Vacation Rentals By Owner in the Florida Keys & Key West

Key West Private vacation home - 4.3 Star Review

*Please note that this home is available for 28+ night stays only.*

The location of La Casita cannot be beaten -- right in the heart of Old Town yet on a quiet lane, only steps to Duval Street. This property is a monthly rental only. Sleeps 4 people.
Once here, you can settle in like a local as everything is within walking or biking dista.......read more

2 Bedroom(s)
Sleeps 4
Private vacation home

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Marathon Cottage

We have a lovely oceanside cottage in Marathon Key, Florida, close to everything with hidden amenities. The cottage has a large yard and plenty of room to park boats, RVs, and wave runners. This modernized cottage is for you if you all need a great place to stay. This quaint and cozy home offers good value and features new furniture and brand-new s.......read more

Studio
Sleeps 4
Cottage

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Key Largo Private vacation home

Treat yourself and your family to a day of fun at one of Key Largo’s many outdoor attractions; the property is moments from world-class diving and fishing charters, as well as water sports, eco-tours, swimming with dolphins, and numerous parks. Key West, Everglades National Park, and the Homestead Motor Speedway are fun-filled day trips, too. We ca.......read more

2 Bedroom(s)
Sleeps 8
Private vacation home

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Marathon Private vacation home - 4.3 Star Review

VACA-22-368
Welcome to the beach house! Enjoy the Southeast Exposure with the sun all day,  while having your toes in the sand of your private beach (a rarity in the Keys) or jump in the private pool whenever you feel like it! 
This oceanfront property is Florida Keys living at its finest. It offers a private swimming pool, a covered patio an.......read more

4 Bedroom(s)
Sleeps 10
Private vacation home

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Marathon Private vacation home - 4.7 Star Review

Marathon Magic

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'

What's better than a Marathon getaway when it comes to coastal adventures and dreamy days of sweet sunshine? Treat yourself to a perfect getaway and make this stunning retreat your hom.......read more

4 Bedroom(s)
Sleeps 8
Private vacation home

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Tavernier Private vacation home - 5.0 Star Review

134 Tequesta Street - Get ready to dive into your Islamorada Winter Retreat! Move in ready today!
This beautiful three-bedroom three bath pool home is located at mile marker 89 on a deep-water canal. Bring your boat (20' or less only please) and fish Islamorada in the winter while your family and friends dig their way out of the snow.
When y.......read more

3 Bedroom(s)
Sleeps 6
Private vacation home

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Summerland Key Private vacation home - 5.0 Star Review

This Summerland Key home is perfect for the avid fisherman. Deep Water Canal with easy access to both the Gulf and Atlantic. Sea Wall has room for (1) 24' boat. This home can sleep 7 adults and 2 small children. There are 4 bedrooms and 4-1/2 bath. Fully stocked modern kitchen, great out door space and a separate apartment for privacy. Swimmi.......read more

4 Bedroom(s)
Sleeps 10
Private vacation home

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Cudjoe Key Private vacation home - 4.9 Star Review

This Chic style home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. Our home is fourth from the waters edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on one of two balconies, dock or poolside, wher.......read more

2 Bedroom(s)
Sleeps 6
Private vacation home

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Marathon Private vacation home

This One Has It All
On the inlet at Sister's Creek
This 4 bedroom, 3 bath beachfront pool home has magnificent ocean views! One of the few locations in the Middle Keys where you can have the best of all features for the perfect vacation. A natural sandy beach at your back door, boat dockage, a freshwater swimming pool, spa and great views of.......read more

4 Bedroom(s)
Sleeps 10
Private vacation home

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Tavernier Condo - 4.9 Star Review

With thoughtful and creative touches both inside and out mixed with a keen attention to the smallest of details, this oceanfront condo exudes a breezy sense of magic, whimsy and laid back Florida Keys style.

Upon entering the home you’ll be greeted by the blue-green colors of the Atlantic and lush mangroves of the protected nature preserve........read more

2 Bedroom(s)
Sleeps 6
Condo

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Key West Condo - 5.0 Star Review

Beautifully renovated 2 bedroom island view Condo. Conveniently located for easy access
King in the Master Bedroom, Queen in the Guest with a Queen sleeper sofa. Stainless Appliances.
You get one assigned parking space with the unit for a vehicle under 6ft 2 inches.
1800 Atlantic has an olympic size heated pool, a 20 person jacuzzi out by.......read more

2 Bedroom(s)
Sleeps 6
Condo

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Little Torch Key Mobile home - 1.0 Star Review

Pirates Pleasure is a family owned home in a small neighborhoood community on the bay side of our hidden gem...Little Torch Key. Pirates Pleasure is a comfortable 2 bedroom one bath home with a queen sleeper sofa in living room. Full kitchen and utensils so no need to bring anything. Drop your bags and enjoy Paradise! A beautifully decorated privat.......read more

2 Bedroom(s)
Sleeps 6
Mobile home

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Key West Apartment - 5.0 Star Review

Summary:
This elegant, elevated 2nd story loft with vaulted ceilings has been designed for your next dream Key West getaway. Tastefully decorated with trendy decor and modern furnishings, this property has a welcoming and clean feel. Comprised of two lofts on Duval, this recently renovated compound is perfect for up to 12 guests.

With a p.......read more

4 Bedroom(s)
Sleeps 12
Apartment

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Marathon Private vacation home - 4.8 Star Review

THE LOCATION is Marathon Island in the heart of the fabulous Florida Keys. Marathon Island has everything to offer from the best charter fishing to the best beach in the Keys right around the corner, Sombrero Beach, which is within walking distance from the property! Don't forget about all the 5-star dining and a great selection of Tiki Bars and lo.......read more

14 Bedroom(s)
Sleeps 28
Private vacation home

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Key Largo Private vacation home

One Hour drive from Miami, close to John Pennekamp, Great Restaurants, boat ramp nearby. Great community! Close to Adam’s Cut - short boat drive to Atlantic Ocean. Jacuzzi and ice maker on property. Tranquil street. .......read more

2 Bedroom(s)
Sleeps 4
Private vacation home

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Stock Island Condo - 4.9 Star Review

A slice of paradise just for you. Quietly enjoy a quintessential view of the Atlantic Ocean and mangrove estuary that will make your Key West vacation one that you will never forget. Newly furnished and tastefully decorated with Key West tropical lifestyle in mind. Located in the Southwest corner of Stock Island just steps away from Oceanside Marin.......read more

3 Bedroom(s)
Sleeps 6
Condo

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Marathon Private vacation home - 4.5 Star Review

Piece of Paradise is a beautifully decorated one bedroom & one bathroom condo in Skipjack Resort. There a king bed in the bedroom and futon in living room. There is a flat screen TV in the living room as well as the bedroom. There is a balcony off the bedroom. The bathroom features a shower with upgraded vanity and sink. There are two barstools loc.......read more

Studio
Sleeps 4
Private vacation home

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Marathon Private vacation home - 4.9 Star Review

This spacious 4 bedroom, 3 bathroom, open waterfront home is located at the south end of Marathon, near the base of the Seven Mile Bridge, directly on the Atlantic Ocean with Gulf access in minutes. It has spectacular open water views!
*This home is on direct open water and does not provide protection for your boat if it's windy. Your boa.......read more

4 Bedroom(s)
Sleeps 8
Private vacation home

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Key Largo Condo - 5.0 Star Review

Enjoy the panoramic view this tropically decorated, fifth-story unit has to offer of the Atlantic Ocean and the adjacent Wildlife Sanctuary. The unit affords its guests the spectacular sunsets the Florida Keys are famous for, right from your balcony and living room.

Kawama Yacht Club is situated at mile marker 100 right on the ocean. This ga.......read more

2 Bedroom(s)
Sleeps 6
Condo

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Key West Private vacation home - 4.8 Star Review

A SWEET SURPRISE JUST OFF DUVAL...
Private single family home with off street parking totaling three bedrooms, two and half baths plus outdoor shower. Enjoy an open floor plan with double French doors that open off the kitchen to a backyard oasis with large sunny and heated pool surrounded by tropical vegetation and spacious decks for sunbathing.......read more

3 Bedroom(s)
Sleeps 8
Private vacation home

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Key West Condo - 4.9 Star Review

Summary:
Time to relax! Bring your family & friends to this 1350 sqft Waterfront condo home. Boat slips available on site with commercial ice machine, fish cleaning station and BBQ grills. Located in historic Downtown Key West. Walk/Bike everywhere 1mi to Duval Street, Historic Seaport, Hemingway House, etc. On-site amenities: heated pool, tiki .......read more

2 Bedroom(s)
Sleeps 6
Condo

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Key West Private vacation home - 4.9 Star Review

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!

Traveling to Key West with a group deserves the ultimate vacation rental home: plenty of space to stretch out and enjoy time together, separate rooms and bathrooms to enjoy privacy, a private saltwater pool and of course, outdoor lounge .......read more

3 Bedroom(s)
Sleeps 8
Private vacation home

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Marathon Private vacation home - 5.0 Star Review

Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse yourself in long leisurely days of boating, lounging by the pool and watching spectacular sunsets from your back porch. Located just 90 miles south of Miami and 45 miles from Key West, the resort overlooks the Gulf of Mexico with f.......read more

3 Bedroom(s)
Sleeps 8
Private vacation home

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Key West Private vacation home

Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of three sparkling pools, and enjoy the fresh modern design of the newly built property. Each unit features 2 Queen beds and accommodates 4 guests. The p.......read more

2 Bedroom(s)
Sleeps 8
Private vacation home

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Key West Private vacation home

Historic 1880's home awarded by the Historic Florida Keys Foundation in a prime old town location. A mere 5 blocks from famous Duval Street and just minutes from the Historic Seaport and restaurants. Completely renovated with stunning interior design including many works by local artists, antiques, oriental rugs and a large modern chef's kitchen. .......read more

Studio
Sleeps 4
Private vacation home

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Key Largo Private vacation home - 5.0 Star Review

Completely remodeled
1st floor - 90’ TV, recliner, full size bathroom, kitchen
2nd floor, 2 bedrooms, 2 bathrooms, kitchen and balcony
Every room has a TV with cable
Restaurants near by
Balcony on the 2nd floor.......read more

2 Bedroom(s)
Sleeps 4
Private vacation home

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Key West Villa - 5.0 Star Review

The Poolside Queen Room is a hotel-style bedroom and bath unit that offers the amenities of our Key West villas for those travelers who do not need a suite or kitchen. With one queen-size bed, this accommodation is perfect for romantic vacations and weekend getaways for two.

* 1 Queen Bed
* Sleeps up to 2 People
* Flat Screen TV with.......read more

Studio
Sleeps 2
Villa

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Key West Private vacation home - 5.0 Star Review

This house is a 3 bedroom stand alone unit with 2 king bedrooms upstairs with balconies and own bathrooms and the bedroom downstairs has two twin beds which could be converted into a king upon request and also has it's own bathroom. There is a queen sleeper sofa with a screen divider for privacy if needed. Pool is just across the way in.......read more

3 Bedroom(s)
Sleeps 8
Private vacation home

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Islamorada Private vacation home

Welcome to this stunningly renovated 5-bedroom, 3-bathroom home situated on a picturesque canal, offering a seamless blend of modern luxury and serene waterfront living. Nestled in a sought-after neighborhood Port Antigua, this property boasts an array of features that cater to both relaxation and entertainment, making it the ideal oasis for famili.......read more

5 Bedroom(s)
Sleeps 10
Private vacation home

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Marathon Private vacation home

Summary:
Welcome to our stunning waterfront home in Marathon! Min to open ocean and steps to Sombrero Beach.
- 4BR/2BA waterfront home
- Heated saltwater pool with spacious deck for lounging
- 60' of canal front with private dock for direct ocean access and a step down for kayaking
- Open living space with gorgeous canal views
- F.......read more

4 Bedroom(s)
Sleeps 9
Private vacation home

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Marathon Private vacation home

This 3 bed 2 bath waterfront house is centrally located in Marathon near Sombrero Beach. There is 85 feet of dockage with a large boat basin for easy turning and docking. A propane grill, fish cleaning station and outdoor dining area completes the outdoor areas. The house is located on the second floor with beautiful views from the balcony........read more

3 Bedroom(s)
Sleeps 6
Private vacation home

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cudjoe key Private vacation home - 4.7 Star Review

Located in a great neighborhood at 1032 Spanish Main, this home is perfect for your next vacation. We are at the end of a dead end street so it is very private. This very clean and neat 3 bedroom 2 bath home has a new granite kitchen that has just been enlarged, bar top with 3 bar stools, a table for seating as well, dishwasher, large r.......read more

3 Bedroom(s)
Sleeps 6
Private vacation home

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Big Pine Key Private vacation home - 4.0 Star Review

Welcome to boater’s dream location! This lovely staged 3bed 2bath home sits on a 75ft wide/deep canal perfect for large boats. There is a marina at the top of our short canal w/launch, fuel, bait & tackle… Also located at the top of our street is the bus stop to Key West (no need to fight for parking or worry about driving). We are practically walk.......read more

3 Bedroom(s)
Sleeps 6
Private vacation home

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Marathon Private vacation home

Welcome to our family-friendly property! An unforgettable tropical vacation awaits you in the Middle Keys. Our room is perfect for solo travelers or couples looking for a comfortable and convenient place to stay equipped with all the essentials you need, including a refrigerator, coffee maker, microwave, and premium TV channels. You won't have to w.......read more

2 Bedroom(s)
Sleeps 8
Private vacation home

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Key West Private vacation home - 4.9 Star Review

OVERVIEW
The Cigar House is a 100+ year old“Cigar maker’s house”. The recently completely renovated house is charming, spacious, secluded and private. The cottage has a raised vaulted wood ceiling, creating a rustic, Caribbean ambiance. The downstairs floor is the original Dade County Pine. All window, door, and floor trim is turn of the cen.......read more

3 Bedroom(s)
Sleeps 4
Private vacation home

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Key West Private vacation home - 4.9 Star Review

Enjoy an early morning cup of coffee on your private bedroom balcony after being gently woken by the crowing of a wild rooster. After a morning stroll, you are ready to enjoy an alfresco breakfast that was just created in your new kitchen. Sit back, relax, you are now on Key West time!
This 2 bedroom 2.5 bath townhouse is prepared to meet your v.......read more

2 Bedroom(s)
Sleeps 4
Private vacation home

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