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Florida Keys Vacation Rentals

(576 rentals)
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
Marathon House
Sleeps 10, 4 bedrooms, 3 bathrooms
9 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Waterfront 4BR/3BA duplex in Marathon, just a 2 minute walk to Sombrero Beach! Perfect for families, this home features a private heated pool, shared dock for one 30’ boat, and a fenced yard. Enjoy modern comforts, a fully stocked kitchen, and easy access to all the Florida Keys have to offer. Comfortably...

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Featured review

"Family reunion"

Excellent stay, everything in the house worked smoothly, nice big pool, kayaks at our disposal, Sombrero beach, groceries in just few minutes of drive. One ctisism: no garbage recycling option.

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$451
avg per night
Islamorada House
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

Key Amenities

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

About this property

Immerse yourself in the luxury and beauty of Oceanside, a brand-new gated community with 9 beachfront homes nestled in the heart of Islamorada. Our 4 bedroom home invites you to experience modern coastal comfort while its nearly 3000 square feet of indoor space provide ample room for family and friends....

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Featured review

"Beautiful stay"

We had the best time at this house! Giovanna and her husband were wonderful hosts and were on top of everything we needed. The house itself is in a great location close to shops and restaurants. Book the...

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$983
avg per night
Key Colony Beach Villa
Sleeps 10, 4 bedrooms, 4 bathrooms
14 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

The Blue Turtle Villa, located in Key Colony Beach, in the Marathon area, is a gorgeous, brand new, designer decorated canal front duplex with a modern coastal feel! Each side is rented separately and has 4 bedrooms, 4 bathrooms, a private pool with a heater and a chiller, and all the amenities you would...

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$652
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 2 bathrooms
11 reviews

Distance to beach: 0.5 miles to White Marlin Beach

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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Featured review

"Villa Marlin Is the Whole Package"

We had a wonderful week in Islamorada at Villa Marlin. This property has everything you need for a water-focused time, especially a beautiful little beach. It was perfect for our grandsons who could have...

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$643
avg per night

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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
New
Key Largo House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to your brand-new beach home—cozy, stylish, and filled with natural light. This beautiful 3-bedroom, 3-bathroom retreat offers stunning ocean views and an easy, relaxed layout perfect for everyday living.Enjoy an open living space, modern finishes, and peaceful bedrooms designed for...

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$286
avg per night
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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$486
avg per night
Big Pine Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 5 miles to Bahia Honda State Park

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to your very own “Island Escape”! This beautiful home is located in one of Big Pine Key’s most favorable boating neighborhoods with quick ocean or gulf access for most any size boat. It’s only a few lots in from open water! The large 75’ concrete dock offers plenty...

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$258
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 3 bathrooms
2 reviews

Key Amenities

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

About this property

"Wow beyond wow! This place had everything we needed and more. We like to rent a house where we can spend most of our time there enjoying family time. The pool and all the games with the game room and infinity table and the dining turned ping pong was amazing. Eric was very responsive..." -...

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Featured review

"This home was perfect!"

Eric was the perfect host. We escaped a cold and snowy winter for Marathon and this home offered us the perfect get away! It included everything we could have needed…games, pool, grill, plenty of space...

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$674
avg per night
Islamorada House
Sleeps 8, 3 bedrooms, 4 bathrooms
2 reviews

Distance to beach: 0.5 miles to ANNE'S BEACH

Key Amenities

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

About this property

Located in the desirable Islamorada which is know as the “Sportfishing Capital of the World” and where you will find the most beautiful crystal clear waters. The house is just minutes from Channel 5 and Channel 2 which give you quick access to the best ocean and backcountry fishing. You are...

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Featured review

"Perfect vacation home"

You could not ask for a more beautiful and clean vacation home. Everything seems really new and well kept. The moment you walk through the home you see the balcony with the beautiful view of the water....

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$425
avg per night
Islamorada House
Sleeps 10, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Relish ocean serenity in this residence set directly on a secluded beach, where an open-concept design seamlessly merges the living area and gourmet kitchen with a grand terrace, all framed by uninterrupted ocean views. Bask in the heated pool, unwind on the covered patio, or step onto your private dock...

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$1,465
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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$640
avg per night
New
Islamorada Condo
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Hot tub
  • Private pool

About this property

Welcome to Bay Harbour A-304, a waterfront penthouse in Islamorada featuring a private 50 feet deep water boat slip in a protected harbor with direct views of the marina and Atlantic Ocean. Atlantic Ocean views are visible directly beyond the protected harbor. Enjoy immediate Florida Bay access and quick...

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$412
avg per night
Marathon Villa
Sleeps 10, 4 bedrooms, 3 bathrooms
7 reviews

Key Amenities

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

About this property

MARATHON ANGLER'S RETREAT in Marathon is a brand new property with every modern convenience and warm coastal decor! Located right on a canal (just 15-20 minutes from open water) it has its own private dock (can accommodate up to a 30' boat), fish cleaning station, private pool, hot tub, and...

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Featured review

"Wonderful home with a great location"

Meredith and Pineapple Properties were very accommodating, and answered all of our questions. The home, the pool, and the hot tub are all in great working shape, well-maintained, and clean. The property...

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$575
avg per night
Key Largo Villa
Sleeps 7, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Indulge in a tranquil, carefully crafted vacation rental designed as a haven of peace and luxury. Ocean Residences blends modern touches with a secluded retreat atmosphere, providing the ultimate getaway experience. As our guest and a new addition to our family, you'll enjoy seamless comfort and...

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$750
avg per night
Islamorada House
Sleeps 8, 4 bedrooms, 4.5 bathrooms
8 reviews

Key Amenities

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

About this property

Welcome to ‘The Beach House’ at Tarpon Point in Islamorada – This luxurious oceanfront home is in a private gated enclave of 12 houses. This home sits directly on ‘The Beach’. Being the end home, it is nestled next to lush mangroves and the ocean offering a lot more privacy....

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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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$729
avg per night
Key West Condo
Sleeps 2, 1 bedroom, 2 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into 5 condo units. Tony's Conch Retreat, unit 5, is on the 2nd floor, at the top of the stairs, and encompasses the rear of the home from end to end. It has a lovely view of the...

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$150
avg per night
New
Islamorada Estate
Sleeps 16, 7 bedrooms, 7 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Turtle Cove - Turtle Cove is a true hidden treasure in Islamorada. This oceanfront gated estate consists of an enclave of four charming cottages nestled in beautiful landscaping with a total of seven bedrooms and seven bathrooms. When entering through the gate you will feel a sense a tranquility that...

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$2,009
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
Summerland Key House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to Casa Caribe, a comfortable 2 bed, 2 bath vacation home on Summerland Key. Located on one of the best canals on the island, and conveniently across the canal from the Summerland Marina, this home provides quick boating to the blue water as well as the prime diving areas of the Gulf and Looe...

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$155
avg per night
Marathon Estate
Sleeps 6, 3 bedrooms, 2.5 bathrooms
16 reviews

Key Amenities

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

About this property

Mar Azul is a High-end Oceanfront Residence overlooking the tranquil 'Bonefish Flats' of Marathon. Enjoy a Private, Secluded 3-Story Home with Spectacular Views of the Atlantic Ocean! Densely surrounded by Nature, the Property includes a Private In-Ground Pool Deck featuring an Outdoor Gazebo...

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Featured review

"Private Oasis!"

Mar Azul is in a perfect location, accessible to many great restaurants, shops and and one of the best beaches in Marathon, Sombrero Beach. The home is comfortable and serene, with two ensuites! The decks...

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$557
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 4.5 bathrooms
6 reviews

Distance to beach: 1 miles to Sunset Park

Key Amenities

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

About this property

Family-friendly Waterfront Oasis with Private Heated Lazy River Pool and 70' Dock Summary: Welcome to Your Dream Florida Keys Getaway! Bring the family to experience the ultimate Florida Keys vacation! Nestled in family-friendly Marathon—right in the heart of the Keys—our...

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Featured review

"Lazy river, slide, and plenty of space for everyone"

Place was clean and open and had all the stuff needed for a great time. Location and price were great too!

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$593
avg per night
Key Colony Beach Villa
Sleeps 10, 5 bedrooms, 4 bathrooms
2 reviews

Distance to beach: 1 miles to In the Key Colony Beach walking distance

Key Amenities

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

About this property

Hey there, fishing enthusiasts and families!Looking for the perfect Florida Keys getaway? Look no further! My beautiful waterfront home in Key Colony Beach is your dream vacation spot.Imagine this: You wake up to stunning sunrises over the open water, have coffee on the wrap-around porch, and...

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Featured review

"Group Vacation"

Stayed with a group of friends from around the country. The house was very clean and well provisioned Kitchen, bedrooms, bathrooms, outdoor cooking area. Met the host and hostess, who were very pleasant....

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$1,315
avg per night
Key Colony Beach House
Sleeps 4, 2 bedrooms, 2 bathrooms
11 reviews

Distance to beach: 0.2 miles to Cabana Beach Club

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

This is a large stilted duplex located in a tropical paradise. The water view property is located on the island City of Key Colony Beach in the Middle Keys (near Marathon). This is a canal-front unit with a 37.5 step down concrete dock with quick easy access to ocean. Dock comes with ladder access and...

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Featured review

"Great vacation rental"

Our stay was wonderful. There were a couple of glitches that were handled immediately. Everyone was very friendly and accommodating. Accommodations were great. Would highly recommen

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$243
avg per night
Key West House
Sleeps 4, 2 bedrooms, 1 bathroom
3 reviews

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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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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$397
avg per night
Key West House
Sleeps 10, 5 bedrooms, 3 bathrooms
2 reviews

Key Amenities

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

About this property

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

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Featured review

"Perfect in every way."

This is the perfect place for a Florida vacation. It has everything we were looking for and more. Private beach, quiet location, mature trees with coconuts and bananas. Tiki hut with a wet bar and comfy...

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$874
avg per night
Marathon House
Sleeps 12, 5 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to your spacious, five-bedroom waterfront pool home in Marathon, just steps from Sombrero Beach! Enjoy multiple entertaining areas inside and out, with a screened-in patio and sparkling pool (pool heat available for an extra fee). The open-concept interior features cathedral ceilings, a modern...

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$836
avg per night
Key West House
Sleeps 6, 3 bedrooms, 3 bathrooms
5 reviews

Key Amenities

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

About this property

2/2 Main House, 1/1 Bunglow, Large Pool And Hot Tub On Beautiful Old Town LaneMulti-month Discounts availableHidden at the end of one of the most beautiful lanes in Old Town, Casa Escondida awaits you with its tropical seclusion and quiet serenity. Nestled amongst mature tropical landscaping,...

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Featured review

"A little slice of heaven on earth"

The location is perfect - about 3 blocks from Duval, and 3 blocks from Truman, and a short bike ride to Ft. Zachary beach. We did not have a car, and did two Uber runs for groceries at Publix, then used...

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$403
avg per night
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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$330
avg per night
New
Islamorada Condo
Sleeps 6, 2 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

The Artist's Cottage at Anglers Reef #136 - This beautiful home is located in Angler's Reef, a gated oceanfront community located in Islamorada. The owner has shared his own personal artwork throughout the unit for guests to enjoy. Angler's Reef is known for its beautiful tropical landscaping...

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$338
avg per night
Big Pine Key House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

You and your family will feel right at home in this charming Big Pine Key home. The Owners have totally refurbished this 2 bedroom plus den, 2 bath property in 2020. Soft sea colors and coastal décor make this a totally comfortable home away from home.Large and spacious living room, kitchen and...

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$172
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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$222
avg per night
Key West House
Sleeps 6, 3 bedrooms, 3 bathrooms
2 reviews

Key Amenities

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

About this property

Down a very quite lane the house has one off street parking spot. If you are familiar with Key West you understand what a treat it is to have off street Parkin !Enter from gate through lush and colorful walk to front door of main house . Walking over the front porch is the typical Key West style outside...

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Featured review

"A hidden gem in Key West!"

We loved our stay at Hidden Cottage! Located on a perfect bike loop with bike-lane to Duval (one way on Southard to Duval and one way on Fleming home)! Also very close to the boat docks. Hidden Cottage...

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$332
avg per night
Islamorada House
Sleeps 12, 5 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

This grand peninsula retreat is embraced by the Ocean and lush mangroves, offering privacy to the heated pool with its tiki bar, expansive sandy playgrounds and lounge areas. Nestled along the tranquil shores of Florida Bay, its array of indoor and outdoor living areas, BRING YOUR BOAT - dock with ocean-access...

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$2,137
avg per night
Summerland Key House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to Margarita Manor – Your Tropical Escape in the Florida Keys!Set your watch to island time and relax at Margarita Manor, a vibrant waterfront oasis perfectly suited for sun-chasers and boating enthusiasts alike. Located just moments from open Atlantic waters, this breezy retreat offers...

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$255
avg per night
Last Minute Deal
Islamorada Townhome
Sleeps 8, 3 bedrooms, 3 bathrooms
2 reviews

Key Amenities

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

About this property

Front-Row Ocean Views – A Location That Cannot Be ReplicatedWelcome to Paradise Palms—the crown jewel of the exclusive Peaceful Palms gated community. Perfectly positioned just steps from the water, this newly built three-story home offers sweeping panoramic views and a rare third-floor...

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Featured review

"Best stay in the Keys and we have stayed at all of them. Lux!"

Best stay we’ve ever had in the Keys and we booked super last minute. We always choose Islamorada, but this place blew every other stay out of the water. The third-story balcony was insane—hello ocean...

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$706
avg per night
Last Minute Deal
Long Key Condo
Sleeps 4, 2 bedrooms, 2.5 bathrooms
2 reviews

Key Amenities

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

About this property

Enjoy Beachfront Island Life from our condo right on the Atlantic Ocean. We are literally only 10-20’ from the water depending on the tide.Totally remodeled in 2022. All new kitchen with high end appliances. Beautiful master bath with large walk in shower for two.Huge wrap around...

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Featured review

"Fantastic place. Gorgeous views over the ocean."

Clean and fully renovated with wraparound balconies overlooking the sandy beach and palm trees. Amazing sunrises and sunsets over the ocean. South and west facing windows. Great beach and communal pool....

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$186
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 3 bathrooms
1 review

Key Amenities

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

About this property

Welcome to our private stand-alone oceanfront home in a quiet, yet friendly gated community in Marathon, Florida! If you’re looking for a relaxing and low-energy getaway for your family, you’ve found the perfect place.Consider a 14-day stay and receive an 8% discount OR 28-day stay and...

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Featured review

"Great house with fabulous views!"

In summary, fabulous views! From the roof you get both the Atlantic and gulf. Unobstructed 180 degree gulf view. The house is great too. Everything you need to sleep comfortably, relax, cook. Space for...

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$591
avg per night
Key West House
Sleeps 6, 3 bedrooms, 2.5 bathrooms
3 reviews

Distance to beach: 0.5 miles to Higg's Beach

Key Amenities

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

About this property

Private Luxury Key West Home with Private Pool, surrounded by lush tropical landscaping in the Casa Marina neighborhood of Old Town.The fusion of a mid-century Florida home with dramatic Caribbean design, has created an ideal contemporary “Floribbean” style villa in the Casa Marina district...

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Featured review

"Stunning Private Villa in Key West - Fabulous Location!"

We were so impressed with this Key West hidden gem. Along with it's beauty, you feel the love and care the owners have for this private home, as they provided you with all the amenities, plus so much more....

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$374
avg per night
Cudjoe Key House
Sleeps 8, 4 bedrooms, 2 bathrooms

Key Amenities

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

About this property

This vacation home has a spectacular view over Cudjoe Bay to the Atlantic from the upper deck, and from the seats in the heated private pool. Kayaks included in the rental. Home has 4 bedrooms and 2 bathrooms. Property has water access/dock for a small boat, and options to dock a larger or multiple boats...

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$550
avg per night
Marathon House
Sleeps 6, 2 bedrooms, 1.5 bathrooms
1 review

Distance to beach: 3 miles to Sombrero Beach

Key Amenities

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

About this property

This charming oceanfront property is the perfect getaway for your next vacation. Located just steps away from the ocean, this cozy retreat features stunning views, modern amenities, and a spacious deck for outdoor relaxation. Enjoy the convenience of nearby shops, restaurants, and attractions. Book your...

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Featured review

"Oceanfront Property Marathon FL"

Newer, modern, comfortable, and well decorated oceanfront property. Had everything we needed and more. Beautiful views from the deck and very nice outside area. We appreciated that there were great...

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$292
avg per night
Last Minute Deal
Islamorada Condo
Sleeps 7, 3 bedrooms, 3 bathrooms
16 reviews

Key Amenities

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

About this property

Oceanfront Islamorada Townhome with Private Dock, Pool & Sunrise ViewsWake up to panoramic ocean sunrises in Islamorada. This 3-bedroom, 3-bath oceanfront luxury townhome features a private dock, sandy entry for kayaks, and a resort-style pool just steps from your door.Your Keys EscapeSet...

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Featured review

"Great vacation"

We had a great time at peaceful palms. The townhouse was very comfortable and well stocked. Jamie and Charlie were great hosts, very responsive to anything we needed. We had our boat with us and spent most...

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$694
avg per night
Cudjoe Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

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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Featured review

"Perfect boat and pet friendly home in the Lower Keys"

We thoroughly enjoyed our stay at Palmetto Retreat. The home was spotless and had all the amenities we needed. A couple of menial things didn't work, and Christine (Rudy) took prompt care of them while...

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$165
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
Big Pine Key House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to Croton Lane Retreat! This comfortable home is located on a canal with 2 bedrooms (Queen beds) and 2 full bathrooms. It has a beautiful screened-in porch with comfortable seating for relaxing and an outdoor dining table with seating for 6 for comfortable outdoor dining. The house has central...

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$187
avg per night
Key Largo Villa
Sleeps 7, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Indulge in a tranquil, carefully crafted vacation rental designed as a haven of peace and luxury. Ocean Residences blends modern touches with a secluded retreat atmosphere, providing the ultimate getaway experience. As our vacationer and a new addition to our family, you'll enjoy seamless comfort...

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$786
avg per night
Ramrod Key House
Sleeps 8, 4 bedrooms, 2 bathrooms
6 reviews

Key Amenities

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

About this property

Come enjoy the cool clear blue waters of the Florida Keys. The weather is great, lobster season is open from Aug.6th to April 1st. This is a spacious oceanfront home with breathtaking open water views! It is located on beautiful Ramrod Key 85 ft concrete seawall facing the priceless Atlantic ocean teaming...

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Featured review

"Wow! What a View!"

This 4 bedroom, 2 bath is more than a house, it feels like home! From the fully stocked kitchen to the various board games available, this house will keep you busy. You can also rest here as the nights...

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$267
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 3.5 bathrooms
22 reviews

Key Amenities

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

About this property

Welcome to HeartofMorada!Step into a private world in Islamorada's most coveted location. Heart of Morada sits in Coral Cove — a gated community of just 8 homes — giving you a private heated saltwater pool with waterfall, your own boat dock with electric and water hookups, and near-exclusive...

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$766
avg per night
Marathon House
Sleeps 6, 2 bedrooms, 3 bathrooms
15 reviews

Distance to beach: 1 miles to Sombrerro Beach

Key Amenities

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

About this property

Lemon Key CottageWelcome home…Thanks to Hurricane Irma, we now have a beautiful newly renovated home! We've spent over $150K on a complete restoration and modernization. (check out the new pics) Lemon Key Cottage is absolutely stunning with new: bathrooms, kitchen, appliances, flooring,...

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Featured review

"Outstanding!"

Beautifully decorated, quiet, comfortable setting. Kitchen is well supplied and equipped. Large fridge, the whole house looks new. Pool and grounds are spotlessly maintained. Lots of fish around the dock...

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$383
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.