Florida Keys Vacation Rentals

(566 rentals)
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Summerland Key House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$143

avg/night

$143
avg per night
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Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to Buccaneer Boathouse! Pack your floral shirts, swimming gear and sandals and come on down to Little Torch Key in the beautiful Florida Keys. This lovely home is spacious with 2 bedrooms and 2 bathrooms. It offers a large open kitchen, dining and living area for everyone to hang-out and plan ...

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Property Type

Summerland Key House

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Little Torch Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 2 miles to Picnic Island (by Boat)

$165

avg/night

$165
avg per night
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Key Amenities

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

About this property

Beautifully kept private and secure canal front (220' of waterfront) home. Located at the end of a dead end street in a residential neighborhood alLows for privacy and extra relaxation. Fully updated kitchen, fully equipped with coffee maker, espresso maker, blender, bullet blender, etc. Ideally ...

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Property Type

Little Torch Key House

Featured review

"Perfect place"

The property is updated, super comfortable, spacious, and beautifully decorated. We will be visiting again!

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Marathon Villa
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
6 reviews

$499

avg/night

$499
avg per night
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Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

"SOMBRERO HEAVEN" is a canal front 4 bedroom 3 bath attached Villa with neighborhood ocean front beach just down the street! It has a private pool that can be heated or chilled (for a fee), private dock (up to 35' boat), fish cleaning station, bait freezer and 4 new bikes! Additionally, ...

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Property Type

Marathon Villa

Featured review

"Everything you could want in a vaca rental"

Meredith is prompt and helpful. Everything you could want at the beach or for your boat is provided. This is a big plus if flying in. Hope to return here. Highly recommend!

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Islamorada Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$200

avg/night

$200
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • WiFi

About this property

Beautiful oceanfront apartment with easy access to pool, spa, and beach. Dock with boat slips and tiki hut overlooking the Atlantic Ocean. Community exercise room Master Bedroom overlooking the ocean Two bedrooms, two full baths. Gourmet equipped kitchen Laundry room Balcony with spiral stairs ...

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Property Type

Islamorada Condo

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Summerland Key House
7 BR | 5 BA | Sleeps 12 | Quick View
Sleeps 12, 7 bedrooms, 5 bathrooms

$667

avg/night

$667
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Fabulous resort-style living & incredible open water views over Niles Channel at this 7 BR 5 BA home on Summerland Key. Just under an acre boasting a sandy beach w/pretty palms, large custom pool, & deep water dockage w/quick access to ocean, gulf & back country. The open Great Room boasts ...

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Property Type

Summerland Key House

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Key Largo House
2 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 3.5 bathrooms

$200

avg/night

$200
avg per night
View Details

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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Property Type

Key Largo House

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Marathon House
4 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 2 bathrooms
12 reviews

Distance to beach: 3 miles to Sombrero

$404

avg/night

$404
avg per night
View Details

Key Amenities

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

About this property

Manatee Cove-4BR/2BA, Pool/Spa, Tiki, Quick Atlantic access!Escape to the Florida Keys ~ Gorgeous 4BR/2BA Home on the Atlantic side of the canal in Marathon. Our home offers the best pool in our area; who can say no to a hot tub, pool, and bar stools in one? Swim right up to the Tiki and enjoy the ...

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Property Type

Marathon House

Featured review

"Paradise"

My family and I had a wonderful week here. The owner and property manager were both a pleasure to work with. Our favorite amenity was the pool and hot tub. We had plenty of space and all of the beds were ...

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Islamorada House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 3 miles to Anne's Beach State Park

$321

avg/night

$321
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

This 3-bedroom bayfront property is located on Lower Matecumbe in Islamorada. The view is spectacular with sunsets on the water most of the year. There is plenty of room for boat trailers, RVs and other toys inside the fence. There is covered parking for your vehicles and a seawall out front to tie your ...

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Property Type

Islamorada House

Featured review

"Lower Matecumbe"

All I can say is that this place never fails to impress! The views from every inch of the property are the best in all of the keys! Great communication with Rich and his office. Would recommend every ...

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Key West Villa
6 BR | 7 BA | Sleeps 16 | Quick View
Sleeps 16, 6 bedrooms, 7 bathrooms
3 reviews

Distance to beach: 0.3 miles to Ft Zachary Taylor

$1511

avg/night

$1,511
avg per night
View Details

Key Amenities

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

About this property

Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theaters and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a huge, fabulous decks that overlooks the action on ...

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Property Type

Key West Villa

Featured review

"Glenn dinner group get away"

We had 6 couples visiting key west for a week to celebrate milestone birthdays and get away. The houses were perfect for our group. Beautifully decorated,plenty of space for everyone to enjoy and not ...

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Marathon House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
7 reviews

Distance to beach: 2 miles to Sombrero Beach

$395

avg/night

$395
avg per night
View Details

Key Amenities

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

About this property

Our waterfront, single-family home, affectionately named “Turtle Cove”, offers 3 bedrooms, 2 baths, and an 80 ft seawall with quick ocean access! This tastefully furnished Keys home is located on a quiet side street in a residential neighborhood on the Atlantic side of the Island, just 5 houses ...

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Property Type

Marathon House

Featured review

"Great stay"

Our family of 6 spent a wonderful 3 weeks at Turtle Cove. This home with 2 separate living spaces was perfect for us. Everything was very clean when we arrived and the amenities were as described in the ...

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Summerland Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

$278

avg/night

$278
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This home is the ideal getaway for the whole family! The interior of the home is super spacious with an updated kitchen that looks out over the canal and large pool.There are three bedrooms, two bathrooms, and a large family area with a big screen television for your entertainment. Not to be outdone, ...

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Property Type

Summerland Key House

Featured review

"Outstanding location for fishing, boating, & diving!"

Stayed at this gem before and after Lobster mini season. The pool was perfectly refreshing after a day in the sun on the water. There are several free boat ramps nearby. Great proximity to the Looe key ...

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Key Colony Beach House
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms

$219

avg/night

$219
avg per night
View Details

Key Amenities

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

About this property

Canal front, Dock, Hot Tub and Cabana Club AccessWelcome to Orchid House, a lushly landscaped canal front home located on the beautiful island of Key Colony Beach. This property comes with boat dockage , private hot tub and access to the Cabana Club pool and beach.When you first drive up to the ...

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Property Type

Key Colony Beach House

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Islamorada Condo
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
3 reviews

$379

avg/night

$379
avg per night
View Details

Key Amenities

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

About this property

1st I want to thank all our past guests for their great reviews. Bay Harbour Starfish is a luxury condo overlooking a large boat basin with views of the Atlantic Ocean. Situated in Lower Matecumbe Key, Islamorada, the Sport Fishing Capital of the World. This very spacious 3 bedroom, 2 and half bath condo ...

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Property Type

Islamorada Condo

Featured review

"warm retreat"

Bay Harbor was delightful, from the condo unit to the grounds and amenities. We used the hot tub, exercise room and swimming pool, When we left there was 76 degrees, returned to 20 degrees in Pennsylvania.

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Big Pine Key House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$177

avg/night

$177
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

What a great sunset view from this house! Fun in the sun surrounds this spot right on a wide canal with excellent access to fishing either the Gulf or the Atlantic side. Any outdoor enthusiast would be content here as the boating, diving, snorkeling, or kayaking is right out your back door.After a ...

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Property Type

Big Pine Key House

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Islamorada House
3 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 3 bedrooms, 2 bathrooms
16 reviews

$481

avg/night

$481
avg per night
View Details

Key Amenities

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

About this property

''BEAUTIFUL BAYFRONT PROPERTY!!!!''** 2022 Remolded bathrooms, 2021 NEW POOL** Fully furnished, 1 story offering 3bd/2ba. The house can sleep up to 8. There is a 1/1 guest suite attached which does have its own separate and private access with full kitchen and bath. Entire house ...

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Property Type

Islamorada House

Featured review

"The BEST of the BEST in every way!"

By far and away, this was the best rental property we have ever stayed! We have been visiting Islamorada for nearly 20 years and have stayed almost everywhere you can imagine, and we have now struck gold ...

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Key Largo House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
5 reviews

$150

avg/night

$150
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Our home is a unique tropical paradise in Key Largo. Our kids named it Manatee Corner for the friendly visiting Manatees. It’s a three-story duplex, open concept with a wrap around balcony. We are blessed with a canal that opens to the Atlantic Ocean providing direct access to the most incredible ...

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Property Type

Key Largo House

Featured review

"Old school Key’s experience"

The owner is a nice family guy who keeps the place clean and safe. The location is perfect. Ubers or Lyft show up in two/ three minutes. You can walk to restaurants and pubs. Ocean water access is great ...

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Key West House
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1 bathroom
3 reviews

$402

avg/night

$402
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

The Sea View Cottage is a 2 bedroom, 1 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 ...

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Property Type

Key West House

Featured review

"The Perfect Relaxing week!!"

My family booked Seaview Estates for our 25th Anniversary trip! We rented both houses so we had the property to ourselves. Upon arrival, Carol met us at the gate and began our tour of the property. The ...

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Summerland Key House
6 BR | 4 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 4 bathrooms
1 review

$658

avg/night

$658
avg per night
View Details

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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Property Type

Summerland Key House

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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Islamorada House
3 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 3 bedrooms, 3 bathrooms
3 reviews

Distance to beach: 0.3 miles to Anne's Beach

$350

avg/night

$350
avg per night
View Details

Key Amenities

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

About this property

Enjoy this modern and recently updated lagoon front 3 bed/3 bath single-family home on the Gulf side of Islamorada at MM 73.5, minutes from the Channel 2 and Channel 5 Bridges, offering immediate access to the oceanside of Lower Matecumbe Key. Dockage is available for up to a 35' boat, or use the ...

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Property Type

Islamorada House

Featured review

"Paradise Found"

We thoroughly enjoyed our stay at this property. It was exactly as described in the listing. The location is nestled in a quiet neighborhood that allows you to ride your bikes across the street to Anne’s ...

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Summerland Key House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms

$457

avg/night

$457
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

Welcome to Oceanview Oasis, a most spectacular open water home on Summerland Key. This is a completely remodeled, state of the art, waterfront retreat with new oceanside pool, adjacent spa and screened porches on two levels for outstanding views at every turn.Interior living space offers a split floor ...

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Property Type

Summerland Key House

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Summerland Key House
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms
1 review

$264

avg/night

$264
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

Make your memories at the Aloe House on Cudjoe Key! This home is located on a beautiful crystal clear canal with plenty of dockage for up to a 25 foot boat. The canals here provide great access to some of the best fishing in the Florida Key – Bahia Azul, “Bay of Blue” is exactly the ...

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Property Type

Summerland Key House

Featured review

"Great Home to rent on Little Torch Key"

Great home on a canal with easy access to the ocean. The extensive dock is wonderful. Very comfortable home with with a good flow.

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Little Torch Key House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms

$421

avg/night

$421
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • WiFi

About this property

Enjoy a luxurious space and a place to call home during your sunny Florida Keys destination. Located on the open water on Little Torch Key with gorgeous ocean views. The sunrises and moon rises are a delightful sight. Large inground ground pool with attached spa for lounging and swimming. Water toys galore. ...

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Property Type

Little Torch Key House

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Islamorada House
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

Distance to beach: 0.5 miles to White Marlin Beach

$851

avg/night

$851
avg per night
View Details

Key Amenities

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

About this property

Bring your boat and Jet SkisNestled on a canal, less than a 2 minute boat ride to the bay and 10 minutes to the ocean with key access to private White Marlin Beach. New heated pool and hot tub, 70' dock with fish cleaning table, commercial ice machine, double jet ski lift, and two floors facing ...

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Property Type

Islamorada House

Featured review

"Fabulous location, off the beaten path, clean, owner available for questions and very responsive."

We stayed in this home for a month, the location is amazing if you love to paddle board, kayak and discover the many mangrove islands that are a five minute paddle from your dock. The outside area has ...

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Summerland Key House
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms

$417

avg/night

$417
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

Looking for that perfect Florida Keys Get Away? You found it here!Located on prestigious Summerland Key with some of the best deep-water boating, diving and fishing in the Lower Keys. Super easy access to superior fishing spots.This upscale home is complete with 4 bedrooms and 2 baths. Beautifully ...

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Property Type

Summerland Key House

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Islamorada Apartment
5 BR | 3.5 BA | Sleeps 14 | Quick View
Sleeps 14, 5 bedrooms, 3.5 bathrooms

$884

avg/night

$884
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Indulge in the epitome of coastal living in this expansive duplex penthouse boasting ocean views in Islamorada. Relish captivating tranquility with a grand open-concept layout seamlessly blending living, dining, and a wet bar, all framed by panoramic seascapes, a chef's kitchen and access to top-tier ...

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Property Type

Islamorada Apartment

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Islamorada Villa
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
14 reviews

Distance to beach: 5 miles to Anne's Beach

$330

avg/night

$330
avg per night
View Details

Key Amenities

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

About this property

The "Nest" villa (one of 7 privately owned condo residences) sits on a 1 acre lot located on Islamorda's beautiful Florida Bay. Stunning water views and unforgettable sunsets are guarenteed. The property is filled with mature tropical landscaping along a tree lined private gravel driveway ...

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Property Type

Islamorada Villa

Featured review

"Amazing location, view, and super clean!"

My 18 yr old son and I stayed here at the end of September and it was a fantastic trip!We have been going to the keys for 14 years several times a year. This unit is the cleanest we have ever seen! ...

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Cudjoe Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

$160

avg/night

$160
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

This Cudjoe Key home is neat as a pin with all the comforts of home. Bright and shiny kitchen with everything you may need to create wonderful get together. The large comfortable living room has plenty of seating including recliners in the sofa and loveseat. Laminate hardwood floors throughout. 3 large ...

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Property Type

Cudjoe Key House

Featured review

"Wonderful relaxing vacation home"

We recently stayed at the Sunset Bay home and couldn’t have been happier with the rental. Never having rented a home in the Keys I wasn’t sure what to expect but the Action Keys realty team was efficient ...

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Islamorada House
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms
1 review

$300

avg/night

$300
avg per night
View Details

Key Amenities

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

About this property

Beautiful, fully remodeled waterfront home with water on both sides! Ocean and lagoon views from bedrooms, dining room, balconies and kitchen. Cable TV with premium channels and wi-fi internet access. The home is in a quiet neighborhood on a cul-de- sac and very convenient to Tavernier or Islamorada ...

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Property Type

Islamorada House

Featured review

"A rental that exceeded expectation"

A well maintained home in a perfect quiet setting. The owner Patrick was outstanding to work with and made sure that all was in order. He is an excellent communicator. Welcome bottles of wine greeted us. ...

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Summerland Key House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms

$391

avg/night

$391
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

The South House is a superb vacation home on Summerland Key. It offers everything you need to make your Florida Keys vacation truly memorable.The downstairs pool area is private and serene. There are several lounging areas to enjoy suntanning or wonderful afternoon shade. The crystal blue pool is ...

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Property Type

Summerland Key House

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Key Largo House
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1 bathroom
2 reviews

Distance to beach: 6 miles to John Pennekamp State Park

$166

avg/night

$166
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront

About this property

1 BR/1 Bath Rare Find! Lovely oceanfront home with large private boat basin. This ground-level house has two enclosed sleeping areas - a master bedroom with a king bed, and a private alcove providing sleeping space for up to 4, with 2 bunks and a full-sized bed (separated from the living room by an ...

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Property Type

Key Largo House

Featured review

"Peaceful Escape"

A lovely property, a comfortable house with all the amenities and a covered outdoor patio right on the ocean where we spent most of our time reading, sunning, and watching the wildlife fly, swim and crawl ...

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Marathon House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
9 reviews

$535

avg/night

$535
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

DOCKSIDE RETREAT is a 4 bedroom 3 bath canal front home that has a private pool, private dock, fish cleaning station, with a green light under the dock, two paddle boards, a kayak, four bikes, and a Tiki Hut for the ultimate Keys vacation! There are 4 parking spots for vehicles and one boat trailer (you ...

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Property Type

Marathon House

Featured review

"Fantastic Experience"

We had a fabulous stay in your property. We really appreciated all of your amenities. We love to cook some of our meals in and you had a great selection of pots and pans and dinnerware. We also like ...

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Lower Matecumbe Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
4 reviews

$364

avg/night

$364
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This Condo comes with tennis courts, pool, club house, undercover parking and elevators for easy access. Located on quiet Lower Matecumbe Key Bay Harbour is just 7 miles from Islamorada's center with nearby beaches and parks.

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Property Type

Lower Matecumbe Key Condo

Featured review

"Bay Harbour condo review"

Spacious 2 bedroom condo with everything you need. Beautiful view, well equipped kitchen. Comfortable furniture. Well maintained grounds and great pool. You're able to buy fresh lobster/ seafood right off ...

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Islamorada Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
8 reviews

Distance to beach: 5 miles to Anne's Beach

$329

avg/night

$329
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

Enjoy the sunrise from the balcony or from the condo through 50' of glass sliding doors. You can also view the sunset from our walkway on bayside. We have a full kitchen, dishwasher to microwave, washer/dryer, even beach towels. We have wifi,cable TV in living area and all bedrooms, master bath ...

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Property Type

Islamorada Condo

Featured review

"Keys Condo"

Awesome peaceful location,clean and perfect amenities lots of birds and fish at marina manatee, sand sharks ,etc

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Summerland Key House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms

$254

avg/night

$254
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

Welcome to Bow Channel Manor and step back in time to Old Florida! You’ll find this plantation style home remeniscent of Florida past! Enjoy family-style vacationing on a private 4 acre parcel of land on Upper Sugarloaf Key.The grounds are like a playground. There is a full-size heated pool ...

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Property Type

Summerland Key House

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Little Torch Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 23 miles to Marathon

$185

avg/night

$185
avg per night
View Details

Key Amenities

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

About this property

Charming house on a canal with all amenities like home. Bring your own boat and park it on the dock for the duration of your vacation. Convenient located 25 miles before Key West. Nice restaurants and groceries shopping 10 minutes from the house Marathon is only 30 minutes away. A short boat ride ...

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Property Type

Little Torch Key House

Featured review

"Amazing vacation!"

This canal front home is close enough to everything to be convenient, yet far enough away from everything to be private and secluded. Easy access to the Atlantic and Gulf for boating, close to picnic ...

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Marathon Villa
4 BR | 3 BA | Sleeps 14 | Quick View
Sleeps 14, 4 bedrooms, 3 bathrooms

$700

avg/night

$700
avg per night
View Details

Key Amenities

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

About this property

WELCOME TO THE KEYS! Mega tropical oasis with 2 HOUSES! No you are not dreaming. Yes there are 2 houses connected together totaling 5 beds, 3 full bathrooms, 2 outdoor showers , 2 six person Hottub’s and 2 kitchens. Along with kayaks, beach bikes, volley ball, bocci ball, fire pit, corn hole and ...

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Property Type

Marathon Villa

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Cudjoe Key Cottage
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$141

avg/night

$141
avg per night
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Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

A comfortable well priced home away from home. This charming 2-bedroom, 2-bathroom cottage offers a spacious, living/dining area with a fully stocked kitchen only steps away from the shaded patio with a water view and firepit.Experience the coastal charm and serenity of waterfront living while being ...

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Property Type

Cudjoe Key Cottage

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Marathon Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$269

avg/night

$269
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Come enjoy this beautiful OCEAN VIEW condo located in Key Colony Beach on the 2nd floor!!! This two bedroom & two bathroom condo offers all the amenities of home!!! Enjoy a cup of coffee in the morning, or a glass of wine anytime on one of the two ocean view balconies. Coin laundry right outside the ...

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Property Type

Marathon Condo

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Summerland Key House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms

$445

avg/night

$445
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Come live the Salt Life at Salty Retreat! Stay at this luxury top of the Line tropical style home on Summerland Key. Located in a very popular subdivision on Lagoon Drive with deep boating access.This home is 'five stars' the moment you pull into the paver circular driveway. Sitting on two ...

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Property Type

Summerland Key House

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Cudjoe Key Villa
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$393

avg/night

$393
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Looking for a home away from home? Via Villa is the place! This vacation home is located in Cudjoe Gardens on Cudjoe Key, only 20 miles from Key West. Situated on a corner canal, there is ample dockage for large boats, water and electric on the dock, as well as a waterside fish cleaning table. Via Villa ...

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Property Type

Cudjoe Key Villa

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Cudjoe Key House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms

$417

avg/night

$417
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

You will be absolutely delighted to vacation at this remarkable luxury vacation home on Summerland Key. This multimillion dollar home has only the best to offer. The kitchen is a chef‘s dream with top of the line stainless appliances, cook top, built in ovens and gorgeous stone countertops.The ...

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Property Type

Cudjoe Key House

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Cudjoe Key House
4 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 2 bathrooms
5 reviews

$417

avg/night

$417
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

BOAT RENTAL: We offer to rent our personal boats to our guests, only. We own: Flats Boat - 17 ft Ranger with E Tech 75 Bay Boat - 24 ft Bay Scout with 225 HP Yamaha Open Fisherman - 29-ft Ocean Runner with twin 300 HP Verrado's These boats are set up with everything you need to fish the Keys, ...

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Property Type

Cudjoe Key House

Featured review

"Vacation 2024/2025"

Southern Sunset is an excellent place to stay! The hosts are very accommodating and were great to chat with and helped make our stay even better. The property is clean and well kept and has a fabulous outdoor ...

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Ramrod Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$221

avg/night

$221
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

The Coral House is a prime destination spot for a great Florida Keys vacation! Conveniently located on Ramrod Key, mile marker 27. Close to all the choice restaurants and services that the Florida Keys have to offer.This home is beautifully decorated in island style with attention to even the smallest ...

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Property Type

Ramrod Key House

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Key Largo Condo
2 BR | 1.5 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 1.5 bathrooms
1 review

Distance to beach: 175 yards to K Building

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

PLEASE NOTE - This unit is only available for monthly rentals due to the condo by-laws.This beautiful end unit is nestled in the most charming area of the best condominium complex in Key Largo. As you walk up to the front of the unit, you will be pleased by the inviting seating area and the paved ...

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Property Type

Key Largo Condo

Featured review

"Breathtaking sunsets"

Lovely condo, owners great to work with. Wonderful amenities with a beautiful heated pool. breathtaking nightly sunsets.

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Summerland Key House
2 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 2 bedrooms, 2 bathrooms

$252

avg/night

$252
avg per night
View Details

Key Amenities

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

About this property

This is truly an incredible, well-designed, and appointed Summerland Key home! You will love the interior design of this palace, with cathedral ceilings, a sunken living room and a lofted office/additional sleep space. A very large dining room leads into the enormous, updated kitchen, fit for any chef. ...

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Property Type

Summerland Key House

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Islamorada House
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms
8 reviews

$793

avg/night

$793
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

‘The Beach House’ at Tarpon Point in Islamorada- DIRECT RENTAL WITH NO ADMIN OR CC FEES‘The Beach House’ is a luxurious oceanfront home in a private gated enclave of only 12 houses. This end home offers privacy and beautiful ocean views including of Indian Key Historic State ...

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Property Type

Islamorada House

Featured review

"Fabulous place to stay!"

This unit on Islamorada provides wonderful oceanfront views. Our group included five retired women who all worked together in the past. We try to make a reunion vacation happen once a year. This is the ...

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Marathon House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

$341

avg/night

$341
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Welcome to “Take it Keysie” your tropical/waterfront retreat in Marathon, Florida!Located in the heart of the Florida Keys, Take it Keysie, offers the perfect blend of luxury, comfort, and adventure for your vacation getaway. Our waterfront property with quick ocean access offers 3 bedrooms ...

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Property Type

Marathon House

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Marathon House
4 BR | 4.5 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 4.5 bathrooms
22 reviews

Distance to beach: 4 miles to Sombrero Beach

$843

avg/night

$843
avg per night
View Details

Key Amenities

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

About this property

New construction! This spacious and tropically decorated property includes 4 KING bedrooms, each with private ensuite bathrooms. There is an additional half bath for guest use, as well as commercial washer and dryer. State of the art kitchen with quartz counter tops and well appointed living area including ...

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Property Type

Marathon House

Featured review

"A perfect getaway"

We spent a week at this lovely home in Marathon Key, escaping our winter wonderland in Michigan. The 4 bedrooms and baths were ideal for our group of seven. The kitchen is well stocked, the deck has plenty ...

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Big Pine Key House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

$266

avg/night

$266
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

This spectacular home is located in the desirable Pine Channel Estates subdivision located on Big Pine Key. You will be more than delighted with this canal front home. Bring your boat, Pine Channel is only minutes away leading to some of the best boating, fishing, diving, and snorkeling in the Florida ...

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Property Type

Big Pine Key House

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Islamorada House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
10 reviews
owner special
Owner special: Available anytime in April

Distance to beach: 0.5 miles to White Marlin Beach

$643

avg/night

$643
avg per night
Owner special:
Available anytime in April

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Rentals by owner
  • WiFi

About this property

House, 3 Bedrooms, 2 Baths, Sleeps 6 Pure High End Luxury with all the Bells and Whistles Boat Friendly Vacation Rental with DockVilla Marlin , 122 Nautilus Drive, Islamorada, Florida Keys mile marker 74.5 bay side, White Marlin Beach located 75 miles south of Miami and 75 miles North of Key West. ...

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Property Type

Islamorada House

Featured review

"Couldn't be better"

What a beautiful fantastic home!! Perfect location....quiet, peaceful, a 2 minute car ride to a lovely quiet small beach (or a ten minute walk which we preferred). Orlando is just a pure gentleman....kind, ...

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