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Florida Keys Vacation Rentals

(591 rentals)
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
Summerland Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

This vacation rental home “Reel Sunshine” is appropriately named! A bright and airy, canal front home in the highly desired Summerland Cove neighborhood, is waiting for your family to settle in and enjoy your Florida Keys vacation.This three bedroom, two and a half bath is located on a...

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$283
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
Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

3 bedroom, 2 bath gulf front home with amazing views and meticulously manicured lot.Amazing Gulf and sunsets views from almost every room in this tropical retreat! The Palm Tree Resort is a private gated, three quarter of an acre resort located directly on the Gulf in a premier section of Morton...

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Islamorada House
Sleeps 8, 4 bedrooms, 4 bathrooms

Key Amenities

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

About this property

$15,000-$17,500 WeeklyA world-class oceanfront residence, located in the heart of Islamorada in the Florida Keys. This luxurious residence features unsurpassed vistas of the Atlantic Ocean from the master bedroom, grand room, kitchen & oversized living terraces. Arrive by car ~ just a short 90-minute...

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$1,594
avg per night

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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 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 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Charming 3-Bedroom, 2-Bathroom Duplex with Waterfront Views in Key Colony BeachEscape to this inviting ground-level duplex home in the heart of the beautiful Key Colony Beach. With stunning waterfront views, top-notch amenities, and plenty of space, this charming retreat is ideal for families or groups...

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Marathon House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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

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$386
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Fresh, clean, updated and excellent deepwater boating with expansive canal views is what you will find in our newest addition to our Coco Plum Beach neighborhood! Just minutes down the bike path to sandy Coco Plum Beach! This 3 bedrooms 2 bathroom home is just what you've been looking for in a vacation...

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$249
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
Little Torch Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 5 miles to Bahia Honda State Park

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Ground floor 3/2 with garage, lanai, and deep water dock. Great area for fishing, lobstering and boating. Bahia Honda beach and park 8 miles away. 28 miles to Key West. Home features a separate dining room, living room and fully equipped gourmet kitchen. Equipment shed separate from home for fishing,diving...

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$186
avg per night
Key Colony Beach House
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • WiFi

About this property

** SUMMER SPECIAL $1800/WEEK**Relax in this peaceful 2/2 with incredible ocean and sunset views! Welcome to Sunset Paradise!Not 1 but 2 spacious and comfortably furnished decks with a water view. Everything located right on the waterway, complete with a private 40 ft boat dock.Unique Fun...

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Featured review

"Keys Condo"

VERY Nice enjoyed ! clean and lots amenities location was also very easy to get to many restaurants and activities

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$300
avg per night
Key Largo House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi
$171
avg per night
Big Torch Key House
Sleeps 14, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • Pool
  • WiFi

About this property

Welcome to Barefoot Retreat, where you will feel as though you are on your own private island! As you drive through the remote, lush tropical island road to access the estate, drive slow as you might be greeted by the quite friendly protected Key Deer, roaming free about the property.As you approach...

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$833
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 House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to Paradise Point! Indescribable Views! This stunning sanctuary offers Water Frontage on 3 sides giving over 180° of unparalleled Atlantic Ocean Views, Direct Ocean Access from your Private Dock, perfect for boating or fishing right from the backyard After a day on the water, unwind in...

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$675
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
Islamorada House
Sleeps 8, 4 bedrooms, 2.5 bathrooms

Key Amenities

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

About this property

Mile Marker 75 – BaysideLarge, modern 4 bedroom canal front home with pool in Lower Matecumbe Key in Islamorada, Florida Keys. This gorgeous home overlooks the pool and canal.The main selling point of Latitudes is the home’s awesome outdoor area. Pool, Tiki Hut, grill and outdoor seating...

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$800
avg per night
Key Colony Beach House
Sleeps 5, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • WiFi

About this property

Adorable 2 bedroom, 1.5 bathroom half duplex. Conveniently located at the top of 4th Street in exclusive Key Colony Beach. Nicely updated, fresh and bright! Walk to the Cabana Club and enjoy the complimentary membership with a large swimming pool, bar/restaurant, beautiful sandy beach. Excellent deep...

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$221
avg per night
Key Largo Condo
Sleeps 6, 2 bedrooms, 2.5 bathrooms
7 reviews

Key Amenities

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

About this property

Multi-million dollar views and the peace and quiet you expect in the Keys. DIRECT bay front condo, white sandy beach, new gym, sauna, swimming pool, bocce, basketball and tennis courts, non motorized water sports launch area and storage, native tropical paths, numerous hammocks and seating areas on the...

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Featured review

"Gorgeous Condo!"

Absolutely loved my time here! The condo has all updated bathrooms, kitchen and laundry! The master bathroom is beautiful and felt like I was in a hotel! Views are gorgeous and the location is great! Will...

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$195
avg per night
Marathon House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Villa FranchellaEscape to paradise and experience the epitome of luxury living in this new breathtaking 4-bedroom, 3-bathroom waterfront home in Marathon, FL. Located just minutes from the Gulf of Mexico with easy access from the 45' of available dockage, this newly renovated sanctuary offers...

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$575
avg per night
Islamorada Condo
Sleeps 8, 3 bedrooms, 4 bathrooms

Key Amenities

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

About this property

Mile Marker 83 – BayfrontWelcome to your dream waterfront rental home in Islamorada, located in the heart of the Florida Keys. This stunning 4 bedroom, 4 bathroom home sits on the bay and offers breathtaking views of the water and world class sunsets.As you enter the home, you’ll...

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$733
avg per night
Key West House
Sleeps 6, 3 bedrooms, 2 bathrooms
6 reviews

Key Amenities

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

About this property

Private home located in New Town available for 28 day minimum rental. Beautifully landscaped yard with secure private back yard and pool. The home features a kitchen with all appliances and granite counter top. The master suite opens onto the pool deck and is furnished with a king size bed and walk-in...

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Featured review

"Excellent location,beautiful house,outstanding owners!"

We stayed a month in December(2022),had everything we needed,close to shopping,sightseeing, nightlife,beaches and airport. House is completely furnished and nothing is lacking.Pool was heated and had all...

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$150
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Seaside SerenityWelcome to your exclusive luxury retreat in Marathon, Florida. Seaside Serenity is a brand-new, 4-bedroom 4.5-bathroom, private pool home where paradise meets perfection. With 35' of dockage and nestled in close proximity to the Atlantic Ocean, Gulf of Mexico, and Coco Plum Beach,...

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$709
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
Special Offer
Little Torch Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Florida Keys Vacation Rentals – Nestled on a pristine canal-front lot, situated in Little Torch Key, this well-appointed home offers all the amenities you will need to enjoy the casual lifestyle of the Lower Keys. The lovely back yard area has a gas BBQ grill, a dining table with seating for six,...

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$221
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
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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$326
avg per night
Islamorada House
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

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

About this property

Lower Matecumbe waterfront home, pet friendly for 1 dog. New concrete saltwater pool (heated/cooled) in 2022. New 20,000 Lb boat lift in 2022. New paint inside and out 2022. New furnishings in 2022. White Marlin Beach access and quick boat ride to Channel 2 or 5 bridge or to Robbies Marina. Plenty of...

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Featured review

"The Florida Keys at its Best!"

We stayed here in the “Honu Hale” house in August 2024 during the Florida Lobster Season. The property is ideally laid out & set up for boaters, divers & fisherman. There’s plenty of dockage and a...

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$350
avg per night
Marathon Cottage
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to Morton Street Charmer! This coastal cottage, nestled on the open Gulf of Mexico, offers 2 bedrooms and 2 bathrooms, with recently updated furniture for a fresh feel. Enjoy stunning water views and unforgettable sunsets from the spacious dock, perfect for boats up to 30 ft. Don't forget...

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$311
avg per night
Key Largo House
Sleeps 4, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Stilt home on canal providing quick Bay access. Spacious master bedroom and bath. Bright and sunny kitchen and living area. Huge sundeck overlooking canal for ultimate relaxation. Covered patio underneath home, complete with picnic table, BBQ, hammock, outdoor games, and covered parking.Fenced...

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Featured review

"Outstanding rental experience"

I rented this home for three months during the winter/spring and had an incredibly positive experience. The location is excellent- quiet at night but also close to fun bars and restaurants. The house is...

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$189
avg per night
Islamorada Villa
Sleeps 14, 5 bedrooms, 4 bathrooms
1 review

Key Amenities

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

About this property

⭐5 bedroom 4 bathrooms (One bathroom by pool) ⭐Canal home in Venetian Shores with access to bay and ocean ⭐100 foot of dockage on 100 foot wide deep canal. Ask about bringing your own boat ⭐Location of canal is off Snake Creek near MM86 ⭐ Beautiful large pool with hot tub in tropical setting ⭐...

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$478
avg per night
Marathon House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool

About this property

Escape to paradise at our stunning 3-bedroom, 2-bathroom pool home, perfectly situated to offer breathtaking open Gulf views. This inviting retreat is designed for relaxation and enjoyment, making it the ideal getaway for families or friends seeking the ultimate Florida Keys experience.Highlights:Breathtaking...

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$457
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
Islamorada Condo
Sleeps 6, 3 bedrooms, 3 bathrooms
2 reviews

Key Amenities

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

About this property

Sunrise is a spectacular unit within the Maison Matecumbe gated community. Maison Matecumbe is a small 9 unit condo located just off the old road in Islamorada at mile marker 81. Newly done pool and hot tub! 3 bedrooms, 3 baths, sleeps 6, pool, sandy beach.Dockage can be obtainable through Islamorada...

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Featured review

"Beautiful Views"

The home is meticulously clean and spacious. It has all the comforts of home. We cooked several meals and had everything we needed. The views from the balconies are amazing. The complex itself is well maintained....

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$529
avg per night
Cudjoe Key House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to El Paraiso, a true Cudjoe Key gem at an affordable price. This three bedroom, three bath home is nicely updated throughout! Located on Lafitte Drive, right behind the famous Square Grouper restaurant and only 20 minutes from Key West. Don’t forget to bring your boat, there is plenty of...

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$222
avg per night
New
Marathon House
Sleeps 12, 5 bedrooms, 4 bathrooms

Key Amenities

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

About this property

Sunset TidesExperience the ultimate Florida Keys getaway at our luxury waterfront vacation rental in Marathon, FL. This spacious 5-bedroom, 4-bathroom home offers breathtaking open water views of the Gulf of Mexico and Atlantic Ocean, a private heated pool and hot tub, 30-foot dock with power and...

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$528
avg per night
Little Torch Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

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

About this property

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

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Featured review

"Lovely view and relaxing area!"

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

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$534
avg per night
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
Little Torch Key House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to Pirates Quay! This newly remodeled 2 bedroom home in Little Torch Key is one of the nicest, most thought-out properties in the area, and with extra living space downstairs and plenty of storage, it feels much bigger than it is. Its pirate theme can be seen throughout from the decor, colors...

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$184
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
Big Pine Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 7 miles to Bahia Honda State Park

Key Amenities

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

About this property

This newly remodeled home is cozy, yet spacious.This open concept, single family home is located on a canal and just a few seconds from the ocean. Fully furnished with Keys-inspired touches, this home comfortably sleeps 6 people with 3 bedrooms and 2 bathrooms.Spend the day at Bahia Honda State...

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Featured review

"Big Pine Vacation"

We stayed in the rental for February and March of 2024 and loved it.Very quiet with friendly neighbors.Wonderful outside area and perfect boating with easy access to the ocean or gulf.Already have our reservation...

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$225
avg per night
Key West House
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool

About this property

Welcome to Island Paradise, your serene retreat in the heart of Key West, Florida! Located in Old Town, Island Paradise is just a half block from the world-famous Duval Street. This charming property offers 2 bedrooms and 2 bathrooms, perfect for small families or couples looking for a relaxing and convenient...

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$186
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
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
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
New
Marathon House
Sleeps 12, 5 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Emerald TidesWelcome to Emerald Tides – a brand-new luxury vacation rental in Marathon, Florida, located in the exclusive Emerald Flats community. This oceanfront escape offers breathtaking open water views of the Gulf of Mexico, a private pool, premium dockage, and upscale interiors that reflect...

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$672
avg per night
Big Pine Key House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

3bd 3bath Icemaker Deep freezer Dock Water access

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$200
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
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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.