Old Town Florida Vacation Rentals and Vacation Homes

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RentKeyWest.com
 305-294-0990 
Key West, FL Rent a private home, cottage, villa, or condo as an alternative to your typical Key West hotel stay.
Browse 85 Vacation Rentals

Rentalsfloridakeys.com
 305-743-5181, 888-743-5635 
Florida Keys Vacation Rentals manages hundreds of vacation rental properties ranging from luxurious to budget-conscious throughout The Florida Keys including Key West, the Lower Keys, ...
Browse 321 Vacation Rentals

Vacation Homes Of Key W...
 888-404-2802 
From charming little cottages to elegant luxurious estates, experience the original island charm of Key West through our variety of top quality vacation rental properties.
Browse 71 Vacation Rentals

AtHomeKeyWest.com
 888-459-9378 
Located throughout Key West many homes, cottages and compounds are open for vacation rentals. These homes offer a private haven in the tropical beauty of Key West Many different styles...
Browse 84 Vacation Rentals

 34 Rentals in Old Town

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Property 19796

Family Reunion KEYS

  • 12 Bedroom Family Reunion Vacation Rental - Key West
  • House in Key West (Near Old Town)
  • 12 Bedroom(s), Sleeps 22-28
  • 8 Bathroom(s)
  • Weekly Rates from $7,500
Property 19250

Key West Coral Country 30

  • Key West Luxury Home
  • Townhouse in Key West (Near Old Town)
  • 7 Bedroom(s), Sleeps 16
  • 9 Bathroom(s)
Property 19251

Island Rendezvous 5730

  • Island Rendezvous Vacation Rental - Key West
  • Villa in Key West (Near Old Town)
  • 6 Bedroom(s), Sleeps 14
  • 5 Bathroom(s)
  • Weekly Rates from $5,850
Property 19793

Classic Key West Estate

  • Classic Key West Estate Vacation Rental
  • House in Key West (Near Old Town)
  • 6 Bedroom(s), Sleeps 12-14
  • 4 Bathroom(s)
  • Weekly Rates from $5,000
Property 31946

The Watson House

  • Award Winning Victorian Home in the Heart of Old Town Key West.
  • House in Key West (Near Old Town)
  • 6 Bedroom(s), Sleeps 12
  • 4 Bathroom(s)
  • Weekly Rates from $5,400
Property 19246

Victorian Mansion 4379

  • Victorian Mansion Vacation Rental - Key West
  • House in Key West (Near Old Town)
  • 5 Bedroom(s), Sleeps 10
  • 3 Bathroom(s)
  • Weekly Rates from $4,450
Property 19792

Amanda's Dream Suites

  • Amanda's Dream Suites Vacation Rental - Key West
  • House in Key West (Near Old Town)
  • 5 Bedroom(s), Sleeps 8-10
  • 3 Bathroom(s)
  • Weekly Rates from $3,100
Property 10863

Southard Street

  • Key West Vacation Rentals
  • House in Key West (Near Old Town)
  • 4 Bedroom(s), Sleeps 14
  • 4 Bathroom(s)
  • Weekly Rates from $4,760
Property 19243

Amelia's Hideaway 3714

  • Amelia's Hideaway Vacation Rental - Key West
  • Villa in Key West (Near Old Town)
  • 4 Bedroom(s), Sleeps 2-10
  • 3.5 Bathroom(s)
  • Weekly Rates from $3,800
Property 10860

Coconut Cabana

  • KEY WEST "Coconut Cabana" A Tropical Vacation Rental Bungalow
  • House in Key West (Near Old Town)
  • 3 Bedroom(s), Sleeps 6
  • 2 Bathroom(s)
  • Weekly Rates from $2,310
Property 10869

Duval Roost

  • "Duval Roost" A Beautiful Vacation Home With Screened Balcony Overlooking The Pool
  • House in Key West (Near Old Town)
  • 3 Bedroom(s), Sleeps 6
  • 3.5 Bathroom(s)
  • Weekly Rates from $2,660
Property 19788

Ocean View Luxury 208

  • Ocean View Luxury Vacation Rental - Key West
  • Condo in Key West (Near Old Town)
  • 3 Bedroom(s), Sleeps 6
  • 2 Bathroom(s)
  • Weekly Rates from $2,000
Property 19789

Coco's Poolside Retreat

  • Coco's Poolside Retreat Key West Vacation Rental
  • Townhouse in Key West (Near Old Town)
  • 3 Bedroom(s), Sleeps 6-8
  • 2.5 Bathroom(s)
  • Weekly Rates from $1,600
Property 19800

Avant-Garde - Modernistic

  • Avant-Garde - Modernistic Luxury Key West Vacation Home
  • House in Key West (Near Old Town)
  • 3 Bedroom(s), Sleeps 7
  • 3 Bathroom(s)
Property 19801

Island Cosmopolitan

  • Island Cosmopolitan Vacation Rental with Private Pool & High Speed Internet
  • House in Key West (Near Old Town)
  • 3 Bedroom(s), Sleeps 2-6
  • 2 Bathroom(s)
Property 80632

island Breeze

  • Key West Golf Club Vacation Rental
  • House in Key West (Near Old Town)
  • 3 Bedroom(s), Sleeps 8
  • 2.5 Bathroom(s)
Property 88223

easy Livin

  • TRUMAN ANNEX VACATION HOME
  • House in Key West (Near Old Town)
  • 3 Bedroom(s), Sleeps 8
  • 4 Bathroom(s)
  • Weekly Rates from $4,000
Property 10865

Havana Lane

  • "Havana Lane" An Old Town Vacation Rental Retreat
  • Cottage in Key West (Near Old Town)
  • 2 Bedroom(s), Sleeps 4
  • 2 Bathroom(s)
  • Weekly Rates from $2,100
Property 10867

Duval Square

  • "Duval Square" Vacation Rental Condo's Conveniently Located
  • Condo in Key West (Near Old Town)
  • 2 - 4 (vari Bedroom(s), Sleeps 4 - 10 (Var
  • 2 - 4 (Var Bathroom(s)
  • Weekly Rates from $1,330
Property 17013

Spa On Duval

  • Spa on Duval - two bedroom two 1/2 bath townhome on Duval St
  • Condo in Key West (Near Old Town)
  • 2 Bedroom(s), Sleeps 6
  • 2.5 Bathroom(s)
  • Weekly Rates from $1,400
Property 19248

Island Village Cottage 1103

  • Island Village Cottage Vacation Rental - Key West
  • Cottage in Key West (Near Old Town)
  • 2 Bedroom(s), Sleeps 4-6
  • 2 Bathroom(s)
  • Weekly Rates from $1,850
Property 19249

Island Oasis Garden Home 6055

  • Island Oasis Garden Home Vacation Rental - Key West
  • Townhouse in Key West (Near Old Town)
  • 2 Bedroom(s), Sleeps 4
  • 2 Bathroom(s)
  • Weekly Rates from $1,500
Property 19787

Down Island Digs

  • Down Island Digs Vacation Rental in Old Town Key West
  • Cottage in Key West (Near Old Town)
  • 2 Bedroom(s), Sleeps 2-6
  • 2 Bathroom(s)
  • Weekly Rates from $2,050
Property 19794

Tropical Chill

  • Upscale Modern Key West Cottage - Tropical Chill
  • Cottage in Key West (Near Old Town)
  • 2 Bedroom(s), Sleeps 4
  • 2 Bathroom(s)
Property 19795

Southern Sunrise KEYS

  • Key West Southern Sunrise Vacation Rental
  • Condo in Key West (Near Old Town)
  • 2 Bedroom(s), Sleeps 4-6
  • 2 Bathroom(s)
  • Weekly Rates from $1,200


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