Vacation Rentals in Key West Florida

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Avoid costly fees and gain in service by dealing directly with the Vacation Rental Management Company.

KEY WEST


Number of Guests

Bedrooms

Bathrooms
more filters

Price Range

Amenities
  Air Conditioning
  Dishwasher
  Fireplace
  Grill
  Hot Tub (Private)
  Luxury
  Pets Allowed
  Pool (Private)
  Ski-in/Ski-out
  Washer/Dryer
  Wheelchair Accessible

Activities and Interests
  Beach
  Biking
  Boating
  Canoeing
  Casino
  Corporate and Executive
  Fishing
  Deep Sea Fishing
  For Sale
  Golfing
  Group and Reunion
  Honeymoon
  Horseback Riding
  Hunting
  Lake
  Mountain Biking
  State National Parks
  Nightclub and Disco
  Over 55 Community
  Sailing
  Scuba Diving
  Skiing
  Cross Country Skiing
  Snowmobiling
  Spa
  Surfing
  Theatre
  Wedding
  White Water Rafting
  Wineries and Vineyards
  Fly Fishing
  Wind Surfing
  Hang Gliding
  Disney
  LegoLand
  Hiking
  Rental Exchange
  Specials
  Ultra Luxury
  Family Vacations
  Kayaking

KEY WEST AREA DESTINATIONS

Map of Key West

TRENDING IN KEY WEST

Key West Lobster Festival

Key West Lobster Festival
by Anthony Vaarwerk

Key West's Fantasy Fest

Key West's Fantasy Fest
by Anthony Vaarwerk

Annual Hemingway Days

Annual Hemingway Days
by Anthony Vaarwerk

The Vacation Rental Properties listed below are professionally managed by Vacation Rental Management Companies who know the Key West area.

Vacation Rental Management Companies provide local hospitality, professional rental services, and the very best in rates and availability while managing vacation rentals that are safe for you and your family. They will assist you in finding the perfect rental property for your vacation.

BOOK DIRECT

Avoid costly fees and gain in service by dealing directly with the Vacation Rental Management Company.


Key West Florida Vacation Rentals

Casa Key West Key West Florida Historic Key West Vacation Rentals
$4,470/month
Home in Key West Florida
3 Beds • 3 Full Baths • Sleeps 6
Historic Key West Vacation Rentals

Ashe Splashe Key West Florida Rent Key West Vacations
$5,323/month
Home in Key West Florida
3 Beds • 3 Full Baths • Sleeps 6
Rent Key West Vacations

Beach Club #304 Key West Florida Rent Key West Vacations
$350/night
Condo in Key West Florida
2 Beds • 2 Full Baths • Sleeps 4
Rent Key West Vacations

Island Days Key West Florida Historic Key West Vacation Rentals
$299/night
Townhouse in Key West Florida
3 Beds • 3 Full Baths • Sleeps 7
Historic Key West Vacation Rentals

Havana Hideaway
$350/night
Condo in Key West Florida
2 Beds • 2 Full Baths • Sleeps 5
Historic Hideaways

Pete's West Cottage Key West Florida Rent Key West Vacations
$280/night
Home in Key West Florida
2 Beds • 1 Full Bath • Sleeps 4
Rent Key West Vacations

Steamplant 209 Key West Florida Historic Key West Vacation Rentals
$1,575/week
Condo in Key West Florida
3 Beds • 3 Full Baths • Sleeps 7
Historic Key West Vacation Rentals

Banana Key
$310/night
Condo in Key West Florida
2 Beds • 2 Full Baths • Sleeps 5
Historic Hideaways

Casablanca Key West Florida Historic Key West Vacation Rentals
$229/night
Condo in Key West Florida
1 Bed • 1 Full Bath • Sleeps 3
Historic Key West Vacation Rentals

Harry Suite - First Floor Front 2 Bedroom 1 Bath Key West Florida Historic Key West Vacation Rentals
$269/night
Home in Key West Florida
2 Beds • 1 Full Bath • Sleeps 5
Historic Key West Vacation Rentals

Petite Maison Key West Florida Historic Key West Vacation Rentals
$289/night
Home in Key West Florida
2 Beds • 2 Full Baths • Sleeps 4
Historic Key West Vacation Rentals

Casa de Cuba Key West Florida Rent Key West Vacations
$560/night
Home in Key West Florida
3 Beds • 2 Full Baths • Sleeps 6
Rent Key West Vacations

Casa Atlantica Studio Key West Florida Rent Key West Vacations
$210/night
Apartment in Key West Florida
Studio • 1 Full Bath • Sleeps 2
Rent Key West Vacations

La Buena Vida
$3,800/month
Key West Florida
2 Beds • 2 Full Baths • Sleeps 4
Historic Hideaways

La Hacienda
$4,500/month
Home in Key West Florida
2 Beds • 2 Full Baths • Sleeps 4
Historic Hideaways

Fairwinds at the Foundry Key West Florida Historic Key West Vacation Rentals
$1,463/week
Condo in Key West Florida
2 Beds • 2 Full Baths • Sleeps 6
Historic Key West Vacation Rentals

Villa Serena @ Duval Square Key West Florida Rent Key West Vacations
$1,984/week
Villa in Key West Florida
2 Beds • 2 Full Baths • Sleeps 4
Rent Key West Vacations

Truman House
$770/night
Home in Key West Florida
4 Beds • 3 Full Baths • Sleeps 10
Historic Hideaways

Azure Hideaway
$2,990/month
Cottage in Key West Florida
2 Beds • 2 Full Baths • Sleeps 8
Historic Hideaways

Sanctuary on Simonton (Monthly) Key West Florida Rent Key West Vacations
$3,871/month
Home in Key West Florida
2 Beds • 3 Full Baths • Sleeps 4
Rent Key West Vacations

South St. Cottage (Monthly) Key West Florida Rent Key West Vacations
$3,677/month
Cottage in Key West Florida
2 Beds • 2 Full Baths • Sleeps 4
Rent Key West Vacations

Key West 1 bedroom cottage rental close to Duval
$300/night
Cottage in Key West Florida
1 Bed • 1 Full Bath • Sleeps 2
Rent Key West Vacations

Southard Sophistication (Monthly) Key West Florida Rent Key West Vacations
$4,839/month
Home in Key West Florida
2 Beds • 2 Full Baths • Sleeps 4
Rent Key West Vacations

Shipyard
$250/night
Condo in Key West Florida
2 Beds • 1 Full Bath • Sleeps 4
Historic Hideaways

Suite Caroline (Monthly) Key West Florida Rent Key West Vacations
$3,194/month
Home in Key West Florida
1 Bed • 1 Full Bath • Sleeps 2
Rent Key West Vacations

Villa Paradiso Key West Florida Rent Key West Vacations
$480/night
Home in Key West Florida
3 Beds • 3 Full Baths • Sleeps 6
Rent Key West Vacations

Caesar's Palace Key West Florida Rent Key West Vacations
Home in Key West Florida
5 Beds • 6 Full Baths • Sleeps 10
Rent Key West Vacations


BOOK DIRECT

Avoid costly fees and gain in service by dealing directly with the Vacation Rental Management Company.

IDEA DRIVEN VACATIONS

Where to stay around Key West Florida

Our April 2021 property listings offer a selection of 147 vacation rentals near Key West. 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 for a holiday or a weekend are on Find Rentals.


Where are the best places to stay in Key West?

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:

  • Florida Gulf Coast: 2,433 vacation rentals
  • Florida Emerald Coast & Destin Area: 1,880 vacation rentals
  • Florida Keys: 619 vacation rentals

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


What are some fun things to do in Key West?

Find Rentals offers a selection of vacation rentals near parks and other areas of interest in Key West. Some of the most popular places to visit while you're traveling in Key West while on vacation are The Key West Butterfly and Nature Conservatory, Key West Garden Club, C. B. Harvey Rest Beach Park, Higgs Beach Dog Park, Indigenous Park and a few more.

There are many other points of interest around Key West 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 Florida?

  • Florida Keys Vacation Rentals: 282 vacation rental properties
  • Rent Key West: 64 vacation rental properties
  • Vacation Homes of Key West: 0 vacation rental properties
  • Historic Key West Vacation Rentals: 58 vacation rental properties
  • Historic Hideaways: 38 vacation rental properties

Can I rent houses in Key West?

Yes. Find Rentals has 79 houses available for rent in Key West. Our other popular types of vacation rentals in Key West include:

  • Condos : 49 rentals available
  • Cottages : 31 rentals available
  • Villas : 12 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including townhouses and more.


Can I rent fishing rentals in Key West?

Absolutely, Find Rentals has 103 fishing rentals in Key West. You have also many other possibilities in Key West 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?

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.





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