Big Pine Key Vacation Rentals

(20 rentals)
booking message booking message

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 ...

View all property information

Property Type

Big Pine Key House

"Great Family Getaway!"

We were very happy with the house and especially with Jeff and Christine . They were very helpful throughout our stay. Property is wonderful and fully accommodates large groups. The pool is fantastic. ...

See all reviews

Show less

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 ...

View all property information

Property Type

Big Pine Key House

Show less

Key Amenities

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

About this property

Wonderful quiet vacation water front (canal) home I have owned for 10 years and loved as a 2nd home the whole time. Remodeled when we purchased it and again post Hurricane Irma.3 bedrooms/ 1.5 bath. Outdoor shower. Great area for hanging out under house for grilling and drinks.Large canal space ...

View all property information

Property Type

Big Pine Key House

Show less

3 BR | 2 BA | Sleeps 7 | Quick View

$267

avg/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 ...

View all property information

Property Type

Big Pine Key House

Show less

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 7 miles to Bahia Honda State Park

$180

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront
  • Private pool

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 ...

View all property information

Property Type

Big Pine Key House

Show less

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • 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, ...

View all property information

Property Type

Big Pine Key House

"Lovely Home on the Beach"

We stayed here for the month of December and thoroughly enjoyed our time. It is centrally located near stores and restaurants. Especially enjoyed our time fishing off the dock and spending time on the ...

See all reviews

Show less

4 BR | 2 BA | Sleeps 8 | Quick View

3

Distance to beach: 3 miles to Bahia Honda Park

$175

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 ...

View all property information

Property Type

Big Pine Key House

"Our Favorite Place to be!"

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 ...

See all reviews

Show less

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 7 miles to Bahia Honda State Park

$259

avg/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 ...

View all property information

Property Type

Big Pine Key House

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

$155

avg/night

View Details

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 ...

View all property information

Property Type

Big Pine Key House

Show less

3 BR | 2 BA | Sleeps 8 | Quick View

$166

avg/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 ...

View all property information

Property Type

Big Pine Key House

Show less

3 BR | 2 BA | Sleeps 6 | Quick View

$150

avg/night

View Details

Key Amenities

  • Air conditioning
  • 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 ...

View all property information

Property Type

Big Pine Key House

Show less

3 BR | 2 BA | Sleeps 8 | Quick View

$245

avg/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 ...

View all property information

Property Type

Big Pine Key House

Show less

3 BR | 1 BA | Sleeps 6 | Quick View

$123

avg/night

View Details

Key Amenities

  • Air conditioning
  • 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

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

$130

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 ...

View all property information

Property Type

Big Pine Key House

Show less

2 BR | 1 BA | Sleeps 4 | Quick View

$121

avg/night

View Details

Key Amenities

  • Air conditioning
  • 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

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

$146

avg/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 ...

View all property information

Property Type

Big Pine Key House

Show less

4 BR | 2 BA | Sleeps 8 | Quick View

$253

avg/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 ...

View all property information

Property Type

Big Pine Key House

Show less

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 ...

View all property information

Property Type

Big Pine Key House

Show less

2 BR | 1 BA | Sleeps 4 | Quick View

$104

avg/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 ...

View all property information

Property Type

Big Pine Key House

Show less

3 BR | 2 BA | Sleeps 6 | Quick View

$122

avg/night

View Details

Key Amenities

  • Air conditioning
  • 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 ...

View all property information

Property Type

Big Pine Key House

Show less

Map
Expand map Close map
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.