut Beach Resort
- Resorts in Key West
- Villas in Key West
- Flights from Tampa (TPA) to Key West (EYW)
- Flights from Alcoa (TYS) to Key West (EYW)
- Flights to Key West
- Flights from Nashville (BNA) to Key West (EYW)
- Flights from Baltimore (BWI) to Key West (EYW)
- Flights from Detroit (DTW) to Key West (EYW)
- Flights from Milwaukee (MKE) to Key West (EYW)
- Flights from New Orleans (MSY) to Key West (EYW)
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- Condos in Key West
- Hotels near Duval Street
- Visit Fort East Martello Museum and Gallery
- Hotels in Key West Historic District
- Beach Hotels in Key West
- All-inclusive Resorts in Key West
- Hotels in Key West
- Car rentals at Key West Airport (EYW)
- Car rentals in Key West
- Oceanfront Hotels in Key West
- Flights to Key West
- Houseboats in Key West
- Key West vacations
- Cheap Hotels in Key West
- Hotels near Smathers Beach
- Condos in Key West
- Hotels near Duval Street
- Visit Fort East Martello Museum and Gallery
- Hotels in Key West Historic District
- Beach Hotels in Key West
- All-inclusive Resorts in Key West
- Hotels in Key West
- Car rentals at Key West Airport (EYW)
- Car rentals in Key West
- Oceanfront Hotels in Key West
- Flights to Key West
- Houseboats in Key West
- Key West vacations
- Cheap Hotels in Key West
- Hotels near Smathers Beach















