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Florida Keys Vacation Rentals

(574 rentals)
Islamorada Condo
Sleeps 6, 3 bedrooms, 3 bathrooms
2 reviews

Key Amenities

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

About this property

Sunrise is a spectacular unit within the Maison Matecumbe gated community. Maison Matecumbe is a small 9 unit condo located just off the old road in Islamorada at mile marker 81. Newly done pool and hot tub! 3 bedrooms, 3 baths, sleeps 6, pool, sandy beach.Dockage can be obtainable through Islamorada...

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Featured review

"Beautiful Views"

The home is meticulously clean and spacious. It has all the comforts of home. We cooked several meals and had everything we needed. The views from the balconies are amazing. The complex itself is well maintained....

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$500
avg per night
Big Pine Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Come and enjoy a tropical sanctuary at this beautifully remodeled, fully furnished ground level island home located in Big Pine Key, Fl. Situated on a quiet street, this home features a bright, open interior with 3 bedrooms, 2 bathrooms. The yard is a wonderful oasis overlooking the canal with a hot tub,...

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$225
avg per night
Marathon House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to your perfect tropical getaway! This stunning, completely remodeled half duplex in Key Colony Beach offers a blend of modern luxury and coastal charm. From top to bottom, no detail has been overlooked in creating this immaculate vacation retreat.Relax and unwind in the spacious living areas...

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$393
avg per night
Islamorada Apartment
Sleeps 2, 1 bedroom, 1 bathroom
3 reviews

Distance to beach: 1 miles to Anne's Beach

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Secluded Waterfront Apartment with Tiki hut, dock, King bed, 1 Bath, Sleeps 2.Please contact us for all of our rates for different length of stays! For shorter stays, make sure you have a minimum of 28 days entered in your contact form! We do not use the rate feature or the calendar feature on this...

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Featured review

"Beautiful and peaceful"

Wish we could stay longer. Three months was not enough. Enjoyed the proximity to many Keys activities and restaurants, from Key Largo to Key West.

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$250
avg per night
Marathon House
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Distance to beach: 5 miles to Sombrero Beach

Key Amenities

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

About this property

A fisherman's delight! This perfectly located 2 bedroom house with a large loft is a perfect place to bring your family or friends for a great Keys experience. It has a 40' dock with access just yards away from the Atlantic ocean and the 7 mile bridge. The property has a large swim spa, ice...

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Featured review

"Central Location"

Great location to visit both upper and lower keys. Well stocked kitchen and we enjoyed the large deck and swim spa.

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$250
avg per night

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Little Torch Key House
Sleeps 4, 2 bedrooms, 2 bathrooms
4 reviews

Distance to beach: 9 miles to Bahia Honda

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Enjoy the Florida Keys in this beautiful canal front two bedroom two bath house in a beautiful area on Little Torch Key. The house features a master bedroom with a king size bed, flat screen TV, and the second bedroom also has a king size bed. A well designed and fully equipped kitchen with everything...

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Featured review

"Beautiful Escape"

We enjoyed our stay in this extremely comfortable home. Beds were very comfortable and location was close to lots of restaurants and local attractions. Having a place for our boat was the best. We could...

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$150
avg per night
Marathon House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Adorable home just moments to the ocean. Lovely pool 10 X 20 (goes from 3′ to 5′) Pool heat is $200 add’l if paid in advance, or $250 on arrival plus taxes. 8 X 15 tiki to relax under the shade. 4 Flat screen TVs all w/DVD players. 55″ in L/R, 42″ in master bedroom and both...

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$363
avg per night
Marathon House
Sleeps 12, 5 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Emerald TidesWelcome to Emerald Tides – a brand-new luxury vacation rental in Marathon, Florida, located in the exclusive Emerald Flats community. This oceanfront escape offers breathtaking open water views of the Gulf of Mexico, a private pool, premium dockage, and upscale interiors that reflect...

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$695
avg per night
Key Colony Beach House
Sleeps 5, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • WiFi

About this property

Adorable 2 bedroom, 1.5 bathroom half duplex. Conveniently located at the top of 4th Street in exclusive Key Colony Beach. Nicely updated, fresh and bright! Walk to the Cabana Club and enjoy the complimentary membership with a large swimming pool, bar/restaurant, beautiful sandy beach. Excellent deep...

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$221
avg per night
Key Colony Beach House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Reel Therapy, a beautifully updated three-bedroom, three-bathroom ground-level half duplex located on the tranquil side of 9th Street. The spacious bedrooms include a master suite with a king-size bed, a queen bed in the second bedroom, and two doubles in the third bedroom. Entertainment is...

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$371
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

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

About this property

Elegant Florida Keys direct ocean access and some open water views from the dock and balcony. This property is single family elevated home. All rooms and bathrooms are upstairs. 40 foot dock with 4 cleats. Large driveway, parking for at least 6 cars, trailer and RV. 75' of waterfront with wood dock....

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Featured review

"Relaxing Getaway"

Can’t say enough about Maria and Daniel the owners. They catered to us from first contact. The place was spotless and the home is even nicer than the pictures. It was a short visit for my wife and I,...

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$470
avg per night
Key Colony Beach House
Sleeps 14, 5 bedrooms, 4 bathrooms
2 reviews

Distance to beach: 1 miles to Cabana Club

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Lovely full duplex that sleeps 14! Upstairs there are 3 bedrooms, 2 and a half bath’s with a wide open concept. The half bath is off the living room area. Four flat screen TV’s, hi speed wireless internet, gas grill and a lovely pool (heat is $200/wk optional). Pool is 10 X 20 and 4′...

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Featured review

"Lowe’s stay at 350 E4th Key Colony"

The location is great! The home, yard, and pool are beautiful. We would recommend the place to others.Some minor issues that should be addressed: the outside fish / bait cooler was very dirty and unusable...

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$682
avg per night
Key Colony Beach House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Sailfish PointThis beautiful Key Colony Beach home is the ultimate tropical escape, comfortably sleeping up to 8 guests. Enjoy an amazing private pool, great dockage for your boat, and all the amenities you need for a relaxing stay. With spacious living areas, a fully stocked kitchen, and outdoor...

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$574
avg per night
Key Largo House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to your ideal getaway in Key Colony Beach, FL! This charming 2-bedroom, 2-bathroom half duplex is brand new to the vacation rental market and offers everything you need for a relaxing and unforgettable stay. With deep water dockage, you’ll have easy access to the sparkling waters of the...

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$250
avg per night
Marathon House
Sleeps 6, 3 bedrooms, 3 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Property Overview:Prime Location: Caribbean Sunsets is nestled in a quiet and picturesque neighborhood, offering breathtaking waterfront living with open Gulf views. Enjoy lush tropical surroundings and easy proximity to local attractions, dining, shopping, and Sombrero Beach. *Saturday-to-Saturday...

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$483
avg per night
Key West Cottage
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 800 yards to Ft. Zachary Taylor State Park

Key Amenities

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

About this property

Envision yourself relaxing in a beautiful wood framed conch cottage with overhead fans lazily turning below the sloping tin roof in the heart of Old Town in Key West. This is the best value in Key West as it is no cookie cutter small rental condo but a private town home (one of only seven available for...

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Featured review

"Perfect condo in a perfect location!!"

Our stay for the month was perfect. A Touch of Bermuda has everything a guest could want in a perfect Key West location. However, the best part of our stay was dealing directly with the owner (Jack) throughout...

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$400
avg per night
Cudjoe Key House
Sleeps 6, 2 bedrooms, 3 bathrooms
44 reviews

Distance to beach: 15 miles to Bahia Honda

Key Amenities

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

About this property

This luxurious home overlooking Cudjoe Bay on the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with 11 total homes. This is #107 and I also rent 109 and 111 in case you need more than one. We are 140 feet from the water's edge facing Southwest. Lounge...

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Featured review

"John V"

Susan & Jennifer are great to deal with, this was our 3rd trip to the property, and we can't wait to go back!!

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$445
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

4BR 4.5BA Home w/ Fantastic Outdoor Entertainment Area, Outdoor Bar and Private Heated Pool!Casa Del Mar This stunning vacation rental features 4 spacious bedrooms, each with en-suite baths, including two master suites with king-sized beds and patio access. The open great room boasts a chef's...

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$547
avg per night
Key Largo Mobile home
Sleeps 4, 2 bedrooms, 2 bathrooms
5 reviews

Key Amenities

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

About this property

***SERIOUS INQUIRIES ONLY**** This house can only be rented for a minimum of 28 days, as per city of Key Largo rules.This cozy and spacious home located in the heart of Key Largo has available water access in the backyard. Located centrally in the Cross Kay Waterways neighborhood near shops, restaurants,...

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Featured review

"Belmont Beauty"

Located directly on a canal- right near Adams Cut for Ocean access, Canal opens to Blackwater Sound - offering access to gulf side also. From our seawall we saw manatee, dolphin, tarpon, needle fish, &...

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Marathon House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Updated two bedroom, two bathroom half duplex on 11th street. Excellent location towards the end of the canal yielding instant access to Vaca Cut and the Open Atlantic, 37 ft of deepwater dockage on an extra wide canal is perfect for fisherman and families alike! Enter through the street-side screened...

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$357
avg per night
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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$150
avg per night
New
Cudjoe Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Welcome to Palms & Pina Coladas where you will enjoy a beautifully remodeled waterfront paradise. Located in coveted Cudjoe Gardens, this ground level home comes equipt with everything you need for a relaxing Florida Keys Vacation! Private heated & cooled in-ground pool, fenced yard, 80 ft of...

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$325
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
24 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, pickleball, heated pool, private beach, and dockage for...

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Featured review

"Very Good place"

We stayed in unit 102. Glenn was a great guy to rent from, very helpful and followed up for any questions.a very nice condo, private bathroom for two main bedrooms. Most everything needed for making meals...

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$187
avg per night
Marathon House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Tropical Canalfront Retreat Near Sombrero Beach – 2 Bed / 2 BathEscape to paradise at this beautifully appointed 2-bedroom, 2-bathroom vacation home located in the heart of Marathon, Florida. Nestled on a deep, wide canal, this waterfront getaway offers the perfect blend of comfort, convenience,...

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$307
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • WiFi

About this property

Mile Marker 74 – Bayfront – Beachfront – Handicap Assessable – Dockage for 30′ boatThis amazing beachfront home is a must see! Located on one of the few white sand beaches in the Florida Keys, Gulfview is a private home located on Lower Matecumbe Key in Islamorada in...

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$433
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
Cudjoe Key House
Sleeps 6, 2 bedrooms, 3 bathrooms
50 reviews

Distance to beach: 15 miles to Bahia Honda

Key Amenities

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

About this property

This luxurious home overlooking Cudjoe Bay on the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with 11 total homes. This is #111 and I also rent 109 and 107 in case you need more than one. We are 40 feet from the water's edge facing Southwest. Lounge...

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Featured review

"Nice Condo"

Well kept clean condo and good host. The host has a nice binder with information and local things to do with mile markers. I would have liked to have the list emailed to me before we came to plan more...

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$514
avg per night
Islamorada House
Sleeps 12, 6 bedrooms, 4 bathrooms

Key Amenities

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

About this property

Mile Marker 77 – Oceanfront – Lower Matecumbe Key.Six bedroom/ four bath luxurious oceanfront premier rental estate on Lower Matecumbe Key in Islamorada. Enjoy a walk around the lush, native garden or take a dip in the oceanfront pool. Catch palm tree shade or sun on the private beach,...

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$573
avg per night
Key Colony Beach House
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Lovely and spacious 3 bedroom, 2.5 bath half duplex on Key Colony Beach. Very spacious townhouse style on the shady side of 9th St. All tile floors downstairs, with an open concept, large well equipped kitchen with a nice size bar that seats 5, along with a separate dining table. There is an adjacent...

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Featured review

"Wonderful"

We have been staying in Key Colony for many vacations. Each time we have stayed in a different house, reason being that I usually wait too long to make reservations. This house definitely was by far the...

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$251
avg per night
Last Minute Deal
Marathon House
Sleeps 10, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

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

About this property

Stay right on Bonefish Bay in this spacious 4BR / 3BA waterfront home with two master suites. Bring your boat and enjoy a 70-ft dock (40 ft available for use) with quick ocean access just 1 mile away. Relax in the private heated pool, fish from the dock, and enjoy peaceful waterfront views. Perfect for...

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Featured review

"Ma920"

Great place!! Loved it . Parking is tight, They do have trailer storage offsite. Jessica was easy to work with and highly recommend contacting her!!!

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$399
avg per night
Cudjoe Key House
Sleeps 4, 2 bedrooms, 2 bathrooms
4 reviews

Key Amenities

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

About this property

House - 2 Bedrooms, 2 Bathrooms, Sleeps 4. Come enjoy our hidden retreat in upscale Cudjoe Gardens. This home is conveniently located only blocks away from Cudjoe Gardens Marina. This single level home is situated on a crystal clear flow through deep water canal. The home features an in ground private...

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Featured review

"Perfect Keys Home"

We absolutely loved this home! We've been traveling to the Keys for 15 years and this is one of our favorites. A quiet neighborhood which is fantastic. Fred is excellent with communication.

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$217
avg per night
Cudjoe Key House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

You will be absolutely delighted to vacation at this remarkable luxury vacation home on Summerland Key. This multimillion dollar home has only the best to offer. The kitchen is a chef‘s dream with top of the line stainless appliances, cook top, built in ovens and gorgeous stone countertops.The...

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$417
avg per night
Big Pine Key House
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 10 miles to Bahia Honda

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Our spacious custom built 2 bedroom and 2 bathroom newly renovated home awaits you. Located in the heart of the National Key Deer Wildlife Refuge. On the water with direct access to the Gulf of Mexico or to the Atlantic Ocean. Concrete Seawall with step down easy boat and kayak access. Fish Cleaning...

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$167
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 4 bathrooms

Key Amenities

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

About this property

The Sea Glass House~LUXURY Oceanfront Estate~Pool Dock Views Jacuzzi Game Room FirePit Office More!The Sea Glass House is a Luxury Exclusive Oceanfront Treasure with more than 100’ of dock and stunning ocean views from virtually every room. Located perfectly in the Middle Keys with direct access...

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$2,350
avg per night
Key West House
Sleeps 8, 4 bedrooms, 2.5 bathrooms
3 reviews

Distance to beach: 600 yards to Simonton Street Beach

Key Amenities

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

About this property

Enjoy an unforgettable stay at a one-of-a-kind ship-builder's home in the heart of Old Town Key West. You will be on a quiet lane in the most desirable neighborhood, just a few short blocks from dining, boating, fishing, galleries, theatre and entertainment. Unique features include open air kitchen...

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Featured review

"Excellent experience"

Management was informative and responsive. The home was perfect for our needs. Everything was pristine and well cared for. I would give this rental and the management the highest recommendation.

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$243
avg per night
Marathon House
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Key Lime Sunrise Watch the sunrise & feel the tropical breezes while sipping your coffee from the comfort of the upstairs screened terrace of this lovely and neatly maintained two bedroom two & a half bath home situated on Sombrero Beach Road. This charming getaway is within walking/biking distance...

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Featured review

"We had a very nice visit."

171 10th St. The duplex was very neat. We loved the screened in back porch (had to keep the fans going because of the heat). The pool chairs lacked comfort but we had seen that in the pictures and brought...

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$299
avg per night
Key Colony Beach House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

No detail spared in this completely renovated, top of the line stilted half duplex on 9th Street in highly sought after Key Colony Beach. Excellent end of the canal location makes for instant access to Vaca Cut! Head to the open waters of the Gulf or Atlantic! Open concept living and kitchen area overlooking...

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$293
avg per night
Big Pine Key House
Sleeps 5, 2 bedrooms, 1 bathroom
3 reviews

Key Amenities

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

About this property

Stay where the palm trees meet the ocean. The Egret House is a quaint and charming home nestled in the lower Florida Keys. This spectacular home is in the perfect location in the highly desirable side of the island. Cozy 2 bed, 1 bath property with open water access, heated and cooled saltwater pool,...

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Featured review

"Wow, just Wow"

We stayed from middle of June to middle of July this year and can tell you, you will not find a more relaxing vacation spot that this one. Scott was incredible from the first day we connected until we...

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$433
avg per night
Plantation Key House
Sleeps 10, 4 bedrooms, 4 bathrooms
1 review

Key Amenities

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

About this property

Sanctuary in Paradise Unique property featuring: ~1BR 1BA main house ~2BR 2BA downstairs apt. ~1BR CottageWhether your ideal vacation is relaxing in a hammock in view of the ocean with a good book or hosting parties late into the night, Sanctuary in Paradise can accommodate you. We have a quiet...

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Featured review

"It was a wonderful Florida keys vacation"

Andy was a wonderful host and his property was gorgeous. My family, including kids and grandkids took full advantage of the water access and all of the fun amenities. There was plenty of room for our two...

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$900
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 4.5 bathrooms
1 review

Distance to beach: 3 miles to Sombrero Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

4BR 4.5BA Home w/ Fantastic Outdoor Entertainment Area w/ Full Kitchen, Yard Games, Bikes, Kayaks, Paddleboards!Casa PlayaWelcome to Casa Playa, a luxurious 4-bedroom, 4.5-bathroom home in Marathon, Florida. Nestled behind gates in a 4-home enclave, this custom-designed retreat offers an element...

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Featured review

"Great week in marathon"

We had an amazing stay at this property from the moment we arrived, we were impressed with how immaculately clean and upscale the house was. The decor was beautiful, and everything felt fresh and well-maintained.The...

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$747
avg per night
Marathon House
Sleeps 8, 4 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Paradise Palms! This stunning 4-BR retreat has it all. Boating right from your private dock, easy open-water access, waterfront views, unwinding in your private heated pool Fire up the grill for a sunset BBQ, challenge friends to cornhole or game room fun, and set off on a kayak adventure...

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Featured review

"Great time"

We have a great vacation, the house fit our needs perfectly. There recommended places to visit and eat at were great. Had a small issue with the dryer, we called them and they responded quickly.

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$397
avg per night
Islamorada House
Sleeps 8, 4 bedrooms, 2.5 bathrooms

Key Amenities

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

About this property

Mile Marker 75 – BaysideLarge, modern 4 bedroom canal front home with pool in Lower Matecumbe Key in Islamorada, Florida Keys. This gorgeous home overlooks the pool and canal.The main selling point of Latitudes is the home’s awesome outdoor area. Pool, Tiki Hut, grill and outdoor seating...

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$800
avg per night
Marathon Apartment
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Escape to paradise at this stunning 3-bedroom, 3-bathroom single-family home in Key Colony Beach! Nestled in a prime location, this spacious home offers everything you need for a relaxing and unforgettable getaway. Whether you're a boating enthusiast, a pool lover, or just looking to unwind in the...

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$457
avg per night
Key Colony Beach House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Escape to tranquility in this charming two-bedroom, two-bath half duplex located on the shaded side of 9th St. Newly installed, the sparkling 9 X 16 pool offers a relaxing oasis with therapy jets in the seating area. Indulge in comfort with a king-size bed in the master bedroom, while the guest bedroom...

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$274
avg per night
Duck Key Cottage
Sleeps 2, 1 bedroom, 1 bathroom
18 reviews

Distance to beach: 9 miles to Coco Plum Beach

Key Amenities

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

About this property

Our vacation rental is an historic 1 BR/1 BTH waterfront cottage in prestigious Duck Key in the Florida Keys. There are plenty of outdoor amenities on the more than 1/4 acre property. These include a 15 X 34 foot saltwater swimming pool, hot tub, and grill with prep and dining area. The backyard perimeter...

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Featured review

"Perfect lil get away!!"

We loved our stay here—it was absolutely perfect. The place was spotless, with ice-cold A/C and a very private setting. It features its own pool and hot tub, plus the best part: a boat dock on a deep-water...

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$157
avg per night
Marathon Townhome
Sleeps 6, 2 bedrooms, 2.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Quiet, secluded townhouse that has amazing views of the tropical surroundings. The unit has two levels, so that no one is living above or below you. The two spacious wrap around decks reveal the Canal feeding in from the Gulf of Mexico and the heated swimming pool. There is a large 10 slip Gulfpointe...

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Featured review

"Marathon vaca"

Great place to stay . Good location. Very nosey tenant's made the stay a little uncomfortable at times.

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$287
avg per night
Marathon Bungalow
Sleeps 8, 3 bedrooms, 3 bathrooms
1 review

Distance to beach: 3 miles to Sombrero Beach

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Start planning your perfect escape to the Florida Keys! Blue Ocean Bungalow is ideally located on a wide, deep-water canal with easy access to world-class fishing in the Atlantic and the Gulf. Enjoy all the amenities needed for a perfect island vacation: airy open living areas with canal views, cozy sunroom...

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Featured review

"Wonderful keys retreat!"

Thank you . We had a great time..we fished, snorkeled and spent a wonderful time with family and friends.. we all highly recommend!!

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$305
avg per night
Marathon House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Villa FranchellaEscape to paradise and experience the epitome of luxury living in this new breathtaking 4-bedroom, 3-bathroom waterfront home in Marathon, FL. Located just minutes from the Gulf of Mexico with easy access from the 45' of available dockage, this newly renovated sanctuary offers...

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$634
avg per night
Key West House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

This estate has it all waterfront, large sun-filled pool and seawall dockage for your boat with over 3,800 sf of living space and 13,600 square feet of lush landscaped grounds. This private residence gives you the space and comfort one needs to relax and entertain your guests. The home was recently rented...

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Featured review

"Historic Downtown Vacation Stay"

Perfect spot to vacation!! Family friendly. This adorable house is downtown and close to everything!! I loved the yard and the porch was a favorite. Can't wait to return!

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$372
avg per night
Summerland Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

This vacation rental home “Reel Sunshine” is appropriately named! A bright and airy, canal front home in the highly desired Summerland Cove neighborhood, is waiting for your family to settle in and enjoy your Florida Keys vacation.This three bedroom, two and a half bath is located on a...

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$283
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.