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Florida Keys Vacation Rentals

(574 rentals)
Islamorada House
Sleeps 9, 4 bedrooms, 5.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

PROPERTY NAME: Bella 109 Valencia Drive Tavernier, FL 33036LOCATION: Bayside Canal home located in the popular Islamorada neighborhood of Venetian ShoresMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 86DESCRIPTION: Luxurious 4-Bedroom...

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$500
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, 4 bedrooms, 3 bathrooms
4 reviews

Key Amenities

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

About this property

This beautiful, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. Situated in a beautiful upscale neighborhood of all waterfront homes, the house is equipped with all the comforts of home. It is extra clean and modernly furnished.Upstairs...

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Featured review

"Perfection in paradise!"

This was a perfect house! Easy and quick access to ocean and gulf, docked 35’ boat right at the house, large pool with hot tub, plenty of parking for vehicles and trailers, very clean, well stocked, tiki...

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$634
avg per night
Cudjoe Key House
Sleeps 6, 3 bedrooms, 3 bathrooms
1 review

Key Amenities

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

About this property

Tropical Paradise has been a popular and romantic vacation rental getaway since 2003. This house includes all the elements you need for an amazing vacation. There are kayaks for adventures, a dipping pool and private beach for relaxation, a floating dock for fishing and docking a boat, (up to 24'...

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Featured review

"Peace and Tranquility. Amazing sunrises and sunsets"

The location was exactly what I had hoped. It was secluded, but close to everything. The water views were worth every penny!

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

Key Amenities

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

About this property

The Cottage is a free-standing 2 bedroom/2 bath villa located on a small resort property nestled in a native hammock on Florida Bay. The Cottage is a “conch-style” cottage which was just completely remodeled and renovated and is completely new, from the tile floors to the new tongue-and-groove...

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$275
avg per night

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Marathon House
Sleeps 10, 4 bedrooms, 4.5 bathrooms

Distance to beach: 0.5 miles to Sombrero Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Exclusive Sombrero Beach vacation retreat is located just up the street from one of the best beaches in the Florida Keys. Sombrero Beach is a large sandy beach that offers something for everyone in the family including playground, volleyball swimming and picnic tables. The beach is also a great place...

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$1,424
avg per night
New
Tavernier House
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Key Amenities

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

About this property

Bayfront Serenity | Seasonal Waterfront Retreat | 4 En-Suite Bedrooms | Pool, Dock & Sunsets | Tavernier, Village of Islands (Islamorada)Welcome to Bayfront Serenity, a private waterfront retreat in Tavernier’s exclusive Village of Islands in Islamorada, where sweeping bay views, breathtaking...

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$733
avg per night
Marathon House
Sleeps 5, 2 bedrooms, 2 bathrooms
3 reviews

Key Amenities

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

About this property

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

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Featured review

"Peaceful palms winter retreat"

We had a great time escaping the cold weather up north. Accommodations were excellent as were our hosts Jamie and Charlie, they were very responsive to any questions we had and made us feel welcome. We...

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$250
avg per night
Tavernier House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

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

About this property

Recently built from the ground up. Three bedroom, three bathroom piece of paradise on a saltwater canal with easy access to the ocean. 50’ dock, pool, outdoor kitchen, plenty of parking. Close to super market, hospital, and many amazing restaurant’s. Full kitchen with everything you may need....

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$288
avg per night
Cudjoe Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • WiFi

About this property

This Cudjoe Key home is neat as a pin with all the comforts of home. Bright and shiny kitchen with everything you may need to create wonderful get together. The large comfortable living room has plenty of seating including recliners in the sofa and loveseat. Laminate hardwood floors throughout. 3 large...

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Featured review

"Perfect boat and pet friendly home in the Lower Keys"

We thoroughly enjoyed our stay at Palmetto Retreat. The home was spotless and had all the amenities we needed. A couple of menial things didn't work, and Christine (Rudy) took prompt care of them while...

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$165
avg per night
Ramrod Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Clean, Tropical 3/2 on open canal in quiet residential neighborhood on a cul-de-sac. House is on Gulfside with quick access to Miles Channel Bridge towards ocean or bayside. 50’ concrete dock with fish cleaning station.Master Bedroom has a queen size bed, shower and indoor jacuzzi tub. Second...

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Featured review

"Wonderful Times!"

Alex and I had a wonderful time in your beautiful home. Loved eating dinners (breakfast and lunch too!) sitting outside. Peaceful and lovely. The storage room downstairs was perfect for storing all our...

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$180
avg per night
Big Pine Key House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

This unique home is situated on a quiet street, with a desirable corner canal location in Port Pine Heights, Big Pine Key. Bringing your boat along? No problem, plenty of dock space here! And quick and easy access to Pine Channel for excellent boating, fishing, diving and snorkeling!The exterior has...

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$207
avg per night
Summerland Key House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to Buccaneer Boathouse! Pack your floral shirts, swimming gear and sandals and come on down to Little Torch Key in the beautiful Florida Keys. This lovely home is spacious with 2 bedrooms and 2 bathrooms. It offers a large open kitchen, dining and living area for everyone to hang-out and plan...

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$157
avg per night
Key West Cottage
Sleeps 4, 2 bedrooms, 1 bathroom
3 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

The Mile Zero House is a MONTLY VACATION RENTAL. Rent one or more months comes completely furnished. Charming conch home with true Key West character. Fenced for privacy with a open style front porch to enjoy the local flavor along with a passing Conch Train. Full size kitchen that is nicely stocked with...

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Featured review

"Amazing Location!"

Historic Conch House Located Downtown Key West near Duval St and restaurants beach and many attractions ! Private Yard fully locked and fenced with beautiful plants Sitting on the front Porch you feel...

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$124
avg per night
Summerland Key House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to the Snow Grouper, a classic and comfortable vacation rental home in the much sought after Summerland Cove on Summerland Key.This two-bedroom, two-bathroom home is completely remodeled, with a layout that is welcoming, from the open concept kitchen and living room, to the beautifully furnished...

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$250
avg per night
Key West Townhome
Sleeps 4, 2 bedrooms, 1.5 bathrooms

Key Amenities

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

About this property

Welcome to your Key West escape! Nestled in the heart of 'Old Town', this charming townhouse is part of a wonderful twelve townhouse community with a lush, tropical garden courtyard that provides a tranquil, resort-like feel. You're just a half-block from the quiet end of Duval Street,...

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$150
avg per night
Summerland Key House
Sleeps 14, 6 bedrooms, 4 bathrooms
1 review

Key Amenities

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

About this property

Beautiful Ocean Front Home with six bedroom/Four bath. New memory foam mattresses in King and Queen rooms. Enjoy the heated pool, dock and beach. Located on Cudjoe Bay with panoramic view of the Atlantic and deep water swimming. Kayaks are provided for your enjoyment. There is a huge screened in porch...

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Featured review

"We would do it again!"

We enjoyed a family vacation for one week at this "villa". The view was spectacular and the interior spacious. There were plenty of spaces for all of us to sit and visit with each other. The pool was fun...

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$658
avg per night
Sugarloaf Key House
Sleeps 10, 5 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Sea Magic on Marlin – Panoramic Open Water Views & Spacious5-bedroom HouseYour Sugarloaf Key adventure begins at this beautifully located waterfront home. Panoramic water views and access allows for boating, swimming, kayaking, snorkeling, and fishing and this 5-bedroom house welcomes...

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$429
avg per night
Tavernier Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

From sunrise to sunset you can enjoy the many activities our Florida Keys resort has to offer. Fine restaurants and shopping are just minutes away, along with boating, fishing, snorkeling, diving, Everglades eco-tours, glass bottom boat reef trips, para-sailing, wave runners, and swimming with the dolphins....

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Featured review

"Outstanding!!"

The incredible view! The kitchen has everything (though we didn't intend to do a lot of cooking!). The unit has a short walk to the pool, snackbar/bar, and the restaurant/bar. There is also a small natural...

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$250
avg per night
Key Largo House
Sleeps 10, 5 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Private pool
  • WiFi

About this property

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

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$650
avg per night
Cudjoe Key House
Sleeps 9, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

***We are taking the recommended steps as presented by the Center for Disease Control and Prevention (CDC) for cleaning, disinfecting, and preparing this home for your arrival. We are following the protocols laid out by the CDC and using the EPA-approved disinfectants for Hard (non-porous) Surfaces, Soft...

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$479
avg per night
Marathon Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to Turtles Nest! A beautiful 2-bedroom 2 bath condo in the heart of Marathon complete with 40' boat slip and a private boat ramp! 30 steps to the water and heated pool, this 2/2 condo is ready for your changes in attitudes, changes in latitudes!Community/Location: - beautiful canal-front...

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$232
avg per night
Ramrod Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

The Coral House is a prime destination spot for a great Florida Keys vacation! Conveniently located on Ramrod Key, mile marker 27. Close to all the choice restaurants and services that the Florida Keys have to offer.This home is beautifully decorated in island style with attention to even the smallest...

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$222
avg per night
Key West Yacht
Sleeps 6, 3 bedrooms, 3.5 bathrooms
4 reviews

Key Amenities

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

About this property

Lady Grace will not be in Florida for the 2025-2026 season. Come visit her in the BAHAMAS!Bahama Cruise with exploration in the Exuma IslandsFor guests who want to enjoy a vacation on the move, our cruise aboard Lady Grace is for you. Nassau, Bahamas is the center of our winter cruise program,...

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Featured review

"Girls trip"

The Lady Grace was awesome and Kelly and Capt Jamie were phenomenal. Everyone loved the yacht and everything she had. Plenty of beds bathrooms and gathering places. The sunset cruise was excellent and so...

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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.