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Florida Keys Vacation Rentals

(591 rentals)
Marathon Apartment
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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

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$457
avg per night
Marathon House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Tropical Canalfront Retreat Near Sombrero Beach – 2 Bed / 2 BathEscape to paradise at this beautifully appointed 2-bedroom, 2-bathroom vacation home located in the heart of Marathon, Florida. Nestled on a deep, wide canal, this waterfront getaway offers the perfect blend of comfort, convenience,...

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$307
avg per night
New
Key Colony Beach House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Sailfish PointThis beautiful Key Colony Beach home is the ultimate tropical escape, comfortably sleeping up to 8 guests. Enjoy an amazing private pool, great dockage for your boat, and all the amenities you need for a relaxing stay. With spacious living areas, a fully stocked kitchen, and outdoor...

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$696
avg per night
Key West House
Sleeps 6, 3 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner

About this property

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

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$500
avg per night
Key West Cottage
Sleeps 2, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to the cutest little Conch Cottage in the Florida Keys! Located in the Seaside Resort Community, only ten minutes to Key West! You won’t find a more affordable and comfortable location than this! The resort has not one, but two large pools, one that overlooks the open water! Other amenities...

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$120
avg per night

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Big Pine Key House
Sleeps 6, 2 bedrooms, 1 bathroom

Key Amenities

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

About this property

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

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$122
avg per night
Summerland Key House
Sleeps 12, 7 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

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

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$667
avg per night
Marathon House
Sleeps 6, 3 bedrooms, 3 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Property Overview:Prime Location: Caribbean Sunsets is nestled in a quiet and picturesque neighborhood, offering breathtaking waterfront living with open Gulf views. Enjoy lush tropical surroundings and easy proximity to local attractions, dining, shopping, and Sombrero Beach. *Saturday-to-Saturday...

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$584
avg per night
Key Largo House
Sleeps 12, 5 bedrooms, 6 bathrooms

Key Amenities

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

About this property

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

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$750
avg per night
Marathon Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
7 reviews

Key Amenities

  • Air conditioning
  • Pool

About this property

Welcome to Coastal Charm, your serene seaside retreat located in Marathon, Florida! This charming condo offers 2 bedrooms and 2 bathrooms, making it ideal for families, couples, or small groups seeking a relaxing getaway.*Saturday-to-Saturday Rentals Only Property Overview:Prime Location: Situated...

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Featured review

"Great Great Great!!"

This place was nice, quiet, clean and on a private beach. Had plenty of room and we sat out on the balcony for several dinners and had great ocean views. Loved the area it was in. Condo and town were really...

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$205
avg per night
Key Colony Beach House
Sleeps 14, 5 bedrooms, 4 bathrooms
2 reviews

Distance to beach: 1 miles to Cabana Club

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Lovely full duplex that sleeps 14! Upstairs there are 3 bedrooms, 2 and a half bath’s with a wide open concept. The half bath is off the living room area. Four flat screen TV’s, hi speed wireless internet, gas grill and a lovely pool (heat is $200/wk optional). Pool is 10 X 20 and 4′...

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Featured review

"Lowe’s stay at 350 E4th Key Colony"

The location is great! The home, yard, and pool are beautiful. We would recommend the place to others.Some minor issues that should be addressed: the outside fish / bait cooler was very dirty and unusable...

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$719
avg per night
Ramrod Key House
Sleeps 6, 3 bedrooms, 2.5 bathrooms
1 review

Key Amenities

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

About this property

Mermaid House was just recently renovated and is a brand new second level vacation rental! This home is in a great central location, not far from Winn-Dixie, Bahia Honda State Park and Key West!Decorated with a warm coastal feel, this home has an open floor plan with large glass windows! The home...

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Featured review

"Just book it!"

I cannot say enough good things about our month-long stay at Mermaid House, so I'll keep it simple, just book it!!! The outside living area was our most favorable spot. (There is one caveat... be VERY...

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$385
avg per night
Special Offer
Marathon House
Sleeps 10, 4 bedrooms, 3 bathrooms
5 reviews

Key Amenities

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

About this property

Stay right on Bonefish Bay in this spacious 4BR / 3BA waterfront home with two master suites. Bring your boat and enjoy a 70-ft dock with quick ocean access just 1 mile away. Relax in the private heated pool, fish from the dock, and enjoy peaceful waterfront views. Perfect for boaters, anglers, and families...

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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
Marathon House
Sleeps 8, 4 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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

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Featured review

"Great time"

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

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$471
avg per night
Marathon House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Adorable home just moments to the ocean. Lovely pool 10 X 20 (goes from 3′ to 5′) Pool heat is $200 add’l if paid in advance, or $250 on arrival plus taxes. 8 X 15 tiki to relax under the shade. 4 Flat screen TVs all w/DVD players. 55″ in L/R, 42″ in master bedroom and both...

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$360
avg per night
Key Colony Beach House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Escape to tranquility in this charming two-bedroom, two-bath half duplex located on the shaded side of 9th St. Newly installed, the sparkling 9 X 16 pool offers a relaxing oasis with therapy jets in the seating area. Indulge in comfort with a king-size bed in the master bedroom, while the guest bedroom...

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$279
avg per night
Islamorada House
Sleeps 10, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

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

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$440
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 4 bathrooms

Key Amenities

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

About this property

The Sea Glass House~LUXURY Oceanfront Estate~Pool Dock Views Jacuzzi Game Room FirePit Office More!The Sea Glass House is a Luxury Exclusive Oceanfront Treasure with more than 100’ of dock and stunning ocean views from virtually every room. Located perfectly in the Middle Keys with direct access...

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$2,300
avg per night
Marathon House
Sleeps 6, 3 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Open concept meets modern elegance in this stunning canal-front pool home located on sought after Coco Plum in the heart of the Florida Keys. No detail has been spared, from its spacious design to its functionality and huge outdoor living space, this home is sure to be your dream vacation location! Dedicated...

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$500
avg per night
Marathon Cottage
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • WiFi

About this property

4 Bikes 2 Kayaks Hot Tub Covered Outdoor Space 37 Ft of Dockage Fresh Interior Well-Equipped Kitchen Quick Walk to Sombrero Beach Lots of ParkingCozy and comfortable Sombrero Beach cottage! This light and airy single family home offers an open concept living, kitchen and dining area with large...

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Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

The Toasted Coconut ~ your private paradise in beautiful Marathon, the heart of the Florida Keys! Gorgeous 3BR home. Your own private pool, gas grill, bikes, beach chairs, all await you for your beautiful day in the Florida Keys! Less than 10 min to Sombrero Beach, Dining & Local Bars. We have everything...

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$271
avg per night
Big Pine Key House
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 10 miles to Bahia Honda

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Our spacious custom built 2 bedroom and 2 bathroom newly renovated home awaits you. Located in the heart of the National Key Deer Wildlife Refuge. On the water with direct access to the Gulf of Mexico or to the Atlantic Ocean. Concrete Seawall with step down easy boat and kayak access. Fish Cleaning...

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$168
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

4BR 4.5BA Home w/ Fantastic Outdoor Entertainment Area, Outdoor Bar and Private Heated Pool!Casa Del Mar This stunning vacation rental features 4 spacious bedrooms, each with en-suite baths, including two master suites with king-sized beds and patio access. The open great room boasts a chef's...

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$575
avg per night
Marathon Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

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

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$300
avg per night
Key Largo Mobile home
Sleeps 4, 2 bedrooms, 2 bathrooms
5 reviews

Key Amenities

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

About this property

***SERIOUS INQUIRIES ONLY**** This house can only be rented for a minimum of 28 days, as per city of Key Largo rules.This cozy and spacious home located in the heart of Key Largo has available water access in the backyard. Located centrally in the Cross Kay Waterways neighborhood near shops, restaurants,...

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Featured review

"Belmont Beauty"

Located directly on a canal- right near Adams Cut for Ocean access, Canal opens to Blackwater Sound - offering access to gulf side also. From our seawall we saw manatee, dolphin, tarpon, needle fish, &...

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$153
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

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

About this property

Stay right on Bonefish Bay in this spacious 4BR / 3BA waterfront home with two master suites. Bring your boat and enjoy a 70-ft dock (40 ft available for use) with quick ocean access just 1 mile away. Relax in the private heated pool, fish from the dock, and enjoy peaceful waterfront views. Perfect for...

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Featured review

"Ma920"

Great place!! Loved it . Parking is tight, They do have trailer storage offsite. Jessica was easy to work with and highly recommend contacting her!!!

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$399
avg per night
Marathon Villa
Sleeps 8, 3 bedrooms, 2.5 bathrooms
9 reviews

Distance to beach: 3 miles to Sombrero Beach

Key Amenities

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

About this property

*Modern updates, new furniture, new docks, pool etc- updated photos on mgmt site!* A spacious bayside 3 BR 2.5 BA retreat within Indigo Reef, a private resort community of Marathon FL- offers many extras for anglers, families, snowbirds, or tourists! Beautiful views from both levels of canals, spacious...

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Featured review

"Fantastic location"

Our stay at Indigo Reef was fantastic. Perfect weather and a perfect location. The unit had everything that we needed and was very comfortable for 5 adults. We truly hope to be back for a longer stay in...

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$424
avg per night
Marathon House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

NEW!!! FULL BACKYARD REMODEL!!! NOW OPEN FOR BOOKING!!! INGROUND POOL INSTALLED - HEATED! AND THE HOTTUB PRICES STILL REFLECT PRE RENOVATION PRICES HURRY IN BEFORE THEY GET RAISED! ***New backyard photos coming soon.***Welcome to your dream Serenity Oasis in the heart of the Florida Keys! This...

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Featured review

"Named correctly"

The name of this property, Serenity Oasis, is exactly how you feel when you are here. Stunning decorated house in a very quiet neighborhood. The pool is wonderful with several different levels of built-in...

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$421
avg per night
Summerland Key House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

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

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$445
avg per night
Key Colony Beach House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Charming Canal-Front Retreat in Key Colony Beach with Exclusive Inch Beach AccessEscape to paradise at this stunning 3-bedroom, 2-bathroom canal-front home in the heart of Key Colony Beach. Perfectly positioned to offer breathtaking water views, this spacious retreat is the ideal vacation getaway...

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$250
avg per night
Marathon House
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to Flamingo Island Paradise!Step into this updated spacious home and enjoy! Tasteful, fresh decor matched perfectly for this relaxation paradise. 2 Master suites with ensuite bathrooms and comfy King Beds. There is a pullout twin in the living area for an extra guest. Updated well stocked...

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Featured review

"Quiet and relaxing"

This is a great location for two couples exploring what the Florida Keys has to offer. We did not have a boat or plan to fish so the residence could’ve accommodated both of those things. We did use the...

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$343
avg per night
Little Torch Key House
Sleeps 8, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to “Summerland by the Sea,” an expansive waterfront property located on the very desirable Summerland Key and pet friendly! Combine the amazing waterfront views with the excellent access to both the Atlantic and the Gulf, it just doesn’t get any better than this!This home...

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$328
avg per night
Duck Key Cottage
Sleeps 3, 1 bedroom, 1 bathroom
12 reviews

Distance to beach: 9 miles to Coco Plum Beach

Key Amenities

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

About this property

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

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Featured review

"Greenbriar house feb.2026"

We had a wonderful stay at Greg and Malinda’s property! The home was exactly as described—clean, comfortable, and beautifully maintained. It had everything we needed for a relaxing vacation, and the...

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$157
avg per night
Islamorada House
Sleeps 8, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Private pool
  • WiFi

About this property

Mile marker 77. Deep Water ocean side canal with direct access to the Atlantic Ocean and a straight shot to Alligator Light House. Sunny Patio and splash Pool. 4 Bedrooms/4 Baths. Sleeps 8. There is no cable package with this home so please bring your passwords for live streaming from the smart TVs.The...

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$364
avg per night
New
Marathon House
Sleeps 12, 5 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Emerald ShoresWelcome to your dream getaway at this direct oceanfront vacation rental in Marathon, Florida Keys. This stunning 5-bedroom, 4-bathroom home offers panoramic Gulf and Ocean views, a private heated saltwater pool, an outdoor kitchen, and a private boat slip at the community marina. Designed...

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$780
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 4.5 bathrooms
1 review

Distance to beach: 3 miles to Sombrero Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

4BR 4.5BA Home w/ Fantastic Outdoor Entertainment Area w/ Full Kitchen, Yard Games, Bikes, Kayaks, Paddleboards!Casa PlayaWelcome to Casa Playa, a luxurious 4-bedroom, 4.5-bathroom home in Marathon, Florida. Nestled behind gates in a 4-home enclave, this custom-designed retreat offers an element...

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Featured review

"Great week in marathon"

We had an amazing stay at this property from the moment we arrived, we were impressed with how immaculately clean and upscale the house was. The decor was beautiful, and everything felt fresh and well-maintained.The...

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$804
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Have a truly blissful vacation at this charming, Gulf Front home that sits on one acre of pristine property on exclusive Morton St. Enjoy the magnificent open Gulf views from nearly every room. This unique home is reminiscent of the way the Keys used to be…..charming! Perfect area for walking,...

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Featured review

"Great house and hot tub/ pool central in Marathon"

Had a great family week at this lovely home with pool, hot tub and tiki hut. The furniture was comfortable and the kitchen was great. We visited many of the local state parks and beaches, the restaurants...

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$377
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
Islamorada House
Sleeps 12, 6 bedrooms, 4 bathrooms

Key Amenities

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

About this property

Mile Marker 77 – Oceanfront – Lower Matecumbe Key.Six bedroom/ four bath luxurious oceanfront premier rental estate on Lower Matecumbe Key in Islamorada. Enjoy a walk around the lush, native garden or take a dip in the oceanfront pool. Catch palm tree shade or sun on the private beach,...

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$646
avg per night
Islamorada Cottage
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

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

About this property

Mile Marker 83 – OceanfrontTwo adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada! This stunning property is truly a tropical paradise with a private, sandy beach and skiff dock. Relax at the beach or cool down in the beachside pool.The front home...

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Featured review

"Osprey Bay January"

Just finished a week at Osprey Bay nice house a little too much up and down with all the steps but spacious Need a larger trash can in the kitchen put it next to the wall near toaster Also new pillows...

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$1,161
avg per night
Little Torch Key House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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

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$334
avg per night
Marathon House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Lovely ocean views at Lindsay Landing…A new ocean front home with views from every room! Right in the heart of Marathon, the location couldn’t be better, this home is close to grocery stores and restaurants, and you can walk to the new Children’s Rotary Park at the end of the street. This...

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$500
avg per night
Key Colony Beach Villa
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Villa Bella an updated cozy 3-bedroom 3 bath duplex with a private heated pool in the heart of Key Colony Beach steps away from Sunset Park. The master bedroom suite has a King size bed with attached bathroom. The second bedroom is a Queen size bed, and the third bedroom offers 2 twin beds....

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$343
avg per night
Marathon House
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Key Lime Sunrise Watch the sunrise & feel the tropical breezes while sipping your coffee from the comfort of the upstairs screened terrace of this lovely and neatly maintained two bedroom two & a half bath home situated on Sombrero Beach Road. This charming getaway is within walking/biking distance...

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Featured review

"We had a very nice visit."

171 10th St. The duplex was very neat. We loved the screened in back porch (had to keep the fans going because of the heat). The pool chairs lacked comfort but we had seen that in the pictures and brought...

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$314
avg per night
Marathon House
Sleeps 10, 5 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to 137 Mockingbird Cove! Modern, expansive home built in 2022, offering incomparable boating! Quick walk or ride from Sombrero Beach. Each of the 5 bedrooms features its own ensuite bathroom, offering ultimate privacy and comfort. Includes a private heated/chilled pool, 2 paddleboards, 4 bicycles,...

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$857
avg per night
Summerland Key House
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Distance to beach: 6 miles to Baja Honda

Key Amenities

  • Air conditioning
  • Oceanfront
  • Rentals by owner
  • WiFi

About this property

Conchcanary is located on Little Torch Key, in the heart of the Florida Keys. Come relax in our hammocks with a tropical beverage or bring your boat for some fantastic fishing.Enjoy your morning coffee with a canal views from the screened balcony. Newly updated kitchen with top of the line appliances,...

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Featured review

"Honeymoon in the Keys"

My wife and I spent the first 7 days of our married life living it up in the Keys. We loved it. Kayaking in the bay. Trips to the beach (very different from other beaches). Snorkeling in the ocean! Live...

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$183
avg per night
Summerland Key House
Sleeps 10, 4 bedrooms, 5 bathrooms

Key Amenities

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

About this property

This Summerland Key home is perfect for the avid fisherman. Deep Water Canal with easy access to both the Gulf and Atlantic. Sea Wall has room for (1) 24' boat. This home can sleep 7 adults and 2 small children. There are 4 bedrooms and 4-1/2 bath. Fully stocked modern kitchen, great out door space...

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$428
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 3.5 bathrooms

Key Amenities

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

About this property

Beautiful bayfront house, private pool and dock, right in Downtown Islamorada Relaxing is made easy at Coral Cove 8, moving from open, airy living spaces to your own private pool. Bright modern finishes meld with traditional Key West style, Coral Cove 8 offers island living in style. This retreat is...

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$1,250
avg per night
Marathon House
Sleeps 12, 5 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Paraíso Del MarIntroducing our newest luxury vacation rental nestled in the prestigious community of Marathon. This brand-new build epitomizes elegance and sophistication, offering an unparalleled experience for those seeking the epitome of luxury in the Florida Keys.Set amidst lush tropical...

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$797
avg per night
Cudjoe Key House
Sleeps 12, 5 bedrooms, 3 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • 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

"Great House and Service"

We came down from Ohio to get away from the cold weather and had a wonderful time in fandango! We really enjoyed the kayaks, the swimming pool and the hot tub! The house had a wonderful kitchen , hot tub...

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$658
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.