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Big Pine Key

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Vacation Rentals in Big Pine Key, Florida Keys

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Big Pine Key Vacation Rental

Big Pine Key and its neighboring islands are some of the most popular vacation destinations for families who want to rent a beachfront house or condo. The climate in this part of Florida is delightful and very similar to the warm and pleasant climates of the Caribbean. The crystal blue waters and the white sandy beaches in Big Pine Key make this an impressive location for your next vacation rental.

Things to Do

Big Pine Key is a fantastic place to come if you want to get away from all the troubles and stress of day-to-day life. The vacation houses and condos available here are designed for rest and relaxation. The main appeal of Big Pine Key is the tranquil environment and beautiful scenery. There are plenty of outdoor activities that you can enjoy when you’re not in your rental home, such as fishing, walking and biking, and seeking out wildlife.

Many people visiting Big Pine Key enjoy getting out into the ocean for excellent snorkeling and diving. Looe Key is located approximately 7 miles off shore and provides the perfect location to see stunning sea life. It is widely regarded as one of the clearest and best reefs for snorkeling and diving in the Keys.

Family Fun

If you’re visiting Big Pine Key with children, there are numerous wonderful activities that will get them out of the rental home for the day. The Theater of the Sea and the National Key Deer Refuge are great options for the whole family. If you would like to spot some of the many alligators that reside in the area, then you should head to the Blue Hole.

Delicious Dining in Big Pine Key

If you’re staying in a vacation home in Big Pine Key, you may choose to dine in and enjoy a quiet intimate or pizza with the family. There are many local groceries where you can purchase fresh seafood and produce to prepare a meal in your condo or villa. However, if you do fancy a meal out, you can take a trip to Rob’s Island Grill, The Big Pine Restaurant, or The China Garden. All of these restaurants are local and provide culinary delights.

Benefits of Big Pine Key Rentals

Unlike a hotel, staying in a Big Pine Key vacation rental provides you with complete privacy and tranquility during your vacation. Enjoy the space and security you can get from your own beautiful rental home.

 
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Nearby rentals
Marathon (54)
Key Colony Beach (40)
Cudjoe Key (9)
Summerland Key (5)
Sugarloaf Key (4)
Little Torch Key (3)
Ramrod Key (1)
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Traveller Rating | Price / nt | Price / wk | Bedrooms | # of photos | # of reviews | Just Added
1-20 of 23
Bed and Breakfast on Big Pine Key in Florida Keys, Big Pine Key
Florida, Florida Keys, Big Pine Key Holiday Rentals
Bed and Breakfast on Big Pine Key in Florida Keys
Slideshow
4 of 5 stars 2 reviews
  • Guest Room
  • 4 Bedrooms, sleeps 2
  • 4 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
159 AUD - 210 AUD
Minimum rental - 2 nights
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Fishermans Paradise. Fun for everyone. Pure Bliss., Big Pine Key
Florida, Florida Keys, Big Pine Key Holiday Rentals
Fishermans Paradise. Fun for everyone. Pure Bliss.
Slideshow
4.5 of 5 stars 2 reviews
  • Holiday Rental House
  • 5 Bedrooms, sleeps 10
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Week:
3,592 AUD - 5,131 AUD
Month:
14,368 AUD
Minimum rental - 1 week
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Quiet Canal Front Home, Big Pine Key
Florida, Florida Keys, Big Pine Key Holiday Rentals
Quiet Canal Front Home
4 of 5 stars 1 review
  • Holiday Rental House
  • 1 Bedroom, sleeps 4
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
2,053 AUD
Month:
2,053 AUD - 2,566 AUD
Minimum rental - 1 night
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Captain Ron's Keys Caribbean Retreat, Big Pine Key
Florida, Florida Keys, Big Pine Key Holiday Rentals
Captain Ron's Keys Caribbean Retreat
Slideshow
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Week:
1,001 AUD - 1,078 AUD
Month:
2,566 AUD - 2,771 AUD
Minimum rental - 5 nights
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Big Pine Key Bay view canal front home, Big Pine Key
Florida, Florida Keys, Big Pine Key Holiday Rentals
Big Pine Key Bay view canal front home
Slideshow
  • Holiday Rental House
  • 3 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Month:
3,284 AUD
Minimum rental - 30 nights
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The following rentals are within 15 kilometres of Big Pine Key, Florida Keys, Florida.

A tropical paradise in the florida keys, Cudjoe Key
Florida, Florida Keys, Cudjoe Key Holiday Rentals
A tropical paradise in the florida keys
Slideshow
4.5 of 5 stars 2 reviews
  • Holiday Rental House
  • 2 Bedrooms, sleeps 4
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
133 AUD - 220 AUD
Week:
924 AUD - 1,539 AUD
Month:
3,079 AUD - 3,592 AUD
Minimum rental - 1 week
Check availability
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Little Sleeves End, Little Torch Key
Florida, Florida Keys, Little Torch Key Holiday Rentals
Little Sleeves End
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 3 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
205 AUD
Week:
1,334 AUD
Month:
5,131 AUD
Minimum rental - 4 weeks
Check availability
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Florida Keys Waterfront Getaway, Ramrod Key
Florida, Florida Keys, Ramrod Key Holiday Rentals
Florida Keys Waterfront Getaway
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
205 AUD
Week:
1,437 AUD
Month:
3,695 AUD
Minimum rental - 1 week
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Lower Keys Paradise- 2/2 on water near Key West, Cudjoe Key
Florida, Florida Keys, Cudjoe Key Holiday Rentals
Lower Keys Paradise- 2/2 on water near Key West
Slideshow
4.5 of 5 stars 6 reviews
  • Holiday Rental House
  • 2 Bedrooms, sleeps 4
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Week:
924 AUD - 1,026 AUD
Minimum rental - 3 nights
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Island Living, Summerland Key, FL
United States, Florida, Summerland Key Holiday Rentals
Island Living
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 3 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
292 AUD
Month:
5,131 AUD
Minimum rental - 1 night
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Tropical Paradise Oceanfront Home with Pool, Cudjoe Key
Florida, Florida Keys, Cudjoe Key Holiday Rentals
Tropical Paradise Oceanfront Home with Pool
Slideshow
4.5 of 5 stars 3 reviews
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
338 AUD
Week:
2,360 AUD
Minimum rental - 1 night
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Beautiful spacious home with pool and ocean views, Cudjoe Key
Florida, Florida Keys, Cudjoe Key Holiday Rentals
Beautiful spacious home with pool and ocean views
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 3 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Month:
5,131 AUD - 6,158 AUD
Minimum rental - 1 week
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White Ibis Inn, Oceanview Private Estate, Cudjoe Key
Florida, Florida Keys, Cudjoe Key Holiday Rentals
White Ibis Inn, Oceanview Private Estate
Slideshow
4.5 of 5 stars 10 reviews
  • Holiday Rental House
  • 6 Bedrooms, sleeps 14
  • 3 Bathrooms
  • Owner
EMAIL OWNER
Night:
530 AUD
Week:
3,489 AUD - 4,310 AUD
Minimum rental - 5 nights
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Secluded Hideaway, Summerland Key, FL
United States, Florida, Summerland Key Holiday Rentals
Secluded Hideaway
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
235 AUD
Week:
1,642 AUD
Minimum rental - 1 night
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Oceanfront 5 star Home Beach area Heated Pool, Cudjoe Key
Florida, Florida Keys, Cudjoe Key Holiday Rentals
Oceanfront 5 star Home Beach area Heated Pool
Slideshow
4.5 of 5 stars 13 reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 10
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Night:
359 AUD
Week:
1,847 AUD - 3,028 AUD
Minimum rental - 1 week
Check availability
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Oceanfront Rental on Summerland Key, Florida, Summerland Key, FL
United States, Florida, Summerland Key Holiday Rentals
Oceanfront Rental on Summerland Key, Florida
Slideshow
4.5 of 5 stars 2 reviews
  • Holiday Rental House
  • 4 Bedrooms, sleeps 10
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Week:
2,258 AUD
Month:
6,158 AUD
Minimum rental - 1 week
Check availability
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Family Retreat Oceanfront Home with Pool, Cudjoe Key
Florida, Florida Keys, Cudjoe Key Holiday Rentals
Family Retreat Oceanfront Home with Pool
Slideshow
3.5 of 5 stars 1 review
  • Holiday Rental House
  • 6 Bedrooms, sleeps 12
  • 4 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
440 AUD
Week:
3,079 AUD
Minimum rental - 1 night
Check availability
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Barry Beach - 4/3 Keys Cottage, Open Water, Pool, Little Torch Key - JUST ADDED
Florida, Florida Keys, Little Torch Key Holiday Rentals
Barry Beach - 4/3 Keys Cottage, Open Water, Pool
Slideshow
  • Holiday Rental House
  • 4 Bedrooms, sleeps 8
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
513 AUD
Week:
3,079 AUD
Month:
8,210 AUD
Minimum rental - 3 nights
Check availability
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Oceanfront Estate on Beautiful Summerland Key, Summerland Key, FL
United States, Florida, Summerland Key Holiday Rentals
Oceanfront Estate on Beautiful Summerland Key
Slideshow
  • Holiday Rental House
  • 3 Bedrooms, sleeps 10
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Week:
2,566 AUD - 4,618 AUD
Month:
7,697 AUD - 13,855 AUD
Minimum rental - 1 week
Check availability
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Pool, Dock, Sandy Beach, Privacy, Open Water, Summerland Key, FL - JUST ADDED
United States, Florida, Summerland Key Holiday Rentals
Pool, Dock, Sandy Beach, Privacy, Open Water
Slideshow
  • Holiday Rental House
  • 7 Bedrooms, sleeps 14
  • 5 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
1,026 AUD
Week:
5,644 AUD
Month:
20,525 AUD
Minimum rental - 3 nights
Check availability
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1-20 of 23

Big Pine Key Holiday Rental Advice

Things to do on Big Pine Key
Posted by ErnestD, 23 Dec 2008
... keys: if you prefer a vacation rental to a motel or B&B, the local authorities have made it so you can't rent a house for less than a month. If you find someone who will rent you their house for a week or whatever, they are doing it ... more
First time visit to Miami and Florida keys
Posted by bornwithwheels, 20 Apr 2012
... somewhere like the Reef Resort Condo's in Marathon, Conch Key Cottages or Coral Bay in Islamorada would work for you. Those places are more old Florida style. There are resorts like Tranquility Bay & Cheeca Lodge but I like the smaller places myself. There are flights to the Bahama's ... more
fishing/spearfishing/lobstering around Big Pine
Posted by waterdaughter, 13 Dec 2007
... and I have rented a condo on Big Pine at the end of Feb. 2008. We stayed on Ramrod last year and had a great time! There was some conflicting advice as far as locations appropriate for fishing/spearing and lobstering (read that to mean LEGAL locations! The Coast Guard ... more
Key West Vacation Rentals
Posted by brodieDublin, 20 Jan 2012
www.historichideaways.com www.athomeinkeywest Or check holiday Rentals to the left! ... more
kays in april
Posted by flipflopsrule, 8 Jan 2012
Contact Andi Saylor at Keys Holiday Rentals. ... more
Is TravelFurnish.com a reputable agency?
Posted by jess j, 11 Feb 2012
... whole experience renting from a vacation rental by ... ... that people think renting a vacation rental by owner is like going to a hotel and it is not. When I checked in I was told that this condo does not operate like a hotel. The owners here are renting them out ... more
Posted by Julius C, 20 May 2012
... was trying to find a vacation rental through flipkey, and found this gorgeous apartment in Times Square area for 259/night, so I decided to ask for the availability. The owner/host Dave Jennings replied back with a gmail account (tripolot@gmail.com) and linked me to travelfurnish.com for ... more
Friends of Bill Wilson
Posted by Stephen H, 30 Apr 2012
Any friends of Bill Wilson renting Condo? We are 4 non-drinkers, non-smokers looking for vacation rental with 2 BR and 2 BA 8/11/2012 - 8/18/2012. Thanks & Peace! ... more
Chosing where to stay for 1 week, help!
Posted by bluewater, 30 Apr 2012
No all inclusives (except Little Palm Island). A resort or vacation rental? That's really up to you and what you like and don't like. It's best to stay with what you like. You can wander at will with a resort too. ... more
dove creek lodge, key largo marriott, or hampton inn
Posted by Kimdrake26, 23 Apr 2012
Check out the vacation rentals on TA, My boyfriend and I went in this same circle trying to choose betwene these 3 hotels (none looking too spectacular, especially for the price they wanted!). Out of curiosity I started looking at what a vacation rental would cost. We wound up booking ... more
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