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Key West 3 Bedroom Vacation Rental

Things To Do In Key West Fl

Disney’s Old Key West 3 Bedroom Grand Villa – Room 1923 from DVC-RENTAL 4K

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.

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.

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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Vacation Home Inkey West Florida

2 Kings, 2 Twin beds
  • Daily Rates from $480to $711per night
  • Weekly Rates from $3,220to $5,250per week

Availability details can be found on the Rent Key West Vacations – Key West Florida Accommodations, Property Management, and Real Estate Listings! website.

Book Direct through the website for maximum savings!

What Is The Best Area To Stay When Traveling To Key West

Cayo Calypso: Old Town Key West House Rental with pool 3 Bedrooms and ...

Whether you’re traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Key West:

  • Key West Historic District: 1,318 vacation rentals
  • Historic Seaport: 969 vacation rentals
  • Uptown – Upper Duval: 323 vacation rentals
  • Old Town Key West: 1,297 vacation rentals
  • New Town: 538 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

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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.

Vacation Rentals & House Rentals In Key West

  • Swing set or jungle gym
  • Table tennis
  • Private fishing lake or river
  • Trampoline

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 26 minutes

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2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 35 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 21 minutes

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2 bedrooms / 2 bathrooms / sleeps 6

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Key West house

10 bedrooms / 6 bathrooms / sleeps 20

Responds fast! avg. 2 hours 35 minutes

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Key West house

5 bedrooms / 4 bathrooms / sleeps 12

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Admire Local Talent At Studios Of Key West

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.

Important Events Worth Visiting For

Craig & Cindy Key West Beachside Resort Condo (Waterfront 3 Bedroom 3 Bath) Version 2021-2

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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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.

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

Our Key West vacation rentals put you right in the middle of the action near some of the biggest must-see destinations in the Keys. Step back in time during a visit to the Ernest Hemingway Home and Museum or experience the relaxing waves at Smathers Beach. See stunning nature at the Key West Butterfly and Nature Conservatory or take a picture in front of the Key West Lighthouse. No matter what youre interested in, you can find it in Key West!

The 10 Best Restaurants Close To Your Key West Accommodation

Keys Kokomo

1. Blue Heaven

Enjoy alfresco garden dining with live music in this restaurant dishing out American, Caribbean and Mediterranean specialties. Try the Caribbean BBQ shrimp with Red Stripe beer glaze.

2. Hogfish Bar and Grill

Devour hogfish-based dishes like the “Killer” sandwich, hogfish fingers, or fried hogfish tacos in this open-air restaurant at Safe Harbor Marina. There’s plenty of chilled beer and live entertainment too.

3. Bad Boy Burrito

This joint features Mexican-style organic homemade specialties like Key West pink shrimp, taco trio, ancho chili relish, and various fresh salads, smoothies, and juices.

4. B.O.’s Fish Wagon

Come to this restaurant for seafood favorites, like the grouper sandwich served on soft Cuban bread, seafood platters, and conch fritters.

5. Latitudes

Spend a special occasion in this upscale restaurant on Sunset Key. Savor the freshest fish delicacies while feasting your eyes on the beautiful sunsets outside.

6. Better Than Sex

Dig your sweet tooth into award-winning desserts like Peanut Butter Perversion, Cookie Nookie Pie and Tongue Bath Truffle. It’s the ultimate in decadence.

7. Onlywood Pizzeria Trattoria

Hidden away on Duval Street, this is where you’ll eat the most authentic Italian pizza around. Watch it being freshly made and baked in an oak-fired oven before digging in.

8. Matts Stock Island Kitchen & Bar

9. El Siboney

10. Conch Republic Seafood

More Information About Key West Cuisine

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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!

Things To Do In Siesta Key

Our condo rentals in Siesta Key put you right in the middle of the action. Theres plenty to see and do for every interest. Between the swimming at Siesta Beach, the mouthwatering food at Café Gabbiano, and the local vendors at the farmers market, youre sure to find a new favorite around every corner! Youre also just minutes away from Sarasota, boasting even more fun for every member of the family.

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Key West’s Best Rental Company

Welcome to Key West, Florida’s 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 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.

Connect with Key West’s Old Town Locals

In 2020, Rent Key West Vacations continues to grow. This year, we’ve gained many new properties, and we’re ready to connect you with Key West’s best vacation rentals, condos, cottages, and historic homes. For the lowest rates possible, book directly with Key Wests vacation rental experts.

Make Key West Your Next Getawaychoose From 148 Great Vacation Rentals

Craig & Cindy Key West Beachside Resort Condo (Waterfront 3 Bedroom 3 Bath) Version 2021-1

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.

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Catch Key West’s Fantasy Fest Celebrations

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.

Monthly Vacation Rentals In Key West

Historic Key West Vacation Rentals’ monthly vacation rental properties are the perfect option for an extended stay in our tropical paradise of Key West. Our Key West Monthly rentals require 28-night minimums. Please keep this in mind when selecting your dates to be sure you meet this minimum night stay rule in order to bring up available options . Immerse yourself in the warm and tropical vibes all month long and experience what local living in Key West can offer. Historic Key West Vacation Rentals offers numerous luxury properties to make your stay hassle-free and filled with the best that Key West and the Florida Keys have to offer.

Discounts are often available for monthly vacation rentals, especially in the off-season or if staying for multiple months, so please ask! Monthly vacation rentals include utilities such as electricity, water, and propane. Please read our rental policies for other rules & items specifically related to monthly vacation rentals.

Reservations occurring during “Peak Season” require check-in dates on the 1st of the month and can only be rented in monthly increments.

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Key West Beachfront Rentals

  • Pool

About this property

3 bedroom, 2 bath in private Beachside Resort, yet close to Old Town Key West, just steps to the beach, just a bike ride to all that Key West has to offer. Keys to Paradise will not disappoint. Direct ocean front condo that features 1 master suite with a king size bed, jacuzzi and luxurious walk in shower. …

3 BR | 2 BA | Sleeps 6 |

Distance to beach: 30 feet to property 20 yards from ocean, 4 mile white sand be


  • Private pool

About this property

Notice: Due to Corona Virus We suggest you purchase “Cancel For Any Reason Insurance”. CSA Insurance In the event you purchase the insurance and cancel,It costs a little over 10% of the total trip costs. Great for people with health problems or in this case “Pandemics”Here …

Key West Condo

“Great Escape”

2 BR | 1 BA | Sleeps 6 |

  • Rentals by owner

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 …

Key West Yacht

“Didn’t stay here”

I did not stay at this property, but had inquired about it and would have loved to check it out. Sadly, we only hit Key West once while we stayed in Key Largo. This site believe I did stay there, so I …

2 BR | 2 BA | Sleeps 6 |


  • Oceanfront

About this property

3 BR | 2.5 BA | Sleeps 8 |



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