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Florida Keys Vacation Rentals

(588 rentals)
Islamorada House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Rentals by owner

About this property

The moment you step inside this calming retreat in exclusive Venetian Shores you feel on vacation with permanently assigned boat slip in private marina just around the corner. All new kitchen, baths, porcelain tile flooring, fully furniture and LOTS more. Three bedrooms, two bath home on a peaceful plugged...

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$217
avg per night
New
Summerland Key House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

The Shores of Sugarloaf Luxury Waterfront Home with Gorgeous Pool, Tiki Bar and SunsetsWelcome to the Shores of Sugarloaf, the perfect Florida Keys Island Getaway. Check-in to this gorgeous coastal home and enjoy a lovely vacation on one of the Florida Keys most desirable keys-Sugarloaf. This house...

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$495
avg per night
Key West Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Hot tub
  • Pool
  • WiFi

About this property

CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 Please be advised that a balcony restoration project will be underway at 1800 Atlantic from May 2025 through Spring 2026. Important Notes: -Units available for booking will...

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$350
avg per night
Marathon House
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

Inquire for monthly discounts.The happy house 339 at ghee mail. Quaint and charming home nestled in the Florida Keys. Secluded single family property with open water access. Private Dock, Beach, kayak launch area with kayaks and bikes available to use. Very private tranquil location. See manatees/fish...

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Featured review

"Great House - Great Location"

The house was comfortable and clean. Enjoyed the kayaks and the dock. Saw a Momma manatee with a baby on two occasions. Caught fish off the dock, nothing big enough to keep but very entertaining. Grocery...

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$316
avg per night
Cudjoe Key House
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to your ideal vacation getaway in the heart of the Florida Keys! Located in the serene Cudjoe Key, this charming home offers luxurious amenities and a perfect blend of comfort and style. Imagine waking up in a cozy, beautifully decorated home and enjoying your coffee on a private deck surrounded...

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Featured review

"FABULOUS!"

This was the best vacation I have ever had in Florida. The house was beautiful and it was very peaceful sitting out on the canal. Only 20 miles to Key West makes for easy day trips. We went 5 times! The...

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$186
avg per night

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Islamorada House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

PROPERTY NAME: Villa Riolo 130 Columbus Drive, Islamorada, FLLOCATION: Gated Oceanside House on canalMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 76.5DETAILS: "Villa Riolo" is an updated single family stilt home and perfect...

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$192
avg per night
New
Key West House
Sleeps 8, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • WiFi

About this property

The welcoming views at Coral Cove are waiting for you! This brand new two-bedroom, two-bathroom home is located on the open water and canal on Saddlebunch Key, just a stone’s throw from the famous “Baby’s Coffee.” You’re at Milemarker 15 and Key West is just minutes away!This...

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$200
avg per night
Marathon House
Sleeps 8, 4 bedrooms, 3.5 bathrooms

Distance to beach: 4 miles to Sombrero Beach

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Our Dome home is a beautifully designed geodesic dream home., a unique spherical structure made with love on the water in the heart of Marathon. (Sleeps 8)This newly built and beautiful 4/3.5 Geodesic Dome home with dockage is in a very quiet established neighborhood. It accommodates a 28-30ft boat...

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$435
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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$587
avg per night
Marathon House
Sleeps 6, 2 bedrooms, 1.5 bathrooms
2 reviews

Distance to beach: 3 miles to Sombrero Beach

Key Amenities

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

About this property

The Cozy Conch is ideally located, just walking distance from the historic 7 mile bridge. Take a bike ride along Overseas Highway, enjoy the nearby beaches or spend the day at our pool. Have a cozy night by the fire pit at the dockside lounge and BBQ area or the hammock park. The lower levels offers...

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Featured review

"We are fans!"

My husband and I just returned from a 5 week vacation in Marathon. Our vacation was unbelievable, due mostly for the lovely home that we stayed in. Cozy Conch is amazing! The location in phenomenal,...

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$189
avg per night
Key Largo House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

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

About this property

This is one of the most unique homes in all of the upper keys! What makes it special is that it's located on a peninsula so very private while at the same time offers stunning views of the Key Largo Bay.The home was recently updated to include all new flooring, new stainless steel kitchen appliances,...

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$1,000
avg per night
Islamorada House
Sleeps 12, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

PROPERTY NAME: Martin Family Fish Camp 106 Madeira Rd., Islamorada, FloridaLOCATION: 2 Houses Located on a private peninsulaMINIMUM STAY: WeeklyMILE MARKER: 81.9DETAILS: The Martin Family Fish Camp is located on a private peninsula and offers two houses named Bonefish and Tarpon. Each...

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$643
avg per night
Summerland Key House
Sleeps 10, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

The South House is a superb vacation home on Summerland Key. It offers everything you need to make your Florida Keys vacation truly memorable.The downstairs pool area is private and serene. There are several lounging areas to enjoy suntanning or wonderful afternoon shade. The crystal blue pool is...

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$383
avg per night
Key West Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Luxury island resort style living in Key West. 1800 Atlantic offers a private sandy sunning beach, Olympic style pool, gym, three tennis courts (one is clay), fitness center, community clubhouse, picnic areas and more. This condominium is updated and turnkey . Open living and dining spaces, eat-in kitchen...

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$216
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
Key West Condo
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • WiFi

About this property

CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 Please be advised that a balcony restoration project will be underway at 1800 Atlantic from May 2025 through Spring 2026. Important Notes: -Units available for booking will...

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$790
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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Big Pine Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Beautiful 3-BR house located directly on canal with easy access to the Gulf of Mexico or Atlantic Ocean. On-property pool and private outside shower. 75-ft dock for boat. Home of the Key Deer and Blue Hole (the deer will walk past house daily).Located 35 miles north of Key West, and 20 miles south...

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$210
avg per night
Key Largo Townhome
Sleeps 10, 4 bedrooms, 4 bathrooms

Key Amenities

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

About this property

*TOP 1% HOME* GUEST FAVORITE* This Key Largo 4 BED/ 4 BA Trendy & Modern Home is just steps to 2 Oceanfront Pools, Pickleball, Jacuzzis, BYOB Speakeasy Game Room, Tennis & Basketball Courts and Marina. A Coffee Bar, Private Balconies, Instagram LED Photo Wall and private en-suite baths await...

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$766
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
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
Islamorada Apartment
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

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

About this property

Beautiful ocean front apartment with easy access to pool ,spa and beach. Dock with boat slips and tiki hut overlooking Atlantic Ocean. Community exercise room Master Bedroom overlooking the ocean Two bedrooms, two full baths. Gourmet equipped kitchen Laundry room Balcony with spiral stairs...

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Featured review

"Unit 205 Beacon Reef"

Love Beacon Reef and the unit was very comfortable and well equipped. Very close to the pool and the staircase from the balcony was convenient

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$183
avg per night
Key Largo Townhome
Sleeps 6, 2 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner

About this property

Welcome to "Sol y Sal" in Buttonwood Bay. Brand new 2 bedrooms + den/ 2 1/2 bath townhouse. This unit was just redone in 2024 and includes fantastic, high-end finishes. Spacious living room with 70 in. tv, dining room with seating for 8, and kitchen with stainless steel appliances, and powder...

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$183
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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$433
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

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

About this property

Traditional coastal cottage styling built in 2017 and the Pool was added in 2020. Large backyard beach and only steps to the turquoise waters of the Atlantic Ocean. Kayak, paddle board, or kite ski from your backyard! Plenty of parking out front and private gated access; fencing around the perimeter....

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$688
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: 88.5DETAILS: "Twice the Charm" is a gorgeous newly remodeled single family...

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$333
avg per night
Little Torch Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • WiFi

About this property

Florida Keys Vacation Rentals – Set sail for a glorious Florida Keys vacation at the Blue Marlin. Spacious and comfortable for 6 in this 3-bedroom 2 bath Little Torch Key home. Located down a private lane and overlooking the crystal blue waters of Pine channel, gulf side. All the rooms are spacious...

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$239
avg per night
Marathon House
Sleeps 12, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Rentals by owner
  • WiFi

About this property

Welcome to your slice of paradise in Marathon! Nestled in the heart of the Florida Keys, this vibrant waterfront escape offers direct ocean access, stunning sunsets, and laid-back island vibes you’ll never forget.️ 3 Bedrooms | 2 Bathrooms | Ocean Access | Dock | Sunset ViewsImagine...

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$317
avg per night
Key Colony Beach Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

$2,,400 - $3,200/wk., depending on season. 7 night minimum stay. Saturday-to-Saturday only during high season.Key Colony Beach is called the “Gem of the Keys,” and for good reason! Our very well-appointed and recently updated 2BR, 2BA condo is DIRECT beach front, on one of the most beautiful...

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Featured review

"SNOW BIRD's Stress Relief"

Just what the Wife Ordered:) We own a Little Bar in West Mich. Called Cocktailz Sports Bar & Grill Plus Myself Ernie is a Realtor. We always try to get away in March every year to a Special Place that...

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$387
avg per night
Islamorada Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
9 reviews

Distance to beach: 0.9 miles to Founders Park

Key Amenities

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

About this property

Oceanfront gated community. Offers pool overlooking the ocean, pier which you can fish off of, clubhouse, sauna, exercise room, and very clean bathrooms by the pool. 2 Bed, 2 Bath. Master bedroom offers queen bed, sitting room, coffee, 50 inch smart tv, storage, master bath separate toilet. 2nd Bedroom...

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Featured review

"Super comfortable condo - amazing location - wonderful host!"

We spent a month in Sharon's condo (January 2025). Upon arrival we had everything we needed for the month! She goes above and beyond stocking the kitchen, cleaning supplies, pantry etc. The bedrooms are...

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$175
avg per night
Big Pine Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Barracuda Bungalow in Big Pine Key! This quaint ground level home is reminiscent of old Florida Keys with some new and improved upgrades like the brand new inground pool and spa. If you’re looking for that laid-back island feel, in a nice quiet neighborhood where you can watch the key...

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$185
avg per night
Key Colony Beach House
Sleeps 5, 2 bedrooms, 2 bathrooms

Distance to beach: 0.6 miles to Cabana Club

Key Amenities

  • Pool
  • WiFi

About this property

Salt & Seaglass- Porch, Dock, Pool Club. Sept 28 - Oct 10 Open & Big discount This welcoming, modern canal front duplex home provides a relaxing and comfortable atmosphere for your vacation in the Florida Keys!The home features 2 large bedrooms and 2 bathrooms, a modern kitchen with large...

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$292
avg per night
Sugarloaf Key House
Sleeps 10, 5 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

This pet-friendly home completed in 2012 has 5 rooms, 3 king-size beds, and 4 twins plus a twin sofa bed and three full bathrooms. The home has a huge kitchen with custom made wood cabinets and top of the line stainless steel appliances including an indoor gas grill and a standing freezer: to keep the...

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Featured review

"Take Your Vacay from 0 to 60 in 2.5 seconds"

SIX STARS * * * * * *This is a wonderful home with channel access right behind the house. It's perfect for the whole family, very spacious. The owners are very accommodating, making sure everything...

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$279
avg per night
Key West Condo
Sleeps 8, 3 bedrooms, 2.5 bathrooms

Key Amenities

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

About this property

CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 Please be advised that a balcony restoration project will be underway at 1800 Atlantic from May 2025 through Spring 2026. Important Notes: -Units available for booking will...

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$710
avg per night
Summerland Key House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to Casa Caribe, a comfortable 2 bed, 2 bath vacation home on Summerland Key. Located on one of the best canals on the island, and conveniently across the canal from the Summerland Marina, this home provides quick boating to the blue water as well as the prime diving areas of the Gulf and Looe...

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$158
avg per night
Tavernier House
Sleeps 7, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Rentals by owner

About this property

This beautiful waterfront home was recently updated and features 3 bedrooms with a spacious master bedroom and 2 bathrooms. The home has a very large kitchen with an island and two refrigerators. The kitchen is fully equipped with pots, pans, utensils, plates and more. We also provide a coffee machine...

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$127
avg per night
Key Largo Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 3 miles to John Pennekamp State Park

Key Amenities

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

About this property

Enjoy the panoramic view this tropically decorated, fifth-story unit has to offer of the Atlantic Ocean and the adjacent Wildlife Sanctuary. The unit affords its guests the spectacular sunsets the Florida Keys are famous for, right from your balcony and living room.Kawama Yacht Club is situated at...

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Featured review

"Boys week"

Great atmosphere, two minutes to the Atlantic. Jose great host, very clean. Thank you Jose for sharing your home.

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$287
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
Key Largo Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
10 reviews

Key Amenities

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

About this property

Congratulations, you have just discovered one of the most unique properties in the heart of Key Largo. This OCEAN FRONT condo is located inside Kawama Yacht Club, a beautiful Hawaiian Island style resort that is situated along the southern border to the most popular park in all of the Keys, John Pennekamp...

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Featured review

"Great place!"

Very nice place. Clean, comfortable, enjoyed the lagoon, and view. Rented the golf cart and enjoyed getting around with it.

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$344
avg per night
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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$289
avg per night
Key West Apartment
Sleeps 2, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • WiFi

About this property

Galveston Porches Stylish one bedroom apartment in the heart of Old Town. Totally renovated and beautifully decorated. Everything you will need for your perfect Key West extended stay. 1 assigned parking space with the apartment. Full kitchen and washer dryer, Central AC and wifi access. The owners have...

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$193
avg per night
Summerland Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Casa Turquesa is the jewel of Summerland Key. Located directly on the beautiful crystal blue keys waters with deep water boat access for the avid angler and plenty of dockage for all the water toys.FLORIDA KEYS VACATION RENTALS! This stylish home is outfitted in Florida tropical style with cool and...

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$296
avg per night
Summerland Key Villa
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to Margarita Villa! Located in Jolly Roger Estates on Little Torch Key, where you’ll find some of the best deep water boating in the Lower Keys!Decorated in fine island-style this private home is definitely a 5-star property. Tile floors, open and airy kitchen, living and dining area...

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Featured review

"Nice home, greatl canal good to work !"

Not my first time with action keys, always had good result with everyone at this company! Wish they would rework there utilities policy , it’s hard enough to pay rent for a month.

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$203
avg per night
Key Colony Beach House
Sleeps 10, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Plentiful. Key Colony Beach 4 bedroom with 37 Ft Dock, Pool Club. Sleeps 10 Spacious, 2200 sq ft duplex home on a wide canal with dock in beautiful Key Colony Beach.Includes free use of nearby, ocean-front beach club with a huge, temp-controlled pool and Hot Tub!!Lower Level - 1 bedroom, 1 bathroom...

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$438
avg per night
New
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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$216
avg per night
Cudjoe Key House
Sleeps 8, 3 bedrooms, 2.5 bathrooms
1 review

Key Amenities

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

About this property

Private Beach, ocean front home with pool on Cudjoe Key.Home includes;- Master bedroom suite with 32' flat screen TV, full bathroom including tub and shower for 2, sliders open to private Master Suite deck with ocean view and private beach.- 2 additional bedrooms with Jack-n-Jill bath-...

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Featured review

"Fantastic view"

We really enjoyed the large house. The easy to launch kayak area was very convientant. Location was great - 25 minutes to Key West. The sunsets were breathtaking. House was well equipped with every you...

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$283
avg per night
Summerland Key House
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 100 feet to our back yard...steps away from the house

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

The Key-ver beach house is an oceanfront vacation rental in the world-famous Florida Keys on the southern end of Summerland Key, mile marker 25. The house is an open floor plan with panoramic Atlantic Ocean views and a large wrap-around deck. Two bedrooms (the oceanside bedroom has a king bed and the...

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Featured review

"Excellent Location - Excellent Hosts"

Fantastic location, the view from the sunroom is fantastic. Postcard sunrises to start the day! House was very well equipted with everything we needed during our stay, hosts reached out to check on us...

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$233
avg per night
Big Pine Key House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • 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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$205
avg per night
Islamorada Condo
Sleeps 4, 1 bedroom, 2 bathrooms

Distance to beach: 4 miles to Founders Park

Key Amenities

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

About this property

Bayside is a first floor apartment overlooking the water. Bayside is located on a small resort property nestled in a native hammock on Florida Bay. An easy 90 minute drive from Miami International Airport, this property is located in the heart of Islamorada, directly on Florida Bay. Bayside is fully air...

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$290
avg per night
Key West Apartment
Sleeps 4, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • WiFi

About this property

Historic 2-Bedroom Cigar Maker’s Cottage – A Key West Gem!Step back in time and experience Old Key West charm in this delightful 2-bedroom Cigar Maker's Cottage, built in the 1880s. Nestled at 1008 Whitehead Street, the cottage sits just across from where a bustling cigar factory...

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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.