Key West Area Florida Vacation Rentals

The Vacation Rentals listed below are represented by Professional Property Management Companies who know the Key West Area and have access to several properties.

These property managers provide local hospitality, additional services, and the very best in rates and availability while managing properties that are safe for you and your family. They will assist you in finding the perfect vacation rental for your vacation.


Showing 1-27 of 318 Rentals

Louisa's Hideaway
Cottage in Key West Florida
$600/night

Sundrenched Reflections
Condo in Key West Florida
Sundrenched Reflections is located on the water at Sunset Marina...
$213/night

Cayo Calypso
House in Key West Florida
The fully fenced private back pool area with chaise lounges and outdoor dining..
$206/night

Beach Club #112
Condo in Key West Florida
$350/night

La Petite Penthouse
Townhouse in Key West Florida
La Petite Penthouse is elegantly furnished...
$220/night

By The Beautiful Sea
Condo in Key West Florida
$480/night

Southard Queen Conch Suite
House in Key West Florida
$300/night

Kemp House
House in Key West Florida
Kemp House
$600/night

Villa Cubana
Cottage in Key West Florida
Villa Cubana is a tropical 2-story cottage located in the heart of Old Town...
$220/night

Shang-Ri-La
Condo in Key West Florida
Shang Ri La has breathtaking views from the balcony...
$220/night

A Dream Come True (30 Night...
House in Key West Florida
A Dream Come True
$5,000/month

Havana Lane
Cottage in Key West Florida
$360/night

Blue Heron's Cove
Townhouse in Key West Florida
The living room has plenty of seating and opens up to a private deck...
$220/night

Casa Feliz
House in Key West Florida
Casa Feliz has a spacious pool surrounded by a generous patio area...
$259/night

Fantasy Resort Villa
Villa in Key West Florida
$850/night

Caribbean Cottage
Cottage in Key West Florida
$425/night

Windswept Palms
Condo in Key West Florida
The views from your wraparound balcony are spectacular...
$402/night

Campbell Cottage (30 Night...
House in Key West Florida
Living Area
$2,400/month

Duval Square
Townhouse in Key West Florida
Private Spa Patio
$280/night

Island Days
Townhouse in Key West Florida
$299/night

Sweet Home Angelita
House in Key West Florida
Sweet Home Angelita is a renovated historic home, made up of two condos...
$556/night

Flower Power House
House in Key West Florida
$1,000/night

Conch in Training
Condo in Key West Florida
Welcome to Paradise!
$214/night

Casa Oliviana
House in Key West Florida
The pool at Casa Oliviana is surrounded by a large deck with 4 seating areas...
$413/night

Baileys Mango Mansion
House in Key West Florida
Key West 4 bedroom pet friendly monthly vacation home rental with private pool
$330/night

Casa Victoria
House in Key West Florida
Key West pet friendly 5 bedroom vacation home with pool
$770/night

Villa Tropicale
House in Key West Florida
$880/night

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Where to stay around Key West Area Florida

Our December 2018 property listings offer a selection of 318 vacation rentals near Key West Area. Find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Key West Area for a holiday or a weekend are on Find Rentals.


Where are the best places to stay in Key West Area?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Key West Area:


For nearby neighborhoods, please use our search to access the selection of vacation rentals available in and around Key West Area.

There are many other points of interest around Key West Area listed on Find Rentals where you can find a great place to stay. Try out the search to find a large selection of vacation rentals available near the city or region you're traveling to.


Which vacation rental managers have properties for rent in Key West Area Florida?


Can I rent fishing rentals in Key West Area?

Absolutely, Find Rentals has 103 fishing rentals in Key West Area. You have also many other possibilities in Key West Area area, including:

Please use our search bar to access the selection of vacation rentals.


How can I find a vacation rental manager in Key West Area?

Find Rentals is the premiere guide for Vacation Rental Managers. We work with management companies from all over the world to provide you with the most robust selection of professionally managed rentals. Use the search to access the selection of management companies and rentals available.