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Florida Keys Vacation Rentals

(562 rentals)
Islamorada Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
8 reviews

Distance to beach: 5 miles to Anne's Beach

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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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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$329
avg per night
Summerland Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Bitter End Vacation Rental –This Summerland Key beauty is the one you have been looking for. Located on Summerland Key with superb boating and access to deep water. Just the perfect spot to see sunset views and peaceful water vistas. Feel free to bring your pet along too!!The interior is...

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$290
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 3 bathrooms
12 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Tingler Retreat is a tastefully decorated 3 bedroom, 3 bath home with a pull-out couch, has a peek-a-boo view of the ocean and is seconds to open water in your boat! It has an open floor plan and is ground level with plenty of natural light and a fully fenced yard! Available for guest use are 2 bikes,...

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Featured review

"Perfect vacation house"

My husband and I hosted our daughter, son in law and 2 grandkids for a week. They loved the pool and the closeness to sombrero beach. It’s at nice quiet neighborhood with a lot of parking. The house is...

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$573
avg per night
Islamorada Apartment
Sleeps 2, 1 bedroom, 1 bathroom
47 reviews

Key Amenities

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

About this property

The Jetson's House apartment (Located on the prestigious White Marlin Beach - which is considered one of the nicest natural sand beaches in the Florida Keys) features great swimming, snorkeling, and spectacular sunsets right off the beach! Have fun exploring an artificial reef! What makes the beach...

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Featured review

"Like A Dream"

Our stay in Islamorada at Jerry and Lisa's was nothing short of magical. The private beach was a slice of paradise, with palm trees perfectly placed to provide just the right amount of shade. The hammock...

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$179
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

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Key Largo House
Sleeps 8, 2 bedrooms, 2 bathrooms

About this property

The Main House is a fully furnished, two-bedroom, two-floor house facing the bay that can sleep up to two adults and six children.On the second floor, the master bedroom is at the top of the stairs and contains two queen-size beds, a large closet, and access to the full-size bathroom, which is also...

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$445
avg per night
Cudjoe Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning

About this property

Florida Keys Vacation Rentals – Need a private space to call home during your sunny stay in the Florida Keys? Conchy Joe’s is the place! This beautiful home has 3 bedrooms and 2 bathrooms. The interior is fully furnished and decorated in Florida Keys fashion with plenty of space for friends...

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Featured review

"Island getaway"

Always enjoy our stays in Keys when we find such a lovely place to have family come to join us. Some homes have a great location some have great amenities, but finding one like this, that has both is...

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$267
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2.5 bathrooms
3 reviews

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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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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$399
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
Cudjoe Key House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Lafitte Landing is the perfect destination for your Florida Keys vacation. Very nicely appointed 2 bedroom, 2 bathroom canal front home is very comfortable and spacious. This home offers a living-dining-kitchen great room floor plan with comfortable seating and a flat screen TV. Double sliding doors to...

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$150
avg per night
Little Torch Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

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

About this property

Our Cancellation policy is: Cancellation: If you cancel your reservation in writing 90 days or more before your arrival, you will receive a full refund, less a cancellation fee of $25.00 and Administrative fee. If you cancel less than 90 days before arrival, your payment and any prepaid rent will be...

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Featured review

"Lovely view and relaxing area!"

This property is about a half hour north of Key West....perfect for relaxing but close enough to go to town and enjoy the party and any boat trips you might want to take. We would consider renting it again....

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$534
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 2.5 bathrooms
6 reviews

Distance to beach: 2 miles to Founders Park

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Welcome to your dream getaway in Islamorada! This 3-bedroom, 2.5-bath paradise boasts a gourmet kitchen with a Viking gas stove, a spacious dining area, and Internet-ready TVs for game days or movie nights.On the first floor, you will find two bedrooms, a full bathroom and a large entertainment area...

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Featured review

"Awesome House & Canal"

We had a wonderful time here. The location is perfect. Close to restaurants, shops, and attractions. We spent a lot of time floating and frolicking in the canal. The house was spotless. The kitchen was...

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$430
avg per night
Islamorada Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 100 feet to Front door

Key Amenities

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

About this property

MINIMUM STAY: 30 daysSpacious and beautiful 2 bedroom/2 bath ocean front condo unit with unobstructed ocean views. BOAT SLIP is available upon request for up to a 46 foot boat, low tide draw is 30 inches. There is an additional fee for boat slip.Walk out your front door and go boating.You’ll...

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Featured review

"Pure serenity"

So clean, so quiet, so beautiful! My wife and I loved our stay at Ocean Harbour. Looking forward to next year!

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$786
avg per night
Key Colony Beach House
Sleeps 10, 4 bedrooms, 4 bathrooms

Key Amenities

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

About this property

Weekly rentals in the Keys {and generally elsewhere } are based on a Saturday to Saturday occupancy. Check - in is on Saturday at 4:00 PM, and check - out is on the following Saturday at 9AM . If other times are required \ requested , please inquire. This house is usually not available from the end of...

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$717
avg per night
Last Minute Deal
Islamorada Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Tropically furnished condominium with amazing views of the Gulf of Mexico, located at the Futura Yacht Club in the Village of Islamorada. Futura Yacht Club is a gated community located on the Gulf of Mexico and consisting of 70 units. It is centrally located, with easy access to Restaurants, shopping...

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Featured review

"Loved it."

We had great time. The weather was perfect and everyone there was friendly and help full. Also are host Nancy was very help full from start to finish. We did some great fishing in the gulf; everglades and...

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$196
avg per night
Key West Condo
Sleeps 4, 2 bedrooms, 1 bathroom
2 reviews

Distance to beach: 0.8 miles to Fort Zachary Taylor State Park and Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Here in Key West we believe in One Human Family where everyone is welcome and treated like family.Our condo has always received great reviews on cleanliness and the bright citrus pallet is welcoming, there are 2 bedrooms (1 King & 1 Queen), one bathroom with couples walk in shower, The small but...

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Featured review

"KWTrip"

Top notch place in great location. Very clean. Would definitely stay in this unit again sometime in the future.

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$388
avg per night
Key Largo House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Cute, 2 bedroom half duplex located on beautiful 8th Street in Key Colony Beach. Extra wide canal and 37 feet of deep water dockage! Shaded dock area perfect for cleaning your catch of the day. Just minutes through the tranquil Key Colony Beach canals to the open Atlantic and Vaca Cut to access the open...

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$207
avg per night
Key West House
Sleeps 10, 4 bedrooms, 3 bathrooms
4 reviews

Key Amenities

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

About this property

The home (also known as Margaux's Hideaway) was built in 1890's, with a farmhouse charm, and porches off of every bedroom. It is light and airy, with gorgeous and comfortable indoor and outdoor living spaces. It's perfect for family gatherings, or just a quiet escape. Each room is sunny...

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Featured review

"Beautifully Appointed Historic Home in Old Town"

I really can't rave enough about this home and the hospitality of the owners. The house is a beautiful historic home in old town that has been lovingly restored. The outdoor living space and the open to...

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$637
avg per night
Duck Key Townhome
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 8 miles to Sombrero Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to Marlin House – your perfect Keys getaway! This 2-bedroom, 2-bath coastal retreat offers the perfect balance of comfort and adventure. Relax in your own private plunge pool, enjoy fully stocked amenities for a stress-free stay, and make yourself at home with thoughtful touches throughout.Step...

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Featured review

"Marlin House"

We had the most wonderful stay at Marlin House on Duck Key . Thank you Paola ! You were such an exceptional host !!!! The townhome is tastefully appointed , clean, great location, lovely patio with private...

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$344
avg per night
New
Islamorada House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 0.3 miles to White Marlin

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Guests at 253 Gulfview can safely launch their boat using the private boat ramp or dock the boat in deep water using the 14K boat lift. Home has a screened-in porch, a garage covered parking. Fully renovated kitchen with new appliances. Large open concept living area with large dining table. 1st bedroom...

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$421
avg per night
Little Torch Key House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to Calypso Corner! This spacious, tropical home that sleeps 6+, sits on a large corner canal lot and has a huge dock that can accomodate most size boats. Located in sought after Jolly Rogers Estates, the canals are large, flow through and swimmable and open water is only a few minutes away with...

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$218
avg per night
Marathon House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Privacy galore at this great location on Sombrero Beach Rd with a brand new POOL! Famous Sombrero Beach is approximately half mile down the dedicated bike path from this stilted 3 bedroom single family pool home with dockage! Open concept living with expansive decks on both floors that boast open water...

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$386
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 2.5 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Blue Shell is a delightful new canal front vacation home with a pool, just a minute to the ocean and open water and lots of fun amenities! It is also about 10 minutes from both Coco Plum Beach and Sombrero Beach.The dock is 50' and there is parking on the side of the house for truck and trailer....

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$410
avg per night
Last Minute Deal
Key Colony Beach House
Sleeps 8, 3 bedrooms, 3 bathrooms
1 review

Key Amenities

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

About this property

Watch dolphins play in Shelter Cove while swimming in our oversized poolRelax in the private pool with the Spectacular Shelter Bay in the background...Our home is located directly on Shelter Bay in Key Colony Beach with some of the most spectacular views of open water a guest can ask for. We have...

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Featured review

"Absolutely Wonderful"

We enjoyed are stay at this well appointed and conveniently located vacation home. The setting is perfect and the home was loaded with every convenience you would need. Margie, the property owner, is...

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$491
avg per night
Marathon House
Sleeps 6, 3 bedrooms, 3.5 bathrooms
19 reviews

Key Amenities

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

About this property

We would love for you to come visit our renovated ground level Florida Keys home! We decided to call our home "TIGHT LINES", because my wife loves to fish. Our conch home consists of 3 bedrooms with king size beds with ensuite bathrooms. A half bath for guests. We have a 60 foot dock with...

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Featured review

"Exceeded expectations!"

I can’t say enough about this property and the owners. From the ease of booking to our entire stay, we were more than happy. The home is top notch, great beds and very well stocked. The owners were...

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$467
avg per night
Islamorada House
Sleeps 8, 4 bedrooms, 4 bathrooms
4 reviews

Distance to beach: 2 miles to Founders Park

Key Amenities

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

About this property

This tropical waterfront beauty has it all...heated pool, spa, dock and custom elevator. Beautifully appointed and fully equipped for your ultimate holiday rental. Located on a deep water canal with direct access to the Bay or Ocean. Enjoy unforgettable sunsets while relaxing on one of several patios...

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Featured review

"The Home Had Everything and it all Worked"

This was the nicest home overall I have rented. If you have a boat, don't look elsewhere. Everything in the house functioned and the house had everything one would need, even for people who do cook while...

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$648
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
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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$450
avg per night
New
Key Largo House
Sleeps 10, 0 bedrooms, 3 bathrooms

Key Amenities

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

About this property

Welcome to your private slice of paradise in Key Largo. Nestled in a quiet, well-protected canal-front neighborhood, this beautiful four-bedroom home offers the perfect escape for those seeking comfort, space, and the laid-back charm of the Florida Keys. Designed to accommodate up to 10 guests, the home...

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$400
avg per night
Key Largo House
Sleeps 6, 3 bedrooms, 2 bathrooms
11 reviews

Key Amenities

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

About this property

Play all day in Key Largo! If you like fishing, snorkeling, diving, kayaking, paddle boarding, wakeboarding, and nature, you can do it all here at Easy Livin’! Bayfront home on open water with dock and private ramp. Love fishing? House is close to Flats, Backcountry, Reefs and Offshore. Dock your...

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Featured review

"A special place!"

This is our 5th year spending a winter month in Key Largo... our first at Easy Livin. We are very pleased to have found it. It's tucked away from the route 1 traffic, but easy access to everything we need/want....

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$280
avg per night
Key West Townhome
Sleeps 7, 3 bedrooms, 3 bathrooms
2 reviews

Key Amenities

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

About this property

Relax with family and friends in your own tropical paradise at this spacious townhome in Key West's beautifully landscaped & maintained Golf Club. Located in a private gated community with resort style amenities, it is just minutes away from the beaches, world class restaurants, water sports...

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Featured review

"our vacation at Key West Golf Club"

We had wonderful time enjoying the beautiful weather and the beauty of all the attractions at Key West. Our condo was all we needed to fulfill our stay. It was clean and we enjoyed being right on the golf...

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$208
avg per night
Marathon Condo
Sleeps 4, 1 bedroom, 1.5 bathrooms
2 reviews

Key Amenities

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

About this property

Newly Built,1 Bedroom 1 Bathroom unit, Marina, Largest Olympic Pool in the Keys overlooks the Atlantic Ocean, Fun and Sun. Great amenities, close to everything.Outdoor bar b q grills, great Sunsets from the Pool, Tikis and Docks.

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Featured review

"Cozy, Comfortable Marina Condo"

Neat, clean and very comfortable condo for the two of us. The pool, gazebo, sheltered deck and marina provided a variety of areas to lounge, swim and read during the wonderful 80 degree weather. Plenty...

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$221
avg per night
Islamorada House
Sleeps 10, 3 bedrooms, 3 bathrooms
5 reviews

Distance to beach: 0.3 miles to Anne's Beach

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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Featured review

"On a scale of 1-10 this property is a 12 overall !"

We have rented this property for 3 years and have been extremely pleased with all aspects from great hosts, nicely appointed house, heated pool, canal/dock access , easy out to ocean or bay, plenty of...

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$359
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 100 yards to Port Antigua Private Beach

Key Amenities

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

About this property

This spectacular 3/Bed 2/Bath canal front home is located in Lower Matecumbe Key, a part of Islamorada island. Enjoy the exclusive neighborhood of Port Antigua—just a 5 minute walk to our private beach.The house is nautically designed, with a spacious and open floor plan. There's a large...

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$303
avg per night
Islamorada Apartment
Sleeps 2, 1 bedroom, 1 bathroom
5 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • WiFi

About this property

The apartment is in a house on the canal and across from the beach with beach access. It is situated on the ground floor of a two storey Keys house where you would be the only residents. All the amenities would be yours and you would have space, tranquility and privacy in the tropically planted landscape....

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Featured review

"Perfect rental for one couple"

This is the perfect apartment for one couple. Wonderful location on the oceanside with ocean views across the street. Has a great dock for your boat with great ocean access. Fish cleaning table is under...

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$132
avg per night
Key Largo Townhome
Sleeps 6, 2 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 100 feet to 4 on site

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

This is a 2 story, 2 bedroom, 2 bathroom townhouse that comfortably sleeps 6 in a 24 acre Resort / Condo complex.WE FOLLOW THE CDC GUIDELINES FOR CLEANING AND SANITIZING THIS PROPERTY.Included in the price are Taxes, Cleaning, WiFi, a Golf Cart, Kayaks, Paddle Boards, Bikes, Fishing Gear, Snorkeling...

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Featured review

"Great Unit and Excellent Host"

My family and I booked 9 days in the condo by the lagoon. I was a bit leery as there is a mix of good and not-so-good reviews for Norman. I found him personable and responsive on the phone whenever I...

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$297
avg per night
Key West Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Just a few houses off Duval, this wonderful retreat occupies the ground level of an almost 100-year-old home in one of the most desired locations in Old Town Key West. A large covered front porch welcomes you to sit and watch the Key West world go by, imagining what life was like in the early days of...

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$244
avg per night
Islamorada Townhome
Sleeps 6, 2 bedrooms, 2.5 bathrooms
2 reviews

Key Amenities

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

About this property

Lazy Daze Beach House is a piece of paradise literally on the Beach! Gorgeous and all new! One King plus set of Full/Twin bunk beds, spacious gourmet kitchen with glass atrium dining. Completely renovated, designer finished, all new gorgeous home, no expense spared! Private oceanfront townhouse located...

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Featured review

"Lazy Daz Beac House"

Excellent couple to work with. Great communication. The rental was beautiful and clean. We had a problem with the rental and they communicated with us and together we solved the problem. They went over...

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$357
avg per night
New
Tavernier House
Sleeps 11, 4 bedrooms, 3 bathrooms

Distance to beach: 4 miles to Founders Park

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Coral Key!Discover a refined yet relaxed waterfront retreat in the heart of Plantation Key at Mile Marker 90. Thoughtfully designed for comfort, relaxation, and effortless entertaining, this spacious home offers everything you need for a memorable Florida Keys escape.Upon entering,...

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$566
avg per night
Islamorada House
Sleeps 10, 3 bedrooms, 2 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Newly renovated 3/2 Canal front home with brand new pool, deck and front gates for privacy!The house is perfect for those traveling with different age groups, in-laws, teenagers or 2 families. The house is extra clean and has modern furnishings. It has 3 bedrooms, 2 baths. Upstairs there are 2 bedrooms,...

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Featured review

"We love this house!"

2022 was our 2nd time renting this wonderful home. The location is fantastic, and the house and property offer everything you can imagine. Outside is a paradise with a refreshing pool (with fun lights...

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$500
avg per night
New
Islamorada House
Sleeps 10, 3 bedrooms, 3 bathrooms

Key Amenities

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

About this property

Welcome to One Ten Palms!Escape to paradise at this private oceanfront estate in Islamorada, where the laid-back spirit of the Keys meets resort-style comfort. Set on more than two acres of lush tropical grounds, the property is graced with 110 swaying palms and 250 feet of natural oceanfront beach,...

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$1,086
avg per night
Ramrod Key House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Come enjoy this newly listed property on Beautiful Ramord Key house with a southern view of Newfound Harbor and the Atlantic !! House has a 60 ft+ dock for your water toys. Enjoy lobster season, fishing (back water and deep sea great snorkeling and dining all minutes away. Ramrod is easy boating...

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$267
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms

Distance to beach: 4 miles to Sombrero Beach

Key Amenities

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

About this property

Welcome to The Butterfly Cottage – Where Nature's Magic Meets Keys ComfortEscape to a truly unique Florida Keys experience at our certified Monarch Butterfly Garden sanctuary! This charming traditional conch cottage offers families a peaceful retreat where butterflies dance through native...

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$199
avg per night
Key Largo Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
10 reviews

Distance to beach: 0.0 miles to On Site

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

This 2 bedroom, 2 bathroom, Ocean Front Condo has spectacular Ocean, Marina, Beach & Park views from the Living Room, Dining Room, Kitchen, Master Bedroom, Balcony and even the master bathroom.THIS CONDO IS CLEANED & SANITIZED TO THE NEW CDC STANDARDS.Included at no extra charge are free...

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Featured review

"Wonderful location"

The condo has new furniture, beds are comfy, bathrooms are nice. We had everything we need for a great week. Restaurants, beach and shopping all close by. The owner has lots of extra items available to...

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$298
avg per night
Tavernier Apartment
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

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

About this property

Simply relax in this One bedroom One bathroom Oceanfront Condo at Ocean Pointe Suites in Tavernier.The comforting living room features a FLAT SCREEN TV, comfy pull out QUEEN SLEEPER SOFA and sliding glass doors that open to the step-out lanai offering sweeping views of the Atlantic.Visit delicious...

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$250
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

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

About this property

Beautiful views from this condo!Bay Harbour is a gated community located at MM 77.5 bayside in Islamorada, FL.We are new owners of this condo that has never been in the rental pool. (that is why few reviews)Complete remodel with no expense spared!The location is quiet with the most beautiful...

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$643
avg per night
New
Plantation Key House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Property #27839 - silverEscape to your own Keys hideaway with cozy island‑inspired home, coastal décor and a bright open living/kitchen area that flows onto a huge screened terrace. Relax in your own private pool, tiki hut-gazebo, shaded lounge areas and serene canal views, perfect for lazy mornings,...

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$400
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
3 reviews

Key Amenities

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

About this property

This condo is located in a tropical paradise overlooking the fabulous Florida Bay in idyllic Islamorada in Futura Yacht Club. FYC is a private 70-unit, gated community with a 53-slip marina and accommodations available for that tranquil tropical getaway you've always imagined. This condo offers...

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Featured review

"Location"

We have been searching for a unit in this area and found this. Islamorada has many restaurants, from fast food to white tablecloths, from waterfront dining to sports bars.

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$198
avg per night
Marathon House
Sleeps 12, 5 bedrooms, 6.5 bathrooms

Key Amenities

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

About this property

Gulf-Front Modern Luxury | 5BR w/ Rooftop Deck, Infinity Pool, Dock & More! Indulge in an unparalleled luxury experience in this breathtaking 5-bedroom, 5.5-bathroom estate in Marathon, Florida. With direct Gulf views, high-end amenities, and a sleek modern design, this home is a dream getaway for...

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$1,200
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 4 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Villa Sombrero – Private Waterfront Living with Sunset Views in the Florida KeysVilla Sombrero is a peaceful waterfront retreat overlooking Boot Key Harbor, offering breathtaking sunsets to the west and refreshing island breezes flowing in from the east through Sisters Creek. A natural waterway...

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Featured review

"Nice comfortable place..... Quiet except for construction work going on across the street."

It's the little things...... We had to call concerning changing the water filter on the refrigerator. The pool needed water added so that the filter and heater would work. The strainer was full of debris.......

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$655
avg per night
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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.