Key West Area Florida Vacation Rentals

The Vacation Rentals listed below are represented by Professional Management Companies who know the Key West Area area and have access to several properties. They will assist you in finding the perfect rental for your vacation.



Showing 1-27 of 318 Rentals

Southard Rooster Conch Suit...
Condo in Key West Florida
$2,660/week

Americana Tropicale
House in Key West Florida
The living room is spacious; the French doors keep the house light and breezy...
$660/night

Margaret Suite - First Floo...
House in Key West Florida
$265/night

Conch in the Treetops
Condo in Key West Florida
The living room has plenty of seating & triple sliding glass doors to balcony...
$220/night

Driftwood Dreams
Condo in Key West Florida
Driftwood Dreams is a fully renovated 2 bedroom, 2 bathroom condo...
$112/night

Ashe Splashe
House in Key West Florida
$5,323/month

Ultimate Pool Cottage (30 N...
House in Key West Florida
Ultimate Pool Cottage
$5,500/month

Southernmost Solace
House in Key West Florida
Southernmost Solace is a charming private home that is located on Elizabeth Street, just steps from the Southernmost Point...
$125/night

La Brisa #401N Blue Heron H...
Condo in Key West Florida
$3,871/month

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

Townhomes on Windsor #6
House in Key West Florida
$595/night

Petite Maison
House in Key West Florida
$289/night

Reynold's Retreat
Cottage in Key West Florida
$5,613/month

Villa Tropicale
House in Key West Florida
$880/night

Shipyard Palms
Condo in Key West Florida
Key West vacation rental with pool
$1,570/week

Louisa House
House in Key West Florida
$590/night

The Artists' Muse
House in Key West Florida
The Artists' Muse has been recently redesigned to celebrate art, culture, and the upscale island life...
$464/night

Azure Hideaway (30 Night Mi...
Cottage in Key West Florida
Azure Hideaway
$3,500/month

Chick-a-Pea's Cottage
Cottage in Key West Florida
$510/night

Puerta Coralina
House in Key West Florida
Puerta Coralina is a classic conch cottage located on a quiet residential street...
$314/night

The Emerald Orchid
House in Key West Florida
The dramatic 22 foot ceilings provide a wonderful sense of light and airiness...
$305/night

Solares (30 Night Minimum)
House in Key West Florida
Solares
$1,950/month

Conch Casa Grande
House in Key West Florida
Conch Casa Grande has a spacious and private sunny pool area...
$737/night

The Commodore's Manor
House in Key West Florida
The Commodore's Manor is a beautiful 5 bedroom 3,500 sq ft townhome that is located directly on the water at Garrison Bight Marina...
$1,001/night

Sea Captain's Haven
Townhouse in Key West Florida
Sea Captain's Haven has open indoor and outdoor living spaces...
$237/night

Little Red Pool
Cottage in Key West Florida
$4,000/month

Casa Angelina (30 Night Min...
House in Key West Florida
Casa Angelina
$4,500/month

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Where to stay around Key West Area Florida

Our October 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.