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At Home Key West Vacation Rentals

Cozy Cottage In The Calm White Street Art District

Paradise Place Monthly Vacation Rental by At Home in Key West

In the mellow White Street Art District neighborhood of historic Key West, this marshmallow-white, one-bedroom cottages charm more than makes up for what it misses in size. The cobalt blue Smeg fridge in the kitchen is a colorful contrast to the spaces white-meets-lightwood decor, with vintage beach photos completing the retro-glam vibe. Rent a bike or scooter from a nearby shop and you can zip to all the island’s best sites in a hurry.

Recreational Lodging Vacation Rentals

TAKE NOTE: Click HERE to visit the MWR & CYP Covid-19 Update page. You will find the most accurate and up to date information on facility closures and on our efforts to mitigate the spread and keep our patrons and staff healthy and mission ready.

HERE to view Recreational Lodging Vacation Rentals 2022 rate increase, effective 1 January. Please note, all preexisting reservations will be honored at the rate they were booked at.

The Recreational Lodging Vacation Rentals is open for leisure travel.

  • For reservations call the Vacation Rentals Office: 305-293-5000/5001
  • Cottages will not be available until further notice

Recreational Lodging Vacation Rentals, located on Trumbo Point, provides the best quality and value in lodging for leisure travel to Key West. Vacation Rentals offers 3 bedroom/1.5 bathroom townhouses as well as 2 bedroom/1 bathroom cottages. Each unit is fully furnished and includes cable TV. Active Duty may make reservations up to 1 year in advance, retired military, eligible veterans, and DoD civilians may reserve up to 6 months in advance.

Managing & Renting The Finest Vacation Rental Homes In Key West

Through Historic Hideaways, you can rent and enjoy a Key West Vacation Rental for the same amount of money…or less…than it costs to rent a hotel room! Choose from private and historic Key West Vacation Rental homes with private pools, or a cozy cottage, or condominiums or townhomes with a shared pool. Each of the unique and charming Key West Vacation Rentals on our website has a detailed description, along with great interior and exterior photos, a list of amenities, and a map location.

In addition to the convenience of our Online Booking and Real Time availability check, our website can answer your most Frequently Asked Questions. You can also get information on our Rental Rules and Procedures, see copies of our Rental Contracts, and even get some information on the benefits of the Travel Insurance we offer. We think you’ll enjoy looking through some of the beautiful Key West Vacation Rentals that Historic Hideaways is proud to represent.

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Book Boutique Vacation Rentals In Key West

Welcome to Key West, a sunny and picturesque island town in the Florida Keys. Find yourself in paradise with our luxury Key West vacation rental homes, condos, and cottages. Our properties are mainly located in the Key West Historic District, on the western side of the island. This desirable area has charming architecture, as well as top points of interest.

Admire Local Talent At Studios Of Key West

Vacation Home Luxury Key West Vacation Rental, FL ...

Free-spirited Key West has long been a haven for artists and creatives. There’s no better place to discover the scene than The Studios of Key West, a 3-story space showcasing works from local artists. Continue the theme at Hemingway House, a handsome Spanish Colonial estate that was once a sanctuary for the American novelist. If you want to meet one of Key West’s most passionate eco-activists, head to Nancy Forrester’s Secret Garden. From chirpy parrots to multicolored macaws, this backyard oasis offers a unique opportunity to get up close and personal with exotic Floridian birds.

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Choose A Key West Vacation Rental For An Unforgettable Beach Vacation

Key West is the place to go if you’re looking for fantastic diving and snorkeling whilst maintaining all the benefits of a city break. It is ideal for any type of stay, from a weekend getaway to a longer vacation. Relish a quiet seaside break and soak up the Caribbean vibes by staying in a Key West vacation rental. Key West has it all, from tranquil seaside nooks to lively entertainment.

Book Your Vacation With At Home In Key West

In business since 1997 and located in the heart of Old Town Key West, At Home in Key West offers a wide variety of vacation rentals available for nightly, weekly, or monthly stays. Our Key West rentals range from historic Conch homes with high ceilings and wraparound balconies to brand new condos overlooking the breathtaking vista of the Atlantic Ocean. Stay in the center of it all, or enjoy privacy and quiet. Our vacation rentals in Key West can accommodate groups of all sizes and needs, whether youre looking for a home with a pool or a place to bring your dog along for the trip.

Our local team lives and plays on the island and knows everything Key West has to offer. Don’t hesitate to reach out to us for help finding your ideal Key West vacation rental and planning the perfect vacation.

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Where Is Key West Fl

Our Key West vacation rentals, condos, and cottages are on the last island of the Florida Keys chain, about 160 miles from Miami and 98 miles from Key Largo. Whether you chose to arrive at this interesting island via plane, ferry, or car, the first sight of the expansive Atlantic Ocean promises to take your breath away. With its vibrant wildlife, you may even be lucky enough to spot a few dolphins splashing around and welcoming you to Key West.

Activities Near Key West Vacation Homes

Tumi’s Time Out Monthly Vacation Rental by At Home in Key West

As the sun starts to set, Mallory Square gears up for a night of family-friendly fun. It’s essentially one big street party, with fire breathers, tightrope walking dogs, tumbling acrobats and more. You’ll also find plenty of action on Duval Street, a lively strip lined with neon-lit bars, theaters, galleries and boutiques. For a quieter scene, why not retreat to the deck of your Key West vacation rental villa for fruity Rum Runner cocktails and Floridian sunsets? For more action, you can snorkel at coral reefs, kayak in crystal-clear water, swim with dolphins, sail on catamarans and more.

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At Home In Key West Inc

Welcome home to Key West! At Home in Key West offers you all the comforts of home, whether it’s a cute cottage in Old Town, a townhome …

Welcome home to Key West! At Home in Key West offers you all the comforts of home, whether it’s a cute cottage in Old Town, a townhome in the Truman Annex or a condo over looking the Atlantic Ocean. Why stay in a small, cramped, expensive hotel room when you can relax in a home of your own. We have accommodations to suit any style, location or price you need.Built on a reputation of customer service and friendly and fair dealings At Home has been happily providing accommodations in Key West since 1997.Our reservation staff will work with you to help you choose the perfect rental home for your special getaway. Whether you would like to be in Old Town experiencing the hustle and bustle of Duval Street or in one of our quieter neighborhoods, we’ll make sure to match you with the perfect island home.

Office located in

Faqs When Booking A Vacation Rental In Key West

How much is a vacation rental in Key West?

KAYAK users have found vacation rentals in Key West for as cheap as $584 in the last 3 days. The average price is $1,177.

How much is a vacation rental in Key West for tonight?

In the last 72 hours, users have found Key West vacation rentals for tonight for as low as $453.

Which are the most popular Key West neighborhoods to stay in?

Vacation rentals in Old Town North of Truman, Old Town South of Truman and Truman Annex have the most searches on KAYAK. For more information about Key West’s different neighborhoods, check out our Key West’s City Guide.

How can I find vacation rentals near me in Key West?

Take a look at our vacation rentals map to find the best vacation rental homes near you.

Which Key West vacation rental offers outdoor activities?

If you want to enjoy outdoor activities while away on vacation, consider staying at Key West Villas. The accommodation offers a tennis court along with tennis equipment, including rackets and balls. There is also a trainer always present for anyone wishing to learn the game’s rules, with first aid services also available at all times.

Which vacation rental provides laundry services?

Old Town Suites is one of several Key West house rentals that offer laundry services. Book a stay at this establishment to save yourself from the inconvenience of traveling back home with dirty laundry. Moreover, guests with families and business travelers find these services incredibly convenient.

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Make Key West Your Next Getawaychoose From 144 Great Vacation Rentals

For an island that is only two miles long and four miles wide, you’d think it would be a quiet place, demanding long trips outside the immediate area to reach attractions, good food, and historical sites. However, that’s far from the case when you book one of our Key West vacation rentals! With a vibrant arts culture, a variety of opportunities for outdoor adventures, and a welcoming small-town attitude, Key West promises a unique and memorable beach vacation.

Vacation Rentals Sales & Key West Awesomeness

Casa, Suite Casa: Monthly Vacation House Rental in Old ...

Get to know Last Key Realty, our unique approach to luxury vacation rentals, and our vision for your stay in Key West when you choose to spend it in a Last Key vacation home.

We are Last Key Realty, a Key West Vacation Rental broker, a Buyers Broker, and a Property Manager in Key West, FL. We are a company of people who are passionate about Key West, and who feel a special responsibility to those visiting the Keys, those pursuing the purchase of property in the Keys, and those in need of property management services for their rental homes in the Keys. We want our guests and clients to come away feeling the same magic that we felt ourselves when we first came to Key West, and the same magic that has kept us here since.

Each of the homes on our website have been designed and furnished with that unique Conch Republic flavor, but also with the idea that our guests should feel right at home. With so many vacation homes making do with the barest of essentials, each of the homes we have to offer will come as a pleasant surprise. We also pride ourselves in the service we provide for our guests, whether its just recommending a great restaurant, or dealing with a maintenance issue in the least amount of time possible. If you have any questions, you can call us at any time.

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Outdoor Activities In Key West Fl

With so many diverse outdoor activities near our Key West condos and cottage rentals, it might be difficult to decide where to start. However, one thing is for surewater is Key West’s playground. Book a charter with Sunset Sail Key West and admire the wildlife or catch one of those famous Florida sunsets. With early morning sunrise cruises, starlit float trips, snorkeling, and themes like “Cruise Concert” and “Wine and Wind” at dusk, there’s something for everyone.

While sandy beaches are not as common in the Keys due to the reef barrier, there are a few favorites that are worth a visit, including Smathers Beach, Ft. Zachary Taylor State Park, and the Dry Tortugas National Park, home to epic sandy beaches and historic Fort Jefferson.

The natural beauty of Key West has been preserved thanks to the recent emphasis placed on ecotourism. With options for kayaking, scuba diving, or snorkeling, you’ll be able to admire wildlife in its natural habitat while helping conservation efforts to maintain the Keys. View the reef up close with a trip on a glass-bottom boat, or try a dolphin-viewing charter.

A beach vacation destination that combines the modern conveniences and comforts of home with a growing environmental awareness , this beautiful island offers a glimpse into all that Florida has to offer. Plan a visit to one of our Key West beach house rentals for a memorable trip full of relaxation, exploration, and unforgettable experiences.

Important Events Worth Visiting For

1. Super Boat Races

Key West rentals fill up fast in the fall, when the annual Super Boat International World Championships take place. Races last for 3 days, while events go on for 7 days. Hire your own private boat to enjoy the races right on the water. Admire the powerboats on display during the Duval Street Party, and participate in fun parties and parades.

2. Half Marathon

Another good time to visit is during the Key West Half Marathon, held in balmy mid-January. Get your running shoes on for this scenic race covering the regions historic Old Town and the beautiful waterfront.

3. Fantasy Fest

Held every last week of October, live music from different genres and fancy costumes are at the core of this event. Book your accommodation in advance if visiting during this 10-day event. This adults-only event has been held every year since 1979. Be a part of the merrymaking, filled with creative costumes, libations, and parades.

4. Lobsterfest

Celebrate summer with fresh lobster, great drinks, and live music during this 4-day festival. Sample delicacies like Caribbean lobster ceviche, grilled lobster, lobster rolls, and much more.

5. Fourth of July in Key West

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Blue Waters Key West Vacation Home 28 Day Rental Or More

New sleepers in the great room – Upgraded mattress for comfort – SO RELAXINGNew Accessories and New Cushions on Dining, Barstools and Chairs all in SUNBRELLA FABRIC!Also now ROKU on all Televisions: Watch You Tube to see Key West AdventuresReserve your dates today!

Thank you very much for sharing such a beautiful place with us! A great house in a great location. Quiet area, but close to all the action when we wanted it. There was plenty of space for the six of us no matter what we were doing. We all enjoyed having the use of the bikes, paddle boards, kayak and hammock. There was always something to do. At the dock, the water was clean and clear right to the bottom. Sometimes it was fun just sitting on the dock and watching the fish swim by. After all the fun during the day, we would sit, relax and watch a beautiful sunset while talking about all the fun we had. The onsite ice machine made it so convenient to fill up the coolers for the day. When we didn’t need to run to the store every day to get ice, it is quite a luxury. Occasionally we would have “Beyond Amazing Key West” bring their 37′ boat right up to the dock and pick us up for a great day out on the water.

Amazing place that’s close enough to Key West yet still offers a little seclusion with a sunset view in the evening. 2 minute ride from the canal to the ocean.

What Are The Popular Point Of Interests Near Where I Can Stay When Traveling To Key West

Paradise Palms Monthly Vacation Rental by At Home in Key West

Vrbo offers a large selection of vacation rentals near lovely places in Key West. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Key West Golf Club: 2,096 vacation rentals
  • Harry S. Truman Little White House: 1,895 vacation rentals
  • Southernmost Point: 1,894 vacation rentals
  • Mallory Square: 1,895 vacation rentals
  • Nancy Forrester’s Secret Garden: 1,900 vacation rentals

But there are many other points of interest around Key West listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

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Experience The Beaches & Culture Of Key West

Located at the southern tip of the Florida Keys, Key West is a tropical oasis steeped in rich culture and history, world-famous nightlife and entertainment, and stunning beaches. Visit the Southernmost Point of the Continental U.S., see the famous 6-toed cats at the Ernest Hemingway Home & Museum, or stroll through the historic streets of Old Town. No matter how you like to vacation, Key West is a destination with tons to offer.

Wherever you choose to stay, all our Key West rentals are infused with the irresistible charm of the islands, the tang of the salt air, and the nagging desire to leave your old life and sink your toes permanently in the warm beach sands. Legend has it that if you get Key West sand in your shoes, youll always come back.

Top Rental Accommodation Types In Key West


Pro Tip: RentByOwner makes it easy to compare the best listings on RBO homes from online vacation rental OTAs, including and more. Use the Advanced Filter feature at the top to easily flip between RBO homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Key West.

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Duplex With Traditional Key West Architecture

Right in the heart of the White Street Gallery District in Old Town Key West, just a 15-minute walk to Higgs Beach and 20 minutes by foot to Duval Street, this updated conch house is the rear unit of a duplex and one of the best Airbnbs in the area. With one bedroom and one bathroom, its got all a pair of travelers need to enjoyincluding a shaded patio for grilling out or kicking back after a days fun. Hardwood floors throughout and high ceilings pair with an open chefs kitchen for a clean and modern vibe. And the price? So, so right.

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