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Florida Keys Vacation Rentals

(588 rentals)
Islamorada Villa
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Mile Marker 75 – Bayside4 bedroom 3 bathPalm Cottage South, is a charming, modern home directly on the canal with a heated, private pool, dockage, and access to the Port Antigua community sandy beach. Dockage for 24′ boat max on the lift pictured.Elevated for great breezes and...

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Featured review

"House was great with all the amenities!"

Great house, pool, and area. Lots of attractions and wonderful restaurants. Also, great people to work with.

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$500
avg per night
Little Torch Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 5 miles to Bahia Honda State Park

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Ground floor 3/2 with garage, lanai, and deep water dock. Great area for fishing, lobstering and boating. Bahia Honda beach and park 8 miles away. 28 miles to Key West. Home features a separate dining room, living room and fully equipped gourmet kitchen. Equipment shed separate from home for fishing,diving...

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$201
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

3 bedroom, 2 bath gulf front home with amazing views and meticulously manicured lot.Amazing Gulf and sunsets views from almost every room in this tropical retreat! The Palm Tree Resort is a private gated, three quarter of an acre resort located directly on the Gulf in a premier section of Morton...

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Key West House
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool

About this property

Welcome to Island Paradise, your serene retreat in the heart of Key West, Florida! Located in Old Town, Island Paradise is just a half block from the world-famous Duval Street. This charming property offers 2 bedrooms and 2 bathrooms, perfect for small families or couples looking for a relaxing and convenient...

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$202
avg per night
Ramrod Key House
Sleeps 6, 2 bedrooms, 2 bathrooms
10 reviews

Distance to beach: 8 miles to Bahia Honda State Park in the keys

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

Ocean access waterfront canal with 40’ dock and all the fixins. Looe key reef straight out canal. 2/2 house with nice size porch

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Featured review

"A MONTH IN THE KEYS! WHATS NOT TO LIKE!"

I was really worried house was going to be too small, as it is a 2 bedroom. We ended up having plenty of room. Beds were very comfortable and A/C would freeze us . Dock was plenty big for our 35’ center...

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$124
avg per night

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Islamorada House
Sleeps 12, 6 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Tea Table Key Private Island Estate and Wedding Venue An extremely rare and stunning private island, accessible by car, Tea Table Key is a gated Caribbean Island located at Mile Marker 79.7 in Islamorada.Jutting into the blue-green waters of the Atlantic Ocean, Tea Table Key features a 2,000′...

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$3,910
avg per night
Summerland Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Summer never ends in the Florida Keys! Endless Summer is located on Summerland Key in the very desirable Summerland Cove neighborhood. This is a two bedroom, two bathroom comfortable home with additional and very accommodating living space on the lower level.Upstairs is open concept living with a...

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$225
avg per night
Big Pine Key House
Sleeps 6, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

Escape to paradise in this beautiful newly remodeled 2 bedroom 1 bath duplex unit on a canal nestled in the heart of Big Pine Key. Perfectly located near a grocery store, great local restaurants, parks, and just minutes from the famous Bahia Honda State Park. Whether you're looking to relax or...

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$125
avg per night
Big Torch Key House
Sleeps 14, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • Pool
  • WiFi

About this property

Welcome to Barefoot Retreat, where you will feel as though you are on your own private island! As you drive through the remote, lush tropical island road to access the estate, drive slow as you might be greeted by the quite friendly protected Key Deer, roaming free about the property.As you approach...

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$833
avg per night
Key West House
Sleeps 6, 3 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner

About this property

A phrase the locals use quite often here in Key West is that we are "Living the Dream" - if you come and spend some time here you will see why! Steps away from the Key West Seaport and just a few blocks from world famous Duval Street this property is located on Eaton Street in Old Town Key...

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Islamorada Condo
Sleeps 8, 3 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Mile Marker 83 – BayfrontWelcome to your dream waterfront rental home in Islamorada, located in the heart of the Florida Keys. This stunning 4 bedroom, 4 bathroom home sits on the bay and offers breathtaking views of the water and world class sunsets.As you enter the home, you’ll...

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$733
avg per night
Key Colony Beach House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

No detail spared in this completely renovated, top of the line stilted half duplex on 9th Street in highly sought after Key Colony Beach. Excellent end of the canal location makes for instant access to Vaca Cut! Head to the open waters of the Gulf or Atlantic! Open concept living and kitchen area overlooking...

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$293
avg per night
Cudjoe Key House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to El Paraiso, a true Cudjoe Key gem at an affordable price. This three bedroom, three bath home is nicely updated throughout! Located on Lafitte Drive, right behind the famous Square Grouper restaurant and only 20 minutes from Key West. Don’t forget to bring your boat, there is plenty of...

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$225
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

Elegant Florida Keys direct ocean access and some open water views from the dock and balcony. This property is single family elevated home. All rooms and bathrooms are upstairs. 40 foot dock with 4 cleats. Large driveway, parking for at least 6 cars, trailer and RV. 75' of waterfront with wood dock....

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Featured review

"Relaxing Getaway"

Can’t say enough about Maria and Daniel the owners. They catered to us from first contact. The place was spotless and the home is even nicer than the pictures. It was a short visit for my wife and I,...

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$398
avg per night
Little Torch Key House
Sleeps 8, 4 bedrooms, 4 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

The Conch House is a very special little piece of paradise located at mile marker 28.5 on Little Torch Key. You can dock your boat right in your own front yard!! It sits on the open water on Pine Channel on the Gulf side of the Keys. The newly constructed cement L shaped dock can accommodate up to a 32’...

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Featured review

"Good times"

House was great, nice layout, pool and view. We had a wonderful time. I would have liked a dock to fish in deeper water from, more reeks and grass beds here. Beautiful though, great host

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$658
avg per night
Key Largo House
Sleeps 12, 5 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

YOU ARE JUST ONE STEP AWAY FROM A DREAM VACATION IN THIS ONE OF A KIND CUSTOM HOUSE. IT FEATURES A HEATED POOL AND 100' DOCK. LOCATED ON ADAMS CUT , THIS LUXURIOUS PROPERTY HAS 5 BEDROOMS ( 4 LARGE MASTER SUITES ) AND 6 FULL BATHROOMS. EACH OF THE 4 MASTER SUITES HAS A PRIVATE BATHROOM AND LARGE...

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$750
avg per night
New
Islamorada House
Sleeps 10, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

This quaint Keys-style home offers timeless charm in a premier waterfront setting on an ocean-access canal. The open-concept living, kitchen, and dining area flows effortlessly through the terrace to the backyard, where a private dock invites boating and fishing, and an outdoor bar and dining area offer...

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$514
avg per night
Marathon House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Updated two bedroom, two bathroom half duplex on 11th street. Excellent location towards the end of the canal yielding instant access to Vaca Cut and the Open Atlantic, 37 ft of deepwater dockage on an extra wide canal is perfect for fisherman and families alike! Enter through the street-side screened...

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$357
avg per night
Big Pine Key House
Sleeps 7, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Rentals by owner
  • WiFi

About this property

Come and enjoy a tropical sanctuary at this beautifully remodeled, fully furnished ground level island home located in Big Pine Key, Fl. Situated on a quiet street, this home features a bright, open interior with 3 bedrooms, 2 bathrooms. The yard is a wonderful oasis overlooking the canal with a hot...

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$330
avg per night
Key West House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

This estate has it all waterfront, large sun-filled pool and seawall dockage for your boat with over 3,800 sf of living space and 13,600 square feet of lush landscaped grounds. This private residence gives you the space and comfort one needs to relax and entertain your guests. The home was recently rented...

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$481
avg per night
Big Pine Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to Paradise Palm, a home away from home that encourages outdoor fun and relaxation with its unforgettable exterior amenities! Nestled in a quiet neighborhood, this beautifully furnished home offers a perfect blend of comfort and luxury.Step outside and be greeted by an excellent space that...

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$281
avg per night
Marathon Townhome
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Private pool
  • WiFi

About this property

Check out Anglers at Sombrero Canal Front Townhome with a private pool and 30 ft of dockage! Just minutes to the stunning Sombrero Beach, this Villa-style home is perfectly located in the heart of the Florida Keys. This newer built villa offers beautiful views of the canal and surrounding neighborhood....

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$458
avg per night
Duck Key Cottage
Sleeps 3, 1 bedroom, 1 bathroom
7 reviews

Distance to beach: 9 miles to Coco Plum Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Our vacation rental is an historic 1 BR/1 BTH waterfront cottage in prestigious Duck Key in the Florida Keys. There are plenty of outdoor amenities on the more than 1/4 acre property. These include a 15 X 34 foot saltwater swimming pool, hot tub, and grill with prep and dining area. The backyard perimeter...

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Featured review

"Escaping Reality."

Quaint cottage with lots of Florida Keys charm. In times when life gets overwhelming our stay was an escape from reality. Cottage was clean, comfortable and relaxing. The outdoor area was amazing with...

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$157
avg per night
Key West House
Sleeps 8, 4 bedrooms, 4 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to Casa Rosa, your tropical sanctuary nestled in the vibrant heart of Key West, Florida.*Saturday-to-Saturday Rentals OnlyProperty Overview:Prime Location: Casa Rosa is situated in a picturesque neighborhood, just one block away from Key West's renowned Duval Street. Casa Rosa...

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$1,042
avg per night
Marathon House
Sleeps 8, 4 bedrooms, 3 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to Tropical Sunsets, your tropical oasis in the heart of Marathon, Florida! This stunning 4-bedroom, 3-bathroom home offers a serene escape with breathtaking Gulf views and a perfect location for relaxation and adventure.*Saturday-to-Saturday Rentals OnlyProperty Overview: Prime Location: Tropical...

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$655
avg per night
Key Largo House
Sleeps 6, 2 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

Water front upstairs Duplex with 38 feet of deep water Dockage ,minutes from open Ocean. two bedroom and 3.5 bath house plus living room with two sofas beds completely renovated, centrally located in prestigious Port Largo Neighborhood, minutes from all water activities imaginable. Enjoy Deep Sea Fishing,...

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$150
avg per night
Key Colony Beach House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Experience the epitome of coastal living in this exceptional half-duplex located in the prestigious Key Colony Beach. Situated on the picturesque blue waters of Key Colony Beach, this property seamlessly combines modern luxury with the relaxed charm of island life. With 3 spacious bedrooms and 3 beautifully...

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$300
avg per night
Cudjoe Key House
Sleeps 12, 6 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

This brand new 5/6 bedroom 4 bath oceanfront home has a private pool and will share dock space, kayaks and the gazebo with Blue Palms Retreat home. There is 1 double and 3 single kayaks. Bring your boat- up to 24’ and your snorkel gear. Relax on one of the porches overlooking The Atlantic Ocean...

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$658
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
24 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, pickleball, heated pool, private beach, and dockage for...

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Featured review

"Very Good place"

We stayed in unit 102. Glenn was a great guy to rent from, very helpful and followed up for any questions.a very nice condo, private bathroom for two main bedrooms. Most everything needed for making meals...

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$189
avg per night
Summerland Key House
Sleeps 8, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This extraordinary island castle will make you feel like the royal family! With four bedrooms and five bathrooms you will not have to share your space! Start your day boating, fishing or kayaking and then return for a cool dip in the pool! Relax on the expansive screened in porch with a drinks and appetizers...

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$459
avg per night
Marathon Villa
Sleeps 6, 3 bedrooms, 2.5 bathrooms
76 reviews

Distance to beach: 5 miles to Sombrero

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Indigo Reef #41 is the BEST KEPT SECRET in the Florida Keys!! This home is spectacular in every sense of the word and not one detail has been overlooked. It is every renter's dream.Luxury and tranquility await you in this beautiful 3BR, 2.5 BA home at Indigo Reef Marina, named one of Marathon,...

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Featured review

"Most Amazing Stay"

Indigo Reef #41 quickly became our family’s new favorite place to stay. This was our second trip to the Keys and this house was amazing. The attention to detail cannot be overlooked. The owner (Toni)...

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$496
avg per night
Big Pine Key House
Sleeps 4, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

Welcome to Kokomo Palms – Your Island Escape!Discover the perfect slice of paradise at Kokomo Palms, a charming 2-bedroom, 1-bath vacation home nestled in Big Pine Key. Located in a peaceful canal-front neighborhood, this getaway offers everything you need for a relaxing and adventurous stay....

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$160
avg per night
Marathon Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This charming property offers 3 bedrooms and 2 bathrooms, ideal for families or groups looking to enjoy the beauty and tranquility of the Florida Keys.*Saturday-to-Saturday Rentals OnlyProperty Overview:Prime Location: Bird of Paradise offers stunning views of the Atlantic Ocean. Bird of...

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$344
avg per night
Marathon House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Villa FranchellaEscape to paradise and experience the epitome of luxury living in this new breathtaking 4-bedroom, 3-bathroom waterfront home in Marathon, FL. Located just minutes from the Gulf of Mexico with easy access from the 45' of available dockage, this newly renovated sanctuary offers...

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$602
avg per night
Cudjoe Key House
Sleeps 6, 3 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Tropical Paradise has been a popular and romantic vacation rental getaway since 2003. This house includes all the elements you need for an amazing vacation. There are kayaks for adventures, a dipping pool and private beach for relaxation, a floating dock for fishing and docking a boat, (up to 24'...

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Featured review

"Peace and Tranquility. Amazing sunrises and sunsets"

The location was exactly what I had hoped. It was secluded, but close to everything. The water views were worth every penny!

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$500
avg per night
Cudjoe Key House
Sleeps 9, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

***We are taking the recommended steps as presented by the Center for Disease Control and Prevention (CDC) for cleaning, disinfecting, and preparing this home for your arrival. We are following the protocols laid out by the CDC and using the EPA-approved disinfectants for Hard (non-porous) Surfaces, Soft...

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$500
avg per night
New
Summerland Key House
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to the Key House, a completely charming, canal front home located in the ultra popular Jolly Roger Estates on Little Torch Key.A cute tropical them from the outside in, you know you are in the Florida Keys! The exterior boasts an immaculately kept grounds with ample storage for your gear,...

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$193
avg per night
Islamorada House
Sleeps 16, 8 bedrooms, 9 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Introducing Maison Residences Full floor for rent – Oceanfront & Poolside… — UP TO 32’ BOAT SLIP MAY BE AVAILABLE —Units 201 and 203 rented together. Private steps to pool, beach and Atlantic Ocean! 8 bedrooms, 8 full baths, 2 half baths, 2 full kitchens, 2...

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$3,155
avg per night
Marathon Apartment
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Escape to paradise at this stunning 3-bedroom, 3-bathroom single-family home in Key Colony Beach! Nestled in a prime location, this spacious home offers everything you need for a relaxing and unforgettable getaway. Whether you're a boating enthusiast, a pool lover, or just looking to unwind in the...

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$457
avg per night
Marathon Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

2/2.5 Condo Unit, Direct Gulffront views - Wrap-around balconiesOsprey Point at Gulfpointe II is a wonderful vacation property that boasts 180-degree views of the Gulf of Mexico and Vaca Cut, an inlet that joins the Gulf of Mexico and the Atlantic Ocean as well as a view down the boat/fishing dock....

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$300
avg per night
Marathon House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to your perfect tropical getaway! This stunning, completely remodeled half duplex in Key Colony Beach offers a blend of modern luxury and coastal charm. From top to bottom, no detail has been overlooked in creating this immaculate vacation retreat.Relax and unwind in the spacious living areas...

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$393
avg per night
Islamorada House
Sleeps 8, 4 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Mile Marker 75 – BaysideLarge, modern 4 bedroom canal front home with pool in Lower Matecumbe Key in Islamorada, Florida Keys. This gorgeous home overlooks the pool and canal.The main selling point of Latitudes is the home’s awesome outdoor area. Pool, Tiki Hut, grill and outdoor seating...

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$800
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Lovely home with lots of glass windows looking towards the ocean. 50 ' of dockage with instant ocean access. 12 Therapy jets in the 14 X 30 pool that ranges from 3' to 5' in depth. The pool overlooks the canal and the ocean. Pool heat is add'l if paid in advance, $200 or $250 on arrival. Three...

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$429
avg per night
Marathon House
Sleeps 8, 4 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Paradise Palms! ️ This stunning 4-BR retreat has it all. Boating right from your private dock, easy open-water access, waterfront views, unwinding in your private heated pool Fire up the grill for a sunset BBQ, challenge friends to cornhole or game room fun, and set off on a kayak adventure...

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Featured review

"Great time"

We have a great vacation, the house fit our needs perfectly. There recommended places to visit and eat at were great. Had a small issue with the dryer, we called them and they responded quickly.

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$511
avg per night
Islamorada House
Sleeps 8, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • WiFi

About this property

$15,000-$17,500 WeeklyA world-class oceanfront residence, located in the heart of Islamorada in the Florida Keys. This luxurious residence features unsurpassed vistas of the Atlantic Ocean from the master bedroom, grand room, kitchen & oversized living terraces. Arrive by car ~ just a short 90-minute...

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$1,720
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to Paradise Point! Indescribable Views! This stunning sanctuary offers Water Frontage on 3 sides giving over 180° of unparalleled Atlantic Ocean Views, Direct Ocean Access from your Private Dock, perfect for boating or fishing right from the backyard After a day on the water, unwind in...

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$661
avg per night
Summerland Key House
Sleeps 14, 6 bedrooms, 4 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Beautiful Ocean Front Home with six bedroom/Four bath. New memory foam mattresses in King and Queen rooms. Enjoy the heated pool, dock and beach. Located on Cudjoe Bay with panoramic view of the Atlantic and deep water swimming. Kayaks are provided for your enjoyment. There is a huge screened in porch...

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Featured review

"We would do it again!"

We enjoyed a family vacation for one week at this "villa". The view was spectacular and the interior spacious. There were plenty of spaces for all of us to sit and visit with each other. The pool was fun...

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$658
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 3.5 bathrooms
1 review

Distance to beach: 2 miles to Sombrero

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Start planning your perfect escape to the Florida Keys! Flamingo Palms Cottage is ideally located on a deep-water canal with 35’ of dockage and easy access to world-class fishing in the Atlantic and the Gulf. Enjoy all the amenities needed for a perfect island vacation: airy open living areas,...

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Featured review

"Blue Ocean Bungalow"

The home was very comfortable, and clean, it was so nice to look out the windows and see the water. Everything you need for cooking in is provided as far as dishes and pots and pans. Also, the Canopy...

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$340
avg per night
Little Torch Key House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Meet your perfect vacation getaway, Maracaibo Manor! Located on Little Torch Key in the highly desirable Jolly Roger Estates neighborhood, with excellent deep water access for boating, diving, fishing and snorkeling at the famous Looe Key Reef.This roomy home has two bedrooms and two bathrooms upstairs,...

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$320
avg per night
Cudjoe Key House
Sleeps 4, 2 bedrooms, 2 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

House - 2 Bedrooms, 2 Bathrooms, Sleeps 4. Come enjoy our hidden retreat in upscale Cudjoe Gardens. This home is conveniently located only blocks away from Cudjoe Gardens Marina. This single level home is situated on a crystal clear flow through deep water canal. The home features an in ground private...

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Featured review

"Perfect Keys Home"

We absolutely loved this home! We've been traveling to the Keys for 15 years and this is one of our favorites. A quiet neighborhood which is fantastic. Fred is excellent with communication.

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$217
avg per night
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Map

FAQ

Location & Specific Keys

What is the difference in atmosphere between the Upper, Middle, and Lower Keys?

The Upper Key has a relaxed vibe with a lot of nature preserves and parks to see. The Middle Keys have a laid-back vibe along with popular places to snorkel, dive, and swim. The Lower Keys, along with Key West, have an energetic vibe.

Which Key is best for nightlife and attractions versus quiet relaxation?

The Lower Keys have a vibrant nightlife, while the Middle Keys offer a relaxing atmosphere.

How do I choose the right Key to stay on for my vacation goals?

One of the simplest ways to choose a Key is to decide which attractions you want to see. Then, choose the Key that gives you the easiest access to those attractions.

Are there any lesser-known Keys that offer good rental options?

Sugarloaf Key, Little Torch Key, and Tavernier Key are lesser-known Keys with houses and other types of vacation rentals.

Activities & Lifestyle

Which Key is the best home base for fishing, diving, or snorkeling trips?

The Middle Key is your best bet for fishing, diving, and snorkeling fun, particularly off the coast of Marathon.

What are the "must-do" activities when staying in the Florida Keys?

Some “must-do” activities include snorkeling and swimming around the reefs, visiting the Hemingway Home and Museum, touring Marathon Marine Park, and visiting Dolphins Plus Bayside.

Are the rentals close to good restaurants, marinas, and public beaches?

Yes. Many Florida Keys vacation rentals are close to restaurants, marinas, and public beaches. Some properties are close to shopping areas, state parks, boat rentals, and breweries as well.

What is the best way to get around the Keys – is a car necessary?

Though there is public transportation like the Freebee Shuttle, renting a car is a great way to take in the sights around the Keys.

Booking & Logistics

What are the pros and cons of renting directly from an owner versus a property manager?

One pro of renting directly from an owner is flexibility. You may be able to negotiate on rent or fees with a property owner, whereas a property manager isn’t likely to negotiate. However, a property owner may not be as quick as a property manager to address rental issues, including maintenance.

What are the best websites for finding "For Rent By Owner" (FRBO) properties in the Keys?

Florida Rentals is one of the best websites to find FRBO properties.

How can I protect myself from scams when booking directly with an owner?

One way to protect yourself is to conduct an address search to ensure the property exists. Also, don’t pay the rent with a gift card, cash, check, or wire transfer. Be suspicious of a large property with lots of amenities and very low rent.

Do rentals by owner offer more flexibility on price or stay dates?

Yes. Rentals by owner offer more flexibility regarding price and stay dates. While a property management company has to answer to the owners, the owner of a rental can make changes at will.

Property Type & Communities

What types of houses are common for rent in the Keys (e.g., stilt homes, bungalows, canal-front homes)?

Canal-front homes, bungalows, and cottages are common rentals in the Florida Keys.

What is the benefit of renting a house on a canal versus one that is oceanfront?

A house with a canal gives you a place to boat and fish in still water right in front of the property. Renting an oceanfront home offers a great view of the ocean, but not a convenient place for fishing and boating.

Do most house rentals come with private boat dockage?

Yes, many house rentals in the Florida Keys include private docks.

Are there large houses available that can accommodate multiple families or big groups?

Yes, there are large houses in the Florida Keys suitable for big groups. Use the search filter to find a rental that can accommodate all of your guests.

Amenities & Features

What are the essential amenities for a Keys rental (e.g., boat slip, fish cleaning station, outdoor seating)?

Essential amenities for Florida Keys rentals include a patio or deck, boat slip, Wi-Fi, heated pool, and kitchen.

Is a private pool a common feature for house rentals in the Keys?

Yes, a private pool is a common sight in a description of house rentals in the Keys.

What should I look for in terms of parking, especially if I'm bringing a boat trailer?

Look at the property’s description to see if there is parking available. Some owners have parking areas for boat trailers. If you don’t see any information about trailer parking, message the property owner to get specifics.

Are kitchens in these homes typically well-equipped for cooking a fresh catch?

Yes. Along with a fish cleaning station, many rentals have a well-stocked kitchen with appliances for cooking seafood.