Big Pine Key Vacation Rentals

(24 rentals)
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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Rentals by owner

About this property

Family House in Big Pine Key, Fl on the water. Bring your Boat and have easy access to the most beautiful waters of the Keys. Boat dock on the back of the house, and house comes with everything, it will make you feel at home.Welcome to your Ultimate Luxury Island Escape! This beautiful waterfront ...

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Property Type

Big Pine Key House

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3 BR | 2 BA | Sleeps 7 | Quick View

1

$247

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Enjoy breathtaking views of ISLAND TIME PARADISE (our nickname) in Big Pine Key. Its our spacious 3 bedroom 2 bathroom ISLAND TIME PARADISE HOUSE that will accommodate a total of 8 people. You will see it as the perfect blend of tranquil beach living and modern convenience. This home is the ideal place ...

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Property Type

Big Pine Key House

"Wonderful home"

Loved staying at this home! Very comfortable! Owners were great to work with and extremely easy to work with! Got our security deposit back within a good time frame! I have no complaints except for the ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Welcome to Big Pine Breeze! Charming and tastefully decorated 2/2 home with beautiful sunset views from the large walk-around deck on the upper level with a large screened deck overlooking the canal for a relaxing time for cocktails and space for outdoor dining. This home is super clean and neat! Fully ...

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Property Type

Big Pine Key House

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Key Amenities

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

About this property

Beautiful 3-BR house located directly on canal with easy access to the Gulf of Mexico or Atlantic Ocean. On-property pool and private outside shower. 75-ft dock for boat. Home of the Key Deer and Blue Hole (the deer will walk past house daily).Located 35 miles north of Key West, and 20 miles south ...

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Property Type

Big Pine Key House

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3 BR | 2 BA | Sleeps 6 | Quick View

3

Distance to beach: 7 miles to Bahia Honda State Park

$225

avg/night

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Key Amenities

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

About this property

This newly remodeled home is cozy, yet spacious.This open concept, single family home is located on a canal and just a few seconds from the ocean. Fully furnished with Keys-inspired touches, this home comfortably sleeps 6 people with 3 bedrooms and 2 bathrooms.Spend the day at Bahia Honda State ...

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Property Type

Big Pine Key House

"Big Pine Vacation"

We stayed in the rental for February and March of 2024 and loved it.Very quiet with friendly neighbors.Wonderful outside area and perfect boating with easy access to the ocean or gulf.Already have our reservation ...

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Key Amenities

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

About this property

Beautiful house in Big Pine Key, Fl on the water. Bring your boat and have it in the water in the back of the house. Comes with everything needed for your amazing stay. There is an ice maker for your use as well. Also you are only 30 miles away from the world famous Key West.

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Property Type

Big Pine Key House

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Key Amenities

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

About this property

Introducing "Turtle Cove" - Your Serene Florida Keys Retreat with Water Access and Pool!Escape to a world of tranquility and indulgence at "Turtle Cove," where the allure of the Florida Keys' vibrant tropical paradise meets the luxurious charm of a newly renovated vacation ...

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Property Type

Big Pine Key House

"Great New Place"

I want to start by saying Joao and family are fantastic, helpful and fair hosts. Like the previous review ( 1st ever renter, me 2nd ) they have done a spectacular job refurbishing this Florida stilt home! ...

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 7 miles to Bahia Honda State Park

$265

avg/night

View Details

Key Amenities

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

About this property

This newly remodeled home is cozy, yet spacious.This open concept, single family home is located on a canal and just a few seconds from the ocean. Fully furnished with Keys-inspired touches, this home comfortably sleeps 6 people with 3 bedrooms and 2 bathrooms.Spend the day at Bahia Honda State ...

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Property Type

Big Pine Key House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Welcome to our home, “Reel’em Inn” Big Pine Key, an excellent location for a relaxing vacation with family and friends 31 miles from Key West’s Mile Marker 0. This spacious 5 bedroom home is located on a double lot with plenty of parking and 150 feet of seawall. There is a step ...

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Property Type

Big Pine Key House

"Great place to stay, especially for fisherman"

Lots of rooms and places to spread out large families. Great facilities, particularly well suited to fisherman. The owner is very helpful and flexible.

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3 BR | 2 BA | Sleeps 6 | Quick View

$141

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

About this property

This lovely waterfront home has it all. This fantastic community is one of the most unique places in the world. In minutes you can explore the beautiful back country or Ocean by kayak or boat. Marine Life sightings and fishing is the best in this area. You can lay back and relax, away from it all and ...

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Property Type

Big Pine Key House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Rentals by owner

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 ...

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Property Type

Big Pine Key House

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2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 10 miles to Bahia Honda

$171

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

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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Property Type

Big Pine Key House

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4 BR | 2 BA | Sleeps 8 | Quick View

$273

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

A get away to "Our Island Thing" will be unforgettable vacation for everyone. Huge 1,900 square-foot house with lots of room for the whole family and kids. Four bedrooms and two bathrooms, this two level concrete home is roomy and airy.The second floor has a huge kitchen, living and dining ...

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Property Type

Big Pine Key House

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

2

$150

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

Welcome to the beautiful Canal-facing newly rebuilt rambler home. Located at Big Pine key that is easily accessible to Key West, Marathon, Bahia Honda State Park, 7 mile Bridge, and many other hidden treasures of the keys. This is a contemporary styled home with amazing views of the Canal from the Master ...

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Property Type

Big Pine Key House

"Enjoy Big Pine Key and don't break the bank"

We were very pleased with the house, its location and the price. The kitchen/living room area is open and comfortable. The kitchen is spacious and well equipped. The 2 bedrooms and bathrooms were comfortable ...

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3 BR | 2 BA | Sleeps 6 | Quick View

$253

avg/night

View Details

Key Amenities

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

About this property

Florida Keys Vacation Rentals – Come and enjoy a magnificent vacation with open water views at this beautiful Big Pine Key home. This home boasts décor by award winning Key West decorator and is super roomy, with three bedrooms and two bathrooms. A large, well-appointed eat-in kitchen will ...

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Property Type

Big Pine Key House

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2 BR | 1 BA | Sleeps 4 | Quick View

$133

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

Simple and sweet with no muss, no fuss. It’s all right here – Gulf Side! This quaint two bedroom vacation home offers views, a deep-water boating and swimming canal and a protective seawall. This home offers 2 queen-size beds and an additional sleeper sofa.A glassed-in porch and all the ...

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Property Type

Big Pine Key House

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2 BR | 2 BA | Sleeps 4 | Quick View

$171

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

What a great sunset view from this house! Fun in the sun surrounds this spot right on a wide canal with excellent access to fishing either the Gulf or the Atlantic side. Any outdoor enthusiast would be content here as the boating, diving, snorkeling, or kayaking is right out your back door.After a ...

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Property Type

Big Pine Key House

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2 BR | 1 BA | Sleeps 4 | Quick View

$105

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

Just the perfect Florida Keys get a way. Cute and super comfortable 2 bedroom 1 bath ½ duplex in Big Pine Key.All totally updated in 2018 with new appliances, furnishings and accessories for a comfy place to enjoy our wonderful area. Flat screen TV and WiFi included. The canal is clean and ...

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Property Type

Big Pine Key House

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2 BR | 2 BA | Sleeps 4 | Quick View

$166

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly

About this property

You and your family will feel right at home in this charming Big Pine Key home. The Owners have totally refurbished this 2 bedroom plus den, 2 bath property in 2020. Soft sea colors and coastal décor make this a totally comfortable home away from home.Large and spacious living room, kitchen and ...

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Property Type

Big Pine Key House

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3 BR | 2 BA | Sleeps 8 | Quick View

$258

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool

About this property

This spectacular home is located in the desirable Pine Channel Estates subdivision located on Big Pine Key. You will be more than delighted with this canal front home. Bring your boat, Pine Channel is only minutes away leading to some of the best boating, fishing, diving, and snorkeling in the Florida ...

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Property Type

Big Pine Key House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Welcome to Barracuda Bungalow in Big Pine Key! This quaint ground level home is perfect for your next Florida Keys getaway. There's plenty of space with 3 bedrooms and 2 baths, it's pet friendly, has a brand new pool and hot tub and sits on a great boating canal! Bring the whole family and the ...

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Property Type

Big Pine Key House

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

1

$146

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly

About this property

This relaxing retreat is situated in a very private part of Port Pine Heights on Big Pine Key. Great boating, fishing, and snorkeling can be easily accessed, just a short boat ride down the canal to Pine Channel. There is plenty of space to park your boat on the concrete dock and clean your catch on the ...

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Property Type

Big Pine Key House

"Great house!"

The house was very spacious for our family of four and our little furry companion.The kitchen was huge and easy to work around. The deck was awesome being screened in and with fans!It was complicated ...

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3 BR | 2 BA | Sleeps 8 | Quick View

$197

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly

About this property

This unique home is situated on a quiet street, with a desirable corner canal location in Port Pine Heights, Big Pine Key. Bringing your boat along? No problem, plenty of dock space here! And quick and easy access to Pine Channel for excellent boating, fishing, diving and snorkeling!The exterior has ...

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Property Type

Big Pine Key House

Show less

4 BR | 2 BA | Sleeps 8 | Quick View

5

Distance to beach: 3 miles to Bahia Honda Park

$200

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Modern 4 bedroom 2 bath stilt home centrally located in Big Pine. Heated salt water swimming pool. Corner canal front lot with 120 ft of dockage. 5 min. to the Gulf and 10 min. to the Atlantic. Close to the Winn Dixie grocery store. Free public boat ramp 5 min away. Room on property to park 6+ cars ...

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Property Type

Big Pine Key House

"Croton house"

Well, we think the house is very nice and clean. Great location, lovely neighbors nice quiet place we have only positive things to say and nothing negative so have a great day

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Big Pine Key Vacation Rentals

Big Pine Key Weather

 | 

7524°  6518°
JANUARY
Ocean 7222°
7624°  6619°
FEBRUARY
Ocean 7222°
7926°  6921°
MARCH
Ocean 7423°
8127°  7222°
APRIL
Ocean 7826°
8529°  7624°
MAY
Ocean 8127°
8831°  7926°
JUNE
Ocean 8328°
8932°  7926°
JULY
Ocean 8529°
8932°  7926°
AUGUST
Ocean 8731°
8831°  7826°
SEPTEMBER
Ocean 8529°
8529°  7624°
OCTOBER
Ocean 8328°
8127°  7222°
NOVEMBER
Ocean 7926°
7725°  6719°
DECEMBER
Ocean 7524°

Enjoy a Sunny Beach Vacation in Big Pine Key Vacation Rentals

Looking to get away from it all with a relaxing oceanside vacation? You can’t do much better than Big Pine Key, FL. This gorgeous shorefront town is the perfect place to slow down and enjoy a variety of fun and relaxing activities, including surfing, scuba diving, snorkeling, shopping, or simply lying on the glittering white beach to get your tan on.

Nestled roughly 30 miles from Key West and 100 miles from Miami, Big Pine Key enjoys a notable distance from many of Florida’s big cities, which provides its residents and visitors with a desirable separation from the hustle and bustle of city life and the chance to truly relax.

Before you rush to book an expensive hotel stay for your next trip to the area, stop and consider Big Pine Key vacation rentals instead. At Florida Rentals, we feature a wide variety of local homes available for rent, ranging from quaint oceanside cottages to expansive beachfront villas to suit any family’s needs and budget.

Hotels can be tightly packed and loud, preventing you from enjoying the peace and quiet you deserve on your vacation. With a vacation rental from Florida Rentals in Big Pine Key, you’ll be able to live like a local during your stay and experience the town’s unique neighborhoods and architecture firsthand.

Tips for Travel in Big Pine Key

Florida enjoys more than 200 days of sun and clear skies each year, which means that oceanside towns like Big Pine Key don’t have an off-season when it comes to enjoying a beach vacation. Whatever your favorite time of year is, the Florida Keys can accommodate you.

However, keep in mind that the highest rates of precipitation and lowest temperatures are typically recorded in the winter months of December, January, and February. The best times of the year to enjoy pleasant weather ideal for outdoor activities are March, April, and May, as well as late October and November.

Spend your spring break by the beach, or shake up your Thanksgiving plans with an oceanside getaway in Big Pine Key house rentals!

Things to Do in Big Pine Key

As a beachfront community in the Florida Keys, it’s no surprise that Big Pine Key’s best activities involve the water. However, you don’t need to be a water sports fanatic to enjoy everything that Big Pine Key has to offer.

The region is home to Bahia Honda State Park, one of the most scenic white sand beaches in the Florida Keys. The park is open from 8:00 a.m. to sundown all year long and offers some of the most gorgeous views in the Keys. There are also plenty of dining spots, along with rentals for snorkeling equipment and kayaks. 
If kayaking is your passion, make sure to visit Big Pine Kayak Adventures. Create the ultimate adventure by choosing one of the company’s specialized backcountry tours, including full- and half-day nature tours in the kayak, extended kayak rentals, skiff tours, shallow-water fishing, and much more. 
You can’t get much closer to Florida Keys wildlife than by scuba diving, and you can do just that in Big Pine Key with Huckleberry Finn Tours by Captain Matt Finn, Ph.D.

Captain Finn is a specialist in ecological science and an expert on local ecosystems, not to mention a highly trained scuba diver who runs custom tours for vacationers of all experience levels. 

Annual Events Near Big Pine Key Rentals

Due to the town’s small size and sleepy nature, you won’t find very many big festivals and gatherings in Big Pine Key on a regular basis. However, visitors to the area can still enjoy plenty of large-scale celebrations year-round throughout the Florida Keys.

Wildlife lovers and birdwatching enthusiasts are sure to have a blast at the Annual Florida Keys Birding and Wildlife Festival, which takes place each September in Marathon. 
The event occurs at the same time as the Raptor Migration Count, hosted by Hawk Watch International, which celebrates and studies the migration of around 17 species of raptors through the Florida Keys.

Some of the best annual festivals in the Florida Keys are centered on the region’s delicious seafood, and nowhere is this better illustrated than at the Annual Key West Lobsterfest each August. Here, you’ll find some of the freshest seafood dishes in all of the coastal cities, as well as plenty of cold refreshments and live music acts to enjoy.
Wining and Dining in Big Pine Key

When you’re not scuba diving, snorkeling, swimming, or lying on the sand, you’ll need to grab a bite to eat. Luckily, Big Pine Key is home to a variety of distinctive local eateries sure to satisfy every taste and craving.

For classic American fare in a casual, inviting setting, don’t miss a visit to Big Pine Rooster. This establishment features warm wood paneling and outdoor dining options with an expansive menu of juicy steaks, seafood dishes, and savory pastas to choose from.

You’ll have to visit at least one waterfront eatery during your Big Pine Key vacation to get the full Florida Keys experience, and there are several you can choose from in town.

Kiki’s Sandbar Bar & Grille is considered to be one of the best in the area. Located right on the water in Big Pine Key, Kiki’s features classic pub food as well as imaginative cocktails, beer, and wine.


FAQ

How many vacation rentals are there in/around Big Pine Key?

There are 24 Big Pine Key vacation rentals available on FloridaRentals.com. From house rentals to rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Big Pine Key?

There are vacation rentals available in Big Pine Key for as low as $105 per night with an average price per night of $199.

Can I find a vacation rental in Big Pine Key?

Yes, you can find vacation rentals in Big Pine Key close to Bahia Honda State Park, National Key Deer Refuge, and Blue Hole. Don't forget to stop in to Calusa Beach or Artists in Paradise Gallery.

Do any vacation rentals in Big Pine Key have a pool?

Yes, there are 12 vacation rentals with a pool in Big Pine Key on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Big Pine Key vacation rentals on the ocean?

There are 3 oceanfront rentals in Big Pine Key available on FloridaRentals.com. Use our filters to search and book yours today!