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Vacation Rentals Near Key West Florida

Make Key West Your Next Getawaychoose From 148 Great Vacation Rentals

Florida keys vacation rental home on Ramrod Key near Key West

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.

Group And Family Vacation Rentals

The 1, 2, and 3 bedroom historic Rose Lane Villas are generously equipped for your family reunion, guys fishing trip, romantic honeymoon, or destination Key West wedding. Each of the Key West vacation rentals include updated kitchens, living areas with flat screen TVs, key-less entry and separate bedrooms. Youll feel right at home, except the daily housekeeping is a bonus reminder that youre in Key West on vacation!

Experience our friendly staff, swimming pool, generously appointed villas and fully equipped kitchens at Rose Lane Villas.

Vacation Rentals In Florida Keys Florida

Avoid costly fees and gain in service by dealing directly with the Vacation Rental Management Company.

The Vacation Rental Properties listed below are professionally managed by Vacation Rental Management Companies who know the Florida Keys area.

Vacation Rental Management Companies provide local hospitality, professional rental services, and the very best in rates and availability while managing vacation rentals thatare safe for you and your family. They will assist you in finding the perfect rental property for your vacation.

Avoid costly fees and gain in service by dealing directly with the Vacation Rental Management Company.

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Before You Travel To The United States

With specific exceptions, noncitizens who have been in certain countries during the past 14 days may not enter the United States, either as immigrants or nonimmigrants. For more information, visit Travelers Prohibited from Entry to the United States.

For information about COVID-19 requirements for land travel, visit the U.S. Department of Homeland Securitys Fact Sheet: Guidance for Travelers to Enter the U.S. at Land Ports of Entry and Ferry Terminals.external icon

Visit The Ernest Hemingway House And The Key West Lighthouse

Sisters of Cedar Key Vacation Rentals in Cedar Key

The Ernest Hemingway House was home to the famous author of A Farewell to Arms and For Whom the Bell Tolls for about ten years. The rooms in the house contain artifacts detailing the authors’ life and works.

The Key West Lighthouse is tiny, but the climb up the 88 steps to its top rewards you with incredible views. The museum houses photographs and other items related to the history of lighthouses in the Florida Keys.

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

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.

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Things To Do In Key West Fl

When you book one of our Key West, Florida beach house rentals, you’re not just booking a vacationyou’re booking an experience! Although the island is relatively small, the number of attractions are vast and varied. Key West has a diverse arts and history culture, including plenty of galleries, delicious restaurants, and landmarks that are as unique as the Keys themselves. The Hemingway Home, located in Old Key West, is a historical treat for guests who enjoy literature . With look-out towers and detailed exhibits of the wrecking business, the Shipwreck Museum is definitely worth a visit.

Other points of interest on the island include the Southernmost Point, and Wyland’s Whaling Wall, a gorgeous mural of some of Key West’s local aquatic residents. Key West has a laid-back attitude, but its nightlife isn’t lacking! Let loose on Duval Street, starting in Mallory Square with its famous Sunset Celebration and working your way down the main drag to the famous Sloppy Joe’s.

Feeling hungry after a long day full of excitement and adventure? Our Key West lodging is conveniently close to many dining options, including restaurants like Help Yourself, an organic cafe and juice bar, and Square One, a fine-dining establishment.

What Are Some Fun Things To Do In Florida Keys

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Find Rentals offers a selection of vacation rentals near parks and other areas of interest in Florida Keys. Some of the most popular places to visit while you’re traveling in Florida Keys while on vacation are The Key West Butterfly and Nature Conservatory, Key West Garden Club, C. B. Harvey Rest Beach Park, Higgs Beach Dog Park, Nancy Forrester’s Secret Gardenand a few more.

There are many other points of interest around Florida Keys listed on Find Rentals where you can find a great place to stay. Try out the search to find a large selection of vacation rentals available near the cityor region you’re traveling to.

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Things To Do In Key Largo

Barefeet Rentals is here to help you plan your Key Largo activities. Charter a boat to snorkel our exotic coral reefs or dive our incredible shipwrecks . Swim with the dolphins. Experience the thrill of the catch and release of the big one on a deep-sea fishing excursion. Take an airboat tour of the Everglades National Park for a cherished experience.A cant-miss tour is Garls Coastal Kayaking for a unique and unforgettable eco-adventure through the Florida Keys and Everglades. See the one-of-a-kind manatee in its natural habitat! Stop in at The Florida Keys Wild Bird Sanctuary, visit an alligator farm close by, take a glass-bottom boat ride and witness the amazing 9 bronze statue of Christ in its unusual setting beneath the ocean at Key Largo Dry Rocks. Created by the artist to symbolize peace of mankind and to inspire all who explored and loved the sea.As the evening wanes, set sail on a sunset cruise or, just go native dig your toes in the sand and relax watching the most gorgeous sunsets in the world ending your evening while listening to live entertainment offered at many of our restaurants and pubs.

Vacation Homes In The Upper Florida Keys

Barefeet Rentals is located in the upper Florida Keys. Our Key Largo vacation rentals are situated just a short drive to Islamorada and surrounded by beachfront views of the azure waters of the Atlantic and the calm waters of the northern Gulf of Mexico, known locally as Florida Bay.Barefeet Rentals offers Florida Keys vacation rentals to fit any budget. Private rental homes and condos – modest to magnificent. We even offer Key Largo vacation homes with docks!

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Top Rental Accommodation Types In Florida Keys


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 Florida Keys.

Where Are The Best Places To Stay In Florida Keys

**BAHAMIAN BAMBOO @ THE ANNEX** Chic Home By Duval &  Beach ...

Whether you’re traveling with family or friends, here are the areas with the largest selection ofvacation rentals for a holiday trip or just for a weekend in Florida Keys:

  • Key West Area: 139 vacation rentals
  • Islamorada Area: 50 vacation rentals

For nearby neighborhoods, please use our search to access the selection of vacation rentals available in and around Florida Keys.

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Key West Vacation Rentals

Last Key Realty offers luxurious fully stocked vacation rentals in various locations throughout Key West. Search for rentals in Historic Old Town, 1800 Atlantic, Truman Annex, and Sunset Marina. We also have vacation rentals on Duval Street and rentals near Duval Street. Our Key West rentals are available to book Nightly, Weekly and Monthly.

Popular amenities including fully equipped kitchens, rentals with private pools, outdoor dining areas, and complimentary concierge services. Our guests can rent nightly or monthly. We also have pet-friendly rentals so that you can bring your dog on vacation too! Our newest homes are fully furnished, fully stocked, and fully equipped with everything youll need to enjoy a relaxing vacation in paradise! Our condo rentals in Key West Fl, come fully stocked and are in a variety of locations for you to choose from. Resort-style amenities include on-site pools, spas, access to tennis courts, and more!

Key West Regulations require homes to have a transient rental license in order to be rented for less than a month at a time. Transient licenses are hard to come by in Key West. Thus making the nightly and weekly rentals vs Monthly rentals at a higher rate per night. If you enter the exact dates in the search, will produce the results available for those dates. If you want to compare rates, simply click flexible rates in the search bar. It will return both sets of dates.

% of our inventory is booked.

  • 139 properties returned

Can I Rent Houses In Key West

Yes, of course. Vrbo has 797 Houses in Key West. Our other popular types of vacation rentals in Key West include:

  • Cottages: 57 rentals available
  • Bungalows: 57 rentals available
  • Condos/Apartments: 704 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Villas and more.

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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

We Can Help Maximize Your Investment Home In Key West

Vacation Homes Of Key West – Privately Owned Vacation Rental Company in Key West, FL

Key West Hideaways is the premier rental property management company in Old Town Key West. Our staff have the training and resources to offer each property owner and guest with a stress free beginning-to-end solution to renting and staying in the Florida Keys.We are here to manage every aspect of keeping your Key West vacation rental booked and ready for guests to enjoy. We want you to make the most out of your investment in the Keys without having to do the busy work involved with managing it.What that means for you is we take professional photos, write descriptions, and offer marketing to potential guests to fill your calendar. We also manage the logistics such as reservations, payments, check-in and check-out, housekeeping, light upkeep, and dispatch of any emergency maintenance.

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Key West Vacation Rentalscondo House Estate Boat Rentals & Property Management

Search these listings for Key West Condo Rentals, House, Estate, Boat and Private Rentals to find your perfect Key West vacation rental.

For Key West Vacation Rentals, Vacation rental condos, houses, private rentals and property management, has every Vacation Rental property listings to choose from.

Vacationing in Key West? Why not experience it in your own Key West Vacation Rental? You can find our own unique, one-of-a-kind vacation rental that fits your accommodation needs. Why not enjoy the perfect alternative to a hotel on your next vacation stay in Key West? We have plenty of vacation accommodation choices for condo vacation rentals, or a house vacation has all of the information you will need to find the perfect Vacation Rentals on the island.

Whether youre here to party on the world famous Duval Street, enjoy some of Key Wests famous world class fishing, explore the historic seaport, enjoy Key West watersports such as snorkeling, diving, or going on a sunset sail around the island, there are many Key West Vacation Rentals to choose from. See our listings above for all of your Key West vacation rental needs.

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.

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Vacation Rentals Sales & Key West Awesomeness

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.

Hemingway Days And New Year’s Eve

Key West Style Villa near Downtown in Naples

The New Year’s Eve celebrations in Key West are world famous. The biggest party is on Duval Street, where you can watch a conch shell drop at midnight at Sloppy Joe’s or head to Bourbon Street Pub to watch a drag queen named Sushi lowered from the rooftop in a giant red high heel.

Hemingway Days, held in July, celebrate the famous author. The festival includes writing, fishing, and look-a-like contests.

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