Old Town (Key West, Florida) Vacation Rentals

(23 rentals)
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

$138

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Rentals by Owner

About this property

This Simonton Studio is neat, sweet and complete. * Pet friendly for additional flat fee of $45 * WiFi included * King size bed * Check-out cleaning included * Outdoor table and two chairs * spacious shower * excellent loctaion for walking Old Town * Duval Loop bus passes this adress for free ...

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Property Type

Key West 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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Key West Old Town Sanctuary- Huge Private Pool- Quiet Lane- Monthly Rental

$183

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

Looking to ‚Äč Relax Renew Recharge? We got you. Your own Key West Sanctuary awaits! Escape to a classic Conch family home perfectly tucked away for privacy yet, only 5 Blocks from famous Duval Street. The best of both worlds! Morning yoga class on the deck, late night dip in the pool, and sunset ...

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Property Type

Key West House

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"Southard Comfort"

2 BR | 2 BA | Sleeps 6 | Quick View

4

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

$153

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool
  • Rentals 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 the guest who wants to feel like a local and enjoy ...

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Property Type

Key West House

"Loved It"
Reviewed February 20, 2019

We've been coming to Key West almost every year since 1986, staying for longer visits as we've left more and more of work behind. We spent a month here in 2018 and loved it. Due back this April. The front ...

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The 6 bedroom Duval Street 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
  • Full Kitchen
  • Rentals by Owner

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 huge, fabulous decks that overlooks the action on ...

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Property Type

Key West Villa

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Ocean View condo steps to Beach, rates include all tax and fees

$189

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

The Jungle Breeze condo at LaBrisa Condominiums is a 1 bedroom, 1 bath apartment * Rates include all taxes and fees * King size bed in the bedroom * queen size sleeper sofa in the living area *accommodates 2 adults of family of 4 * WiFi inlcuded * Parking included *Central AIr Conditioning * ...

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Property Type

Key West Condo

"AMAZING"
Reviewed January 30, 2019

There truly aren't enough adjectives to describe the level of service Pam provided. At the very beginning, she answered all my questions, in less than an hour. Her customer service was amazing. She provided ...

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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

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Rentals by Owner

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. * Pet Friendly for flat fee of $45 * King size bed * WiFi included * check-out cleaning included * 2 wall AC units * flat screen TV * Shared gas grill * porch with ...

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Property Type

Key West Condo

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Parrot Dice --"MONTHLY," 2 bedroom (+den), 3 bath, Pool & Hot Tub, Private Drive

2 BR | 3 BA | Sleeps 6 | Quick View

Distance to beach: 0.5 miles to Higgs Beach

$150

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

"MONTHLY" RENTAL ONLY: Old Town Tropical Oasis, Private Pool, Hot Tub, Private Driveway. Meticulously restored and maintained home featuring: 2 bedrooms + den with sleep sofa (can be a 3rd bedroom) and 3 full en suite bathrooms. Our favorite part of this property is the lush & extremely ...

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Property Type

Key West House

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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
  • Full Kitchen
  • Private Pool
  • Rentals 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 landscaping, the main 2/2 house features an indoor/outdoor ...

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Property Type

Key West House

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

$193

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

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 perfect spot to enjoy all that Key West has to offer.Why ...

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Property Type

Key West House

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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
  • Full Kitchen
  • Kid Friendly
  • Pool

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 Street and just 5 tiny tropical island sized ...

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Property Type

Key West Villa

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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

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

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 Street and just 5 tiny tropical island sized ...

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Property Type

Key West Cottage

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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

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront

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 View Villas boast the single Finest Location in ...

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Property Type

Key West Villa

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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
  • Full Kitchen
  • Pool

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 Street and just 5 tiny tropical island sized ...

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Property Type

Key West Villa

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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
  • 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 Street and just 5 tiny tropical island sized ...

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Property Type

Key West Villa

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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
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool

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 View Villas boast the single Finest Location in ...

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Property Type

Key West Villa

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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
  • Full Kitchen
  • Rentals by Owner

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'.The original local artwork throughout the ...

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Property Type

Key West Cottage

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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
  • Full Kitchen
  • 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.Located just 2 blocks off Duval Street and just 5 tiny tropical island sized ...

View all property information

Property Type

Key West Villa

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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
  • Full Kitchen
  • Kid Friendly
  • Pool

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 Street and just 5 tiny tropical island sized ...

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Property Type

Key West Villa

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A Touch of Bermuda at Truman Annex SPECIALS AUG 31 TO OCT. 5

$300

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Rentals by Owner

About this property

$500 OFF THESE WEEKS ONLY 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 private town home (one ...

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Property Type

Key West Cottage

"A Touch of Bermuda"
Reviewed August 19, 2019

Jack is an excellent host! We were there all week and had a great time with the location of this house. We were able to walk everywhere.

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Townhouse, 1/2 Block from Duval in Old Town. Monthly Only**

$75

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Rentals by Owner

About this property

**Available for rent by the month. Although you rent it for a month, you may of course come late and/or leave early. The monthly price will generally be the same as for a comparable unit rented by the day for 10-14 days. It does however give you a lot more options and freedom.Located on a side ...

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Property Type

Key West Townhome

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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 | 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
  • Full Kitchen
  • Kid Friendly
  • Private Pool

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 Park & Beach. Duval Street is just 3 blocks ...

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Property Type

Key West House

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A Touch Of Cuba In Key West $500/WEEK OFF SEPT 7-OCT. 5

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
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

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 over sized two bedroom, one bathroom condominium is located on picturesque ...

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Property Type

Key West Condo

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Duval Balcony Rentals - Suite Mischief

1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 1 miles to Fort Zachary Taylor, Higgs Beach, Smathers Beach

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

Located in the heart of Key West, this unique property offers a central location to the Key West landmarks and sights. Enjoy all Key West has to offer from a historic building with a private balcony overlooking Duval St. For Fantasy Fest, this property offers an ideal location from where you can enjoy ...

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Property Type

Key West Apartment

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Old Town (Key West, Florida) Vacation Rentals