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Florida Keys Vacation Rentals

(570 rentals)
Cudjoe Key Cottage
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 15 miles to Bahia Honda State Park

Key Amenities

  • Air conditioning
  • Oceanfront
  • Rentals by owner
  • WiFi

About this property

Minimum Rental is 28 Days to a single family or party (no subleases allowed).PLEASE DO NOT REQUEST for less than 28 night rental. A fine of $16,000.00 is imposed by Monroe county for less than 28 nights. Less than 28 nights is simply non-negotiableNO PETS ALLOWED. IF YOU WANT TO BRING PETS,...

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Featured review

"Beautiful Sunsets"

The home was clean and full of amenities. Great place to spend a month escaping harsh Wisconsin winters. Owners were attentive and easy to deal with. A great boat launch should you need one. Neighborhood...

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$167
avg per night
Islamorada House
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

Key Amenities

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

About this property

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

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Featured review

"Beautiful stay"

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

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$943
avg per night
Key Colony Beach House
Sleeps 10, 4 bedrooms, 4 bathrooms
3 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

"Very comfortable and spacious."

INTERESTING LOCATION on an active canal in Key Colony Beach…Lots of space and privacy for a group of eight.Can accommodate ten.Good parking and boat accommodation.GARAGE WITH TONS OF STORAGE AND SECURITY..private...

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$564
avg per night
Key West House
Sleeps 6, 3 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Tropical seclusion and privacy at its very best. Located just 15 miles from Key West. This luxury rental consists of 2 full suites. The first floor has a roomy living room, huge screen porch, queen sleeper sofa, bath and bedroom connected by an exterior staircase to the second floor. The second floor...

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Featured review

"Soon to be there"

I have not stayed there yet, but will gladly take $5 for this review. I hope is as nice as it its described

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$208
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

PROPERTY NAME: Ocean Harbour K31 87851 Old Highway, Islamorada, FloridaLOCATION: Ocean Front CondoMINIMUM STAY: 28 Days, MILE MARKER: 87.8DETAILS: Gorgeous 3 bedroom ocean front condo with unobstructed ocean views from the screened balcony. Check out the photos! The kitchen was completely...

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$300
avg per night

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Big Pine Key House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

The name says it all, find your dream vacation home at Million Dollar View! Located on Big Pine Key, this perfectly placed piece of paradise sits on a convenient corner lot, providing ample space for boats, and some of the fastest access to water you can get anywhere in the Keys! When you aren’t...

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$327
avg per night
Marathon House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 1 miles to Sombrero Beach

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Beautifully updated 3 bedroom, 2 bathroom stilted home on exclusive Flamingo Island in the high-demand Sombrero Beach area. This home will not disappoint. Fantastically lush and meticulously landscaped yard by local famous design artist featuring a large, brand new heated/chilled pool with plenty of built...

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$400
avg per night
Key Largo House
Sleeps 10, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

PROPERTY NAME: Twice the Charm 214 S. Ocean Shores Dr, Key LargoLOCATION: Oceanside Canal Front HomeMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 98.5DETAILS: "Twice the Charm" is a gorgeous newly remodeled single family...

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$333
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 3 bathrooms
10 reviews

Key Amenities

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

About this property

4 bedroom/3 bath Canal front home.7 nights minimum. Enjoy coastal breezes in this canal front Villa. Beautifully decorated. 4 Bedrooms/3 Baths. Two King Master Suites with attached baths. One on first floor. Fully stocked Gourmet Kitchen. Dining area seats 10. Flat screen Satellite TV's in each...

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Featured review

"Well Done"

Very Clean, stocked with the right amenities, great location, very fun time, Would highly recommend for those looking for a central location in the Keys

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$446
avg per night
New
Islamorada House
Sleeps 10, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Venetian shores 4 bedroom 3 bath, pool, hotub, 300lbs ice machine with 20K and 8k boat lift, Master has a double walk-in shower, separate 1 bedroom with full bath on lower unit great for privacy, full kitchen with all stainless appliances..28 day minimum

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$540
avg per night
Key Colony Beach House
Sleeps 4, 2 bedrooms, 2 bathrooms
4 reviews

Key Amenities

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

About this property

Come vacation at our 2 Bedroom, 2 Bathroom, canal front property located on the Island of Key Colony Beach in the Middle Keys. Our house sleeps 4 people including kids and has dockage right our back for up to a 40-foot boat. You can fish right off our dock on the Island's largest, deepest, most private...

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Featured review

"Perfect Vacation Getaway!"

We had a wonderful stay and highly recommend this vacation rental! The property was very clean, and the kitchen was well equipped with everything we needed. We especially enjoyed fishing from the dock and...

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$165
avg per night
Cudjoe Key Villa
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Looking for a home away from home? Via Villa is the place! This vacation home is located in Cudjoe Gardens on Cudjoe Key, only 20 miles from Key West. Situated on a corner canal, there is ample dockage for large boats, water and electric on the dock, as well as a waterside fish cleaning table. Via Villa...

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$393
avg per night
Islamorada House
Sleeps 8, 3 bedrooms, 3.5 bathrooms
2 reviews

Key Amenities

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

About this property

Welcome to the coastal home of your dreams in the relaxed residential retreat of Coral Cove. As soon as you pull into our driveway, you’ll be able to walk, bike or paddle everywhere in town. Our newly constructed two-story house has 3 spacious bedrooms, a study area with bunk beds, plus 3 and...

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Featured review

"Bayside Paradise Perfection"

Our family has been traveling to Islamorada for Spring Break for the last 4 years and this was by far our favorite place to stay! Our family enjoyed the private oasis that the townhome provided. We felt...

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$871
avg per night
Islamorada House
Sleeps 10, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • WiFi

About this property

Seeing is believing. The Captain's Quarters is a direct, oceanfront home on the Atlantic shoreline of Islamorada. For your planned getaway, come enjoy truly private and relaxing oceanfront living in the heart of Islamorada, in a unique home boasting a treasure-trove of Florida Keys history. The...

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$667
avg per night
Islamorada House
Sleeps 8, 4 bedrooms, 4.5 bathrooms
2 reviews

Key Amenities

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

About this property

Named one of the most romantic destinations in the world, this Magnificent brand new home in the heart of Islamorada is nestled between Cheeca Lodge Resort and Caribbean Resort offers a unique and luxurious experience for those looking for a private getaway. This 4 bedroom/4.5 bath home services from...

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Featured review

"Great House, Great location"

Had a great time! The house was amazing and well-appointed. We grilled, we cooked, amd we walked to several great dinner spots. The pool was excellent with the grandchildren. Highly recommended!

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$963
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 2 miles to Founder's Park

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Long-term rental available in the beautiful Venetian Shores community of Islamorada, Florida. This 3-bedroom, 2-bath home sits on a secluded plugged canal by the water. Enjoy a large master bedroom, a spacious open layout, and a generous outdoor deck ideal for entertaining. Additional features include...

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$235
avg per night
Big Pine Key House
Sleeps 8, 5 bedrooms, 3 bathrooms

Key Amenities

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

About this property

Tropical Oasis on the Canal: Tiki Bar, Heated Pool & Outdoor Grills Big Pine Key, FL | 5 BR, 3 BA | 28-Day Minimum Stay Escape to the ultimate Florida Keys retreat! This expansive, fully fenced canal-front estate offers a resort-style experience designed for families and groups seeking privacy,...

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Islamorada House
Sleeps 5, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

PROPERTY NAME: The Bungalow House 32 Park Rd Islamorada, FloridaLocation: Bayside Very close to the Publix Shopping CenterMINIMUM: 28 Days, All stays must be the whole month (s), No Partial Months AllowedMile Marker : 82Details: This home is absolutely beautiful with your own pool and...

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New
Key Largo Condo
Sleeps 4, 2 bedrooms, 1.5 bathrooms

Key Amenities

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

About this property

Welcome to your tropical escape in the heart of the Florida Keys! This beautifully appointed condo at Moon Bay Condominium offers the perfect blend of relaxation, comfort, and island adventure. Nestled along the bay in sunny Key Largo, this peaceful retreat is ideal for couples, families, remote workers,...

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Inquire for rates

New
Islamorada House
Sleeps 6, 3 bedrooms, 3.5 bathrooms

Key Amenities

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

About this property

Gated Home | Dock, Heated Pool & 2 Pools | Pet-OK Welcome to HeartofMorada!Step into a private world in Islamorada's most coveted location. Heart of Morada sits in Coral Cove — a gated community of just 8 homes — giving you a private heated saltwater pool with waterfall, your...

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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.