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Key West Vacation Rentals By Owner

The Owner Rental Group

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

Looking For Key Largo Vacation Rentals?

Look no further than the captivating community of beautiful, Ocean Reef. Located on the northernmost tip of Key Largo in the Florida Keys, it is truly a vacationers paradise with 2,000 acres of private, tropical vegetation bordered on three sides of pristine water.

Where We Come In

The Owner Rental Group is a full service rental company that was founded by Russell Post in 2006. ORG features luxury vacation properties, ranging in size from 1 bedroom condos to 5 bedroom homes.

As an intimate company, ORG is more in touch with their guests needs and does not compromise on quality or service. Known for complete customer satisfaction ORG strives to create a worry free vacation by providing the following amenities: Housekeeping Services, 24 hour On-Call Maintenance with Real-Time Response, Grocery Provisioning, Golf Cart Rentals, Airport Transportation and more.

Contact us to request more information about Ocean Reef Rentals in Key Largo.

United St Key West Fl 33040

  • –applicationsCentury old, completely renovated house, in what is considered to be the best part of Key West Old Town. Moments from Southernmost Beach and Point, and across the road from the famous Butterfly Museum. Duval Street is literally a few steps away. No need for a taxi all the bars and restaurants along Duval are walking distance. Completely furnished. The house itself has had no expense spared in creating the fantastic historic timepiece with modern flair. Start your day with a coffee on the front porch or second floor balcony and watch Key West wake up. Modern kitchen with everything you will need to cook your local catch. There is even a professional wine cooler to keep your champagne at the right temperature whilst you laze in your private sun-filled pool or you could cook your shrimp and steaks outside on the grill with additional shaded seating for meals under the sun or stars. Two sets of washer dryers provides for the essentials. Location, location, location is where it is at and where you should be.Renter pays cleaning fees and sales and tourism tax in addition to monthly rent.Show more
  • Find Vacation Rentals In Or Near Key West

    Discover more than 1716 vacation rentals in Key West that are perfect for your next trip. Whether you are traveling with a group, family, friends, or couples retreat in Key West, RBO has all types of rental properties with top amenities, including indoor/outdoor/private swimming pools, Wi-Fi, hot tubs, self-catering, and more.

    Rent By Owner offers vacation rentals near Key West for all types of travelers, whether you are looking for a luxury home, villa, resort, condo, cabin, cottage, RV rental, or pet friendly accommodation in Key West. Rent By Owner makes it easy to find and compare vacation rentals, matching you with rental properties from different vacation rental websites. By comparing these rental properties, RBO helps you find the best deals in Key West. Luxury vacation rental prices start from $ 79 per night and affordable condos in Key West start from $ 79 per night.

    RBO offers a large selection of vacation rentals from top leading sites such as Booking.com, Airbnb, VRBO, Trip.com, RV Share, Outdoorsy, and many more providers. Filter your search dates and discover Key West vacation homes for your next trip.

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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.

    Key West ~ Weekly Vacation Rentals

    Key West Beachfront Rentals

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

    Key West weekly rentals hold a special City of Key West transient license which allows these properties to be rented weekly or nightly. Most weekly rentals have a minimum stay of 3 to 5 nights and during some months require a week minimum stay.

    Weekly rentals are decorated Key West island style, reflecting the unique tastes of property owners. Some are furnished luxuriously, and some more simply. All are equipped with 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

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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

    What Are The Top

    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.

    Read Also: Key West 3 Bedroom Vacation Rental

    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.

    Best Time To Visit Key West

    Key West Wabi Sabi- 4Br/3BA Key West Vacation Rental

    The best time to visit Key West is between March and May. During this time, the weather remains moderate and there are the least chances of rainfall and snowfall. The minimum temperature is as low as 45°F and the maximum temperature is as high as 85°F . The average daily temperature hovers between 55°F to 75°F .

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    The 10 Best Restaurants Close To Your Key West Accommodation

    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

    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.

    Also Check: Vacation Packages All Inclusive With Airfare Included

    Whitehead St Key West Fl 33040

  • –applicationsTHIS IS A 3 BEDROOM 2 BATH HISTORIC HOUSE THIS IS NOT A LONG TERM LEASE – SORRY THIS HOUSE IS OPEN DECEMBER 2022 & MARCH 2023Welcome to Making Memories Key West! from the moment we took our first vacation to the island of Key West we fell in love with the inclusiveness, atmosphere and weather! So welcome to our little piece of paradise. Located one block from Duval street, 4 blocks to the Southernmost point and steps away from the Hemingway House and Key West Lighthouse. This 3 bedroom 2 bath Old Town house will surely provide you the perfect home base to make plenty of Key West memories. The first floor includes a living room, kitchen and two bedrooms along with a full bath. The top floor has a large studio apartment feel with it’s own kitchenette full bath and walkout deck. The house will sleep 6-8 as the sofa in the living room will pull out to a full bed. This home is available for 28 day rentals.DECEMBER $7500 PLUS TAX AND CLEANINGMARCH 2023 $10,000 PLUS TAX AND CLEANING THE HOUSE CAN BE DIVIDED INTO A 2/1 AND A 1/1Show more
  • Find Your Ultimate Key West Accommodations

    Aqua Pearl Crest

    Locals and visitors alike love Key West for its pastel-colored homes, great fishing and fresh seafood, snorkeling and scuba diving, quaint streets, and fun events and nightlife. Our Key West vacation rentals, which range from one to six bedrooms, offer spacious interiors, ideal locations, equipped kitchens, and free high-speed internet. Other convenient amenities include available on-site check-ins, refreshing private pools, and outdoor showers. Some properties are even pet friendly!

    Whether you’re just traveling through or plan to stay a month or more, we have the Key West vacation rental for your needs.

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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.

    Key West Rentals By Owner

    3 BR | 2 BA | Sleeps 6 |

    • Rentals by owner

    About this property

    The Sand dollar is a 3 bedroom, 2 bath home built within feet of the Atlantic Ocean with 180 degree ocean views.The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge.Fishing and diving just steps outside your door. Then at night, Key West is just …

    Key West House

    “Best Oceanfront Rental I ever had”

    If your looking for a Tropical paradise this is your place, The location is great and wow what a view. The best host and has everything you could ask for. We will return.

    5 BR | 3 BA | Sleeps 10 |

    • Rentals by owner

    About this property

    2 rental homes within 5 private gated acres of scenic beauty in the heart of the Florida Keys and 15 minutes to Key West. Located within the keys wildlife preserve, Sea View Estate is just a 15 minute drive to the shopping and nightlife of Key West and just minutes to some of the finest restaurants …

    Key West House

    “Wonderful property wonderful hosts!”

    I just got back from taking my family and a friend’s family to Troy and Carol’s property for a week. The houses were just as described, the location was just what we wanted, quiet and peaceful and away …

    2 BR | 1 BA | Sleeps 4 |

    • Rentals by owner

    About this property

    Key West House

    “Beautiful Paradise”

    Studio | 1 BA | Sleeps 2 |

    Distance to beach: 0.5 miles to South Beach


    • Rentals by owner

    About this property

    Key West Condo

    “Perfect Place to Stay”

    2 BR | 2 BA | Sleeps 6 |



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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.

    Things To Know Before You Visit Key West

    Rent Key West Vacations FL Condos Homes Service Hotels

    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 youll 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 youd rather spend your time shopping, dining, and enjoying the local bar scene, you wont 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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    Best Things To Do In Key West

    Key West boasts many places. Those that you should include in your bucket list include the following:

    Key West Museum of Art & History at the Custom House: Handily located between Mallory Square and the Harry S. Truman Little White House attractions stand the Key West Museum of Art & History. Set in the city’s historic Customs House building, a large and handsome red brick structure built in 1891 it’s well worth a visit.

    Laze on a Key West Beach: Many first-time visitors are blown away to find out that Key West is actually home to a number of great little beaches . Which one you gravitate to will depend largely on your travel habits.

    Key West Lighthouse and Keepers Quarters: The Key West Lighthouse was built in 1847 and opened in 1848 with a female keeper, a rarity at that time. Over the years, its keeper’s quarters and lenses were upgraded until technology rendered both obsolete, and it was decommissioned in 1969.

    Key West Cemetery: Founded in 1847 after the island’s original cemetery was destroyed by a hurricane, the headstones in Key West’s cemetery mark the graves of more than 35,000 people.

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