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Florida Keys Vacation Rentals

(576 rentals)
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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$377
avg per night
Tavernier Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
11 reviews

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

Welcome to your remodeled 2 - bedroom, 2 - bathroom vacation rental that has everything you need! The Master bedroom features a comfortable king size bed with a private bathroom that has a walk-in shower. The second bedroom has 2 twin beds and a connecting bathroom. The kitchen boasts beautiful granite...

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Featured review

"2 week vacay"

Our trip was wonderful! The condo was clean and nicely decorated. We had plenty of room and the view was priceless!

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$245
avg per night
New
Key Largo House
Sleeps 10, 0 bedrooms, 3 bathrooms

Key Amenities

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

About this property

Welcome to your private slice of paradise in Key Largo. Nestled in a quiet, well-protected canal-front neighborhood, this beautiful four-bedroom home offers the perfect escape for those seeking comfort, space, and the laid-back charm of the Florida Keys. Designed to accommodate up to 10 guests, the home...

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$400
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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$198
avg per night
Key West House
Sleeps 8, 4 bedrooms, 2 bathrooms
1 review

Key Amenities

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

About this property

Dos Casas can be the answer to your fabulous Old Town Key West vacation. We've been renting to discerning travelers for over 15 years. Our guests come back over and over, finding the comfortable spaces, stocked with amenities and ideal location the perfect spot to enjoy all that Key West has to offer.Dos...

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Featured review

"Dos Casas"

Beautiful sanctuary centrally located in Old Town. Very comfortable accommodations in a well maintained property. Property manager and Owner were very responsive to any questions or concerns that arose....

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$653
avg per night

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Marathon House
Sleeps 12, 5 bedrooms, 4 bathrooms
13 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Blue Turtle Villa at The Tides of Vaca Cut (Unit #4), is a brand new 5 bedroom 4 bath home with a private pool, boat slip, all the toys for the perfect vacation ~ paddle boards, kayak, giant Jenga, giant connect four, ping pong and more! Perfectly situated on the water with stunning views, sunrise and...

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Featured review

"Beautiful vacation rental"

The home is absolutely beautiful and in a great location, beautiful views and has all the amenities needed for a great family vacation!

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$798
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

Gulf side Gem, 45 ft. Dock, pool , hot tub and moreSpacious 3 Bedrooms and 3 Baths 1,600 sq ft home overlooking a canal with a brand new dock that spans the width of the property complete with a fish cleaning station and private pool and brand new hot tub. The Open Concept Living and Kitchen Area...

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$395
avg per night
Last Minute Deal
Islamorada Townhome
Sleeps 8, 3 bedrooms, 3 bathrooms
2 reviews

Key Amenities

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

About this property

Front-Row Ocean Views – A Location That Cannot Be ReplicatedWelcome to Paradise Palms—the crown jewel of the exclusive Peaceful Palms gated community. Perfectly positioned just steps from the water, this newly built three-story home offers sweeping panoramic views and a rare third-floor...

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Featured review

"Best stay in the Keys and we have stayed at all of them. Lux!"

Best stay we’ve ever had in the Keys and we booked super last minute. We always choose Islamorada, but this place blew every other stay out of the water. The third-story balcony was insane—hello ocean...

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$706
avg per night
New
Islamorada House
Sleeps 6, 3 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Tucked away on a quiet street in Lower Matecumbe, this beautifully furnished canalfront home is everything you imagine when you think of a laid-back Keys escape. Surrounded by lush, tropical landscaping and offering total privacy, this 3-bedroom, 3.5-bath getaway has all the extras—100 feet of dockage,...

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$550
avg per night
Duck Key House
Sleeps 6, 3 bedrooms, 3.5 bathrooms

Key Amenities

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

About this property

This charming family-friendly residence in Duck Key presents a spacious and inviting environment, featuring three comfortably appointed bedrooms and three modern bathrooms, making it an ideal choice for a memorable getaway. Each bedroom is thoughtfully furnished with a plush king-sized bed, ensuring restful...

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$809
avg per night
Marathon House
Sleeps 6, 2 bedrooms, 3 bathrooms
15 reviews

Distance to beach: 1 miles to Sombrerro Beach

Key Amenities

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

About this property

Lemon Key CottageWelcome home…Thanks to Hurricane Irma, we now have a beautiful newly renovated home! We've spent over $150K on a complete restoration and modernization. (check out the new pics) Lemon Key Cottage is absolutely stunning with new: bathrooms, kitchen, appliances, flooring,...

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Featured review

"Outstanding!"

Beautifully decorated, quiet, comfortable setting. Kitchen is well supplied and equipped. Large fridge, the whole house looks new. Pool and grounds are spotlessly maintained. Lots of fish around the dock...

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$383
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
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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$155
avg per night
Key West House
Sleeps 4, 2 bedrooms, 1 bathroom
3 reviews

Key Amenities

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

About this property

The Sea View Cottage is a 2 bedroom, 1 bath home built within feet of the Atlantic Ocean with 180 degree ocean views.The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge.Fishing and diving just steps outside your door. Then at night, Key West is...

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Featured review

"The Perfect Relaxing week!!"

My family booked Seaview Estates for our 25th Anniversary trip! We rented both houses so we had the property to ourselves. Upon arrival, Carol met us at the gate and began our tour of the property. The...

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$397
avg per night
Islamorada House
Sleeps 8, 4 bedrooms, 3 bathrooms

Distance to beach: 3 miles to Founders Park

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Blue Palm Oasis!Escape to paradise at Blue Palm Oasis, a charming 4-bedroom, 3-bath home located on Plantation Key in Islamorada. This contemporary Keys villa seamlessly blends modern comfort with laid-back island charm, making it the perfect place to unwind, recharge, and soak up the sun....

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$537
avg per night
Islamorada House
Sleeps 8, 3 bedrooms, 4 bathrooms
2 reviews

Distance to beach: 0.5 miles to ANNE'S BEACH

Key Amenities

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

About this property

Located in the desirable Islamorada which is know as the “Sportfishing Capital of the World” and where you will find the most beautiful crystal clear waters. The house is just minutes from Channel 5 and Channel 2 which give you quick access to the best ocean and backcountry fishing. You are...

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Featured review

"Perfect vacation home"

You could not ask for a more beautiful and clean vacation home. Everything seems really new and well kept. The moment you walk through the home you see the balcony with the beautiful view of the water....

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$425
avg per night
Key Colony Beach Villa
Sleeps 10, 5 bedrooms, 4 bathrooms
2 reviews

Distance to beach: 1 miles to In the Key Colony Beach walking distance

Key Amenities

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

About this property

Hey there, fishing enthusiasts and families!Looking for the perfect Florida Keys getaway? Look no further! My beautiful waterfront home in Key Colony Beach is your dream vacation spot.Imagine this: You wake up to stunning sunrises over the open water, have coffee on the wrap-around porch, and...

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Featured review

"Group Vacation"

Stayed with a group of friends from around the country. The house was very clean and well provisioned Kitchen, bedrooms, bathrooms, outdoor cooking area. Met the host and hostess, who were very pleasant....

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$1,315
avg per night
Marathon House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Privacy galore at this great location on Sombrero Beach Rd with a brand new POOL! Famous Sombrero Beach is approximately half mile down the dedicated bike path from this stilted 3 bedroom single family pool home with dockage! Open concept living with expansive decks on both floors that boast open water...

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$386
avg per night
Islamorada House
Sleeps 10, 3 bedrooms, 2 bathrooms
17 reviews

Key Amenities

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

About this property

''BEAUTIFUL BAYFRONT PROPERTY!!!!''** 2022 Remolded bathrooms, 2021 NEW POOL** Fully furnished, 1 story offering 3bd/2ba. The house can sleep up to 8. There is a 1/1 guest suite attached which does have its own separate and private access with full kitchen and bath. Entire house...

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Featured review

"Would give it 1,00,000 Stars if I could!"

My stay at our little piece of paradise was nothing short of AMAZING. This homey, cozy stay is the best possible place to come back to and spend time with family and friends after long sunny days spent...

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$480
avg per night
Summerland Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Bitter End Vacation Rental –This Summerland Key beauty is the one you have been looking for. Located on Summerland Key with superb boating and access to deep water. Just the perfect spot to see sunset views and peaceful water vistas. Feel free to bring your pet along too!!The interior is...

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$290
avg per night
Islamorada House
Sleeps 10, 5 bedrooms, 5 bathrooms

Key Amenities

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

About this property

One of the only white sandy beaches in the Fl Keys and 1 mile whole of it!Newly built,state of the art,beautifully done 5 bedroom home, 4 master suites w/ king beds and facing open water! Magnificent indoors and out! Each bathroom is exquisite,very large stone,glass and hand picked tiles. The...

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$785
avg per night
Summerland Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This home is the ideal getaway for the whole family! The interior of the home is super spacious with an updated kitchen that looks out over the canal and large pool.There are three bedrooms, two bathrooms, and a large family area with a big screen television for your entertainment. Not to be outdone,...

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Featured review

"Outstanding location for fishing, boating, & diving!"

Stayed at this gem before and after Lobster mini season. The pool was perfectly refreshing after a day in the sun on the water. There are several free boat ramps nearby. Great proximity to the Looe key...

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$289
avg per night
Big Pine Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 5 miles to Bahia Honda State Park

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to your very own “Island Escape”! This beautiful home is located in one of Big Pine Key’s most favorable boating neighborhoods with quick ocean or gulf access for most any size boat. It’s only a few lots in from open water! The large 75’ concrete dock offers plenty...

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$258
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 100 yards to Port Antigua Private Beach

Key Amenities

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

About this property

This spectacular 3/Bed 2/Bath canal front home is located in Lower Matecumbe Key, a part of Islamorada island. Enjoy the exclusive neighborhood of Port Antigua—just a 5 minute walk to our private beach.The house is nautically designed, with a spacious and open floor plan. There's a large...

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$301
avg per night
Marathon Condo
Sleeps 4, 1 bedroom, 1.5 bathrooms
4 reviews

Key Amenities

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

About this property

Newly Built,1 Bedroom 1 Bathroom unit, Marina, Largest Olympic Pool in the Keys overlooks the Atlantic Ocean, Fun and Sun. Great amenities, close to everything.Outdoor bar b q grills, great Sunsets from the Pool, Tikis and Docks.

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Featured review

"Great stay"

Thank you so much for an amazing stay. We couldn’t have asked for a better rental. The rental had so many amenities that other places have not. Will definitely stay here again.

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$209
avg per night
Key Largo House
Sleeps 6, 3 bedrooms, 2 bathrooms
11 reviews

Key Amenities

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

About this property

Play all day in Key Largo! If you like fishing, snorkeling, diving, kayaking, paddle boarding, wakeboarding, and nature, you can do it all here at Easy Livin’! Bayfront home on open water with dock and private ramp. Love fishing? House is close to Flats, Backcountry, Reefs and Offshore. Dock your...

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Featured review

"A special place!"

This is our 5th year spending a winter month in Key Largo... our first at Easy Livin. We are very pleased to have found it. It's tucked away from the route 1 traffic, but easy access to everything we need/want....

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$325
avg per night
Key West Townhome
Sleeps 7, 3 bedrooms, 3 bathrooms
2 reviews

Key Amenities

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

About this property

Relax with family and friends in your own tropical paradise at this spacious townhome in Key West's beautifully landscaped & maintained Golf Club. Located in a private gated community with resort style amenities, it is just minutes away from the beaches, world class restaurants, water sports...

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Featured review

"our vacation at Key West Golf Club"

We had wonderful time enjoying the beautiful weather and the beauty of all the attractions at Key West. Our condo was all we needed to fulfill our stay. It was clean and we enjoyed being right on the golf...

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$207
avg per night
Islamorada House
Sleeps 10, 3 bedrooms, 3 bathrooms
5 reviews

Distance to beach: 0.3 miles to Anne's Beach

Key Amenities

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

About this property

Enjoy this modern and recently updated lagoon front 3 bed/3 bath single-family home on the Gulf side of Islamorada at MM 73.5, minutes from the Channel 2 and Channel 5 Bridges, offering immediate access to the oceanside of Lower Matecumbe Key. Dockage is available for up to a 35' boat, or use the...

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Featured review

"On a scale of 1-10 this property is a 12 overall !"

We have rented this property for 3 years and have been extremely pleased with all aspects from great hosts, nicely appointed house, heated pool, canal/dock access , easy out to ocean or bay, plenty of...

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$360
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

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

About this property

Beautiful views from this condo!Bay Harbour is a gated community located at MM 77.5 bayside in Islamorada, FL.We are new owners of this condo that has never been in the rental pool. (that is why few reviews)Complete remodel with no expense spared!The location is quiet with the most beautiful...

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$646
avg per night
Ramrod Key House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Come enjoy this newly listed property on Beautiful Ramord Key house with a southern view of Newfound Harbor and the Atlantic !! House has a 60 ft+ dock for your water toys. Enjoy lobster season, fishing (back water and deep sea great snorkeling and dining all minutes away. Ramrod is easy boating...

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$267
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms

Distance to beach: 4 miles to Sombrero Beach

Key Amenities

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

About this property

Welcome to The Butterfly Cottage – Where Nature's Magic Meets Keys ComfortEscape to a truly unique Florida Keys experience at our certified Monarch Butterfly Garden sanctuary! This charming traditional conch cottage offers families a peaceful retreat where butterflies dance through native...

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$199
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

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

About this property

Come have your first sunset drinks compliments on us at Island Fish Company. $100 Gift Certificate to Island Fish Company Included. No Expense Spared! New Construction Bayfront Home With Private Dock and Pool.5 O'Clock Somewhere Bay House is a piece of paradise on the Vaca Cut waterway in Marathon....

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Featured review

"Fabulous vacation rental for our family celebration with all the amenities and comforts of home plus a fabulous view!"

This vacation getaway home had everything we needed plus Lauri was an extremely responsive host. The location was excellent. We could walk to the Aquarium that was across the canal or drive ten minutes...

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$727
avg per night
Tavernier House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Swim. Sleep. Repeat., at Manatee Manor. This 3-bedroom, 2.5-bath home on Plantation Key has something for everyone. Enjoy a drink by the tiki bar, rack ‘em up at the billiard table, or soak up some vitamin D next to the pool. With an entrance just off the carport, the downstairs offers a comfortable...

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$276
avg per night
Key Largo House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to your dream coastal escape! A peaceful and beautifully well maintained home where comfort meets adventure. Beautiful 3-story canal-front home, just 3 houses from the ocean. Boaters Dream!! Including an entertainment room, ideal for an executive office or a private guest retreat with sofa bed....

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$325
avg per night
Islamorada House
Sleeps 10, 5 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Paradise Palms!Located on a cul-de-sac in the charming city of Islamorada, this beautifully- appointed five-bedroom, four and a half-bath home serves as an excellent setting for your tropical getaway. Ideally located in Islamorada on Lower Matecumbe Key, you will have convenient access...

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$576
avg per night
Islamorada Townhome
Sleeps 6, 2 bedrooms, 2.5 bathrooms
2 reviews

Key Amenities

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

About this property

Lazy Daze Beach House is a piece of paradise literally on the Beach! Gorgeous and all new! One King plus set of Full/Twin bunk beds, spacious gourmet kitchen with glass atrium dining. Completely renovated, designer finished, all new gorgeous home, no expense spared! Private oceanfront townhouse located...

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Featured review

"Lazy Daz Beac House"

Excellent couple to work with. Great communication. The rental was beautiful and clean. We had a problem with the rental and they communicated with us and together we solved the problem. They went over...

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$354
avg per night
New
Plantation Key House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Property #27839 - silverEscape to your own Keys hideaway with cozy island‑inspired home, coastal décor and a bright open living/kitchen area that flows onto a huge screened terrace. Relax in your own private pool, tiki hut-gazebo, shaded lounge areas and serene canal views, perfect for lazy mornings,...

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$400
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

Ocean-View | Family-Friendly | Resort Amenities | Tavernier / Upper KeysProperty Overview Welcome to Coastal Ways Suite at Ocean Pointe, a beautifully appointed 900 sq ft, 2-bedroom ocean-view condo in the Upper Florida Keys. Nestled between Key Largo and Islamorada, this resort-style retreat offers...

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Featured review

"Loved ocean Point unit 3210"

Unit was nicely updated and exactly as advertised. The unit was nicely appointed including the kitchen. Close to pool and tennis courts. Loved the beach! We will be back!

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$249
avg per night
Key Largo Estate
Sleeps 16, 6 bedrooms, 6 bathrooms

Distance to beach: 6 miles to Pennekamp

Key Amenities

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

About this property

Recently renovated large 6 bedroom, 7 bathroom Ocean Front House on 5 Acres. Gated from the main road. It can comfortably sleep up to 16 people. Covered parking for up to 6 vehicles and outside parking for several more. This estate is surrounded on 3 sides by park lands and the Atlantic ocean. If...

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$824
avg per night
Islamorada Apartment
Sleeps 4, 2 bedrooms, 1.5 bathrooms
1 review

Key Amenities

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

About this property

Gorgeous 2 bedroom 1 & half condo, two story (townhouse style) HEATED POOL, DOCK FOR FISHING, OCEAN FRONT location. Gated community makes it a perfect getaway for a family for 4 but sleeps 6 to accommodate any short term visitors. Inside our home, you will find all the amenities for an enjoyable stay,...

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Featured review

"Totally Remodeled Oceanside Condo with Great Amenities"

The location of this Complex was perfect for our stay this last January. We were able to visit Founder's Park (Half mile walk) almost daily, for pickleball, volleyball, long walks/running on the exercise...

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$100
avg per night
Key Colony Beach Condo
Sleeps 6, 2 bedrooms, 2.5 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Private pool
  • WiFi

About this property

We are a 50 unit Oceanfront Condominium located on our own private beach, with a heated pool in our center courtyard, protected from the North wind. We have a huge tiki hut on our private beach and plenty of lounge chairs and palm trees for shade. We also have a huge deck on our beach for great sunsets,...

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Featured review

"Absolutely Perfect!"

Cay Condominiums had everything we could possibly want. The beach was beautiful with a great view and plenty of chairs. The pool and the grounds were extremely well cared for. We are already planning a...

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

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Just a few houses off Duval, this wonderful retreat occupies the ground level of an almost 100-year-old home in one of the most desired locations in Old Town Key West. A large covered front porch welcomes you to sit and watch the Key West world go by, imagining what life was like in the early days of...

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$237
avg per night
Key West House
Sleeps 10, 4 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Island Dreaming – Your Luxury Key West Getaway Welcome to Paradise*** Please note for 2027 High Season rentals Jan- February - Arrival after the 5th of January for 6 week minimum is required in order to get accurate pricing***Discover the ultimate island retreat at Island Dreaming, a spectacular...

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$567
avg per night
Key Largo Villa
Sleeps 6, 3 bedrooms, 3 bathrooms
8 reviews

Distance to beach: 0.0 miles to 4 small beaches on site

Key Amenities

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

About this property

3 bedroom, 3 bathroom Ocean Front / Beach Front Villa in Key Largo sleeps up to 6. It was completely renovated in 2020. It has dockage for boats up to 38 feet. This Villa is 35 feet from the Ocean and has a private beach 5 feet from the patio. I provide a Golf Cart, Kayaks, PaddleBoards, Fishing equipment,...

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Featured review

"Spring Break"

This was my first trip since the passing of my husband 5 years ago. It couldn’t have been better. Sun, beach, and good food. The Villa was perfect for me, my son and his fiancé, and three grandchildren...

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$482
avg per night
Tavernier Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

You'll find coastal comfort in our oceanfront condo at Ocean Pointe Suites in Key Largo, located directly on the Atlantic. Situated on 60 lush acres, Ocean Pointe offers a newly renovated pool and jacuzzi, private lagoon beach, outdoor grills, marina, boat ramp, pier, tennis, nature trails, swings...

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$241
avg per night
Tavernier Apartment
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

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

About this property

Simply relax in this One bedroom One bathroom Oceanfront Condo at Ocean Pointe Suites in Tavernier.The comforting living room features a FLAT SCREEN TV, comfy pull out QUEEN SLEEPER SOFA and sliding glass doors that open to the step-out lanai offering sweeping views of the Atlantic.Visit delicious...

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$250
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
13 reviews

Distance to beach: 4 miles to Anne's Beach

Key Amenities

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

About this property

Enjoy the sunrise from the balcony or from in the condo through 50 ft of glass sliding doors. You can also see the sunset from our walkway on bayside. We have a full kitchen from dishwasher to microwave, washer/dryer, even beach towels. We have wifi, cable TV, and a Master Bath with whirlpool tub,...

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Featured review

"Excellent location, wonderful ocean view with full sunrises, clean and well-equipped condo with large balcony."

Condo was well equipped and tastefully decorated in an appropriate style. Direct ocean views from a 50' balcony overlooking docked boots with the occasional manatee swimming by was exceptional. Location...

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$330
avg per night
Tavernier Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

In the heart of Tavernier lies this beautiful 2-bedroom condo that combines the Florida Keys' breathtaking scenery and lively atmosphere. Nestled just a short 19-minute drive from the renowned John Pennekamp Coral Reef State Park, this property offers the perfect base for your tropical getaway.As...

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$244
avg per night
Key West House
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 0.4 miles to Higgs Beach

Key Amenities

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

About this property

Tiki Tango - Your Key West Oasis in the Coveted Casa Marina District!Welcome to Tiki Tango, a grand 2-bedroom, 2-bathroom home that blends island ambiance with modern luxury. Located in the coveted Casa Marina District of Key West, this vacation rental promises a memorable stay with its private pool,...

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$252
avg per night
Marathon Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
11 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

2 bedrooms, 2 bathrooms ideal getaway in Coco Plum Beach, the Florida Keys. Great value and our reviews are excellent! Small Pets OK for downstairs unit.We have two units in the same building.Amazing amenities, that include waterfront swimming pool, boat dockage included for boat up to 40’,...

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Featured review

"Fishing Vacation"

Beautiful condo, great amenities with pool, boat dockage, launch, and trailer parking! Condo is spacious, great decorations, and very comfortable. Everything you need for a wonderful 5 week vacation....

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$237
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.