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Florida Keys Vacation Rentals

(576 rentals)
Key Largo House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • WiFi

About this property

PROPERTY NAME: Bay Therapy 778 Bostwick Dr., Key Largo, FloridaLOCATION: Bayside canal home located in Key Largo MINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 103DETAILS: Owners call this their special getaway "Bay Therapy" for...

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$266
avg per night
Islamorada Townhome
Sleeps 4, 2 bedrooms, 1.5 bathrooms
1 review

Key Amenities

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

About this property

We are delighted to offer this 2 story, 2 bedroom, 1 1/2 bathrooms OCEANFRONT TOWNHOUSE!!! There are a limited number of oceanfront townhomes available at Planation By The Sea! Enjoy the breathtaking views off of all 3 balconies catching the sunrise and sunset. The main living area and upstairs bedroom...

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Featured review

"Beautiful waterfront Condo"

We had a wonderful month in Islamorada at this outstanding waterfront condo with pool and sauna, dock etc. The views were gorgeous from the 3 decks in this corner unit. The area is exciting and near both...

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$140
avg per night
Ramrod Key House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool

About this property

Blue Tranquility will be the perfect destination to get some rest and relaxation for your next Florida Keys vacation. Located directly on the ocean side of South Pine channel, which offers wonderful sunrises and moon rises. Kick back and enjoy the balmy breezes on the serene screened in porch. The pool...

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$275
avg per night
Key Largo Estate
Sleeps 20, 7 bedrooms, 5.5 bathrooms
3 reviews

Key Amenities

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

About this property

Large, very spacious, beautifully appointed 7 BR home with breathtaking ocean views, large dock, pool, 2 jacuzzis, BBQ grill, 4 kayaks, large tiki, two fully equipped kitchens, all new appliances and major upgrades since Irma. Comfortably accommodates multiple families. Very private and secure with property...

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Featured review

"Perfect house for families!! Amazing outdoor space!!"

We loved our stay at Casa Lorelane! We had 18 people and never once felt crowded. The living area on the second floor was amazing. The second kitchen on main floor made it easy to prepare food to enjoy...

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$800
avg per night
Sugarloaf Key House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

Amazing Waterfront Home with Fabulous Pool and Sunset ViewsWelcome to the Sugarloaf Guest House, the perfect Florida Keys Island Getaway. As you enter the gate to this charming seaside cottage, you will experience its charm and relaxing vibes. A gorgeous new pool with graceful waterfalls make it the...

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$395
avg per night

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Key West Condo
Sleeps 2, 0 bedrooms, 1 bathroom
7 reviews

Distance to beach: 0.5 miles to South Beach

Key Amenities

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

About this property

This Simonton Studio is neat, sweet and complete. * Pet friendly for additional flat fee of $90 *Cleaning fee of $90 is additional. * WiFi included * King size bed * Outdoor table and two chairs * spacious shower * excellent loctaion for walking Old Town * Duval Loop bus passes this adress...

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Featured review

"Perfect little getaway for two!"

Fabulous location, great host. Awesome little getaway just big enough for two. Pam is great to work with.

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$205
avg per night
Marathon House
Sleeps 5, 2 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 7 miles to Sombrero

Key Amenities

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

About this property

Great news, we just completed construction of a brand new 60FT dock. We have a kayak launch and plenty of room for your boat.Our indoor upgrades included getting a Tempur Pedic king-size adjustable bed for the master bedroom (raise the head or feet). All the TVs are now 4K smart TVs, which we mounted....

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Featured review

"Everything you want or need."

This house has the latest and greatest of everything. It's beautifully decorated and located on the best part of the island. Over looking a heated pool, it's steps away from an elevated observation deck...

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$205
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
Key Largo Townhome
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

If you want to experience the true meaning of a Key Largo Island vacation, then look no further than our spacious townhouse on the ocean side of the world famous Key Largo, Florida. ... The Dive Capital of the World! This Villa is located inside Kawama Yacht Club, a beautiful Hawaiian Island style resort...

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Featured review

"Great place"

Nice condo in Key Largo. Owner very responsive. Beds comfortable. Would rent again, for sure. Close to a lot of restaurants & stores.

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$226
avg per night
Big Pine Key House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This is truly a hidden gem! A secluded four bedroom, three bath home furnished to the nines! There are three decks off of the home, plus an above ground pool with attached deck, bar and tiki hut. Super private with a fenced in yard! If you want to visit the Lower Keys, but don’t care about being...

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$133
avg per night
New
Big Pine Key House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

This charming 2-bedroom, 2-bath rental home is perfect for your tropical getaway! With a minimum stay of 28 days, it accommodates up to 6 adults and 1 child, making it ideal for families or groups. The master bedroom features a king-size bed, while the guest bedroom offers a queen-size bed. Additional...

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$200
avg per night
Marathon House
Sleeps 4, 2 bedrooms, 1.5 bathrooms
1 review

Distance to beach: 3 miles to Sombrero Beach

Key Amenities

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

About this property

Welcome to DragonFly Lite our home in Marathon, FL in the heart of the beautiful Florida Keys, the house has 2 bedrooms a Queen in the master and 2 twins in the guest room, one bathroom + our outdoor shower, all the towels you will need for the pool or beach (please leave the sand outside). It’s...

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Featured review

"A Magical Place to Isolate"

Though Dragonfly Lite would be a marvelous place to vacation anytime, it proved especially so in a global pandemic. We had everything we needed right there on property. The pool is pristine, the home was...

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$231
avg per night
Key Largo Townhome
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Coastal Themed Villa Retreat in Paradise Awaits for You! Spacious Large Open Floor Plan on 2nd Floor with large Family Room and 2 Large Bedrooms each on opposite sides of the unit. Large Open Kitchen to Family and Dining Area...Bathrooms are also Coastal Themed. Villa is quiet and peaceful surrounded...

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$130
avg per night
New
Big Pine Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Breathtaking sunrises from your balcony at this 3 bedroom, 2 bath home. There's a L shaped floating dock that can host a 24' boat, or you can launch the provided kayaks onsite. The master bedroom has a king bed, a working desk station, balcony access, and a private bath. There is a King bed,...

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$350
avg per night
New
Key West Cottage
Sleeps 4, 0 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to “The Coconut” – Your Slice of Old Town ParadiseTucked into the heart of Old Town Key West, The Coconut is your dreamy island hideaway — where history meets laid-back tropical living.Built in the late 1800s and full of classic Key West charm, this sun-drenched...

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$271
avg per night
Tavernier Mobile home
Sleeps 4, 2 bedrooms, 2 bathrooms
9 reviews

Key Amenities

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

About this property

This property is located on a very unique spot. Very private. Too perfect to describe.During the day you could sunbathe while fishing for snappers, tarpon and lobsters from your private dock. Later on you may want to jump in for a swim or cruise the area on the kayak At early evening you may enjoy...

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Featured review

"Paradise!"

This is an amazing rental and the owners are the nicest people you will ever meet. The home is on the water and one house from the Gulf of Mexico. Sit on your own private dock and watch the Manatees, Dolphins,...

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$180
avg per night
Little Torch Key House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Private pool
  • WiFi

About this property

This 3 bedroom/2.5 bath home is located in a quiet neighborhood on a deep canal with easy boating access to open water.The Master has a King bed, 2nd bedroom has a Queen. There is an extra sleeping area with a queen and twin bunk bed, 1/2 bath and outdoor enclosed shower. 2 beach bikes and 1 double...

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$268
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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$243
avg per night
Key Largo House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Island Tropical Bungalow! This lovingly maintained, delightful and spacious 3/2 with large expanded porch and Boat ramp just crossing the street makes a great getaway. All utilities are included (water, power, wifi, tv) Large shed in back with laundry (washingmachine and dryer). Totally redone...

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$286
avg per night
Key West Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through the Spring of 2026. This construction WILL impact your stay if you are staying during the week days. Please contact All Florida Keys Property Management for more detailed information....

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$165
avg per night
Key Largo Villa
Sleeps 8, 3 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. The property is located in Rock Harbor's most upscale neighborhood. The area has the distinction of being Key Largos newest oceanfront gated destination, with some of the most...

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$393
avg per night
Key Largo Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Beautiful bright Buttonwood Bay Condo. It's one of the few 2000sf units for rent in the community. No stairs inside the unit. It is a spacious corner unit with a single floor plan. Located close to the tennis courts and pool. Our home has new furniture and all new kitchen appliances. From the moment...

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Featured review

"Buttonwood Bay Vacation"

One of the nicer & classier condos we have stayed at in Key Largo. My wife & I walked around the docks for exercise mostly every day except for a few that were too cold, also spent a few days at the heated...

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$187
avg per night
Key Colony Beach House
Sleeps 14, 6 bedrooms, 5 bathrooms

Distance to beach: 0.3 miles to Sunset Park

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This beautiful, modern and stylish home is perfect for families and group vacations and boast 2 full kitchens.It features high quality and modern furniture and beds, a fully equipped kitchens, high-speed wireless internet and a private, heated pool.The Upper side has 3 bedrooms and 2 bathrooms,...

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$992
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms

Distance to beach: 3 miles to Sombrero beach

Key Amenities

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

About this property

If you are looking for a tropical Keyz experience, you have arrived in paradise at this three bedroom two bathroom home on a direct ocean access canal which has all the comforts of home and more. **This is a 3 bedroom 2 full bathroom rental** There is no ground floor apartment or access. This is owners...

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$311
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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$212
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
Full map
Map

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.