Big Pine Key Vacation Rentals

(16 rentals)
ANGELFISH COVE

3 BR | 2 BA | Sleeps 6 | Quick View

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

Pack your floral shirts, swimming gear and sandals and come on down to Angelfish Cove. Fun is the order of the day. Enjoy the beautiful crystal clear swimming pool (heated) or jump in your boat to go explore some of the best fishing and diving the Florida Keys has to offer. This home offers 70 feet of ...

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Property Type

Big Pine Key House

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MANGO HOUSE

2 BR | 1 BA | Sleeps 4 | Quick View

Key Amenities

  • Air Conditioning
  • Full 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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ISLAND TIME 1

2 BR | 1 BA | Sleeps 4 | Quick View

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

Truly remarkable Big Pine Key vacation home. Rare Duplex on over an acre in the Doctors Arm area. A huge boat basin and direct access to Bogie channel. Rent one or both sides for the best family vacation destination in the Keys.Fully fenced for privacy and lots of yard space for everyone to enjoy ...

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Property Type

Big Pine Key House

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Big Pine Key Retreat

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 7 miles to Bahia Honda State Park

$155

avg/night

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Key Amenities

  • Air Conditioning
  • Full 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

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5 Bedroom 4 Bath Canal Front Home Sleeps 12. (28 day min. rental)

5 BR | 4 BA | Sleeps 12 | Quick View

4

Distance to beach: 4 miles to Bahia Honda

$250

avg/night

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Key Amenities

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

About this property

Large home located on a double lot with plenty of parking and 200 feet of seawall. There is a step down platform for getting in and out of your boat. This area also has whip lines to keep you boat off of the seawall. Quiet neighborhood with convenient access to grocery stores and other services. Large ...

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Property Type

Big Pine Key House

"Big Beautiful House"
Reviewed June 30, 2020

We rented this house to celebrate a birthday. It was the perfect venue for our large family gathering. From the swimming pool to the easy ocean or gulf access, it was very enjoyable and relaxing place. ...

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Best location in the Keys, 150-foot dock, coconut palms on the beautiful beach.

$475

avg/night

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Key Amenities

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

About this property

The charming, oceanfront house directly on the beach. Most beautiful spot in the Keys! Very private, like being on your own tropical island. Coconut palms, 150-foot dock, mooring whips for a flats boat. Turtle nesting beach, Key deer, many tropical birds, and great fishing.  Inshore: tarpon, bonefish, ...

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Property Type

Big Pine Key House

"Gem on Long Beach"
Reviewed January 11, 2021

Our family stayed 3.5 months. Charming home, tastefully appointed. Great indoor/ outdoor spaces. Everything works. Owners are very responsive. Beautiful beach. Fantastic dock with mooring whips allows ...

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SUNSET TIKI

2 BR | 2 BA | Sleeps 4 | Quick View

$150

avg/night

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Key Amenities

  • Air Conditioning
  • Full 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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Our Island Thing

4 BR | 2 BA | Sleeps 8 | Quick View

$216

avg/night

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Key Amenities

  • Air Conditioning
  • Full 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

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WATER'S EDGE

2 BR | 2 BA | Sleeps 4 | Quick View

$122

avg/night

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Key Amenities

  • Air Conditioning
  • Full 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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BREEZE SWEPT

3 BR | 2 BA | Sleeps 6 | Quick View

$211

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront
  • Pet Friendly

About this property

Magnificent open water views in this beautiful 3 Bedroom, 2 bath home on Big Pine Key! This home boasts decor by an award winning Key West decorator. Includes fast access Internet for you to surf the internet quickly in addition to a large screen TV.Enjoy a swim in the new, heated pool after a long ...

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Property Type

Big Pine Key House

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Beautiful Canal Front Pool Home

4 BR | 2 BA | Sleeps 8 | Quick View

3

Distance to beach: 3 miles to Bahia Honda Park

$200

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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

"Our Favorite Place to be!"
Reviewed December 4, 2020

Every year we (two 50+ couples) travel to the Keys in search of adventure and relaxation. We have been guests at Mr. Romanella’s home for 6 years now and could not imagine staying anywhere else! We tried ...

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Big Pine Bliss

2 BR | 2 BA | Sleeps 6 | Quick View

$150

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

One look and anyone would love this exceptional vacation rental on Big Pine Key. This home was just completed in 2019 and has the warmth and comfort of a home well done. Swirling concrete floors with open concept kitchen and top of the line appliances. The large kitchen island is great for entertaining ...

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Property Type

Big Pine Key House

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BLUE HERON

2 BR | 2 BA | Sleeps 4 | Quick View

$105

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

Nice and comfortable 2 bedroom, 2 bathroom vacation home on Big Pine Key in the Eden Pines area. This vacation rental is neat and clean with a 40′ wood boat dock and fish cleaning area to clean all that great, fresh fish you’re gonna catch.Easy ride under some bridges to Pine Channel with ...

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Property Type

Big Pine Key House

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MANATEE BAY

3 BR | 2 BA | Sleeps 6 | Quick View

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

Manatee Bay located in the Port Pine Height area is just the right spot to bring your family and friends for an unbelievable Keys vacation.Great Gulf-side boating is at your fingertips and just a short run out to the Atlantic to fish and dive all the great reef spots. The gulf side waters are full ...

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Property Type

Big Pine Key House

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CONCH OUT

3 BR | 2 BA | Sleeps 6 | Quick View

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

“Conch Out” on your tropical vacation at this spacious and comfortable 3 bedroom, 2 bathroom canalfront home on Big Pine Key.Relax on a swing under your private tiki hut, entertain in the large screened porch with your own built-in grill, or take advantage of the quick, excellent boating ...

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Property Type

Big Pine Key House

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ISLAND TIME 2

3 BR | 1 BA | Sleeps 6 | Quick View

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

Truly remarkable Big Pine Key vacation home. Rare Duplex on over an acre in the Doctors Arm area. A huge boat basin and direct access to Bogie channel. Rent one or both sides for the best family vacation destination in the Keys.Fully fenced for privacy and lots of yard space for everyone to enjoy ...

View all property information

Property Type

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°

Endless fun and nature in Big Pine Key

If you're looking for a low-key vacation, Big Pine Key is the place for you. In Big Pine Key, about 100 miles south of Miami and 30 miles north of Key West, you'll find relaxing, water-borne activities such as boating, fishing, scuba diving and snorkeling. Fishing, of course, means seafood, and you'll find some of the nation’s best seafood restaurants in Big Pine Key and on nearby keys.

When staying in one of our Big Pine Key vacation rentals instead of a traditional hotel, you’ll have much more space and privacy, plus cost savings when booking a property for a large group. Some of our Big Pine Key rentals even come with special amenities like a backyard pool, washer/dryer units, and bicycles. Whether you’re looking for a beach condo with amazing views, or a larger home for space for the entire family, you can find it on our site.

Climate

Whether you visit Big Pine Key during peak summer time or in the middle of the winter, you’re likely to experience beautiful weather. Big Pine Key climate is similar to that of the Caribbean Islands, and temperatures here average 75 degrees Fahrenheit during the winter and in the upper-80s during the summer months. Abundant sunshine and warm water temperatures also appeal to visitors looking for a relaxing getaway. 

Top activities and attractions in Big Pine Key

The main allure of Big Pine Key is its tranquil and scenic environment. The National Key Deer Refuge is home to many endangered species, including fish, plants, birds, and of course, Key deer. This refuge also features a popular area called The Blue Hole, which is a freshwater quarry that sustains many types of wildlife. The area is made up of close to 9,200 acres (3,723 hectares) of land and consists of salt marsh wetlands, pine rockland forests, and mangrove forests. 

Schedule a Big Pine Key snorkeling trip to experience the color and diversity of Florida’s extensive coral reef system. With a variety of coral, a sunken ship and more than 150 species of fish, Looe Key Marine Sanctuary makes an excellent Big Pine Key diving trip. Adolphus Busch contains a wreck just off Big Pine Key that is fully intact, as an ancient cargo freighter was sunk there in 1998.

Many vacationers also make it a point to visit Bahia Honda State Park. The park encompasses more than 500 acres as well as an offshore island where visitors can snorkel, swim, fish or sightsee from a rented kayak. There is also a bicycle path that families can enjoy, while others prefer to put down a towel at the award-winning beach and spend the day watching the waves roll in. The park also has a gift shop, concession stand, kayak rentals and daily snorkeling tours.

The year-round, perfect weather creates many opportunities for fun events and festivals in Big Pine Key. One of the most unique events is the Underwater Music Festival that takes place just south of Big Pine Key. During the event, divers and snorkelers can explore Looe Key Reef while rocking out to a sub-sea concert. The event encourages coral reef protection while music is piped underwater.

The Big Pine Island Arts Festival is another popular event. It takes place in late November and features live music and crafts made by local artisans. Kids can enjoy activities in the Kids’ Corner, and everyone can indulge in the food and drink available at the yearly festival.

Restaurants and Bars

Get your grub on at Big Pine Rooster, a highly-rated restaurant serving up all sorts of American favorites, including the freshest seafood. Good Food conspiracy is a roadside diner that excels at almost everything. You’ll love the juice bar! For the best coffee and sandwiches, check out Cuba Coffee where you can get some Cuban flavor. Lastly, the reviews of the cobb salad at No Name Pub are particularly glowing - try it!

Why you should book an Big Pine Key rental on FloridaRentals.com

Booking a Big Pine Key vacation rental on FloridaRentals.com can save you up to 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Happy planning!