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Luxury Vacation Rentals in Key Colony Beach

(34 rentals)
Key Colony Beach House
Sleeps 10, 4 bedrooms, 4 bathrooms

Key Amenities

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

About this property

Weekly rentals in the Keys {and generally elsewhere } are based on a Saturday to Saturday occupancy. Check - in is on Saturday at 4:00 PM, and check - out is on the following Saturday at 9AM . If other times are required \ requested , please inquire. This house is usually not available from the end of...

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$700
avg per night
Key Colony Beach House
Sleeps 10, 4 bedrooms, 4 bathrooms
2 reviews

Distance to beach: 3 miles to Coco Plum Beach

Key Amenities

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

About this property

Welcome to your perfect getaway! This beautifully renovated and spotless 4-bedroom, 4-bath vacation home offers the ultimate in comfort and convenience. Enjoy a brand new & spacious in-ground swimming pool with soothing massage jets, perfect for relaxing after a day on the water. Located on a deep-water...

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Featured review

"Wonderful house, great location!"

This house was wonderful, great location, and is well equipped for our week vacation, the pool was clean and well serviced, the location is great and the water access was a short ride to the bay/ocean....

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$802
avg per night
Special Offer
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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$1,228
avg per night
Key Colony Beach House
Sleeps 14, 6 bedrooms, 5 bathrooms

Distance to beach: 0.3 miles to Sunset Park

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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

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$980
avg per night
Marathon House
Sleeps 12, 5 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Paraíso Del MarIntroducing our newest luxury vacation rental nestled in the prestigious community of Marathon. This brand-new build epitomizes elegance and sophistication, offering an unparalleled experience for those seeking the epitome of luxury in the Florida Keys.Set amidst lush tropical...

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$1,000
avg per night

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Marathon House
Sleeps 10, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Seaside SerenityWelcome to your exclusive luxury retreat in Marathon, Florida. Seaside Serenity is a brand-new, 4-bedroom 4.5-bathroom, private pool home where paradise meets perfection. With 35' of dockage and nestled in close proximity to the Atlantic Ocean, Gulf of Mexico, and Coco Plum Beach,...

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$798
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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$720
avg per night
Marathon House
Sleeps 12, 5 bedrooms, 4 bathrooms
5 reviews

Key Amenities

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

About this property

5 Star Modern New Construction Bayfront Home With Private Dock and PoolIsland Dreamz Bay House is a piece of paradise on the Vaca Cut waterway in Marathon. Gorgeous and brand new 5 bedroom, designer decorated, 4 bath single-family home with 36 ft. of assigned dockage. Private pool can be heated upon...

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Featured review

"Island Dreamz a stunning home, lovely view and perfect location in the Keys!"

This was our second stay at Vaca Cut at The Tides. We loved this gorgeous home with its exquisite design and comfort. The house was immaculate ~ kudos to the pros who keep this home clean and well stocked...

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$820
avg per night
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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$730
avg per night
Marathon House
Sleeps 12, 5 bedrooms, 4 bathrooms
14 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Sailfish Villa, unit #6, is a brand new gorgeous, professionally decorated 5 bedroom 4 bath Villa with open water views on Vaca Cut! Enjoy sunrise and sunset colors and direct ocean and Gulf access! It has a private pool and boat slip for a boat up to 35' including motors. There is no additional...

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Featured review

"Grateful"

I have been coming to marathon with family for many years and have had many rentals.. Meredith I have to say is the best.. she worked with me with every question and plans that I had . Definitely would...

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$725
avg per night
Marathon House
Sleeps 12, 5 bedrooms, 4 bathrooms
7 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Pineapple Tides, located at "The Tides at Vaca Cut" (Unit #8), is a new 5 bedroom 4 bath home with a private pool and boat slip!Perfectly situated on the water with stunning views, sunrise and sunset colors, and direct quick access to both the Atlantic Ocean and the Gulf of Mexico via Vaca...

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$728
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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$780
avg per night
Marathon House
Sleeps 12, 5 bedrooms, 6.5 bathrooms
1 review

Key Amenities

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

About this property

Gulf-Front Modern Luxury | 5BR w/ Rooftop Deck, Infinity Pool, Dock & More! Indulge in an unparalleled luxury experience in this breathtaking 5-bedroom, 5.5-bathroom estate in Marathon, Florida. With direct Gulf views, high-end amenities, and a sleek modern design, this home is a dream getaway for...

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Featured review

"AWESOME BAYSIDE OCEAN LOCATION, PROPERTY AND STUNNING HOME - MARCH/APRIL 2026"

The ocean view from the roof and 5 bedroom modern style home is 2nd to none in the keys! Each bedroom has it's own bathroom and the home is very modern and in excellent condition. The infinity pool is...

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$1,157
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
Marathon House
Sleeps 10, 4 bedrooms, 4.5 bathrooms
28 reviews

Distance to beach: 4 miles to Sombrero Beach

Key Amenities

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

About this property

New construction! This spacious and tropically decorated property includes 4 KING bedrooms, each with private ensuite bathrooms. There is an additional half bath for guest use, as well as commercial washer and dryer. State of the art kitchen with quartz counter tops and well appointed living area including...

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Featured review

"Wonderful experience!"

This was our first time yo Key West, FL. My husband, daughter, and I had a wonderful time. Kraken’s Cove is beautiful with all the amenities and lots of extras too. We went to downtown Key West parts...

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$822
avg per night
Marathon House
Sleeps 14, 6 bedrooms, 5 bathrooms
1 review

Key Amenities

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

About this property

"The furnishings/decor are beautiful. This is one of the nicest houses we have had the pleasure to rent, everything is spotless/brand new. It was hard getting our kids ages 8 and 10 to leave the house each day for adventures. " -Kristie KruegerAs a boating enthusiast, I designed Captain's...

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$1,026
avg per night
Marathon House
Sleeps 14, 6 bedrooms, 6 bathrooms

Distance to beach: 1 miles to Sombrero Beach

Key Amenities

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

About this property

Weekly rentals in the Keys {and generally elsewhere } are based on a Saturday to Saturday occupancy. Check - in is on Saturday at 4:00 PM, and check - out is on the following Saturday at 9:00 AM. Check in directions are emailed to you the week prior to your arrival { please check "spam" } Pups...

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$846
avg per night
Marathon House
Sleeps 10, 5 bedrooms, 5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to 137 Mockingbird Cove! Modern, expansive home built in 2022, offering incomparable boating! Quick walk or ride from Sombrero Beach. Each of the 5 bedrooms features its own ensuite bathroom, offering ultimate privacy and comfort. Includes a private heated/chilled pool, 2 paddleboards, 4 bicycles,...

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Featured review

"Keys Paradise: Waterfront Perfection in Marathon!"

We had an absolutely amazing stay at this waterfront home in Marathon! From the moment we arrived, we knew we had found something special. The location is unbeatable—classic Florida Keys beauty with crystal-clear...

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$857
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 4 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Must See Stunning 3095 Sq. Ft 4/4 SFH on ground level with pool, 45 ft of dockage, outdoor kitchen and access to the ocean by boat.This gorgeous property features an open floor plan with elegant furnishings, state of the art kitchen with Viking appliances and an induction cooktop, quartz countertops,...

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Featured review

"Sunny Daze in Marathon!"

I didn’t know much about Marathon other than it was in the keys. Upon hearing from a family friend that it was the Keys best kept secret we couldn’t resist. The Sunny Daze house was perfect for my family...

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$1,051
avg per night
Marathon House
Sleeps 10, 5 bedrooms, 10 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Escape to paradise at Anglers End Estate the ultimate vacation getaway with unobstructed open water views and an indoor heated pool. This stunning property boasts 5 bedrooms, 3 full bathrooms, and over 3600sq ft of living space, making it perfect for family and friend gatherings. Enjoy the amazing, landscaped...

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$871
avg per night
Special Offer
Marathon House
Sleeps 14, 6 bedrooms, 5 bathrooms
4 reviews

Distance to beach: 0.1 miles to Sombrero Beach

Key Amenities

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

About this property

Waterfront 6 Bedrooms , 5 Baths, canal views. On the HIGHLY sought after Sombrero Beach !!!(We rent weekly only, and our Check-in is on a Saturday and Check-out is on a Saturday dates only so we can optimize our months.)Our houses are safe and clean because we disinfect them with the highest...

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Featured review

"The house was perfect for our fishing trip."

The house was very clean, and location could not be better. The house was more amazing than the pictures showed. The outside tiki hut, (2) barbeque grills and pool made a perfect end to a day of fishing....

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$1,248
avg per night
Marathon House
Sleeps 12, 5 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to your spacious, five-bedroom waterfront pool home in Marathon, just steps from Sombrero Beach! Enjoy multiple entertaining areas inside and out, with a screened-in patio and sparkling pool (pool heat available for an extra fee). The open-concept interior features cathedral ceilings, a modern...

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$835
avg per night
Marathon House
Sleeps 30, 14 bedrooms, 10 bathrooms

Distance to beach: 100 yards to Sombrero Beach

Key Amenities

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

About this property

Seaside Sandpiper is truly a unique property that can accommodate as few guests as you want and up to 30! Rent the 6 bedroom main house by itself or rent the entire 14 Bedroom Main house and Addition! Weddings, family reunions and business retreats are all possible at our home! Our pet friendly home...

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$2,141
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 3.5 bathrooms

Distance to beach: 0.1 miles to Sombrero Beach

Key Amenities

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

About this property

Dreaming of that elusive Keys home with a incredible waterfront views, a private pool, a great beach, and a dock for your boat? Look no further... this newly built 2026 home on a gated Tingler Island might be just for you.Located just one block from Sombrero Beach (Trip Advisor Top 10 Beaches in N....

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$803
avg per night
Last Minute Deal
Marathon House
Sleeps 14, 6 bedrooms, 5 bathrooms
4 reviews

Key Amenities

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

About this property

Great for Family Reuions, and Large Groups vacationing in the Florida Keys! Fabulous 6500 sq ft. vacation paradise. Includes everything you need for a perfect Family Reunion or large destination vacation.Private Vacation Rental Waterfront Home with 6 Bedroom 5 Baths Private Pool and Spa ~Tiki Hut,...

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Featured review

"Family Vacation In The Heart of Paradise"

From beginning to end it was a pleasure working with Liz to secure the week of family fun! The estate was everything that we needed it to be with plenty of room for our children and grand children. The...

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$1,248
avg per night
Marathon House
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Key Amenities

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

About this property

Wide Horizon is a bright beautiful upscale home where you feel immersed in nature. The house was custom designed, by the owners to take full advantage of its unique ocean location. All principal rooms, including bedrooms, have a minimum of 12 foot glass sliding doors to oceanfront balconies. Its...

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$840
avg per night
Marathon House
Sleeps 12, 5 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Emerald ShoresWelcome to your dream getaway at this direct oceanfront vacation rental in Marathon, Florida Keys. This stunning 5-bedroom, 4-bathroom home offers panoramic Gulf and Ocean views, a private heated saltwater pool, an outdoor kitchen, and a private boat slip at the community marina. Designed...

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$932
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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$706
avg per night
Marathon House
Sleeps 8, 4 bedrooms, 3.5 bathrooms
11 reviews

Distance to beach: 900 yards to Sombrero Beach

Key Amenities

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

About this property

"BELLA VISTA" - a Spectacular Oceanfront home in Marathon, Fla. with an Invisible-edge heated salt water pool that overlooks the Atlantic Ocean. Open Water Unobstructed VIEWS. VERY PRIVATE. Newly renovated! This 4 bedroom/3.5 bath home can comfortably sleep 8 people. Three bedrooms have King...

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Featured review

"Perfection!"

Don’t think twice about booking this slice of heaven. My family of seven stayed at this glorious home. Absolutely spotless and very well stocked with everything you need. The views are amazing!! 5...

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$896
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 4.5 bathrooms

Distance to beach: 0.5 miles to Sombrero Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Exclusive Sombrero Beach vacation retreat is located just up the street from one of the best beaches in the Florida Keys. Sombrero Beach is a large sandy beach that offers something for everyone in the family including playground, volleyball swimming and picnic tables. The beach is also a great place...

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$1,377
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

3 bedroom, 2 bath gulf front home with amazing views and meticulously manicured lot.Amazing Gulf and sunsets views from almost every room in this tropical retreat! The Palm Tree Resort is a private gated, three quarter of an acre resort located directly on the Gulf in a premier section of Morton...

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$3,500
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Casa Feliz~ Experience, enjoy, relax, and rejuvenate in luxury accommodations on the Atlantic Ocean.~ Secluded sophistication can be your vacation destination.Welcome to Casa Feliz! We are located on the quiet Grassy Key in the middle of the Florida Keys.Concierge Level Luxury vacation...

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$1,102
avg per night
Marathon House
Sleeps 12, 5 bedrooms, 4 bathrooms

Distance to beach: 60 yards to Onsite

Key Amenities

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

About this property

Welcome to SeaGlass Cove — where barefoot luxury meets the laid-back beauty of the Florida Keys. This newly built, three-story oceanfront home offers over 5,200 sq. ft. of indoor and outdoor space, with 5 bedrooms, a two-car garage, and breathtaking open waters.Located in a gated, oceanfront...

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$876
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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$800
avg per night
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