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Luxury Vacation Rentals in Big Pine Key

(5 rentals)
New
Last Minute Deal
Big Torch Key House
Sleeps 14, 3 bedrooms, 3 bathrooms

Key Amenities

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

About this property

Welcome to Barefoot Retreat, where you will feel as though you are on your own private island! As you drive through the remote, lush tropical island road to access the estate, drive slow as you might be greeted by the quite friendly protected Key Deer, roaming free about the property.As you approach...

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$833
avg per night
Cudjoe Key House
Sleeps 12, 5 bedrooms, 3 bathrooms
2 reviews

Key Amenities

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

About this property

This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1. Located just 20 miles away from Key West. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Downstairs grill, upstairs grill, Jacuzzi. Full WiFi. TVs in every...

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Featured review

"Squillets & Manor Wedding"

We had a great time, we will definitely be back! Fun in the sun! Close to restaurants and grocery store.

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$807
avg per night
Key West House
Sleeps 10, 5 bedrooms, 3 bathrooms
1 review

Key Amenities

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

About this property

2 rental homes within 5 private gated acres of scenic beauty in the heart of the Florida Keys and 15 minutes to Key West. Located within the keys wildlife preserve, Sea View Estate is just a 15 minute drive to the shopping and nightlife of Key West and just minutes to some of the finest restaurants...

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Featured review

"Wonderful property wonderful hosts!"

I just got back from taking my family and a friend's family to Troy and Carol's property for a week. The houses were just as described, the location was just what we wanted, quiet and peaceful and away...

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$1,011
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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$1,141
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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$1,043
avg per night

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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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$1,307
avg per night
Marathon House
Sleeps 8, 3 bedrooms, 3 bathrooms
9 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

WE ARE OFFERING A 5% DISCOUNT THROUGH JANUARY 31ST! IT IS AUTOMATICALLY FIGURED INTO THE QUOTE!Tingler Retreat is a tastefully decorated 3 bedroom, 3 bath home with a pull-out couch, has a peek-a-boo view of the ocean and is seconds to open water in your boat! It has an open floor plan and is ground...

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$781
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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$2,130
avg per night
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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$1,300
avg per night
Marathon House
Sleeps 10, 5 bedrooms, 5 bathrooms

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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$857
avg per night
Marathon Apartment
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
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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$1,014
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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$1,225
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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$907
avg per night
Marathon Villa
Sleeps 10, 4 bedrooms, 3 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

WE ARE OFFERING A 5% DISCOUNT THROUGH JANUARY 31ST! IT IS AUTOMATICALLY FIGURED INTO THE QUOTE!Reel Life 2 has everything! 4 bedroom 3 bathrooms, canal front, private dock (boat up to 35'), large private pool, Tiki Hut with flat screen TV, large grill, 2 bikes, 2 paddle boards, 1 kayak and a...

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$736
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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$727
avg per night
Marathon House
Sleeps 14, 6 bedrooms, 5 bathrooms

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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$1,400
avg per night
Marathon Villa
Sleeps 14, 4 bedrooms, 3 bathrooms

Key Amenities

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

About this property

WELCOME TO THE KEYS! Mega tropical oasis with 2 HOUSES! No you are not dreaming. Yes there are 2 houses connected together totaling 5 beds, 3 full bathrooms, 2 outdoor showers , 2 six person Hottub’s and 2 kitchens. Along with kayaks, beach bikes, volley ball, bocci ball, fire pit, corn hole and...

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$700
avg per night
Marathon House
Sleeps 12, 5 bedrooms, 6.5 bathrooms

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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$1,425
avg per night
New
Marathon House
Sleeps 10, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • 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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$2,600
avg per night
Marathon House
Sleeps 10, 4 bedrooms, 4.5 bathrooms
22 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

"A perfect getaway"

We spent a week at this lovely home in Marathon Key, escaping our winter wonderland in Michigan. The 4 bedrooms and baths were ideal for our group of seven. The kitchen is well stocked, the deck has plenty...

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$850
avg per night
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