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Florida Keys Vacation Rentals

(575 rentals)
Key Colony Beach House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to your perfect waterfront getaway in Key Colony Beach with the Cabana Club Membership! This charming 2-bedroom, 2-bath half duplex is ideally located on 7th St, featuring the only boardwalk and the widest canal in Key Colony. Enjoy the convenience of dockage right out back eith a fish cleaning...

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Key Colony Beach House
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to your dream home in Key Colony Beach! This stunning, waterfront, half-duplex offers breathtaking views, a spacious open floor plan, and has been completely upgraded. With two bedrooms and two bathrooms, you'll have plenty of space to relax and unwind.The kitchen is fully equipped and...

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Key Colony Beach House
Sleeps 7, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Private pool, sleeps 7, 5min access to Ocean, 37.5ft dock, shelter bay view. JUST REDUCED, SPECIAL RATE FOR MINI LOBSTER AND LOBSTER OPENING WEEK.ONE-OF-A-KIND, EAST FACING, 2/2 WITH SPACIOUS LOFT THAT HAS TWO TRUNDLE BEDS, PERFECT FOR CHILDREN. JUST 7 HOUSES IN FROM THE ENTRANCE OF THE CANAL! QUICK...

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Key Colony Beach House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

2/2 HALF DUPLEX IN KEY COLONY BEACH ON SADOWSKI CAUSEWAY. COMES WITH CABANA CLUB MEMBERSHIP AS WELL. ENJOY THE POOL, BEACH OR BAR. THIS BEAUTIFULLY REMODELED HOME (2012) IS LOCATED WITH DIRECT BAY VIEWS. TOMMY BAHAMA DÉCOR, STAINLESS STEEL APPLIANCES AND GRANITE TOP COUNTERS. FULLY EQUIPPED HOME...

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Key Colony Beach House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

2/2 half duplex located on West Ocean Dr in Key Colony Beach.This unit has a king bed in the master and two twins in the guest room that will combine to a king. This 936 sq. Ft home will sleep 4 people maximum. You will have cabana club membership and can use the pool and beach on property. Central...

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Marathon House
Sleeps 10, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Slack Tide- 4 bedroom waterfront home with Private Pool,Outdoor Kitchen and DockWelcome to "Slack Tide", your dream vacation getaway in the heart of the Florida Keys! This luxurious 4-bedroom, 4.5-bath single-family home offers everything you need for an unforgettable stay. Nestled in a...

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Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

We welcome you to our piece of paradise in the heart of the Florida Keys! This ground level, SFH with a brand new pool & spa will guarantee to impress. Enjoy a cup of coffee or a cocktail while out back watching the birds, fish, manatees and sunrises/sunsets. This beautiful home offers 3 bedrooms...

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Key Colony Beach House
Sleeps 10, 7 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to the Key Colony Beach Palm Villa! This stunning 7 bedroom, 4 bathroom home is situated right on the canal, offering breathtaking water views. With 60ft of dockage, it's perfect for boat lovers!Accommodating up to 10 people, this home is ideal for large family vacations offering a split...

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Marathon House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Gorgeous 2/2 half duplex in the Heart of Marathon with quick ocean access! Enjoy the ocean Breeze on the balcony. There is a fully equipped kitchen for all your cooking desires. Master bedroom has a king sized bed and an en-suite bathroom with stand up shower. The guest room has two twins. There's...

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Marathon House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Private paradise! Gorgeous 4/3 Half duplex w/ private pool & dockage!Welcome to paradise at South Creek! This gorgeous 4/3 with a private pool and dockage welcomes you with its nautical decor. Enjoy the stunning sunsets/ sunrises from the balcony off of the living room with outside seating.This...

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Key Colony Beach House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Create amazing memories at this unique, family-friendly home in the Heart of the Fl Keys! This 2/2 has a complete kitchen, stainless appliances, private pool that can be heated for an extra fee, 10,000 lb. boat lift at dock (no additional space), bait freezer, outdoor shower and much more. Enjoy a cup...

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Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Beautifully decorated town-home in a quiet location with a boat slip at your doorstep and sunsets that you will remember for a lifetime on the most comfortable deck furniture. The maximum boat length allowed is 31 ft. I hope you all get an opportunity to visit and for a long time as life doesn't...

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Key Colony Beach House
Sleeps 7, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Your Private Paradise- 3/2 single family home, completely private and fenced!WELCOME TO OUR FLORIDA KEYS RETREAT!ENJOY THE AMAZING WATERFRONT VIEWS AND OCEAN BREEZE FROM YOUR COMPLETELY PRIVATE BACK YARD (Not a Duplex) WHILE RELAXING, DRINKING YOUR MORNING COFFEE OR READING A BOOK. HAVE A COOKOUT...

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Marathon House
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Property DescriptionOriginal Marathon conch house 2 bed 2 bath completely remodeled after hurricane Irma, new kitchen appliances and furniture throughout the house, travel to ocean less than a minute, and bayside less than 5 minutes ,located off of Vaca cut. Has BBQ with tank, fish cleaning table...

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Key Colony Beach House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Key Colony Beach House with Cabana Club membership This is a spacious, canal water front, open layout, 2 bedrooms, 2 baths, ground level home that can accommodate up to 6 guests with plenty of room to spare. It is a short walk from multiple restaurants, bars, waterfront parks, and the Cabana Club. We...

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Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly

About this property

Yellowtail Escape! 3/2 SFH w. 60ft dockageWelcome to Paradise! This beautiful Marathon home on a deep water canal awaits your vacation. This home sleeps 8 people very comfortably. The large master bedroom has a newly renovated en suite bathroom with a stand up shower and a king sized bed. It also...

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Key Colony Beach House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Island Paradise-large 2 bedroom/2 bath SFH with Cabana club and 75ft of dockageRelax and unwind at Island Paradise!Nestled along the serene canal, this exquisite single-family home exudes peace and comfort at every turn. Step inside to discover a spacious haven boasting two large bedrooms, the...

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Marathon House
Sleeps 2, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • WiFi

About this property

Lovely 1/1 condo in Coco Plum with pool, dockage and a boat ramp. This home is spacious and offers a pool and garden view from back screened in patio. You can enjoy a cup of coffee or a cocktail and enjoy paradise. It is just a very short walk to the canal and pool!The condo has a queen sized bed...

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Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Sea Renity~ Large 3/2 SFH, 30ft dockage, Private pool, Hot tub & Huge game roomWelcome to our lavishly appointed, open floor plan, 3/2 Single Family Home with water views from the living room and balcony. Easy boating access, less than 10 minutes from the Ocean. Seas the day and the evening breeze...

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Marathon Condo
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • WiFi

About this property

Imagine waking up to the soothing sound of waves crashing against the shore as you step out onto your private balcony. Welcome to our beautifully remodeled 2 bedroom, 2 bath condominium with blissful beachfront views.This coastal retreat is the epitome of relaxation and style, boasting a nautical-inspired...

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Key Colony Beach House
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

SALTLIFE- Waterfront 2/2 in Key Colony Beach! 30ft of DOCK, Cabana Club & Pool STAY IN PARADISE & ENJOY THE STUNNING SUNRISE OFF THE PIER. DRINK A MORNING CUP OF COFFEE IN THE SCREENED PATIO OR ENJOY EVENING COCKTAILS WITH BAY VIEWS. YOU SIMPLY CANT BEAT THE BEST OFFSHORE FISHING EXPERIENCE!COZY...

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Featured review

"Excellent place to stay in the keys"

The best Place in the keys everything that you will look for is in this place. I highly recommended.

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Key Colony Beach House
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our Peace of Paradise in the Keys! Ocean, beach and private salt pool living at its Best! Enjoy swimming and sun bathing right across the street at Private Inch Beach or at the private salt pool surrounded by tropical plants. As you enter Key Colony Beach, a quiet and peaceful island town,...

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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
New
Key West Townhome
Sleeps 6, 2 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

2 bedrooms and 2 full baths, 2 Balconies has pool view and Ocean view. Sleeps 6 address is 200 Sunset Ln Key West, Florida 33040Kitchen Coffee maker Dishwasher Microwave Oven Refrigerator (full-size) StovetopEntertainment Internet access Telephone TV DVD player Radio or music...

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Key West Cottage
Sleeps 3, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

A beautiful historic cottage, in the complex of Sirena Blue=Blue Mermaid, located in a great area of old town Key West, within walking distance of Duval St. and beaches, available to rent for short term. Recently fully remodeled May of 2023. High end furnishings. 2 bedrooms or an office and bedroom,...

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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.