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Key West Vacation Home Rentals

The 3 Best Beaches Near Your Key West Vacation Home

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

1. Smathers Beach

Boasting close to 2 miles of shoreline, this mangrove-fringed beach is great for families. There’s lots of swimming, parasailing, kayaking, and snorkeling opportunities.

2. Fort Zachary Taylor State Park

Beach Visitors often come here for sunbathing and snorkeling. Walk, run, or bike on the various nature trails. Take a guided tour of the pre-Civil War vintage fort on the grounds.

3. Rest Beach

Although only less than 1,000 feet long, the beach promises a tranquil experience. Visit here on early mornings for spectacular sunrises and beautiful views of the Atlantic. The beach also features a yoga deck where classes are held.

Mango Cottage Vacation Rental In Key West With Private Pool

Location: Key West, Florida

Rates from: $388 per night

Accommodates: 6 guests

Its hard not to be pulled in by the charm of the Mango Cottage, a 2-bedroom rental in Key West with a private pool. The recently-restored historic Conch house has antique Miami-Dade County pine walls and floors, in addition to modern features like an open-concept kitchen, living, and dining area that let in natural light from its vaulted ceilings and glass doors.

The outdoor deck area is a highlight for many, where you can enjoy outdoor dining under umbrella shade, top up your tan on the lounge chairs, or sip cocktails on the deck around the heated pool.

What Are The Best Large Group Vacation Rentals In Or Near Key West

Big groups mean enormous fun. They also mean finding a place that’ll comfortably fit your crew. Check out our large group vacation rentals in or around Key West and get your favorite people together under the same roof:

  • Providing space, privacy and comfort, you’ll get everyone’s seal of approval at “New Photos: Drive To Your Getaway”. Up to 12 people can be accommodated at this property which has 5 bedrooms, a swimming pool and a beach view. This group getaway is around 1 mile to the southeast of Key West.
  • Invite as many as 14 of your favorite people to “William Skelton Home – Heart Of Key West” and fill the place with love and laughter. This top option has 6 bedrooms and is around 0.1 miles to the north of central Key West. It’s packed with features to keep a large group comfortable, including a swimming pool and a garden.

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Discover Weekend Getaways You’ll Never Forget

When you’re looking for a quick escape, there’s nothing quite like a weekend vacation. These trips can introduce you to unforgettable experiences while being remarkably convenient to embark on. Plus, the shortened time frame means that planning is a bit easier than if you were going away for a week. With just 2 or 3 days to explore, you can hit all the top spots or simply relax in a new destination that offers tranquility and fun that home simply can’t match.

When you’re looking for top-quality weekend getaways, your best bet is to book a rental. When you rent a house or cabin, you can enjoy all the comforts of home in a new destination, taking your relaxation to the next level. Houses are particularly helpful for this, but getting a cabin can bring your experience much closer to nature, which is useful for trips to national parks or the beach. You’ll find plenty of variety as well, with rentals suited for whole families and others best fit for romantic outings available in equal measure.

Find Romantic Weekend Getaways

Vacation House in Uptown/Upper Duval

Getting away for the weekend with your partner could be exactly what you need. The hustle and bustle of everyday life will fade into the background when you embark on a weekend adventure to someplace new. You’ll find plenty of romantic destinations all across the country on the east coast, west coast, and everywhere in between. Within all these destinations, you’ll find a wide variety of rentals you can book for the weekend that offer premier comforts that pamper you throughout the trip.

Romantic vacation rentals tend to come with quite a few exciting amenities for you and your partner to enjoy. One of the most common in romance-oriented rentals is a hot tub. You’ll find options with a hot tub inside, but there are some with outdoor hot tubs as well. Outdoor hot tubs are particularly popular in rentals in more remote areas near beaches or in the mountains. They’re also useful for enjoying picturesque surroundings in the winter as the heated water can keep you warm while you’re surrounded by snow-covered natural splendor.

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Explore Cheap Weekend Getaways

Going on a trip over the weekend doesn’t have to break the bank. In fact, you’ll find cheap weekend getaways all across the country, so you’re never too far away from some quick adventure. While cheaper rentals tend to be more isolated and less spacious, this can actually be beneficial depending on the kind of experience you’re looking for. An isolated cabin with room for 2, for example, can be perfect for a romantic getaway to the mountains.

Despite being on the more affordable side of the spectrum, cheap rentals tend to have more amenities than ever before. Central heating and cooling and Wi-Fi are fairly common, even among the most affordable options. Additionally, the more affordable a rental is, the more likely it is to be pet friendly, so you can bring your pup along on a weekend getaway if you like.

Cheap Cottage Rentals In Key West Fl

Compare 3,426 available oceanfront holiday vacation home properties, starts from $32

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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.

Why Should I Use Key West Vacation Properties & Realty As My Key West Property Manager

Rent Key West Vacations FL Condos Homes Service Hotels

Key West Vacation Properties & Realty is in the business to provide the highest level of property management services to our customers. Our company is the most experienced in Key West with the most responsive and fast service. Key West Vacation Properties & Realtys staff has over 28 years of experience in the Key West property management industry. Our success comes from giving our guests an experience that makes them come back year after year. We offer a variety of Vacation Rentals and Long Term Rentals that will meet your financial needs.

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We Can Help Maximize Your Investment Home In Key West

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.

Vacation Rentals & House Rentals In Key West

  • Private fishing lake or river
  • Swing set or jungle gym

1 bedroom / 1 bathroom / sleeps 4

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2 bedrooms / 3 bathrooms / sleeps 6

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1 bedroom / 1 bathroom / sleeps 2

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Key West house

2 bedrooms / 3 bathrooms / sleeps 6

awesome the condo was beautiful. very good location. 2 suggestions. the grill did not have gas . the bed that opens up to king. not so much, mattress is 2 different heights and slides if you try to sleep on it. very very uncomfortable.

Responds fast! avg. 1 hour 59 minutes

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2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 46 minutes

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Perfect place to experience Key West This is a lovely condo with a tropical, quiet view. Many extras are included: beach towels, bikes, and kitchen supplies. The pool area was our favorite spot, and we had coffee every morning on the balcony with chairs for all 6 of us. My husband enjoyed watching March Madness on the large T.V. Kathy did a fantastic job with all communications and provided great tourist tips. We would definitely stay here again!

Responds fast! avg. 2 hours 32 minutes

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2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 14 minutes

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Key West house

5 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 3 hours 57 minutes

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2 bedrooms / 1 bathroom / sleeps 6

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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.

Can I Find Studio Apartments For Rent In And Around Key West

$3000 private pool, south end of duval, 1 king, 1 queen

Studio apartments may be small in size, but they pack a punch when it comes to location and convenience. Plonk your bags down at one of these top studio apartments in or near Key West:

  • After a fun-filled day of urban exploration, come home to the comforts of “Condo In Old Town Key West’s Truman Annex”. A hair dryer and high-speed internet services are among the handy amenities on offer here.
  • An equally fantastic property is “Your Condo By The Beach With Ocean View”. Don’t let its modest size fool you this cozy apartment is filled with handy amenities like a nearby laundromat, an elevator and lots more.

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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 is 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.

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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Vacation Rentals In Old Town Key West 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 Old Town Key West 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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Things To Know Before You Visit Key West

Key West Vacation Rental – William Skelton Home

Getting to Key West is easy. From Miami, you simply hop on Highway 1 and take it all the way to the southern most point in the U.S., the iconic Key West buoy. The drive will be about four hours long but could take much longer if you make stops along the way to the incredible island towns throughout the Florida Keys. If you are flying in, the Key West International Airport is small but efficient and well-suited for travel to this island city.

Key West is known as a great spot for those who love the outdoors, and there are plenty of things to do that will appeal to this type of traveler. Rent a boat and go diving with fish. Snorkel along the many reefs in the area where you’ll find tropical fish as well as unique coral species. Exploring by boat can also give you an opportunity to see rare birds and mangrove islets, as well as the sites used by the Conch Republic in their famous protest against the government.

If you’d rather spend your time shopping, dining, and enjoying the local bar scene, you won’t be disappointed in Key West. A stroll down Duval Street in the historic downtown will give you a plethora of food and entertainment options to choose from.

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Browse This Site For Information About Visiting Key West And View All Of The Vacation Rentals On Avantstay

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.

Riptides Centrally Located Stylish Rental In Key West

Location: Key West, Florida

Rates from: $348 per night

Accommodates: 2 guests

Love birds looking for a stylish space can book a stay at this rental in Key West, located one block from Duval Street. The cozy vacation rental on Simonton Street is perfect for a no-frills romantic getaway in Key West, featuring a queen-size bed, kitchenette, table for two, and separate bathroom.

You wont even need a car for the length of your stay, as everything is within walking or biking distance away. After sightseeing, you can enjoy the small private outdoor deck with patio seating.

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What Are The Best Houses For Rent With A Pool In Or Near Key West

A pool is often an all-important amenity when choosing where to stay on vacation, particularly if you’re taking the kids. Check out these houses with a pool in or near Key West and fill your days with frolicking good fun:

  • Pack your swimming gear and take your gang to “Casa Capri Beautiful Tropical Style House With 3 King Suites Pool 2 Mi To Beach”. There are plenty of other convenient amenities here, including a porch and a fenced pool.
  • Spend leisurely vacation days splashing around or simply unwinding by the water at “Casa Cay West Beautiful Tropical House 3 Bedrooms 2 King Suites Pool 2 Mi Beach”. This vacation home is also a firm favorite and features a porch, a swimming pool and more.

Key West has a tropical savanna climate, with average summertime temperatures ranging from 80 ºF to 85 ºF. But there’s no need to wait until summertime to visit. Check out the search bar at the top of the page and adjust the filters to find the perfect Key West vacation rental and organize your getaway for whatever season you like.

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