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Vacation Homes In Key West

Vacation Rentals & House Rentals In Key West

Rent Key West Vacations FL Condos Homes Service Hotels
  • 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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Can I Find Short Term Rentals In Or Near Key West

From funky studio apartments to extravagant houses, Vrbo has your quick escape sorted. Here are just two of our favorite stays in and around Key West:

  • Close to the center of Key West, “Coconut Sunsets And Open Water Views” welcomes short-term guests. When you’re not chilling out in your comfortable digs, get out and discover all the fun stuff around you.
  • “Cloud 9 ~ It’s Heaven On Earth In This 3b” is also well located. Settle in here and find out why lots of guests rate this property as one of their favorites.

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 Top Vacation Rentals In Or Near Key West

Whatever vacation experience you’re seeking, you’ll find a rental in or around Key West that’s a perfect match. These are some of our top picks:

  • “Sombrero Beach Home On Canal With Private Dock And Heated Pool” is popular with guests. Around 45 miles from Key West, it has 3 bedrooms and lots of amenities to help you feel at home, including a living room and cookware, dishware and utensils.
  • Another great option is “Key West Oasis, Seperate Cottage”, which is around 1 mile from Key West. With 2 bedrooms, towels and air conditioning, it has everything you need to make your stay comfortable.

For even more great options, use the search bar at the top of the page to find the perfect Key West vacation rental for you.

Catch Key West’s Fantasy Fest Celebrations

Little Key West cottage with grand style porch detail.

Craving a dose of winter sunshine? Escape to Key West vacation rentals and you’ll find yourself immersed in a tightknit community of locals. Chances are you’ll soon be sharing key lime pie with your new neighbors. Locals cite spring as a Key West sweet spot. Crowds taper off and temperatures continue to hover around the 80s. Visit in the last week of October and you’ll catch Key West’s raucous Fantasy Fest celebrations. The 10-day street party sees the island come alive with pet parades, burlesque shows, costumed events, street food stalls and more.

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Key West ~ Monthly Vacation Rentals

Your Search Results:Below are Monthly Rentals with no specified number of bedrooms

Key West monthly vacation rentals must be rented for at least a month, but not for more than six months. Monthly rentals are designed for guests who want to experience living in Key West, settle in and enjoy the comforts of a home away from home.

Monthly rentals are furnished and decorated to provide the experience of a well-appointed local. Interior designs reflect the unique tastes of property owners. Some are luxuriously stylized, and some are furnished more simply. All are set with the essential amenities and conveniences of home, including internet, TV, linens, and kitchenware. Read our property descriptions to learn the details.

* PLEASE NOTE: Some properties displayed may not be available for rent due to other inquiries and pending reservations. Please contact our office to be sure of availability. or 305-294-7358 ext. 1

There are no properties available that fit all of your search options. Please contact our office if you would like assistance. or 305-294-7358 ext. 1

Renovated Rental In Key West With Shared Pool & Hot Tub

Location: Key West, Florida

Rates from: $380 per night

Accommodates: 6 guests

This two-bedroom rental in Key West was recently renovated at the Sunrise Suites Resort and includes a brand new interior. In addition to top-of-the-line appliances, fixtures, and furnishings, it features a new Samsung Smart TV in each bedroom and a 60-inch in the living room.

At the end of your day in Key West, sit back and enjoy the sunset views over the salt ponds from your private balcony. You can also take advantage of perks like a Keurig coffee machine, a full-size washer and dryer, and a community pool, hot tub, gym, and tennis court.

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Key West Home Rentals

Last Key offers home rentals in various locations throughout Key West, including Historic Old Town, 1800 Atlantic, Truman Annex, Sunset Marina, Casa Marina, on Duval Street, or near Duval Street. Last Key home rentals are available Nightly, Weekly, Monthly.

Our homes come fully stocked with all of the appliances, linens, and comforts you can expect in a luxury vacation house in the whole Key West area. Our unrivaled guest services give you the peace of mind that should an issue arise during your stay, as often do in private homes, it will be taken care of quickly and personably, so you can focus on enjoying your well-deserved vacation. Our vacation homes are available for Nightly, Weekly, and Monthly rental, in various locations throughout Key West, including Historic Old Town, Truman Annex, Duval Street, Mallory Square, or in the heart of Old Town.

One of the most popular destinations is to take a photo at the southernmost point buoy. It marks the southernmost point in the continental United States, the lowest latitude land of contiguous North American States. Make sure to call up a friend and say hello, because there is a live webcam! If you have any questions about vacation rentals in Key West, feel free to message us! A property manager will get with you shortly. Your island paradise in the Florida keys awaits you!

Faqs When Booking A Vacation Rental In Key West

Historic Hideaways Vacation Rentals 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 $269 in the last 3 days. The average price is $581.

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 $269.

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

Vacation rentals in Old Town North of Truman, Truman Annex and Old Town South of Truman 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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What Are The Best Large Family Vacation Rentals In Or Near Key West

Every family get-together should be memorable. Whether you’re organizing a fun escape with the kids or that long-overdue family reunion, our large family vacation rentals in or near Key West offer a home away from home with enough space for everyone:

  • Sleeping as many as 7 guests in 3 bedrooms, “Cloud 9 ~ It’s Heaven On Earth In This 3b” is the perfect place for some family time. This popular retreat is 0.1 miles to the north of Key West and has amenities that include a swimming pool and a fridge.
  • Another popular option is “Casa Cove Beautiful Tropical Decorated 3 King Suites Pool 2 Mi Beach”. This vacation rental is 4 miles east of Key West and features a stereo, childrens activities and more. With 3 bedrooms accommodating up to 8 people, there’s no need to leave anyone off your invitation list.

If you’re hoping to visit some family-friendly attractions around the area, you’re spoiled for choice. Dolphin Research Center, The Turtle Hospital and Great White Heron National Wildlife Refuge promise lots of fun for all ages.

Vacation Homes In Key West

Are you looking for the perfect place to stay while on vacation? Key West has a wide variety of places to stay, but if you are looking for something unique, why not choose a vacation home? Vacation homes come in all shapes and sizes, and there is one for every budget. Here are four reasons why choosing a vacation home is a great idea:

1. Vacation homes come with all the amenities of home. This means that you can cook your own meals, which can save you money on food.

2. Vacation homes are often located in great locations. For example, many of them are right on the beach or in the heart of the action.

3. Vacation homes are perfect for larger groups. If you are traveling with a group of friends or family, a vacation home is a great option.

4. Vacation homes are often less expensive than other types of accommodation. This is especially true if you are traveling during the off-season.

511 Eaton Street

One Of The Most Cheap Vacation Homes in Key West,Florida

At Rose Lane Villas you’ll be within just a 10-minute stroll of The Ernest Hemingway Home and Museum and close to 7 Artists & Friends Gallery. This accommodation contains climate control, cable channels and a patio.

Located in Duval district, the venue is 3 km from the centre of Key West. The natural history museum “Florida Keys Eco-Discovery Center” is within 1.1 km from the villa. Wendy’s offers American specialities and lies 150 metres away. Rose Lane Villas is set a few minutes’ drive from Fort Zachary Taylor.

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Make Key West Your Next Getawaychoose From 165 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.

Garden Cottage Of Villas Key West

Key West vacation rentals near Duval Street

518 Margaret Street

One Of The Most Popular Vacation Homes for Rent in Key West

Garden Cottage Of Villas Key West is within a few steps of Mile Marker 0 Store and Vandenberg Wreck. The accommodation features climate control, a patio and a sofa in the rooms.

The property lies within 950 metres of the even Southernmost Point. This villa is 0.9 km from The Ernest Hemingway Home and Museum. The centre of Key West is 2 km from the venue. Garden Cottage Of Villas Key West is set a few minutes’ drive from Ripley’s Believe It or Not Museum.

One Of The Coolest 2 Bedroom Vacation Homes in Key West

Key West Villas is located within a 15-minute walk from the Harry S. Truman Little White House and a 10-minute walk away from The Ernest Hemingway Home and Museum. The venue includes TV, an adjoining terrace and smoke detectors in the rooms.

Situated in Duval district, the accommodation right next to the even Southernmost Point and within a few minutes’ drive to the waterfront Mallory Square. It is a 20-minute walk from Key West city centre. Pinchers and Pizza Joe’s offering both food and drinks are 125 metres away. Popular points of interest close to Key West Villas include the downtown commercial zoned Duval Street.

Is Another One Of The Best 2 Bedroom Vacation Homes in Key West For Couples

One Of The Best Cheap Vacation Homes in Key West, Florida

If Youâre Looking For A Cheap Vacation Homes in Key West, Florida, Then You Must Check Out Flagler’S Crossing

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Palms Away Truman Annex Vacation Rental In Key West

Location: Key West, Florida

Rates from: $280 per night

Accommodates: 6 guests

If location is what youre after, this two-bedroom Key West rental home is in the heart of the city. However, this charming rental, set in the highly coveted community of Truman Annex, is surrounded by palm trees and white picket fences.

Unwind in paradise on your private porch or explore the open concept great room with an updated kitchen and breakfast bar. The tropical decor creates a laid-back vibe, while the indoor/outdoor space is great for happy hour cocktails, featuring glass sliding doors that open to a private outdoor area with a dining table and electric grill.

What Are The Best Romantic Weekend Getaways In Or Near Key West

Nothing says “I love you” like a romantic weekend together. If you’d like to spend a couple of relaxing nights away with your sweetie, we’ve got some romantic getaways in and around Key West that will sweep you off your feet:

  • Sneak off on Friday for a couple of passion-filled evenings at “Key West Oasis, Seperate Cottage”. Roughly 1 mile from Key West, this property comes with lots of nice touches, including beauty services and outdoor furniture.
  • “Cloud 9 ~ It’s Heaven On Earth In This 3b” is another wonderful option guaranteed to woo you. It’s about 0.1 miles from Key West and comes with a nearby marina and a swimming pool.

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Sunrise Suites Great Exuma Suite #406

Of All The Cheap Vacation Homes in Key West,Florida, Sunrise Suites Great Exuma Suite #406 May Be The Most Luxurious And Comfortable

Sunrise Suites Great Exuma Suite #406 offers an accommodation within 5 minutes by car from Key West International airport. The venue features a TV, coffee/tea making facilities and ironing facilities at the guests’ disposal.

This villa is 3 km from Edward B. Knight Pier. You can find Key West Butterfly and Nature Conservatory 4.9 km from the property. The centre of Key West is 4 km away. Cow Key Channel is located within walking distance to Sunrise Suites Great Exuma Suite #406.

  • Cookware/ Kitchen utensils

What Are The Top

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

If you’ve been busier than a squirrel in a nut factory, you deserve to escape for a few days. Skip out of work early on Friday and live it up at one of these weekend getaways in or near Key West:

  • Find some peace at “Casa Cove Beautiful Tropical Decorated 3 King Suites Pool 2 Mi Beach”. Located about 4 miles to the east of Key West, this delightful escape has all you need for a chilled out stay, including heating and coffee and tea making facilities.
  • “Starfish – Sunny Townhome In Quiet Truman Annex Two Blocks From Duval St” is another fantastic option to consider. It’s located about 0.1 miles to the southwest of Key West and features coffee and tea making facilities, nearby birdwatching activities and more.

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Key West’s Best Rental Company

Welcome to Key West, Floridas southernmost city known for its vibrant culture, conch-style houses, clear waters, and Old Town neighborhood. Originally founded in 1996, Rent Key West Vacations is one of the longest standing vacation rental companies on the island of Key West. Our office is located right on Duval street, just one block from the Ernest Hemingway Museum. This position at the center of Old Town Key West allows our team to manage both short and long-term rentals for many of Key Wests most famous homes. We connect with every guest to ensure that you find the right place for your Key West Vacation.

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