1 BR | 1 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Located within the gated community of Truman Annex, you are just steps away from the new Truman Waterfront Park and only 2 blocks from the famous Duval St. Enjoy the heart of Old Town Key West and all its charms! Stroll or bike to many of the historic sites such as Hemingway House and Little Truman White ...
Property Type
Key West Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
This home is meticulously cared for and will not disappoint! One story living with an open airy feel in all living and entertaining areas while bathrooms are easily accessible and bedrooms are tucked away for privacy and serenity. Indoor entertaining will not be an issue for the kitchen is newly and beautifully ...
Property Type
Key West House
6 BR | 6.5 BA | Sleeps 16 | Quick View
Distance to beach: 0.3 miles to Ft Zachary Taylor
Key Amenities
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 ...
Property Type
Key West Villa
2 BR | 1.5 BA | Sleeps 4 | Quick View
Distance to beach: 2 miles to Smathers Beach
Key Amenities
About this property
Come stay in a premier development in Key West. This is a great location to stay with a monthly rental minimum. Yearly rates available. You are close to everything Key West has to offer. Renovated 2019. Our house offers many amenities to make your stay comfortable and convenient. Each Bedroom on the ...
Property Type
Key West Townhome
The owners are amazing to work with. The house is newly remodeled and furnished. It was just perfect for 4 people and we had a wonderful time! We were just a few minutes to great restaurants on Stock Island ...
Studio | 1 BA | Sleeps 2 | Quick View
Key Amenities
About this property
Overlooking the Historic Key West Bight, this bright and clean studio features a fully equipped kitchen, renovated bathroom, front loading washer/dryer, 4K smart TV, and one of the best people watching front porches in Key West. Steps from the water, just 3 blocks from Duval street, and surrounded by ...
Property Type
Key West Studio
We stayed at this property for 6 weeks. The location is awesome! It is steps away from the marina, a short walk to a small beach, and just several blocks from Duval Street. The location is also set in close ...
3 BR | 2 BA | Sleeps 6 | Quick View
Distance to beach: 150 yards to Smathers Beach
Key Amenities
About this property
Bluegrass Seabbatical is a Spectacular 3 bedroom 2 bath oceanfront condominium at 1800 Atlantic. Enjoy the incredible ocean front view from all 3 bedrooms and the living room. This property is close to 2000 sq feet and can be your fantastic home away from home. Available for extended stays during the ...
Property Type
Key West Condo
This condo has the most beautiful views. I also love the full kitchen and ammenities. Perfect for a relaxing getaway with a huge balcony overlooking the ocean.
2 BR | 2 BA | Sleeps 6 | Quick View
Distance to beach: 800 yards to Ft. Zachary Taylor State Park
Key Amenities
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 private town home (one of only seven available for ...
Property Type
Key West Cottage
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.
3 BR | 3 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Down a very quite lane the house has one off street parking spot.Enter from gate through lush and colorful walk to front door of main house . Enter into the living room with smart tv ,through to the right into the dinning area. The kitchen is off to the left. There is a large working counter with seating ...
Property Type
Key West House
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Once you see this historic two storey townhouse, you won’t want to stay anywhere else!Filled with natural light, this end unit is ‘tucked away’ in an exclusive, historic Foundry building next to the ‘Truman Little Whitehouse’. There are only 3 residences in our building!There ...
Property Type
Key West Townhome
Yes, this end unit is "One of a Kind"! Many thanks to Rosemary & Mark. Their spacious, quiet & immaculate home has been our great winter escape. This was our third stay at this remarkable townhouse in ...
3 BR | 2 BA | Sleeps 6 | Quick View
Distance to beach: 4 miles to Smathers
Key Amenities
About this property
COVID-19 UPDATE: Key West and Monroe County are opening to visitors June 1! Restuarants will be open at 50% capacity and bars that do not serve food will remain closed. MONTHLY RENTALS ONLY We purchased Bougainvillea Villa in late 2014 as our future retirement home. The villa was built in the early ...
Property Type
Key West House
Nothing is missing from this very clean and very well organized beautiful home situated on a wide lagoon. For us, the highlight is the superb view of the wide lagoon from the window wall across the entire ...
2 BR | 2.5 BA | Sleeps 6 | Quick View
Distance to beach: 0.3 miles to Ft. Zachary Taylor Beach
Key Amenities
About this property
Located in the gated community of Truman Annex: a popular and beautifully landscaped community in Old Town Key West. Enjoy the peaceful tropical landscape and pool while only 2 blocks from the excitement of Duval St. We are just outside the entrance to Ft Zachary Taylor State Park and Beach and so close ...
Property Type
Key West House
Beautiful condo in a great part of town. It was exactly as advertised. Wonderful. We visited the fort, beaches, pool, and numerous restaurants, bars, and shops. It was Fantasy Fest week. We ate at Bagtell’s, ...
1 BR | 1 BA | Sleeps 3 | Quick View
Distance to beach: 0.3 miles to Ft. Zachary Taylor
Key Amenities
About this property
This upscale home has been meticulously renovated with our guests' complete comfort in mind. Located in the gated community of Truman Annex: a popular and beautifully landscaped community in Old Town Key West. Enjoy the peaceful tropical landscape and pool while only 2 blocks from the excitement of Duval ...
Property Type
Key West Condo
This was our first experience staying in a condo instead of hotel and we could not have made a better choice! We got married on Smathers Beach December 5th and stayed 6th-12th. This condo is lovely and ...
4 BR | 4 BA | Sleeps 10 | Quick View
Key Amenities
About this property
Cock-a-doodle-do Vacation Rental, named for Key West's beloved chicken population, is a mid-town oasis! 5 minute drive to Old Town or take Uber for just $ 10!A meticulously updated pool home with beautifully lush landscaped grounds and plenty of space for everyone! The main house is a 3/3 (1 King, ...
Property Type
Key West House
2 BR | 1 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Stay in a beautifully appointed villa or cottage located directly on the Atlantic Ocean. Only a 15 minute drive to Key West's history, restaurants and nightlife, this tropical retreat known as Sea Vista, is as serene as a private island.Enjoy full use of direct TV channels, free current video library ...
Property Type
Key West House
3 BR | 2 BA | Sleeps 6 | Quick View
Distance to beach: 20 yards to Private beach at Marina
Key Amenities
About this property
Beautiful fully furnished floating home. Coconuts is a sturdy steel hull Florida Bay Coaster. She is safely located at the Stock Island Yacht Club and Marina. In a convenient slip. Full marina amenities including pool, grounds, gated and free parking, laundry steps nearby. Full size refrigerator, dishwasher, ...
Property Type
Key West Houseboat
2 BR | 2 BA | Sleeps 5 | Quick View
Key Amenities
About this property
2 Bedrooms, 2 Baths, Sleeps 5This luxury 2 bedroom, 2 bath condominium is located in The Truman Annex Shipyard gated community. Spend your day lounging in the pool just steps from the front door. Take a relaxing stroll through the Truman Waterfront park or catch a show at the new Ampitheatre. Enjoy ...
Property Type
Key West Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Distance to beach: 1 miles to Fort Zachary Taylor, Higgs Beach, Smathers Beach
Key Amenities
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 ...
Property Type
Key West Apartment
3 BR | 2 BA | Sleeps 6 | Quick View
Distance to beach: 30 feet to property 20 yards from ocean, 4 mile white sand be
Key Amenities
About this property
Go to virtual tourIn Key West - Not Islands Away * ** Ocean Front**Ocean View From Every Room *90' Scenic Balcony Huge 2200 Sq Ft under air. **SPECIAL REDUCED RATES FOR ANNUAL, OR OTHER LONG TERM RENTALS **** Notice: Due to Corona Virus We suggest you purchase "Cancel For Any Reason Insurance". ...
Property Type
Key West Apartment
3 BR | 3 BA | Sleeps 6 | Quick View
Key Amenities
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 ...
Property Type
Key West House
2 BR | 1 BA | Sleeps 6 | Quick View
Key Amenities
About this property
The Space Y Knot is a 44 foot trawler yacht with 2 staterooms, a full head with walk in shower, a complete galley complimented by 2 refrigerators, freezer, stove/oven and microwave. Dining booth sits 6 adults. The v-berth stateroom has 3 double berths and 1 single birth. The small stateroom has 2 single ...
Property Type
Key West Yacht
3 BR | 2.5 BA | Sleeps 6 | Quick View
Distance to beach: 0.5 miles to Higg's Beach
Key Amenities
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 ...
Property Type
Key West House
Four of us , and our dog, stayed at Lynda’s beautiful home in Casa Marina area. We had a wonderful month there. The location was great and quiet. We spent most of our time enjoying the covered deck ...
3 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Private home located in New Town available for 4 week minimum rental. Beautifully landscaped yard with secure private back yard and pool. Use of bicycles and four passenger electric car provide flexible transportation all over the island. The home features a modern kitchen with all appliances and granite ...
Property Type
Key West House
What a lovely stay - I heartily recommend and hope that I will be back in the future. The house was great, but I think the pool was my favorite place to be! Really enjoyed the owners’ thoughtful attention ...
3 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
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 ...
Property Type
Key West House
3 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Sea Vista EstateStay in a beautifully appointed villa or cottage located directly on the Atlantic Ocean. Only a 15 minute drive to Key West's history, restaurants and nightlife, this tropical retreat known as Sea Vista, is as serene as a private island.Enjoy full use of direct TV channels, free ...
Property Type
Key West House
4 BR | 2 BA | Sleeps 8 | Quick View
Key Amenities
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 ...
Property Type
Key West House
2 BR | 2 BA | Sleeps 6 | Quick View
Distance to beach: 1 miles to Smathers Beach
Key Amenities
About this property
Enjoy the comforts of home in the midst of paradise.Comfortable, reasonably priced 2-bedroom condominium in Sunrise Suites Resort. The Resort offers concierge service, heated swimming pool, outdoor spa, gym facilities, tennis court and Internet service. The unit is on the 3rd floor, accessible by ...
Property Type
Key West Condo
Trip was cancelled due to covid19 concern. Hopefully will be able to reschedule. I still want to visit Key West and the many sights in the area. The reservations were cancelled without any problem. So ...
1 BR | 1 BA | Sleeps 2 | Quick View
Key Amenities
About this property
Our beautiful deluxe one bedroom condo in Key West Florida on Southard Street is just blocks from the ocean and Duval street. Located in historic old town, the condo is enclosed in a beautiful garden on the ground floor.It is approximately 950 sq ft of air- conditioned luxury. There is a king size ...
Property Type
Key West Condo
3 BR | 3 BA | Sleeps 7 | Quick View
Key Amenities
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 and ...
Property Type
Key West Townhome
2 BR | 2 BA | Sleeps 6 | Quick View
Distance to beach: 1 miles to Fort Zachery Taylor State Park
Key Amenities
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 ...
Property Type
Key West House
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 ...
5 BR | 3 BA | Sleeps 10 | Quick View
Key Amenities
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 ...
Property Type
Key West House
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
Beachfront home located on privately owned Sugarloaf Beach. This gated estate offers 350 feet of private beach and 4 acres of tropical gardens. The gardens have tropical plants and bananas that have been collected from all around the world. This 2 bedroom home is beautifully and fully furnished with central ...
Property Type
Key West House
Our vacation to Sugarloaf Key was amazing!! The location is perfect with stunning views of the water. The fishing off the pier was good. You could catch all the Snapper you wanted. The beach area was ...
2 BR | 1 BA | Sleeps 4 | Quick View
Key Amenities
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 ...
Property Type
Key West House
2 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
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 ...
Property Type
Key West House
2 BR | 1 BA | Sleeps 4 | Quick View
Distance to beach: 0.5 miles to Ft. Zachary Taylor State Park
Key Amenities
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 ...
Property Type
Key West Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Key Amenities
About this property
The Jungle Breeze condo at LaBrisa Condominiums is a 1 bedroom, 1 bath apartment * 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 * Check-out cleaning included * This ...
Property Type
Key West Condo
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 ...
1 BR | 1 BA | Sleeps 6 | Quick View
Key Amenities
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 ...
Property Type
Key West Townhome
Studio | 1 BA | Sleeps 2 | Quick View
Distance to beach: 0.5 miles to South Beach
Key Amenities
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 ...
Property Type
Key West Condo
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 ...
1 BR | 1 BA | Sleeps 2 | Quick View
Key Amenities
About this property
This lovely quiet sun filled resort apartment is located just across the street from Smather's beach and a ten minutes walk from Old Town. Artistically furnished and serviced by an elevator the apartment is located on the second floor facing southwest where you can enjoy a lovely view of the enormous ...
Property Type
Key West Apartment
I loved my stay in 219c Key West by the Sea! It was across the street from the beach where I could take morning walks seeing gulls and pelicans fishing for their breakfast. The apt. Is light, bright, and ...
3 BR | 3 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Tropical seclusion and privacy at its very best. Located just 15 miles from Key West. This luxury rental consists of 2 full suites. The first floor has a roomy living room, huge screen porch, queen sleeper sofa, bath and bedroom connected by an exterior staircase to the second floor. The second floor ...
Property Type
Key West House
Studio | 1 BA | Sleeps 3 | Quick View
Distance to beach: 22 yards to Public use + Private views Waldorf Astoria Resort
Key Amenities
About this property
Welcome to your Ocean Views Studio! Get yourself dates before flights! Art studio is smaller - 2 Base rate room and tax- see listing info. But Before you book any dates! see listing -FAQ's, travel insurance Notes + Additional info for clarity- good knowledge - + no surprises, no refunds, stay ...
Property Type
Key West Studio
This was an amazing place to stay. Great views. Holly was very gracious. Place was very clean. We loved it and plan to make this our spot when w revisit Key West.
Studio | 1 BA | Sleeps 2 | Quick View
Distance to beach: 0.5 miles to South Beach
Key Amenities
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 ...
Property Type
Key West Condo
Stay steps from the sand in your Key West vacation rental
Relaxing, laid-back Key West calls to beach bums who prefer their landscape pristine and untouched. Key West is famous for watersports, nightlife, beaches and historic sites. Don’t miss Duval Street, one of the most energetic strips of shops, bars and cafes in Florida. Whether you prefer culture or the outdoors, Key West has plenty to offer in a relaxed, welcoming atmosphere.
From a romantic bungalow for a couple to a house that can fit your entire family and more, the Key West house rentals are endless. When staying in one of our Key West vacation rentals instead of hotel, you’ll have much more space and privacy, plus cost savings when booking a property for a large group. Some of our condos and villas even come with special amenities like a set of bicycles, chef’s kitchen, and in-home theater. Use the filters to narrow down your choices and choose the property that calls to you, just like Key West does.
Key West, Florida travel advice
Thanks to economic boom and a bustling cigar industry, this area's became quite a hot spot by the turn of the 20th century. Surrounded by the Gulf of Mexico, Key West offers visitors ample natural beauty and great swimming beaches. History buffs love the island’s maritime history and legends of its famous residents, while partygoers can’t get enough of Duval Street. Located closer to Cuba than to Miami, Key West offers endless Latin and Cuban cultural influences from the cuisine to the music and art. Running four miles long and about two miles wide at its widest, this is a small island. The popular Old Town makes up about half of this area.
Climate
Abundant sunshine and gentle breezes make Key West one of the most popular tourist destinations in Florida. With over 320 sunny days per year you’ll most likely get the weather you want, no matter when you visit. Be sure to bring plenty of sunscreen and beach umbrellas as the UV rays can be quite strong here. The sea temperature is almost bath water and you’ll love the turquoise-blue color.
Top activities and attractions
Even getting to Key West is an adventure. The Overseas Highway is one of the most beautiful drives in the country. Completed in 1938, it connects a string of cays and coral rock with 113 miles of concrete roadway. The aptly named Seven Mile Bridge is the longest and most scenic of the entire route.
Key West’s diverse and unique ecosystems are a result of the convergence of two major bodies of water. There’s endless entertainment to be had on the ocean. You’ve got the deep blue Atlantic and its Gulf Stream current to the south and the shallow flats of the Gulf of Mexico to the west. From deep sea fishing to parasailing and even just body surfing, you’ll love a day out on the water in Key West.
Hop on the Conch Tour Train for a fun way to see the surrounding area. You’ll get a narration of the city’s past from an experienced tour guide as you cruise around the streets. Walking tours are one of the best ways to see the city, too. Peek in at the area’s intriguing architecture, courtyards, and gardens.
On the presidential side of life, don't miss a tour of the Harry S. Truman Little White House, a command center during World War I and II as well as the winter home of President Harry S. Truman. Fort Zachary Taylor Historic State Park is a great place to swim, snorkel, and catch the sunset.
Dining and Nightlife
Over 300 restaurants and bars make this city one of the most fun places to be in southern Florida. For those with a sophisticated palate, try the highly-rated Bien restaurant to indulge in Latin & Cuban flavors. For great sandwiches and service, eat at the cleverly named Munch Box to break up your day of adventure. For Korean food that will make you scream “WOW”, pop in to Garbo’s Lunchbox. And lastly, for those who love to brunch, visit Key Plaza Creperie for delicious breakfast foods.
At night, Duval Street is the place to be. The Green Parrot is Key West’s oldest bar but it’s still a rockin’ atmosphere. Famed local Ernest Hemingway loved to get sauced at Sloppy Joe’s bar. (Don’t miss the Ernest Hemingway Home & Museum to get a closer look at what made this famous author tick.) For those who like the legitimate arts, take in a performance at Key West’s Fringe Theater, the Red Barn Theatre, or the Waterfront Playhouse.
For the kids, take the family to Mallory Square, where you’ll find local performers, plenty of fried food, and gorgeous sunset views.
Key West vacation homes on FloridaRentals.com
Vacation rentals in Key West on FloridaRentals.com can save you up to 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Happy planning!
