Daily Rentals & Vacation Rentals in the Florida Keys & Key West

Search for Vacation Rental Homes or Hotels

           
Best Prices Booking


Vacation Places To Stay We have chosen to partner with Booking.com to offer travelers the best choices for vacation properties - No Booking Fees, Last Minute Room Availability, 2,146,000+ hotels, apartments, villas, condo rentals and more....

Rentals in Florida Keys

Don't know Where To Stay? Select your destination and search for discount accommodations.

If you don't see your travel destination, just type it in the box and search for hundreds of Hotels, Resorts, Motels, Homes, Villas or Condos and more!

Cheap Hotels Florida Keys

Trying to save money on your vacation? VacationPlacesToStay.com has great deals and low prices on vacation rentals & hotels, Best Price Guaranteed.

Save when you book directly online for last minute deals with 3 to 5 Star Resorts, Inns, Hotels and more!


Book Direct Here for daily Vacation Home Rentals in the Florida Keys and Key West

Book Your Vacation Homes Directly Online Here and Save!

We have partnered with a major provider for Vacation Rentals by Owner, directly through Vacation Places To Stay. There are many home rentals to choose from, and we now have the selection and value to offer our visitors going to Florida Keys. Browse hundreds of Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer.

Big Pine Key house

Big Pine Oasis

Explore the Keys! Canal Front Property - Beautiful Sunsets

Conveniently located 10 miles from Bahia Honda State Park, 26 miles from Key West, 17 miles from Marathon, washer and dryer, dishwasher, microwave and oven/stove, direct tv, BBQ grill, outdoor shower, 2 car parking, in a quiet safe neighborhood. 52' ....

2 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 4
Big Pine Key, FL

View Vacation Home

Big Pine Key house

Skelley House

Skelley - Quiet Cottage on corner canal

This 3 bedroom 2 bath home located on Big Pine Key is perfect for your Florida Keys Get-A-Way. Tropical canal front resort style home. Enjoy a beautiful open living room and kitchen, large lanai area with views of the canal and tropical landscape. ....

3 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 7
Big Pine Key, FL

View Vacation Home

Big Pine Key house

Casa Del Mar

Welcome to Casa Del Mar

Welcome to "Casa Del Mar" a brand new mid-century modern home in Paradise! This home is a monthly vacation rental that must be rented for 28 days or greater. Quiet neighborhood , pool on deck. You can enjoy stunning oceanfront views from almost ever ....

3 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 12
Big Pine Key, FL

View Vacation Home

Big Pine Key mobile home

Pelican Cove

Keys paradise hidden gem. Only 30 miles from Key West. Relax Relax Relax!

Located just 5 miles from Bahia Honda park rated top 5 beaches in the nation Located just 30 miles from famous Key West. Near Looe Key one of the worlds most beautiful snorling reefs. Enjoy the Key deer as they frequently come through this spacious s ....

3 Bedroom(s) 3 Bath(s) Mobile Home - Sleeps 6
Big Pine Key, FL

View Vacation Home

Big Pine Key house

Captain D's Hideout

Captain D's Hideout - Beautiful waterfront home in the heart of a deer preserve

Beautiful, well maintained canal front home at the end of Big Pine Key. Surrounded by the Key Deer National Refuge. Wake up to Key Deer in your back yard. Only 30 miles from Key West and Duval Street. Concrete, step-down dock. Bring your boat. ....

2 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL

View Vacation Home

Big Pine Key house

Vacation Home

Mickey and Lynn's House of Windows

Secluded two story above garage corner lot gives you a panoramic views of water and near by park. Key deer frequent the property on this lovely sanctuary. Over a hundred feet of dock space and cleaning table. Secluded but convenient, located close ....

3 Bedroom(s) 3 Bath(s) Vacation Rental
Big Pine Key, FL

View Vacation Home

Big Pine Key house

Sunrise on Tropical Bay

Recently remodeled 4 bedroom

Remodeled Ocean front with Boating and a POOL . This 4 bedroom, 3 1/2 bath, fully-furnished home is right on Bogie Channel on Big Pine Key. It has full ocean access and the time you spend exploring the Lower Key’s back country will be time you will ....

4 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 8
Big Pine Key, FL

View Vacation Home

Big Pine Key house

Blue Heron Estate

Awesome Open Water View at Blue Heron Estate

Hurricane repairs are complete for the Blue Heron Estate. This is a 15 acre open water property with a 4 bedroom/4 bath house, a large pool and 70' of protected dockage. The grounds are a little rough but the views from the house of the open water an ....

4 Bedroom(s) 5 Bath(s) Vacation Rental - Sleeps 10
Big Pine Key, FL

View Vacation Home

Big Pine Key house

~CASA AZUL~

~CASA AZUL~ Brand new construction, deep water canal with pool!!!

OPEN WATER VIEWS FROM ALL ANGLES AND BALCONIES! Meticulously designed Keys home with exquisite furnishings throughout home, quartz counter tops and top of the line stainless steel appliances. This brand-new home has a lovely open & entertaining feel ....

4 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 13
Big Pine Key, FL

View Vacation Home

Big Pine Key recreational vehicle

Tropical Caribbean Wonderland

Tropical Caribbean Wonderland

Note: This is a new unit the other RV from the reviews was damaged by Irma and this is the NEW replacement unit it is AWESOME..!!! We are located in a beautiful RV wooded park, with endangered Key Deer everywhere you look. We have a nice Pool and cl ....

2 Bedroom(s) 1 Bath(s) Recreational Vehicle - Sleeps 4
Big Pine Key, FL

View Vacation Home

Big Pine Key house

Big Pine Escape in Doctors Arm

Big Pine Escape Fishing Paradise, Ocean-Access Canal Quiet Doctors Arm

The property has direct access to the Atlantic Ocean or the Gulf in minutes, providing some of the finest bluewater fishing coupled with backwater bonefish and permit fishing rivaled to none. The Loe Key National Park, famous for it's crystal clear ....

2 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL

View Vacation Home

Big Pine Key house

Palm Ave 3/3

Experience the Keys like a Local at this Spacious Canal Front Home with Dock!

This lovely waterfront home is located on mile marker 29, on the ocean side of Big Pine Key. Just 40 minutes from Key West, this hidden gem offers quiet relaxation, while still close enough to enjoy the party atmosphere of Key West! Dock your boat o ....

3 Bedroom(s) 3 Bath(s) Vacation Rental
Big Pine Key, FL

View Vacation Home

Big Pine Key house

Vacation Home

Gulf and Atlantic access fishing and diving paradiss

Large and comfortable home located on canal with direct Bluewater access 10 min to Atlatic. 3 spacious bedrooms, great sleeping setup for kids. 3 minutes to grocery and shopping in big pine including dive store and tackle shops. 25 minute drive to Ke ....

3 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 8
Big Pine Key, FL

View Vacation Home

Big Pine Key house

Vacation Home

New Listing! Beautiful Canal front , Key Deer and jacuzzi.

-Remodeling house 3 bedroom and 3 bath. -Please note that there is a 28 minimum rental period for this property. - Boat lift , dock and fish cleaning station. -Excellent access to Atlantic and Gulf, minutes to the best lower keys fishing in coun ....

3 Bedroom(s) 3 Bath(s) Vacation Rental
Big Pine Key, FL

View Vacation Home

Big Pine Key house

Catlin By The Sea

Catlin By The Sea Excellent Boating Location for Ocean and Back County Access

This canal front comfortable home is nestled in the North East Corner of Big Pine Key. Endangered Key Deer, found only in the keys, roam about the neighborhood as well as many other wildlife species. This property offers excellent boating with dire ....

3 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 6
Big Pine Key, FL

View Vacation Home

Big Pine Key house

Bogie Cottage

Fabulous boating access on Big Pine Key

Great spot for boaters! Newly remodeled and nicely appointed 2 bedroom/2 bath home on Big Pine Key. The master bedroom has a queen-sized bed, en-suite bath and walk-in closet. The second bedroom has two twin beds and ample storage. There's cable TV a ....

2 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 4
Big Pine Key, FL

View Vacation Home

Big Pine Key house

Pine Channel Getaway

BIg Pine Key New House 75 ft dock 250 feet from open waters of Pine Channel

Welcome to our new spacious 3 bedroom 2 full bath home on a wide deep water canal with a 75 foot dock only 250 feet from the peaceful open waters of Pine Channel. Our comfortable 10 ft by 20 ft rear deck offers breath taking expansive views of the pe ....

3 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 8
Big Pine Key, FL

View Vacation Home

Big Pine Key house

Vacation Home

....

5 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 11
Big Pine Key, FL

View Vacation Home


© Reservations Direct, Inc. - Florida Keys & Key West Vacation Rentals, Hotels & Resorts

About Us - Privacy - Top Florida Destinations - Best Vacation Spots - Car Rentals