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Florida Keys Vacation Rentals

(562 rentals)
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
Marathon House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

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

About this property

Off the HookImagine your vacation in this stunning custom-built modern 3-bed, 3-bath pool home, "Off the Hook," on the edge of Marathon. This newly built Florida Keys retreat welcomes you with a striking foyer and floor-to-ceiling windows that blend indoor luxury with outdoor beauty.The...

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$703
avg per night
Summerland Key House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Florida Keys Vacation Rentals – This Summerland Key vacation home is situated on a private, fully fenced lot, with a tastefully decorated interior with great features such as hardwood floors and a beautifully well-equipped, custom kitchen. Spacious living and dining rooms provide ideal entertaining...

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$217
avg per night
Key West House
Sleeps 6, 3 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

This nicely appointed home is located in Key Haven subdivision of fine homes. It offers an expansive living room with upgraded kitchen and appliances. The kitchen is nicely stocked with plenty of room for multiple cooks. The house can accommodate up to six people with 3 bedrooms and 2 full bathrooms....

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Featured review

"Serene and comfortable"

We absolutely love this home! The interior features plenty of space and storage. The kitchen is well equipped with everything you need and more. The bedrooms very comfortable. The shower in the master has...

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$188
avg per night
Islamorada House
Sleeps 4, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

PROPERTY NAME: Marlin House 156 Venetian Drive, Islamorada, FL 33036LOCATION: Bayside Canal home located in the popular Islamorada neighborhood of White Marlin BeachMINIMUM STAY: 90 days, this is a 3 month minimumMILE MARKER: 74.5DETAILS: You will love this charming and cozy Keys Holiday...

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$214
avg per night

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Tavernier Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • WiFi

About this property

Relax amongst the tropical sights and sounds in this charming ocean front condo.Ideal for couples, solo & budget travelers, Key West Road Trippers, Snowbirds, Sea-Foodies, Divers, Snorkelers & AnglersSEAS THE DAY - OR JUST RELAX - YOU'RE ON ISLAND TIME!The space With thoughtful and...

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$235
avg per night
Cudjoe Key House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Available for the 2026 season! (weekly rentals permitted) Affordable piece of paradise! Escape the cold and come enjoy this Venture Out home with open concept, bright and airy rooms, and freshly painted interior! This 2 bedroom 2 bath home is so spacious you’ll be amazed. This fully furnished home...

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$205
avg per night
New
Marathon House
Sleeps 10, 4 bedrooms, 3.5 bathrooms

Distance to beach: 0.1 miles to Sombrero Beach

Key Amenities

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

About this property

Dreaming of that elusive Keys home with a incredible waterfront views, a private pool, a great beach, and a dock for your boat? Look no further... this newly built 2026 home on a gated Tingler Island might be just for you.Located just one block from Sombrero Beach (Trip Advisor Top 10 Beaches in N....

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$822
avg per night
Summerland Key Cottage
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

A comfortable well priced home away from home. This charming 2-bedroom, 2-bathroom cottage offers a spacious, living/dining area with a fully stocked kitchen only steps away from the shaded patio with a water view and firepit. NEW to the Property - Heated Swim Spa!Experience the coastal charm and...

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$214
avg per night
Key West House
Sleeps 8, 3 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Pool
  • WiFi

About this property

Coral Hammock – 3BR/3BA Home with Pool Views in Coral Hammock3 Bedrooms | 3 Full Bathrooms | Sleeps up to 8 | Backs to Community PoolWelcome to Coral Hammock, your home away from home in beautiful Key West! Built in 2004 and meticulously maintained, this spacious 3-bedroom, 3-bathroom home...

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Featured review

"Southern Charm with a boat slip!"

Our family had a wonderful time staying in this townhome style rental. We relaxed and enjoyed the views of the bay and marina from the back porch. The boat slip worked great for our rental boat. This...

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$2,635
avg per night
Marathon Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 1 miles to cocoplum

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Are you ready to Seas the Day? 30 steps to the water and heated pool, this completely renovated 2/2 condo is ready for your changes in attitudes, changes in latitudes!Community/Location: - beautiful canal-front community - steps from heated (and chilled) saltwater pool (easier on eyes, skin and...

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$224
avg per night
New
Big Pine Key House
Sleeps 4, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Welcome to Your Canal-Front Keys RetreatTucked away in the quiet beauty of Big Pine Key, this elevated canal-front home offers the relaxed rhythm of the Florida Keys with room to breathe, unwind, and reconnect with nature. From peaceful mornings on the deck to spectacular sunsets over the water, this...

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$200
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.