Big Pine Key Vacation Rentals

(23 rentals)
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Big Pine Key House
3 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 3 Bedrooms, 2 Bathrooms
1 review

$217

avg/night

$217
avg per night
View Details

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

Featured review

"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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Big Pine Key House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
2 reviews

$125

avg/night

$125
avg per night
View Details

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

Featured review

"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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Big Pine Key House
2 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2.5 Bathrooms

$220

avg/night

$220
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • 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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Big Pine Key House

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Big Pine Key House
3 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 3 Bedrooms, 2 Bathrooms

$330

avg/night

$330
avg per night
View Details

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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Big Pine Key House

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Big Pine Key House
2 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 2 Bedrooms, 2 Bathrooms

$217

avg/night

$217
avg per night
View Details

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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Big Pine Key House

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Big Pine Key House
3 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 3 Bedrooms, 2 Bathrooms
3 reviews

$250

avg/night

$250
avg per night
View Details

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

Featured review

"Great Family Visit"

Had a great trip with the family. House was very clean and well stocked. Canal access was perfect for daily trips out exploring the water! Hoping we can make the time to go back next year.

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Big Pine Key House | On the beach
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 3 Bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront

About this property

A special, calm, and exclusive setting in the lower Florida Keys. Atlantic oceanfront featuring a 150-foot dock with a thatched chickee hut and a naturally occurring sandy beach. Lots with trees encircle the house. Adjacent 200-foot conservation lots are owned by Monroe County. Adjacent to Coupon Bight ...

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Big Pine Key House

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Big Pine Key House
5 BR | 5 BA | Sleeps 13 | Quick View
Sleeps 13, 5 Bedrooms, 5 Bathrooms
3 reviews

$383

avg/night

$383
avg per night
View Details

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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Big Pine Key House

Featured review

"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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Big Pine Key House | On the beach
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms

$145

avg/night

$145
avg per 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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Big Pine Key House

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Big Pine Key House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms

Distance to beach: 10 miles to Bahia Honda

$172

avg/night

$172
avg per night
View Details

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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Big Pine Key House

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Big Pine Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms
3 reviews

Distance to beach: 7 miles to Bahia Honda State Park

$205

avg/night

$205
avg per night
View Details

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

Featured review

"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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Big Pine Key House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms

$175

avg/night

$175
avg per 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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Big Pine Key House

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Big Pine Key House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms
2 reviews

$148

avg/night

$148
avg per 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

Featured review

"Perfect boat and pet friendly home in the Lower Keys"

We thoroughly enjoyed our stay at Palmetto Retreat. The home was spotless and had all the amenities we needed. A couple of menial things didn't work, and Christine (Rudy) took prompt care of them while ...

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Big Pine Key House
2 BR | 1 BA | Sleeps 5 | Quick View
Sleeps 5, 2 Bedrooms, 1 Bathroom

$332

avg/night

$332
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront

About this property

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

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Big Pine Key House

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Big Pine Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms

$150

avg/night

$150
avg per night
View Details

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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Big Pine Key House

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Big Pine Key House
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 2 Bathrooms

$275

avg/night

$275
avg per night
View Details

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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Big Pine Key House

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Big Pine Key House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms

$168

avg/night

$168
avg per night
View Details

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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Big Pine Key House

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Big Pine Key House
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 1 Bathroom

$108

avg/night

$108
avg per night
View Details

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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Big Pine Key House

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Big Pine Key House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 2 Bathrooms

$264

avg/night

$264
avg per night
View Details

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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Big Pine Key House

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Big Pine Key House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms

$150

avg/night

$150
avg per night
View Details

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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Big Pine Key House

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Big Pine Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms

$258

avg/night

$258
avg per 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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Big Pine Key House

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Big Pine Key House
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 1 Bathroom

$135

avg/night

$135
avg per night
View Details

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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Big Pine Key House

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Big Pine Key House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 2 Bathrooms

$197

avg/night

$197
avg per night
View Details

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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Big Pine Key House

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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 23 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 $108 per night with an average price per night of $201.

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 10 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 4 oceanfront rentals in Big Pine Key available on FloridaRentals.com. Use our filters to search and book yours today!