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Key West Vacation Rentals

(74 rentals)
Key West, the last island in the Florida Keys, is a walkable island known for its historic district, exceptional snorkeling, and Sunset Celebration at Mallory Square. Expect Old Town cottages or New Town condos and townhomes, at a median of $286 a night for a condo, $433 for a house.
Key West House
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Looking to ​ 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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Featured review

"Perfect place to relax and unwind!"

We loved our time at Key West Sanctuary! The perfect location to bike to the sights and sounds of Key West; close to one-way roads with a bike lane going to/from Duval. The beautiful and peaceful surroundings...

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$393
avg per night
Key West House
Sleeps 6, 3 bedrooms, 3 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Down a very quite lane the house has one off street parking spot. If you are familiar with Key West you understand what a treat it is to have off street Parkin !Enter from gate through lush and colorful walk to front door of main house . Walking over the front porch is the typical Key West style outside...

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Featured review

"A hidden gem in Key West!"

We loved our stay at Hidden Cottage! Located on a perfect bike loop with bike-lane to Duval (one way on Southard to Duval and one way on Fleming home)! Also very close to the boat docks. Hidden Cottage...

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$507
avg per night
Key West House
Sleeps 8, 3 bedrooms, 2 bathrooms
7 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

TRANQUIL BEAUTY: 3 BR’s, 2 Baths Private Haven paradise with huge private heated pool and landscaped back yard!ENJOY KEY WEST at its peaceful best in your 3BR, 2 bath private hideaway in a quiet neighborhood near Higgs and Smathers beaches and only a 10 minute bike or Uber ride from Duval Street....

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Featured review

"Vacation"

Location was great. Quiet neighborhood, lush garden and good accommodations. The tile in the pool is excessively dirty. Pool guys came several times during our stay and never cleaned them.

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$271
avg per night
Key West Condo
Sleeps 2, 1 bedroom, 2 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into 5 condo units. Tony's Conch Retreat, unit 5, is on the 2nd floor, at the top of the stairs, and encompasses the rear of the home from end to end. It has a lovely view of the...

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$270
avg per night
New
Key West Cottage
Sleeps 3, 1 bedroom, 1 bathroom

Distance to beach: 0.8 miles to Higgs Beach

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Seasonal rental - Fully furnished - beautifully painted in Keyzie colors, 1br/1ba rear cottage in the historic district of Old Town, Key West; 5 blocks to the beach and 4 blocks to the world famous Duval Street with shops, art galleries, restaurants, bars and night clubs.FEATURES: One off street...

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$142
avg per night

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Key West Villa
Sleeps 16, 6 bedrooms, 7 bathrooms
3 reviews

Distance to beach: 0.3 miles to Ft Zachary Taylor

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • 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 huge, fabulous decks that overlooks the action on...

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Featured review

"Glenn dinner group get away"

We had 6 couples visiting key west for a week to celebrate milestone birthdays and get away. The houses were perfect for our group. Beautifully decorated,plenty of space for everyone to enjoy and not...

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$1,712
avg per night
Key West Condo
Sleeps 2, 1 bedroom, 1 bathroom
3 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

The Jungle Breeze condo at LaBrisa Condominiums is a 1 bedroom, 1 bath apartment * King size bed in the bedroom *accommodates 2 adults only * WiFi inlcuded * Parking included *Central AIr Conditioning * Check-out cleaning is $160 * This is not a hotel; it is a privately owned condo facing the...

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Featured review

"The perfect location that has everything..."

Just finished a 2 week stay and I have been renting from Pam for over a decade and she continues to make a great condo even better with her constant upgrades to the unit and she is a wonderful host. The...

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$344
avg per night
Key West House
Sleeps 8, 4 bedrooms, 2 bathrooms
12 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Dos Casas can be the answer to your fabulous Old Town Key West vacation. We've been renting to discerning travelers for over 15 years. Our guests come back over and over, finding the comfortable spaces, stocked with amenities and ideal location the perfect spot to enjoy all that Key West has to offer.Dos...

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Featured review

"Perfect stay"

Our family of 5 visited Dos Casas and had an absolutely wonderful stay! We were warmly welcomed and informed about the property-they were very attentive to details. The compound is beautifully maintained...

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$723
avg per night
Key West Cottage
Sleeps 4, 2 bedrooms, 1 bathroom
3 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

The Mile Zero House is a MONTLY VACATION RENTAL. Rent one or more months comes completely furnished. Charming conch home with true Key West character. Fenced for privacy with a open style front porch to enjoy the local flavor along with a passing Conch Train. Full size kitchen that is nicely stocked with...

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Featured review

"Amazing Location!"

Historic Conch House Located Downtown Key West near Duval St and restaurants beach and many attractions ! Private Yard fully locked and fenced with beautiful plants Sitting on the front Porch you feel...

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$268
avg per night
Key West Townhome
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 528 yards to Fort Zachary Taylor Historic State Park Beach .3 M

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to Casa Del Sol ℠— your luxurious and elegantly appointed 2-bedroom, 2.5-bath island townhome with private carport, nestled within the 45 lushly landscaped acres of the prestigious Truman Annex in the heart of Old Town Key West.Designed for relaxing extended stays, Casa Del Sol℠...

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$435
avg per night
Key West Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Just a few houses off Duval, this wonderful retreat occupies the ground level of an almost 100-year-old home in one of the most desired locations in Old Town Key West. A large covered front porch welcomes you to sit and watch the Key West world go by, imagining what life was like in the early days of...

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$382
avg per night
Key West House
Sleeps 6, 3 bedrooms, 3 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

2/2 Main House, 1/1 Bunglow, Large Pool And Hot Tub On Beautiful Old Town LaneMulti-month Discounts availableHidden 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,...

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Featured review

"A little slice of heaven on earth"

The location is perfect - about 3 blocks from Duval, and 3 blocks from Truman, and a short bike ride to Ft. Zachary beach. We did not have a car, and did two Uber runs for groceries at Publix, then used...

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$614
avg per night
Key West Townhome
Sleeps 4, 2 bedrooms, 1.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to your Key West escape! Nestled in the heart of 'Old Town', this charming townhouse is part of a wonderful twelve townhouse community with a lush, tropical garden courtyard that provides a tranquil, resort-like feel. You're just a half-block from the quiet end of Duval Street,...

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$150
avg per night
Key West Condo
Sleeps 2, 0 bedrooms, 1 bathroom
2 reviews

Distance to beach: 0.5 miles to South Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • 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. * King size bed * WiFi included * check-out cleaning is an additional fee of $100 * Split AC system * flat screen TV * porch with table and 2 chairs This accommodation...

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Featured review

"Great unit"

This small unit had everything we needed. Very clean and convenient to everything we wanted to do. Will rent again! Pam was so easy to work with.

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$287
avg per night
Key West Studio
Sleeps 3, 0 bedrooms, 1 bathroom
8 reviews

Distance to beach: 22 yards to Public use + Private views Waldorf Astoria Resort

Key Amenities

  • Air conditioning
  • Oceanfront
  • Rentals by owner
  • WiFi

About this property

This beach view is beautiful and apartment in town can be yours EVEN IF FOR A SHORT VISIT! Just Blocks from downtown Key West? LIKE NO-WHERE ELSE! Like no where else in Key West, do Come + have YOUR, OWN OCEAN VIEWS! Yes! Secluded but not isolated? Yes!The island is very sensitive. The ocean...

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Featured review

"Amazing location!"

Our stay at the studio was lovely. The proximity to the ocean and beach cannot be beat. The place was very clean, well appointed, comfortable, and creatively decorated too. Our host was very responsive...

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$498
avg per night
Key West House
Sleeps 6, 2 bedrooms, 2 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Adorable historical conch house 2 bdrm, 2 full bath on quiet street with all the modern day amenities & decor in convenient location, relax by your private heated/chilled pool surrounded by decking and palm trees. Enjoy your morning sitting on the front porch watching the breeze travel through the...

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Featured review

"Key West paradise"

Beautiful home on a quiet street and close to everything. No need for a car. You can walk or ride bikes to anywhere on the island. Outdoor area is just right for a group of six. Totally enjoyed the...

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$317
avg per night
Key West Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Just a few houses off Duval, this wonderful retreat occupies the upper level of an almost 100-year-old home in one of the most desired locations in Old Town Key West. The carefully restored Dade County Pine wood walls and Red Oak floors evoke a more relaxed era in the Southernmost City. The home opens...

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$391
avg per night
Key West House
Sleeps 4, 2 bedrooms, 1 bathroom
4 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

The Sea View Cottage is a 2 bedroom, 1 bath home built within feet of the Atlantic Ocean with 180 degree ocean views.The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge.Fishing and diving just steps outside your door. Then at night, Key West is...

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Featured review

"Amazing Week in Paradise"

This gated estate is exceptional. The beach is just steps from the back door, and the ocean views are outstanding. The pool area is stunning and offers a beautiful place to relax and take in the scenery....

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$428
avg per night
Key West Townhome
Sleeps 4, 2 bedrooms, 1.5 bathrooms
2 reviews

Distance to beach: 2 miles to Smathers Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

**Peaceful Paradise in Key West Golf Club – Monthly Stays Welcome**Escape to serenity in this beautifully appointed 2-bedroom townhouse nestled within the gated Key West Golf Club community. Designed for monthly stays of 29 days or more, this home offers the perfect blend of comfort, convenience,...

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Featured review

"Three months in Paradise"

The townhouse and grounds are exactly as pictured and described! Staying on Stock Island was a great experience. Close enough to beaches and downtown Key West and the island itself offers a number of terrific...

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$233
avg per night
Key West Condo
Sleeps 2, 0 bedrooms, 1 bathroom
8 reviews

Distance to beach: 0.5 miles to South Beach

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

This Simonton Studio is neat, sweet and complete. *Cleaning fee of $100 is additional. * WiFi included * King size bed * Outdoor table and two chairs * spacious shower * excellent location for walking Old TownThis accommodation is the perfect location for exploring Key West. So, get out there...

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Featured review

"Superb Cottage"

This property is perfect for a couple or a single wanting a getaway to the vibes of Key West. It has everything you need from a comfortable bed, a cool air conditioner, a functional kitchen with all the...

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$288
avg per night
Key West House
Sleeps 6, 3 bedrooms, 2 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

The Sand dollar is a 3 bedroom, 2 bath home built within feet of the Atlantic Ocean with 180 degree ocean views.The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge.Fishing and diving just steps outside your door. Then at night, Key West is just...

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Featured review

"Paradise"

This is our 2nd stay at this vacation rental. We love the view, pool, dock, house, privacy and the owners. A must for anyone vacationing in the Keys!!

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$505
avg per night
Key West House
Sleeps 10, 5 bedrooms, 3 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

2 rental homes within 5 private gated acres of scenic beauty in the heart of the Florida Keys and 15 minutes to Key West. Located within the keys wildlife preserve, Sea View Estate is just a 15 minute drive to the shopping and nightlife of Key West and just minutes to some of the finest restaurants...

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Featured review

"Perfect in every way."

This is the perfect place for a Florida vacation. It has everything we were looking for and more. Private beach, quiet location, mature trees with coconuts and bananas. Tiki hut with a wet bar and comfy...

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$930
avg per night
Key West Townhome
Sleeps 7, 3 bedrooms, 3 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Relax with family and friends in your own tropical paradise at this spacious townhome in Key West's beautifully landscaped & maintained Golf Club. Located in a private gated community with resort style amenities, it is just minutes away from the beaches, world class restaurants, water sports...

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Featured review

"our vacation at Key West Golf Club"

We had wonderful time enjoying the beautiful weather and the beauty of all the attractions at Key West. Our condo was all we needed to fulfill our stay. It was clean and we enjoyed being right on the golf...

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$233
avg per night
Key West House
Sleeps 6, 3 bedrooms, 2.5 bathrooms
3 reviews

Distance to beach: 0.5 miles to Higg's Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Private Luxury Key West Home with Private Pool, surrounded by lush tropical landscaping in the Casa Marina neighborhood of Old Town.The fusion of a mid-century Florida home with dramatic Caribbean design, has created an ideal contemporary “Floribbean” style villa in the Casa Marina district...

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Featured review

"Stunning Private Villa in Key West - Fabulous Location!"

We were so impressed with this Key West hidden gem. Along with it's beauty, you feel the love and care the owners have for this private home, as they provided you with all the amenities, plus so much more....

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$431
avg per night
Key West House
Sleeps 10, 4 bedrooms, 3 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

The home (also known as Margaux's Hideaway) was built in 1890's, with a farmhouse charm, and porches off of every bedroom. It is light and airy, with gorgeous and comfortable indoor and outdoor living spaces. It's perfect for family gatherings, or just a quiet escape. Each room is sunny...

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Featured review

"The Perfect Home"

I came to this house with friends, completely unsure what to expect from Key West. The island itself moves at this fascinating, slightly calm/chaotic pace, but stepping into this rental felt like entering...

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$846
avg per night
Key West Condo
Sleeps 4, 2 bedrooms, 1 bathroom
2 reviews

Distance to beach: 0.8 miles to Fort Zachary Taylor State Park and Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Due to a change in licensing we are only available for monthly rentals. However I will consider offering a last minute deal pay for 3 and stay for 4. Please contact me directly.Here in Key West we believe in One Human Family where everyone is welcome and treated like family.Our condo has always...

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Featured review

"KWTrip"

Top notch place in great location. Very clean. Would definitely stay in this unit again sometime in the future.

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$397
avg per night
Key West Townhome
Sleeps 4, 2 bedrooms, 2 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to Key West Getaway in Old Town!In the heart of Old Town, Southard Square Condominiums is an award-winning condo development with stunning gardens, a clubhouse with changing rooms/baths, seating area, kitchenette and one of the largest private community swimming pools in Key West. Staying...

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Featured review

"Beautiful home"

Thank you for you help in researching a vacation rental . We love key west an we will be inquiring with you in the future

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$300
avg per night
Key West House
Sleeps 10, 4 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Island Dreaming – Your Luxury Key West Getaway - MONTHLY RENTAL Welcome to Paradise*** Please note for 2027 High Season rentals Jan- February - Arrival after the 5th of January for 6 week minimum is required in order to get accurate pricing***Discover the ultimate island retreat at Island...

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$682
avg per night
Key West Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Suncatcher on the Ocean – Available at 1800 AtlanticWe’re thrilled to introduce Suncatcher on the Ocean to the rental market at the prestigious 1800 Atlantic community. This stunning, newly renovated condo has been upgraded from top to bottom with high-end finishes and thoughtful details...

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$214
avg per night
Key West House
Sleeps 4, 2 bedrooms, 2 bathrooms
6 reviews

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

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

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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Featured review

"Just Perfect"

Southard Comfort is perfectly appointed and comfortable. There is nothing I can suggest to improve the experience. The house is nicely decorated, the kitchen is completely outfitted, the location is great...

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$370
avg per night
Key West House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

This estate has it all waterfront, large sun-filled pool and seawall dockage for your boat with over 3,800 sf of living space and 13,600 square feet of lush landscaped grounds. This private residence gives you the space and comfort one needs to relax and entertain your guests. The home was recently rented...

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Featured review

"Historic Downtown Vacation Stay"

Perfect spot to vacation!! Family friendly. This adorable house is downtown and close to everything!! I loved the yard and the porch was a favorite. Can't wait to return!

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$492
avg per night
Key West Cottage
Sleeps 2, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

This charming one bedroom cottage has everything you need. Full kitchen and living area to relax in. Outdoor backyard patio with gas grill. It is an easy walk to shopping and dining. If you have a car, this property offers a private parking space for your convenience. Please note this is a monthly...

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$133
avg per night
Key West Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

Art-Filled 1,700SF 3BR/2BA Old Town Key West Home with 2 Decks, Pool, Parking,++Large art-filled, two story Key West condo boasts 2 large inviting bedrooms, including a king bed, queen bed, and large office or third bedroom for extra flexibility. Guests enjoy living and dining rooms, 2 full bathrooms,...

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$310
avg per night
Key West House
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to Island Paradise, your serene retreat in the heart of Key West, Florida! Located in Old Town, Island Paradise is just a half block from the world-famous Duval Street. This charming property offers 2 bedrooms and 2 bathrooms, perfect for small families or couples looking for a relaxing and convenient...

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$227
avg per night
New
Special Offer
Key West House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Casa Atlantic is located in the upscale Casa Marina District on a quiet shrub lined street that has very little traffic, because it is not a through street. This luxury house that was built in 2013 with 1,672 sq. ft. of finished indoor space has everything that is needed, except refreshments and food....

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$387
avg per night
Key West Cottage
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 800 yards to Ft. Zachary Taylor State Park

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

SPECIAL OFFER. A GREAT 12 NIGHTS ARE AVAILABLE NOV. 9-21 FOR THE PRICE OF A WEEKAbout This Property A Touch of Bermuda is a privately owned, two-story Bermuda-style conch cottage in the Shipyard section of Truman Annex — one of only seven private townhomes available for rent in this gated,...

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Featured review

"Perfect condo in a perfect location!!"

Our stay for the month was perfect. A Touch of Bermuda has everything a guest could want in a perfect Key West location. However, the best part of our stay was dealing directly with the owner (Jack) throughout...

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$512
avg per night
Key West House
Sleeps 8, 4 bedrooms, 2.5 bathrooms
3 reviews

Distance to beach: 600 yards to Simonton Street Beach

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Enjoy an unforgettable stay at a one-of-a-kind ship-builder's home in the heart of Old Town Key West. You will be on a quiet lane in the most desirable neighborhood, just a few short blocks from dining, boating, fishing, galleries, theatre and entertainment. Unique features include open air kitchen...

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Featured review

"Excellent experience"

Management was informative and responsive. The home was perfect for our needs. Everything was pristine and well cared for. I would give this rental and the management the highest recommendation.

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$437
avg per night
Key West House
Sleeps 6, 3 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner

About this property

A phrase the locals use quite often here in Key West is that we are "Living the Dream" - if you come and spend some time here you will see why! Steps away from the Key West Seaport and just a few blocks from world famous Duval Street this property is located on Eaton Street in Old Town Key...

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$500
avg per night
Key West Condo
Sleeps 5, 2 bedrooms, 1 bathroom
6 reviews

Distance to beach: 0.2 miles to Fort Zachary Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

AMAZING LOCATION in TRUMAN ANNEX: SHABBY CHICKEN - come stay with the large & proud bird in town!! She's not too shabby after all, she is close to the action, but far enough from the riff-raff :) Large front yard and porch to watch Key West pass by. Beautiful and spacious in/outdoors. POOL within...

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Featured review

"Shabby Chicken was perfect"

Shabby Chicken was absolutely perfect. From the location, amenities, interior , exterior, proximity to Truman waterfront , Fort Zachary beach and the Green Parrot. Marie (and Tom) were awesome. Karen and...

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$427
avg per night
Key West House
Sleeps 8, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • WiFi

About this property

The welcoming views at Coral Cove are waiting for you! This brand new two-bedroom, two-bathroom home is located on the open water and canal on Saddlebunch Key, just a stone’s throw from the famous “Baby’s Coffee.” You’re at Milemarker 15 and Key West is just minutes away!This...

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$210
avg per night
Key West House
Sleeps 6, 3 bedrooms, 2 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Private home located in New Town available for 28 day minimum rental. Beautifully landscaped yard with secure private back yard and pool. The home features a kitchen with all appliances and granite counter top. The master suite opens onto the pool deck and is furnished with a king size bed and walk-in...

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Featured review

"Excellent location,beautiful house,outstanding owners!"

We stayed a month in December(2022),had everything we needed,close to shopping,sightseeing, nightlife,beaches and airport. House is completely furnished and nothing is lacking.Pool was heated and had all...

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$133
avg per night
Key West House
Sleeps 8, 4 bedrooms, 4 bathrooms
7 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to Casa Rosa, your tropical sanctuary nestled in the vibrant heart of Key West, Florida.*Saturday-to-Saturday Rentals OnlyProperty Overview:Prime Location: Casa Rosa is situated in a picturesque neighborhood, just one block away from Key West's renowned Duval Street. Casa Rosa...

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$1,001
avg per night
Key West Condo
Sleeps 4, 2 bedrooms, 1 bathroom

Distance to beach: 0.4 miles to Fort Zachary

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Escape the winter and settle into this beautifully renovated 2-bedroom, 1-bath condo in the heart of Old Town Key West — perfect for snowbirds and monthly renters seeking the ideal balance of tranquility and convenience. Located in the prestigious gated community of Truman Annex at the Shipyard...

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$245
avg per night
Key West Cottage
Sleeps 4, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Charming Pool Cottage in the Heart of Old Town Key WestPerfectly situated in historic Old Town Key West, this quaint and inviting pool cottage offers the ideal island escape for a couple, with room for occasional guests. Thoughtfully decorated and impeccably maintained, the home features a newly renovated...

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$173
avg per night
Key West Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Hot tub
  • Pool
  • WiFi

About this property

Beautifully Renovated 2BR/2BA Condo at Exclusive 1800 AtlanticExperience comfort and elegance in this beautifully renovated 2-bedroom, 2-bath condo located in the prestigious 1800 Atlantic community. Each bedroom features a king-size bed, generous closet space, and direct access to a private balcony...

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$190
avg per night
Key West Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

OFFERING A REDUCED RATE FOR JULY AND AUGUST DUE TO POOL RENOVATION. Sammy's Hideaway is located in a gated community with easy beach access. This 2 bedroom/2 bath condo faces the Atlantic Ocean offering wonderful ocean breezes and an oversized balcony with dining set. The open style living room has...

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Featured review

"Beautiful Apartment"

We stayed at 102 S at LaBrisa for Halloween. The apartment was clean and absolutely gorgeous. The view of the Atlantic Ocean was breathtaking. The pool was clean with warm salt water. The grounds were very...

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$251
avg per night
Key West Cottage
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 0.5 miles to Simonton Street Beach

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Welcome to the Dancing Rooster, your charming retreat just 2 blocks from Duval Street in the heart of downtown Key West! Nestled within the historic Simonton Cottage enclave, our recently renovated 3-bedroom, 2-bath home offers the perfect blend of comfort and convenience. You’ll be surrounded by...

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$616
avg per night
Key West Condo
Sleeps 4, 2 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Enjoy the ocean views from this beautifully appointed condo in the exclusive Key West Beach Club.This two-bedroom, two and half-bath waterfront condo that has been newly renovated with casual furnishing and all the comforts of home: central air conditioning, cable TV, washer/dryer, Wi-Fi, and a fully-equipped...

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$533
avg per night
Key West House
Sleeps 8, 3 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Pool
  • WiFi

About this property

Coral Hammock – 3BR/3BA Home with Pool Views in Coral Hammock3 Bedrooms | 3 Full Bathrooms | Sleeps up to 8 | Backs to Community PoolWelcome to Coral Hammock, your home away from home in beautiful Key West! Built in 2004 and meticulously maintained, this spacious 3-bedroom, 3-bathroom home...

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Featured review

"Southern Charm with a boat slip!"

Our family had a wonderful time staying in this townhome style rental. We relaxed and enjoyed the views of the bay and marina from the back porch. The boat slip worked great for our rental boat. This...

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$460
avg per night
Key West Condo
Sleeps 4, 2 bedrooms, 1 bathroom

Distance to beach: 0.4 miles to Fort Zachary Taylor State Park

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Key West is just like the Caribbean, always warm with lovely turquoise waters. It's a short walk to Mallory Square, Hemingway's Home, the Truman White House, Duval Street and Zachary Taylor Park ( do yoga on the beach, swim, snorkel, or hang hammocks between the palms). Walk to shops, restaurants,...

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$149
avg per night
Full map
Map

What staying in Key West actually costs

Florida and Monroe County require a 12.5% tax, which includes a 6% state sales tax, 1.5% county surtax, 4% tourist development tax, and 1% tourist impact tax. The owner sets the cleaning fee, damage waiver, and any additional costs, but because you book directly with them, there isn’t a booking fee on top.

SHORT STAY
3 nights

$2,042

all in
$505/night

$505 × 3 nights$1,515
Cleaning + damage waiver$300
Tax (12.5%)$227
Booking fee$0
Total$2,042

WEEKLY STAY
7 nights

$4,181

all in
$488/night

$488 × 7 nights$3,416
Cleaning + damage waiver$300
Tax (12.5%)$465
Booking fee$0
Total$4,181

MONTHLY STAY
30 nights

$14,681

all in
$425/night

$425 × 30 nights$12,750
Cleaning + damage waiver$300
Tax (12.5%)$1,631
Booking fee$0
Total$14,681

When to visit Key West

The best time to visit Key West is spring, when the air sits in the low 80s and the water has warmed to the high 70s without the risk of summer storms. Winter runs a close second, since the water is still in the low 70s, making Key West a nice escape for snowbirds. Come June, the heat and the afternoon storms arrive together, with the majority of the area’s rain concentrated between June and October.

Peak rates Best value Shoulder Air temperature
MonthMedian nightlyDifference from annualHigh / low air tempWhat’s going on
January$398+33%75° / 65°Literary Seminar; Food and Wine Festival
February$400+33%76° / 66°Art and Craft Festival at Truman Waterfront
March$398+33%79° / 69°Conch Shell Blowing Contest; Taste of Key West; spiny lobster season ends
April$325+8%82° / 72°Conch Republic Independence Celebration
May$295-2%85° / 76°Songwriters Festival; Minimal Regatta, Memorial Day weekend
June$249-17%88° / 81°Pride, closing with the parade down Duval
July$249-17%89° / 80°Hemingway Days, with the look-alike contest at Sloppy Joe's
August$225-25%90° / 79°Spiny lobster season opens
September$250-17%88° / 79°WomenFest; Just a Few Friends; BrewFest
October$283-6%85° / 76°Fantasy Fest, ending the last Sunday; Goombay on Petronia Street
November$3000%81° / 72°Film Festival; Harbor Walk of Lights from Thanksgiving eve
December$318+6%77° / 67°Lighted Boat Parade; New Year's Eve drops

Based on the median Key West nightly rate on FloridaRentals.com.



Where to stay in Key West

You can bike the length of the island in about 30 minutes. Lively Old Town holds the historic district, Duval Street, and the Historic Seaport. New Town runs east toward the airport. It’s more suburban, but the buildings are newer and city code requires each licensed rental to have an off-street parking space, a rule that does not apply inside the historic district.

Map of Key West vacation rental areas
FLORIDA KEYS
Rental areas in Key West: Old Town and 1800 Atlantic. Geometry from US Census TIGER/Line, public domain.
Old Town →
Charming, colorful wooden houses fill Old Town. Duval, the Historic Seaport, and Fausto's grocery are all a walk away, and there’s plenty to see and do.
32 rentals · from $133
1800 Atlantic →
These condos on the Atlantic shoreline have a sandy area out front and shared pools. It’s a short walk to Smathers Beach.
10 rentals · from $183

Things worth doing in Key West

Fort Zachary Taylor Historic State Park
Fort Zachary Taylor Historic State Park
Visit a Civil War fortress, then snorkel on the clear shoreline. Gear is available for rent and bringing water shoes is recommended. There is a modest entry fee per vehicle.
Truman Annex
Mallory Square Sunset Celebration
Mallory Square Sunset Celebration
A tradition since the 1960s, performers and artisans take over the dock every evening, starting about two hours before sunset. Walk the area and enjoy the unique entertainment.
Old Town
Dry Tortugas National Park
Dry Tortugas National Park
Fort Jefferson sits 70 miles west. The ferry leaves the Historic Seaport and runs about 2.25 hours each way. Day trips sell out weeks ahead. You can book campsites for overnight adventures.
Old Town
The Ernest Hemingway Home & Museum
The Ernest Hemingway Home & Museum
Guided tours start every 15 minutes from 9:15 a.m. daily, and reservations aren’t needed. Nearly 60 cats live on the grounds, about half of them six-toed, descended from a cat given to the author in the 1930s.
Old Town
Truman Waterfront Park
Truman Waterfront Park
Kids can play at this scenic park with a playground, trails, and a splash pad. Find it at the end of Southard Street, open 7 a.m. to 11 p.m.
Bahama Village edge

Know before you book

Key West has its own airport.

Seven airlines run scheduled nonstop service into Key West International, three to four miles from Duval and about 15 minutes by car. Driving from Miami is about 160 miles (around 4 hours), and US-1 is the only road in.

Parking can be difficult.

On-street parking in Old Town's commercial blocks is paid through the Passport Parking app, and no vehicle may sit on a city street longer than 72 hours. The Old Town garage at Grinnell and Caroline is open 24 hours, and paying there covers the city bus for everyone in the car.

There’s a tiered storm evacuation system.

While evacuations are rare, if they do happen, Monroe County begins a mandatory visitor evacuation about 48 hours ahead of tropical storm winds and residents about 30 hours out. Key West is Zone 1, farthest from the mainland, and US-1 is the only road off the island.

Licensed rentals post a medallion by the door.

The island has only so many short-stay licenses, so a week can be harder to find than a month. A licensed rental must post a medallion with contact information outside, and the city keeps a public list of licensed addresses.


Key West vacation rental FAQs

Straight answers to what people ask us most.

How much does a vacation rental in Key West cost?

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The median Key West vacation rental cost is $356 a night. A week comes to about $3,416 and a month to about $12,759. On top of the nightly rate you will pay 12.5% tax and, on most listings, a cleaning fee. There is no booking fee because you pay the owner directly rather than through us.

What is the cheapest month to visit Key West?

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August is the cheapest month to visit Key West due to heat, humidity, and the chance of rain. Surrounding summer months are also affordable options with the same tradeoffs. The driest, mildest, most expensive stretch runs December through April.

Does Key West have beaches?

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Yes, but not the kind most people picture. Smathers and Higgs are city beaches on the Atlantic side, both rebuilt with sand trucked from mainland Florida mines. The state lists nearly the whole south shore as critically eroded. Fort Zachary Taylor's is sand and pebbles over a rocky bottom. For a genuinely wide sand beach, Bahia Honda State Park is up US-1, and the nearest rentals are on Big Pine Key.

Why do so many Key West rentals require longer stays?

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The city caps how many short-stay licenses exist, and they change hands rather than being issued new, so the supply is fixed.

Is Key West dog friendly?

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Key West is fairly dog friendly. Dog Beach at 1500 Vernon Avenue is the city beach where dogs can swim, open sunrise to sunset. Higgs Beach has a fenced dog park, though dogs are not allowed on the Higgs sand itself.

Is Key West a good place to visit with kids?

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Yes. Truman Waterfront Park has a free playground, trails, and a splash pad at the end of Southard Street. The Key West Butterfly and Nature Conservatory on Duval keeps 50 to 60 butterfly species, exotic birds, and two flamingos under a glass dome. And the Hemingway Home's cats win over children who would not otherwise sit through a house tour.

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