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Florida Keys Vacation Rentals

(577 rentals)
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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$2,257
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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$1,756
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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$349
avg per night
Marathon House
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

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

About this property

Our wonderful, Oceanside and waterfront home is just two minutes from the Atlantic Ocean and Vaca Cut. No bridges to the Atlantic and super easy to access the Gulf via Vaca Cut.This home is completely remodeled and features brand new furniture throughout. The 55 foot dock is brand new and awaits your...

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Featured review

"Great Vacation Rental"

We came in by boat and had a wonderful stay in this home. Rooms are large and plenty of space to move around. Sunrises are beautiful. Outside freezer for fish and bait was a great asset. Nice area to take...

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$250
avg per night
Key Colony Beach House
Sleeps 5, 2 bedrooms, 2 bathrooms

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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$263
avg per night

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Marathon House
Sleeps 12, 5 bedrooms, 4 bathrooms
13 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

WE ARE OFFERING A 5% DISCOUNT THROUGH JANUARY 31ST! IT IS AUTOMATICALLY FIGURED INTO THE QUOTE!Sailfish Villa, unit #6, is a brand new gorgeous, professionally decorated 5 bedroom 4 bath Villa with open water views on Vaca Cut! Enjoy sunrise and sunset colors and direct ocean and Gulf access! It has...

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Featured review

"Grateful"

I have been coming to marathon with family for many years and have had many rentals.. Meredith I have to say is the best.. she worked with me with every question and plans that I had . Definitely would...

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$942
avg per night
Little Torch Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

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

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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Featured review

"Perfect place"

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

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$165
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 3 bathrooms
5 reviews

Key Amenities

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

About this property

NEW TO MARKET AND AVAILABLE FOR LOBSTER MINI SEASON!!! This new construction has everything. This concrete house is waterfront with great views of Bonefish Bay. The 70 foot dock is built in 10-12 foot water. It is frequented by manatee, dolphin, and numerous mangrove snapper. The large heated pool...

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Featured review

"Great house! Great location! Great management!"

The title says it all. We all agreed we would stay here again in a heartbeat! The house was clean and well maintained. The kitchen was well equipped though we had a little bit of a learning curve figuring...

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$399
avg per night
Islamorada Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
6 reviews

Key Amenities

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

About this property

Luxurious and large 2 bedroom 2 bath condo with balcony, large heated swimming pool, stainless steel appliances, flat screen televisions in every room in the beautiful Florida Keys.Huge ocean front dock with plenty of room for fishing! Wifi, deluxe cable, and restaurants within walking distance.2...

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Featured review

"We had a great stay at Tony & Nancy’s condo at Plantation by the Sea!"

The condo was neat and well furnished. Great location and a beautiful property! Founders park across Rt 1 is a great take with a nice beach and very helpful staff at the visitors center.

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$128
avg per night
Key Largo Townhome
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

If you want to experience the true meaning of a Key Largo Island vacation, then look no further than our spacious townhouse on the ocean side of the world famous Key Largo, Florida. ... The Dive Capital of the World! This Villa is located inside Kawama Yacht Club, a beautiful Hawaiian Island style resort...

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Featured review

"Great place"

Nice condo in Key Largo. Owner very responsive. Beds comfortable. Would rent again, for sure. Close to a lot of restaurants & stores.

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$344
avg per night
Key Colony Beach House
Sleeps 10, 4 bedrooms, 4 bathrooms
2 reviews

Distance to beach: 0.5 miles to Key Colony Cabana Club Beach

Key Amenities

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

About this property

Beautiful 2-story half duplex home on wide canal with boat slip. Sleeps 10 comfortably. 4 bedrooms, bathrooms and lower-level family room with mini kitchen make this a great place for multiple families to have private space or gather together.Plenty of parking for boat trailer and multiple vehicles,...

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Featured review

"Plenty of room and a great location!"

Rare find of 4 full baths and 4 real bedrooms (not a daybed stuck in a sunroom like some rentals market as a bedroom). House comes with everything you need - beach towels, coffee maker, toaster, blender,...

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$571
avg per night
Marathon Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

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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$326
avg per night
Marathon Villa
Sleeps 10, 4 bedrooms, 3 bathrooms
5 reviews

Key Amenities

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

About this property

WE ARE OFFERING A 5% DISCOUNT THROUGH JANUARY 31ST!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 35' boat...

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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
Last Minute Deal
Islamorada House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 2 miles to Anne's Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

House, 3 Bedrooms, 2 Baths, (Sleeps 4-6)Spacious ground level home that will be easy on your legs--NO stairs to climb! The home is fully equipped with linens for the king, queen, and 2 double beds. The master bedroom has its own bath. A separate media room with a flat screen TV as well as a large...

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$300
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

Welcome to Paradise Palms – the crown jewel of the exclusive Peaceful Palms gated community. This newly built, three-story luxury oceanfront home delivers a rare blend of modern elegance and unobstructed ocean views—all just steps from the water. Every detail reflects our commitment to comfort,...

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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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$736
avg per night
Tavernier Mobile home
Sleeps 5, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Located in desirable Hammerpoint in Tavernier Florida. 3 bedroom, 2 bath home on the bay. Hardwood floors throughout. View the amazing sunset in your own private hot tub on the screened porch. Fishing, shrimping, lobstering and snorkling in your own back yard. 57' dock cable internet...

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$160
avg per night
Islamorada House
Sleeps 12, 4 bedrooms, 2 bathrooms
4 reviews

Key Amenities

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

About this property

ALERT: BRAND NEW POOL JUST COMPLETED AND INSTALLED....DOWNSTAIRS IS AVAILABLE TO RENT BUT IS NOT INCLUDED IN THE PRICE feel free to ask about downstairs pricing and availability. Downstairs is an additional 3br and 2ba so the upstairs and downstairs would be a total of 7br & 4ba....THIS LISTING...

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Featured review

"A month in heaven"

My wife and I spent the month of Dec. 2022 at this property in Islamorada (HEAVEN) in the Keys. The property has a pool, a canal and a boat dock that can handle any boat.Let me start of saying that...

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$257
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 2 bathrooms
10 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

"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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$643
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 3.5 bathrooms
19 reviews

Key Amenities

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

About this property

There's a reason why we have ALL 5-star reviews! HeartofMorada is located in the HEART of Islamorada on Upper Matecumbe so you are mere blocks from several restaurants and breweries that you will love! The home is just 3 years old and WELL apportioned with everything you'd need on vacation and...

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$821
avg per night
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
Marathon House
Sleeps 10, 4 bedrooms, 2 bathrooms
12 reviews

Distance to beach: 3 miles to Sombrero

Key Amenities

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

About this property

Plan your Marathon Trip - Stay at Manatee Cove-4BR/2BA vacation home. Pool with 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...

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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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$393
avg per night
Islamorada Condo
Sleeps 7, 3 bedrooms, 3 bathrooms
13 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

"Wonderful place, wonderful people!!!"

The property owners were extremely helpful in every way. If you can't have fun here, you just can't have fun.

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$756
avg per night
Special Offer
Marathon Estate
Sleeps 6, 3 bedrooms, 2.5 bathrooms
15 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

"Amazing"

Great house is equipped with everything you could want or need! Beautiful property and very peaceful. We had a fantastic vacation. Our dog had fun too!! Lisa is great. We plan on visiting again!

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$599
avg per night
Marathon Villa
Sleeps 6, 3 bedrooms, 2.5 bathrooms
76 reviews

Distance to beach: 5 miles to Sombrero

Key Amenities

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

About this property

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

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Featured review

"Most Amazing Stay"

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

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$532
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 3 bathrooms
2 reviews

Key Amenities

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

About this property

Welcome to our waterfront family home located 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 receive...

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Featured review

"Beautiful view"

The property was amazing the views of the water were fantastic. The dock area was super great for fishing off of every day. The elevator was a life savior for getting suit cases and groceries up stairs....

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$633
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 4.5 bathrooms
22 reviews

Distance to beach: 4 miles to Sombrero Beach

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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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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$850
avg per night
Marathon Villa
Sleeps 8, 3 bedrooms, 3 bathrooms
69 reviews

Distance to beach: 4 miles to Sombrero Beach

Key Amenities

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

About this property

Come stay with us! Why?68 FIVE STAR reviews!! It's literally the highest number of reviews for ALL properties listed here on !!! That's right ALL OF THEM!Welcome to the luxurious “Yellowtail” Villa, where luxury meets the Gulf of Mexico! The only problem with this vacation...

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Featured review

"Great time"

Matt was great to deal with. Villa is beautiful. The yellowtail was definitely set up better than the rest of the villa. Matt has it decorated nice and laid out well. There were 6 of us and we had great...

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$528
avg per night
Islamorada House
Sleeps 8, 3 bedrooms, 2.5 bathrooms
1 review

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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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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$300
avg per night
Key Largo Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
10 reviews

Key Amenities

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

About this property

Congratulations, you have just discovered one of the most unique properties in the heart of Key Largo. This OCEAN FRONT condo is located inside Kawama Yacht Club, a beautiful Hawaiian Island style resort that is situated along the southern border to the most popular park in all of the Keys, John Pennekamp...

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Featured review

"Great place!"

Very nice place. Clean, comfortable, enjoyed the lagoon, and view. Rented the golf cart and enjoyed getting around with it.

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$396
avg per night
Islamorada House
Sleeps 3, 1 bedroom, 1.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

PROPERTY NAME: Sunshine Place 84371 Overseas Highway, Islamorada, FLLOCATION: Oceanside HouseMINIMUM STAY: WeeklyMILE MARKER: 84.3DETAILS: "Sunshine Place" is setup perfectly for privacy and convenience. The owners of this wonderful property called Sunshine Place are willing...

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$276
avg per night
Islamorada House
Sleeps 12, 6 bedrooms, 7.5 bathrooms

Distance to beach: 1 feet to on property or at Founders Park

Key Amenities

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

About this property

Beautiful new home on Florida Bay with sandy beach, spacious pool, beautiful views, and sunsets every night. The home accommodates up to 12 guests. Each suite can be rented individually or combined. Please note that there is no smoking and no pets.Sitting on an acre with 6 bedrooms, 7 and 1/2...

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$1,141
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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$241
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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$467
avg per night
Key West Condo
Sleeps 4, 2 bedrooms, 1 bathroom
1 review

Distance to beach: 0.5 miles to Ft. Zachary Taylor State Park

Key Amenities

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

About this property

SUMMER/FALL SPECIAL. $500 OFF MY WEEKLY RATE. So welcome to Key West and the Shipyard section of the Truman Annex. You have many choices of accommodations and since I am not a real estate salesman or property manager, allow me let the photos and description speak for themselves. My oversized two-bedroom,...

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Featured review

"A touch is all you need…"

A touch of Cuba was the perfect little spot. We are now spoiled to the conveniences of renting direct with the owner, having Class A rated efficiencies, Beach, Bikes, Pool, very quiet and well kept area...

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$571
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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$468
avg per night
Islamorada House
Sleeps 12, 4 bedrooms, 3 bathrooms
3 reviews

Key Amenities

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

About this property

PLEASE INQUIRE WITHIN FOR ALL STAYS AND SPECIAL DEALS!!!OCEANFRONT Jewel in the Heart of Islamorada and on Tavernier Creek allows for easy access to everything the Upper Keys have to offer and direct Ocean and Bay access. This Open Water home HAS IT ALL. -Brand New (Sept 2017) Huge, heated...

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Featured review

"Love this house"

Great location! Sunrises and sunsets were amazing. Easy location to open water, kids loved going out on boat. Fishing right off the dock. Lots of wildlife. Everyone loved the outdoor bathroom! Very convenient....

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$525
avg per night
Islamorada House
Sleeps 8, 3 bedrooms, 3.5 bathrooms
31 reviews

Key Amenities

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

About this property

See why we have ALL 5-star reviews. It's named The Oasis for good reason! Located in the HEART of Islamorada on Upper Matecumbe, so you are a block or two from several restaurants and breweries you will fall in love with. The homes are well-apportioned for the discerning traveler.The ONLY pool...

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$1,624
avg per night
Key Largo Condo
Sleeps 6, 2 bedrooms, 1.5 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Look no further than this perfect place in the Keys for your next vacation! Our cozy condominium provides an ideal location to enjoy the best of the Florida Keys and has some of the best views in all of Key Largo!Located on the 5th floor, you are the top floor of the building with no one above to...

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Featured review

"Beautiful Views, Beautiful Condo, Perfect Getaway Spot"

Loved this condo! Amazing views, tastefully furnished, everything we needed was already onsite. Host was very friendly, helpful. Perfect getaway.

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$283
avg per night
Key Largo Cottage
Sleeps 2, 1 bedroom, 1 bathroom

Key Amenities

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

About this property

We call this beautiful Sailfish Cottage our Honeymoon Suite because it is right on the beach and has its own attached tiki hut in the front, which overlooks the bay. It’s the perfect place to have breakfast or sit with a drink and watch the sunset while preparing dinner on the gas grill..It...

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$298
avg per night
Key Largo House
Sleeps 6, 3 bedrooms, 2 bathrooms
6 reviews

Distance to beach: 40 feet to Across the street

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

FAMILY FRIENDLY GORGEOUS HOME WITH DIRECT WATER VIEW OF LARGO SOUND! WATCH THE SUN RISE FROM THE COMFORT OF YOUR LIVING ROOM! 3 BEDROOMS 2 BATHROOMS BEACH AND BOAT LAUNCH INCLUDED IN RATE! THIS IS THE OPPORTUNITY OF A LIFETIME! KING SIZE BED IN MASTER BEDROOM, Queen bed in 2ND BEDROOM AND TWIN...

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Featured review

"The perfect getaway spot"

This place is amazing, beautiful beach right out the front door is why we come here. The host is the best, Nancy catered to all our needs. The home is nicely decorated, it had everything we needed. We will...

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$200
avg per night
Lower Matecumbe Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
4 reviews

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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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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$383
avg per night
New
Key Largo House
Sleeps 12, 4 bedrooms, 3 bathrooms

Key Amenities

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

About this property

Oceanfront Paradise in Key Largo’s 55+ Adult CommunityWelcome to your Key Largo escape — a 4-bedroom, 3-bath oceanfront home with an oceanfront outdoor shower, located in the exclusive gated community of Silver Shores. Perfectly designed for extended families, snowbirds, or guests seeking...

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$317
avg per night
Key Largo Villa
Sleeps 6, 2 bedrooms, 2.5 bathrooms
2 reviews

Key Amenities

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

About this property

An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. The property is located in Rock Harbor's most upscale resort. The area has the distinction of being Key Largos newest oceanfront gated destination, with some of the most unique...

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Featured review

"Best view in the resort!"

The location, pool and setting were spectacular. The condo was clean and had everything we needed. Highly recommend.

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$548
avg per night
Islamorada House
Sleeps 14, 5 bedrooms, 4 bathrooms

Distance to beach: 3 miles to Founders Park

Key Amenities

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

About this property

Welcome to the Conch & Lobster Homes, a rare dual-home getaway located in the heart of Islamorada, just minutes from iconic Alligator Reef. Perfect for large families, multi-generational vacations, or group getaways, this tropical property comfortably sleeps up to 14 guests across two coastal designed...

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$1,018
avg per night
Key Colony Beach House
Sleeps 4, 2 bedrooms, 2 bathrooms
10 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

"Family Vacation"

This was our second year to stay at this property and enjoyed it just as much as the first time. The home was nicely decorated, very clean, and the layout worked perfect for parking our trailer and docking...

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$231
avg per night
Islamorada House
Sleeps 12, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

PROPERTY NAME: Martin Family Fish Camp 106 Madeira Rd., Islamorada, FloridaLOCATION: 2 Houses Located on a private peninsulaMINIMUM STAY: WeeklyMILE MARKER: 81.9DETAILS: The Martin Family Fish Camp is located on a private peninsula and offers two houses named Bonefish and Tarpon. Each...

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$643
avg per night
New
Key Largo House
Sleeps 10, 5 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Private pool
  • WiFi

About this property

This lovely house in Key Largo offers 5 cozy bedrooms with a mix of queen, king, and full beds. Each of the 5 bathrooms is equipped with a refreshing shower. With AC and heating, guests will stay comfortable year-round. The outside living area has a heated pool and built in gas bbq grill. This marvelous...

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$800
avg per night
Little Torch Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 23 miles to Marathon

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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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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$193
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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$1,030
avg per night
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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$213
avg per night
Full map
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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.