Old Town (Key West, Florida) Vacation Rentals

(20 rentals)
1 BR Margaritavilla Beach Cottage at Fort Zachary Taylor - Discounts Available!

1 BR Margaritavilla Beach Cottage at Fort Zachary Taylor - Discounts Available!

1 BR | 1 BA | Sleeps 2 | Quick View

Distance to beach: 0.1 miles to Fort Zachary Taylor Park & Beach

$236

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Communal Pool
  • Kid Friendly
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

About this property

IMPORTANT: A Phone Number Is Required for service. By providing your phone number, we can offer you a weekly stay at a rate equivalent to 5 nights rent. Inquiries without a phone number will not qualify for any discounts. Located just 2 blocks off ...

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Location Information

Key West, Florida, 33040

Property Type

Cottage

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4 BR, 2 BA Margaritavilla Beach Cottage in Old Town - Ask About Our Specials!

4 BR, 2 BA Margaritavilla Beach Cottage in Old Town - Ask About Our Specials!

4 BR | 2 BA | Sleeps 8 | Quick View

Distance to beach: 0.2 miles to Fort Zachary Taylor Park & Beach

$681

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Communal Pool
  • Kid Friendly
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

About this property

IMPORTANT: A Phone Number Is Required for service. By providing your phone number, we can offer you a weekly stay at a rate equivalent to 5 nights rent. Inquiries without a phone number will not qualify for any discounts.Located just 2 blocks off Duval ...

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Location Information

Key West, Florida, 33040

Property Type

Villa

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6 BR, 5.5 BA Luxury Key West Beach House in Old Town at Fort Zachary Taylor

6 BR, 5.5 BA Luxury Key West Beach House in Old Town at Fort Zachary Taylor

6 BR | 5.5 BA | Sleeps 10 | Quick View

Distance to beach: 0.1 miles to Fort Zachary Taylor Park & Beach

$1929

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Wheelchair Accessible
  • Full Kitchen
  • Private Pool
  • Kid Friendly
  • Non-Smoking
  • Free WiFi

About this property

This Luxury 6 BR, 5.5 BA Ocean View Private Pool Home is one of the finest rentals to ever become available in Key West and is crawling distance to everything you are coming to Key West for, including just one home away from entering Fort Zachary Taylor ...

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Location Information

Key West, Florida, 33040

Property Type

House

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Sea Watch 2 BR Open Water Luxury Penthouse - Ask About Our Specials!

Sea Watch 2 BR Open Water Luxury Penthouse - Ask About Our Specials!

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.1 miles to Fort Zachary Taylor Park & Beach

$500

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Wheelchair Accessible
  • Full Kitchen
  • Waterfront
  • Oceanfront
  • Communal Pool
  • Kid Friendly

About this property

IMPORTANT: A Phone Number Is Required for service. By providing your phone number, we can offer you a weekly stay at a rate equivalent to 5 nights rent. Inquiries without a phone number will not qualify for any discounts.These 2 BR and 3 BR Open Water ...

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Location Information

Key West, Florida, 33040

Property Type

Villa

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Key West Seashell Cottage - private home with spa, located on a quiet lane.

Key West Seashell Cottage - private home with spa, located on a quiet lane.

1 BR | 1 BA | Sleeps 2 | Quick View

Distance to beach: 0.5 miles to South Beach

$186

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Non-Smoking
  • No Pets Allowed
  • Managed by Owner
  • Managed by Property Manager

About this property

Forget that 'been there, done that' hotel room; enjoy the comforts of home in Old Town Key West at the Seashell Cottage. Located on a quiet lane, just 1 block to Duval Street, walk to the grocery store, restaurants, museums, beach, and 'Sunset Celebration'. ...

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Location Information

Key West, Florida, 33040

Property Type

Cottage

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A Touch Of Cuba In Key West

A Touch Of Cuba In Key West

2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.5 miles to Ft. Zachary Taylor State Park

$250

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Communal Pool
  • Kid Friendly
  • Non-Smoking

About this property

Welcome to Key West and the Shipyard section of the Truman Annex. You have many choices of accommodations and since I am not a real estate salesman or property manager, allow me let the photos and description speak for themselves. My oversized two bedroom, ...

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Location Information

Key West, Florida, 33040

Property Type

Condo

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4 BR, 3 BA Margaritavilla Beach Cottage in Old Town - Ask About Our Specials!

4 BR, 3 BA Margaritavilla Beach Cottage in Old Town - Ask About Our Specials!

4 BR | 3 BA | Sleeps 8 | Quick View

Distance to beach: 0.2 miles to Fort Zachary Taylor Park & Beach

$697

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Communal Pool
  • Kid Friendly
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

About this property

IMPORTANT: A Phone Number Is Required for service. By providing your phone number, we can offer you a weekly stay at a rate equivalent to 5 nights rent. Inquiries without a phone number will not qualify for any discounts.Located just 2 blocks off Duval ...

View all property information

Location Information

Key West, Florida, 33040

Property Type

Villa

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2 BR, 2 BA Margaritavilla Beach Cottage in Old Town - Ask About Our Specials!

2 BR, 2 BA Margaritavilla Beach Cottage in Old Town - Ask About Our Specials!

2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 0.2 miles to Fort Zachary Taylor Park & Beach

$425

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Communal Pool
  • Free WiFi

About this property

IMPORTANT: A Phone Number Is Required for service. By providing your phone number, we can offer you a weekly stay at a rate equivalent to 5 nights rent. Inquiries without a phone number will not qualify for any discounts.Located just 2 blocks off Duval ...

View all property information

Location Information

Key West, Florida, 33040

Property Type

Villa

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3 BR, 2 BA Margaritavilla Beach Cottage in Old Town - Ask About Our Specials!

3 BR, 2 BA Margaritavilla Beach Cottage in Old Town - Ask About Our Specials!

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.2 miles to Fort Zachary Taylor Park & Beach

$633

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Kid Friendly
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

About this property

IMPORTANT: A Phone Number Is Required for service. By providing your phone number, we can offer you a weekly stay at a rate equivalent to 5 nights rent. Inquiries without a phone number will not qualify for any discounts.Located just 2 blocks off Duval ...

View all property information

Location Information

Key West, Florida, 33040

Property Type

Villa

Show less

Sea Watch 3 BR Open Water Luxury Penthouse - Ask About Our Specials!

Sea Watch 3 BR Open Water Luxury Penthouse - Ask About Our Specials!

3 BR | 3 BA | Sleeps 7 | Quick View

Distance to beach: 0.1 miles to Fort Zachary Taylor Park & Beach

$714

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Wheelchair Accessible
  • Full Kitchen
  • Waterfront
  • Oceanfront
  • Kid Friendly
  • Non-Smoking

About this property

IMPORTANT: A Phone Number Is Required for service. By providing your phone number, we can offer you a weekly stay at a rate equivalent to 5 nights rent. Inquiries without a phone number will not qualify for any discounts.These 2 BR and 3 BR Open Water ...

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Location Information

Key West, Florida, 33040

Property Type

Villa

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The Duval Compound

The Duval Compound

6 BR | 6.5 BA | Sleeps 16 | Quick View

Distance to beach: 0.3 miles to Ft Zachary Taylor

$1250

per night

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Key Amenities

  • Air Conditioning
  • Hot Tub
  • Full Kitchen
  • Non-Smoking
  • No Pets Allowed
  • Managed by Owner
  • Free WiFi

About this property

Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theaters and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a ...

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Location Information

Key West, Florida, 33040

Property Type

Villa

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2 BR, 1 BA Margaritavilla Beach Cottage in Old Town - Ask About Our Specials!

2 BR, 1 BA Margaritavilla Beach Cottage in Old Town - Ask About Our Specials!

2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.2 miles to Fort Zachary Taylor Park & Beach

$393

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen

About this property

IMPORTANT: A Phone Number Is Required for service. By providing your phone number, we can offer you a weekly stay at a rate equivalent to 5 nights rent. Inquiries without a phone number will not qualify for any discounts.Located just 2 blocks off Duval ...

View all property information

Location Information

Key West, Florida, 33040

Property Type

Villa

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Dos Casas - 2 Houses 2 blocks from Duval in beautiful Old Town -- Monthly Rental

$193

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Managed by Owner
  • Free WiFi

About this property

Dos Casas can be the answer to your fabulous Old Town Key West vacation. We've been renting to discriminating travelers for over 10 years. Our guests come back over and over, finding the comfortable spaces, stocked with amenitites and ideal location the ...

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Location Information

Key West, Florida, 33040

Property Type

House

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Townhouse, 1/2 Block from Duval Street in Old Town Key West

$100

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Pet Friendly
  • Managed by Owner
  • Free WiFi

About this property

Available for rent by the month, managed by owner. Located on a quiet side street off Duval and Truman Avenue, this newly remodeled two story townhouse is one in a gated cluster of twelve surrounding a beautiful award winning courtyard. You are within ...

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Location Information

Key West, Florida, 33040

Property Type

Town Home

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Tropical Seclusion On Old Town Lane With Pool And Detached Bungalow.

$193

per night

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Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Non-Smoking
  • No Pets Allowed
  • Managed by Owner

About this property

2/2 Main House, 1/1 Bunglow, Large Pool And Hot Tub On Beautiful Old Town LaneHidden at the end of one of the most beautiful lanes in Old Town, Casa Escondida awaits you with its tropical seclusion and quiet serenity. Nestled amongst mature tropical ...

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Location Information

Key West, Florida, 33040

Property Type

House

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"Southard Comfort"

"Southard Comfort"

2 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 1 miles to Fort Zachery Taylor State Park

$157

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Kid Friendly
  • Non-Smoking
  • Managed by Owner

About this property

924 Southard Street... an Old Town cottage made famous by Country Home magazine! Featured in Country Home , in June 2001, this one-of-a-kind cottage was formerly owned and decorated by well known decorator Mary Emmerling. Southard Comfort is perfect for ...

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Location Information

Key West, Florida, 33040

Property Type

House

"Great Time At Southard Comfort"
Reviewed July 5, 2018

Super comfortable. Love the pool and the back patio. Great location. Close walk to several great restaurants. Far enough from the Duval madness that you can ignore it completely and close enough to walk ...

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A Touch of Bermuda at Truman Annex

$257

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Pet Friendly
  • Communal Pool
  • Kid Friendly
  • Non-Smoking
  • Managed by Owner

About this property

Envision yourself relaxing in a beautiful wood framed conch cottage with overhead fans lazily turning below the sloping tin roof in the heart of Old Town in Key West. This is the best value in Key West as it is no cookie cutter small rental condo but a ...

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Location Information

Key West, Florida, USA

Property Type

Cottage

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Simonton Studio, an Old Town get-away for 2

Simonton Studio, an Old Town get-away for 2

Studio | 1 BA | Sleeps 2 | Quick View

1

Distance to beach: 0.5 miles to South Beach

$152

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Pet Friendly
  • Non-Smoking
  • Managed by Owner
  • Free WiFi

About this property

This Simonton Studio is neat, sweet and complete. This pet friendly accommodation is the perfect location for exploring Key West. So, get out there and live it up in Key West and come home to a king size bed and everything you need to fix your own cocktails ...

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Location Information

Key West, Florida, 33040

Property Type

Condo

"Excellent location - would definitely stay there again!"
Reviewed April 7, 2018

This little gem had everything we needed and was just perfect for a getaway for two. We appreciated the tips left by the owner, giving recommendations for dining and activities, and it was fun to have ...

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My Condo by the Beach with Ocean View

$169

per night

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Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Non-Smoking
  • No Pets Allowed
  • Managed by Owner
  • Free WiFi

About this property

The Jungle Breeze condo at LaBrisa Condominiums is a 1 bedroom, 1 bath apartment with a king size bed in the bedroom and a queen size sleeper sofa in the living area. It accommodates 2-4 people. This is not a hotel; it is a privately owned condo facing ...

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Location Information

Key West, Florida, 33040

Property Type

Condo

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Superb Location, Affordably Priced - The TwoSim Suite

Superb Location, Affordably Priced - The TwoSim Suite

Studio | 1 BA | Sleeps 2 | Quick View

Distance to beach: 0.5 miles to South Beach

$135

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Pet Friendly
  • Non-Smoking
  • Managed by Owner
  • Free WiFi

About this property

This Studio is a lovely charmer nestled in a 6 unit compound in a residential neighborhood in the center of Old Town Key West. This pet friendly accommodation is the perfect location for exploring Key West. You can walk to the Hemmingway House, the Butterfly ...

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Location Information

Key West, Florida, 33040

Property Type

Condo

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Old Town (Key West, Florida) Vacation Rentals