Florida Keys Vacation Rentals

(273 rentals)
Sand in your toes

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.1 miles to Coco Plum

$243

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool

About this property

Walk the Beach! Beautiful 2 bedroom, 2 bath Ocean front condo at Coco Plum Beach Villas, nicely decorated and furnished. Leather recliners in the main living area overlooking the Atlantic Ocean. King in master, 2 twins in 2nd. Pull Out couch in living room. Deck, master bedroom and the livingroom overlook ...

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Property Type

Marathon Condo

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Beacon Reef #522 - Oceanfront 5th floor (top floor) condo at Beacon Reef.

$147

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days NEW ON THE RENTAL MARKET. PHOTO UPDATES COMING SOON. "Beacon Reef 522" offers magnificent 180 degree oceanfront views. Enjoy the sea breezes as your relax on your private balcony and gaze at the water. Whether staying one month or more you will be more than happy ...

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Property Type

Islamorada Condo

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Key West Beach Front Rental! Beach Studio Ocean views

Studio | 1 BA | Sleeps 3 | Quick View

Distance to beach: 22 yards to Public use + Private views Waldorf Astoria Resort

$289

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront
  • Rentals by Owner

About this property

NEWS FLASH! Please Attention!!!!! Art studio is smaller phone for inquiry,, Key West and the Keys HAVE NO RED TIDE OR ALGAE! We are 110% free from this impact from nature…Need proof? Call Chamber Of Commerce Key West. Get yourself dates before flights! Happy to hold for you a short ...

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Property Type

Key West Studio

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Islamorada water front with free boat tie-up. Available weekly, Saturday to Sat

1 BR | 2 BA | Sleeps 4 | Quick View

8

Distance to beach: 5 miles to Anne's Beach

$185

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Rentals by Owner

About this property

The Osprey Nest (MM 82.3) is a private condo residence which is wonderfully maintained. It is the total upper floor of the building in the foreground. It is operated under FL DBPR license # MOT 5403060 and is inspected annually. This Non-Smoking home is professionally cleaned prior to your arrival. ...

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Property Type

Islamorada Condo

"Mark and Dolly"
Reviewed July 15, 2018

Absolutely fantastic place to stay, we will definitely be back

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Kens Cozy Conch Key Cottage-2Br/2Bth Getaway + Optional motor boat rental

2 BR | 2 BA | Sleeps 5 | Quick View

1

Distance to beach: 4 miles to Long Key or Curry Hammock

$250

per night

View Details

Key Amenities

  • Air Conditioning

About this property

We are a small romantic cottage on a tropical island named Conch Key. A quaint Old Florida Keys style lobster fishing village located about 10 miles from Marathon and close to various state parks and beaches.Sorry but we are a NO SMOKING , NO PET, NO PARTY HOUSE OR LARGE GATHERING RENTAL.Centrally ...

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Property Type

Marathon Cottage

"Relaxation vacation"
Reviewed January 27, 2019

Our first visit to the keys was stress free with this cottage rental. From first inquiry to end of vacation, Ken made this so easy. The cottage had everything we needed. After a day of exploring it was ...

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Seaglass-20 feet from the Gulf

2 BR | 2.5 BA | Sleeps 6 | Quick View

$185

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront
  • Pool
  • Rentals by Owner

About this property

Seaglass-Paradise on the Gulf is located in the heart of the the beautiful Florida Keys. The Keys are a series of 40 islands connected by 40 bridges , off the southern most tip of Florida. The chain of islands extends 120 miles into the Atlantic Ocean and Gulf of Mexico. The area is famous for its Caribbean ...

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Property Type

Marathon Condo

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Casa Lorelane

7 BR | 5.5 BA | Sleeps 20 | Quick View

$667

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront
  • Private Pool
  • Rentals by Owner

About this property

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

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Property Type

Key Largo Estate

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Moon Bay A410 - End unit in one of Key Largo's finest bay front condo complexes

$150

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Minimum Rental: 7 Days"Moon Bay #A410" is a 4th floor end unit in one of Key Largo's finest bay front condominium complexes offers a beautiful view of the Florida Bay and lots of natural light. You'll love the updated kitchen with granite counters, new cabinetry and appliances. New linens ...

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Property Type

Key Largo Condo

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The 6 bedroom Duval Street Compound

6 BR | 6.5 BA | Sleeps 16 | Quick View

Distance to beach: 0.3 miles to Ft Zachary Taylor

$1250

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theaters and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a huge, fabulous decks that overlooks the action on ...

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Property Type

Key West Villa

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Palms #214 - Lovely condo with panoramic views of the Atlantic Ocean.

$73

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days "The Palms #214" is a gorgeous 2 bedroom, 2 bath condo. This is a gated complex located directly on the Atlantic Ocean. This unit has unobstructed views of the ocean from the master suite and the balcony. Wake up every morning, open the curtains and view a panorama ...

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Property Type

Islamorada Condo

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Conch Cottage

2 BR | 1 BA | Sleeps 4 | Quick View

$414

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Stay in a beautifully appointed villa or cottage located directly on the Atlantic Ocean. Only a 15 minute drive to Key West's history, restaurants and nightlife, this tropical retreat known as Sea Vista, is as serene as a private island.Enjoy full use of direct TV channels, free current video library ...

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Property Type

Key West House

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Tropical Oasis - Exceptional single family home designed for tropical living.

$292

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Minimum Rental: 28 Days "Tropical Oasis" is an exceptional single family home designed for tropical living - charming interior and extraordinary outdoor living areas. Open concept living area on the middle level of the home offers a formal dining with 8 chairs and 3 bar stools at the kitchen ...

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Property Type

Key Largo House

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Panoramic Ocean View, Pool, Hot Tub, Tennis & Fishing

2 BR | 2.5 BA | Sleeps 6 | Quick View

Distance to beach: 5 miles to Sombrero Beach

$342

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Pool

About this property

Entering our luxurious condo, you will be impressed with expansive ocean views, literally from every room. Corner-sited and on the 1st floor (above parking), the wrap around private balcony, with all-new wicker lounge furniture, is but a stone toss to the ocean. Travertine tile floors and granite counters ...

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Property Type

Key Colony Beach Condo

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CASA LAGO MAR - KEY COLONY BEACH 3/2

3 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 5 miles to Sombrero Beach, Marathon

$314

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

Waterfront 3/2 "ANOTHER DAY IN PARADISE" Seventy miles and one left turn from the mainland brings you to Key Colony Beach. 54 miles to Key West!Enjoy the tropical Florida Keys at their best! Fly, drive, or skipper your vessel to this exquisitely-appointed, three bedroom, two full ...

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Property Type

Key Colony Beach House

"Beyond great"
Reviewed May 1, 2018

Super well kept, this two story home is fully stocked, clean and has the most comfortable mattresses. Sunsets from the second story balcony are quintessential other words, perfect! Rental included access ...

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Sombrero Heaven

4 BR | 3 BA | Sleeps 10 | Quick View

$225

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

"SOMBRERO HEAVEN" ~ Brand New, Designer Decorated and Perfectly Appointed 4-Bedroom (1 King, 3 Queens), 3-Bath Private Heated Pool Villa with Neighborhood Ocean Front beach and Second Story Screened Balcony that Over Looks Private Pool and Canal! Everything you need for the perfect keys vacation ...

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Property Type

Marathon Villa

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Palm Villa

2 BR | 2 BA | Sleeps 4 | Quick View

1

$471

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Beachfront home located on privately owned Sugarloaf Beach. This gated estate offers 350 feet of private beach and 4 acres of tropical gardens. The gardens have tropical plants and bananas that have been collected from all around the world. This 2 bedroom home is beautifully and fully furnished with central ...

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Property Type

Key West House

"Isla. Gulfview"
Reviewed March 2, 2019

Small but exceptional. Gorgeous view. Quiet. Clean. We will go back if possible. This is in lower Matecumbe.

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Private House Facing the Ocean with New Heated Swim/Pool/Spa LOC LOC LOC

$357

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Private Pool
  • Rentals by Owner

About this property

Come enjoy the cool clear blue waters of the Florida Keys. The weather is great, lobster season is open from Aug.6th to April 1st. This is a spacious oceanfront home with breathtaking open water views! It is located on beautiful Ramrod Key 85 ft concrete seawall facing the priceless Atlantic ocean teaming ...

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Property Type

Ramrod Key House

"Fabulous vacation home"
Reviewed August 21, 2018

The home was amazing, plenty of room, lots of fun stuff to do at the home. Beyond amazing cross breezes. Swim spa was really nice. The bikes were great. And the kayaks were a lot of fun. We found lobsters ...

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Luxury Florida Keys Estate

3 BR | 3 BA | Sleeps 8 | Quick View

$714

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

Ocean Front, Lush Gardens, Private Beach, Deep-Water Dockage, Brand new Pool with Spa.This luxurious and newly renovated home is situated on the very desirable Lower Matecumbe Beach in Islamorada. This gated home offers supreme peace and privacy overlooking the Atlantic Ocean. Over 4,000 sq feet of ...

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Property Type

Islamorada House

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RHCP8 - Bayfront townhouse located in a lush tropical setting.

$90

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

MINIMUM STAY: 28 Nights. Bayfront townhouse located in the lush tropical setting of Rock Harbor Club in Key Largo. You'll love the open water views from the two oversized screened balconies - one off the main living area and the other off the master suite. There's something for everyone at Rock Harbor ...

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Property Type

Key Largo Townhome

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Beba's Reef House - Capture your imagination the moment you enter this home .

$150

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Minimum Rental: 28 Days"Beba's Reef House" will capture your imagination the moment you enter the home and rise to the main living level through the reef painted on the walls of the stair well and the photos of fish captured by the owner during numerous dives here in the Keys. This is a ...

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Property Type

Tavernier House

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Manatee Manor - Opportunity to experience The Florida Keys at its best.

$198

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Minimum Rental: 28 Days"Manatee Manor" is a 3 Bedrooms and 2 ½ Baths home with POOL, Dock, and all new furnishings make this your opportunity to experience The Florida Keys at its best. Conveniently located on a deep and wide canal with easy access to the Bay or a short ride to Tavernier ...

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Property Type

Tavernier House

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PARADISE FOUND! BRING YOUR BOAT! HOME WITH ACCESS TO BEACH AND BOAT RAMP!

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 40 feet to Across the street

$153

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Rentals by Owner

About this property

FAMILY FRIENDLY GORGEOUS HOME WITH DIRECT VIEW OF LARGO SOUND! WATCH THE SUN RISE FROM THE COMFORT OF YOUR LIVING ROOM! 3 BEDROOMS 2 BATHROOMS BEACH AND BOAT LAUNCH INCLUDED IN RATE! THIS IS THE OPPORTUNITY OF A LIFETIME! KING SIZE BED IN MASTER BEDROOM, 2 TWIN BEDS IN 2ND BEDROOM, AND QUEEN SIZE ...

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Property Type

Key Largo House

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Waterfront Get Hooked

4 BR | 3 BA | Sleeps 10 | Quick View

$364

per night

View Details

Key Amenities

  • Air Conditioning

About this property

Waterfront Home in the heart of the Florida Keyes. Come relax and enjoy the beautiful waters of Sombrero and Bahia Honda Beaches. Both nearby. There is plenty of room and comfort in our 4 bedroom, 3 bath home. Two King Master Suites with attached baths. Satellite Flat Screen TV's in each bedroom. Fully ...

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Property Type

Marathon House

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Oceanfront End Unit, Pool, WiFi, Panoramic Ocean Views

2 BR | 2 BA | Sleeps 4 | Quick View

1

Distance to beach: 1 miles to Harry Harris

$139

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

Welcome to this 5th floor end unit condo in an art deco inspired building right on the Atlantic Ocean in a peaceful neighborhood. Enjoy full panoramic ocean views right from your own condo and balcony. Oceanfront clean heated pool and private covered parking space. Free high speed WiFi included. Sandy ...

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Property Type

Islamorada Condo

"Great Views, Comfortable Condo, Great Bargain!"
Reviewed September 9, 2018

My wife and I stayed here the first week in September, 2018 and wouldn't you know it, we got a tropical storm! It was just one rainy day however. This condo is on the 5th floor of a 7 story building, ...

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Anglers Reef-Rent Now for Summer- May/June Special

$243

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

Welcome to Anglers, a newly renovated luxurious escape for your vacation needs. Perfect for families, couples, or a friends getaway. Located in Anglers Reef, a gated community with heated swimming pool and two private beaches. Our availability calendar is always up to date and current.Our beautiful ...

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Property Type

Islamorada House

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A Touch of Paradise.. pool, close to beach & Duvall. 2 FULL baths, 7 night Min.

2 BR | 2 BA | Sleeps 5 | Quick View

Distance to beach: 0.1 miles to Ft Zachery Taylor Beach

$242

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Rentals by Owner

About this property

Best Location!! .. ...This Key West Getaway, with beachy decor, is so close to all the local Key West bars & restaurants and museums, just take a short stroll or jump on a bike and a way you go...google KeyWest296! 1 block to Green Parrot Music bar or Blue Heaven restaurant/bar/music , and only 2 ...

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Property Type

Key West Condo

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Beacon Reef #310 - Beautiful condo with lovely views of the ocean.

$107

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days"Beacon Reef 310" is one of the most desirable condominium complexes in the Upper Keys. Located in Islamorada it is convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more. Picture yourself relaxing on your ...

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Property Type

Islamorada Condo

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Beautiful Ocean Sunrise Views!

3 BR | 2.5 BA | Sleeps 6 | Quick View

3

$293

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Rentals by Owner

About this property

Enjoy the sunrise over the Atlantic ocean or relaxing on a private, sunny lanai. Take a cruise around the many canals or out to Florida Bay to capture the sunset. A 30' boat slip is included with the rental. Beautifully furnished living spaces, large dining area, granite counter tops and stainless ...

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Property Type

Islamorada Condo

"Beautiful Condo"
Reviewed August 15, 2018

We love Bay Harbour Condos! We've stayed in the community 3 times so far and this condo- WILL NOT DISAPPOINT. It's beautifully decorated and very spacious. Owners are sweet and communicate very well! We ...

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Truman Annex Shipyard Condo-1BR/1BA w/Loft

$185

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool

About this property

1BR/1BA w/ Loft in Truman Annex close to Ft Zachary Taylor beachThis condo easily accommodates both couples and small families with its unique layout. It features a private bedroom, loft area and sleeper sofa for flexible sleeping accommodations. Located within the gated community of Truman Annex, ...

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Property Type

Key West Condo

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MA869

6 BR | 5 BA | Sleeps 14 | Quick View

$514

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

***PLEASE NOTE 7 night minimum***All holidays and lobster weeks are $5200*** Room for everyone with 3 master suites, each with a king size bed and an ensuite bath. One guest room has a queen. There is a small bunk bedroom for the kids. In addition, off one of the master bedrooms there is a twin bedroom ...

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Property Type

Marathon House

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Ocean Front building with Ocean Front pool in beautiful Islamorada!

$129

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool
  • Rentals by Owner

About this property

Luxurious and large 2 bedroom 2 bath condo with balcony, large heated swimming pool, stainless steel appliances, flat screen televisions in every room in the beautiful Florida Keys.Huge ocean front dock with plenty of room for fishing! Wifi, deluxe cable, and restaurants within walking distance.2 ...

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Property Type

Islamorada Condo

"Wonderful location and hosts."
Reviewed January 10, 2019

This home was perfect for our family of five. Spacious bedrooms, living area and bathrooms. We also had use of the storage unit for our fishing gear and coolers. The pier is breathtaking. Our thoughtful ...

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Chillax

4 BR | 3 BA | Sleeps 10 | Quick View

$425

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

"Chillax" in the Keys is a gorgeous brand new beautifully decorated 4 bedroom 3 bath canal front Villa (pull out couch)! You can rent one or both sides! With a private dock that can accommodate a boat up to 40', private pool, plenty of parking for cars and boat trailer and a two minute drive ...

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Property Type

Marathon Villa

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Island Conch Cottage

2 BR | 1.5 BA | Sleeps 4 | Quick View

1

Distance to beach: 0.5 miles to Anne Beach

$125

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Rentals by Owner

About this property

Island Conch Cottage A quaint ground level conch style cottage located at the end of a private street in a very quiet setting. Cottage and grounds have privacy fence and gate. The grounds are displayed as a sand beach setting. This property has 60’ of canal frontage located on an extra wide canal ...

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Property Type

Islamorada House

"Second time Around"
Reviewed September 29, 2018

This is the second time we stayed at this island conch Cottage, this is a beautiful home the neighborhood is very quiet and the locals are always friendly. We caught a variety of snapper just off the patio ...

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LUXURY HOME WITH DOCK, POOL, HOT TUB, AND ELEVATOR

3 BR | 3 BA | Sleeps 8 | Quick View

3

Distance to beach: 1 miles to Coco Plum & Sombrero Beach

$271

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool
  • Rentals by Owner

About this property

This new gated Marathon home is 2 levels with an elevator. 3 Bedroom / 3 Bathroom , Sleeps 8 people, with all the comforts of home. This home offers nothing but the best in home furnishings and security. Panoramic water views from private decks off the living room and master bedroom. Master / King bed; ...

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Property Type

Marathon House

"Beautiful place on earth"
Reviewed January 28, 2019

Larry has the most beautiful, restful and comfortable vacation home ever. He thinks of everything to make your stay the best ever. Very clean and all the comforts you could ever ask for.

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Welcome to Paradise

2 BR | 3 BA | Sleeps 6 | Quick View

$125

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool

About this property

Heart of StoneHalf way between Miami and Key West and nestled between 2 oceans (the Atlantic Ocean and the Gulf of Mexico) is the 'Heart of Stone'. The perfect destination in the Florida Keys. Where can you drive on a highway that divides two Oceans? The Gulf of Mexico on the west and The Atlantic ...

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Property Type

Long Key Mobile Home

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Beacon Reef 406 - Charming condo with lovely views of the ocean and pool.

$100

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly
  • Pool

About this property

Minimum Rental: 28 Days NEW ON THE RENTAL MARKET. "Beacon Reef 406" is an excellent choice for your vacation getaway, whether you're planning on staying a month or the entire season, this is a great unit. Beacon Reef is centrally located in the Heart of Islamorada making it convenient ...

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Property Type

Islamorada Condo

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Brock Haus - Bayfront Weekly Townhome with Boat Slip, Pool, Beach.

$225

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

Minimum Rental: 7 Days (Saturday to Saturday)"Brock Haus on the Gulf" is an end unit townhouse on the water's edge with water views on 3 sides! The main living area faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces the marina. The panoramic ...

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Property Type

Plantation Key Condo

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This beautifully furnished waterfront home with ocean views

$167

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

This beautifully furnished waterfront home with ocean views will thrill the most ardent diver or fisherman and his family. You will love the luxury of a heated pool, magnificent view, and protected deep water dockage for multiple boats. It is located on a large harbor with multiple sailing yachts and ...

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Property Type

Islamorada House

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Villa Riolo - Updated home and perfect for your next holiday in Islamorada

$117

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly

About this property

Minimum Rental: 28 Days"Villa Riolo" is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 6 in two bedrooms. This home has been meticulously cared for over the years and for the first time the owners are offering you an opportunity ...

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Property Type

Islamorada House

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30 night minimum stay, SUNSET KEY, LUXURY UPSCALE HOME RIGHT ON THE BEACH,

$399

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Private Pool

About this property

30 day stay minimum, 3000 SF, 3BDR, 2.5BATHS, SLEEPS 6 Treat yourself to a dream vacation in our beachfront residence on the private island of Sunset Key, located in the middle of Key West Harbor. Our tastefully designed upscale villa has beautiful ocean views, private pool, and 2 hot tubs for our guests ...

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Property Type

Key West House

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Paradiso Sul Mare

2 BR | 2 BA | Sleeps 6 | Quick View

$200

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool
  • Private Pool

About this property

Kawama Yacht Club, a beautifully landscaped gated resort, is set on an unspoiled peninsula between the untouched habit of a bird sanctuary to the south and the beautifully preserved John Pennekamp Marine Coral Reef State Park to the north.Located on the 4th floor of the prestigious oceanfront 5 story ...

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Property Type

Key Largo Condo

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Brand New 6 Bedroom 5 Bath 65 Foot Deep Water Dock, Heated Pool Outdoor Kitchen

6 BR | 5 BA | Sleeps 14 | Quick View

Distance to beach: 0.1 miles to Sombrero Beach

$857

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

Brand New Construction, 6 Bedroom , 5 Bathroom canal views, On the HIGHLY sought after Sombrero Beach !!! 100 Foot Deep Water Dock (my 23 foot boat sits in a lift so you get 65 foot to use) 10 minute ride through the famed Sisters Creek to the open ocean, 15 minute to the seven mile bridge, six NM to ...

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Property Type

Marathon House

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Sea Grape - Serene, quaint part of paradise that the entire family will enjoy..

$400

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly

About this property

*******THIS PROPERTY IS NOT CURRENTLY AVAILABLE FOR RENT*******MINIMUM STAY: 28 DAYSFABULOUS BEACH HOUSE located directly on a mile long sandy beach. The original "Sea Grape" was destroyed by Hurricane Irma in September 2017. The decision was made to tear down and rebuild. The ...

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Property Type

Islamorada House

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Conch Bar South - 4 Bedroom Waterfront Home with Swimming Pool

4 BR | 3 BA | Sleeps 10 | Quick View

Distance to beach: 3 miles to Founders Park Beach

$298

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

***FALL SPECIAL*** RECEIVE 20% OFF RENT FOR ALL BOOKINGS IN NOVEMBER AND DECEMBER. Minimum Rental: 28 Days"Conch Bar South" is a magnificent home is located at the mouth of a wide canal in Plantation Key and offers phenomenal open water views. The furnishings are new and provide a comfortable ...

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Property Type

Tavernier House

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NEW 3/2 POOL HOME

3 BR | 2 BA | Sleeps 6 | Quick View

$300

per night

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Key Amenities

  • Air Conditioning
  • Private Pool

About this property

30 MINUTES TO KEY WEST. BEAUTIFUL LOT WITH COCONUT TREES. BEAUTIFUL BRAND NEW FURNISHINGS. 65" LCD TV IN LIVING ROOM 50" LCD IN MASTER BEDROOM. WORLD FAMOUS LOOE KEY JUST OFF SHORE. TWO QUEEN BEDS AND TWO TWIN BEDS IN THREE BEDROOMS. SONOS MUSIC SYSTEM WITH KLIPSH OUTDOOR SPEAKERS. RELAX IN ...

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Property Type

Big Pine Key House

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Villa Serena Duval Square

2 BR | 2 BA | Sleeps 4 | Quick View

$275

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Open the door to Villa Serena and find yourself transported to a peaceful sanctuary. Recently renovated in February 2018, Villa Serena is the perfect space for your relaxing vacation.The downstairs living area is decorated in soothing cobalt and beachy sand tones and provides plenty of space for ...

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Property Type

Key West Condo

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Casa de Cuba

3 BR | 2 BA | Sleeps 6 | Quick View

$501

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval Street in the historic district, the location can't be beat. The home's history is rich; neighboring the historic Gato Cigar factory which is now restored ...

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Property Type

Key West House

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Mobile Home, 2 Bedrooms, 2 Baths, (Sleeps 2-4)

$120

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

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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Property Type

Tavernier Mobile Home

"We found out paradise !"
Reviewed March 5, 2019

We loved staying here. The location is great for shopping and very safe. The house is immaculate, everything you need is here. Sit out under the tiki hut and watch the beautiful sunsets. Watch all the manatees ...

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Key Lime Sunrise 526 Sombrero Beach Road Marathon, FL

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 1 miles to Sombrero Beach

$243

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

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 1,440 sq. ft. two bedroom two & a half bath home situated on Sombrero Beach Road. This charming getaway is within walking/biking ...

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Property Type

Marathon House

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W. Plaza del Lago - Promises to be a favorite!

2 BR | 2 BA | Sleeps 5 | Quick View

Distance to beach: 0.3 miles to Port Antigua Neighborhood Beach

$133

per night

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Key Amenities

  • Air Conditioning
  • Kid Friendly

About this property

Minimum Rental: 28 Days"West Plaza Del Lago" promises to be a favorite. Beautifully remodeled roomy single family stilt home with vaulted ceilings and located in prestigious Port Antigua on a deep and wide canal. You will love the interior of this home as much as the exterior! As you enter ...

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Property Type

Islamorada House

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