Big Pine Key Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Big Pine Key

Old Wooden Bridge Resort and Marina
2.5 star property
8.6 out of 10, Excellent, 133 reviews
"We enjoyed our stay at Old Wooden Bridge. "
The price is AU$235
per night
23 June - 24 June
Old Wooden Bridge Resort and Marina
Tropical Caribbean Wonderland
9.2 out of 10, Wonderful, 75 reviews
"Property was excellent and host was very responsive. Rained for most of our trip and this place was our safe haven for the week. The restaurant next door also had great food and friendly staff and was within walking distance. Would definitely stay here again."
Tropical Caribbean Wonderland
Keys 3 Bedroom Corner Home near Beach & Key West
9.4 out of 10, Exceptional, 3 reviews
"Absolutely lovely property. The only thing we regretted was not having more time to spend there. We loved the nearby restaurant called “The Boardwalk Pub & Grill. They have a very friendly staff and they’re very accommodating in the changes they make to their menu."
The price is AU$1,091
per night
26 June - 27 June
Keys 3 Bedroom Corner Home near Beach & Key West
Save an average of 15% on thousands of hotels when you're signed in
Skipjack Resort & Marina
3.0 star property
8.6 out of 10, Excellent, 1,100 reviews
"Good hotel ! Rooms are in great condition "
The price is AU$387
per night
23 June - 24 June
Skipjack Resort & Marina
Aqua Lodge Rentals At Coconut Cay
3.5 star property
9.6 out of 10, Exceptional, 106 reviews
" Very cool and very clean place. We saw a dolphin one morning off the back, a jelly fish and a huge manatee another day. A/C was great and place was furnished with all the essentials. Our only complaint was the shower, very poor water pressure and drained slowly as well. Other than that we enjoyed our stay for something different than a standard hotel. Would stay here again "
The price is AU$366
per night
24 June - 25 June
Aqua Lodge Rentals At Coconut Cay
Tropical Cottages
3.0 star property
8.4 out of 10, Very good, 697 reviews
"Was only 1 night as we traveled through the area. Was clean, people were friendly. "
The price is AU$218
per night
23 June - 24 June
Tropical Cottages
Yacht Haven Marina
3.5 star property
9.8 out of 10, Exceptional, 52 reviews
"House boat on the water"
The price is AU$276
per night
24 June - 25 June
Yacht Haven Marina
Knight's Key Suites
3.0 star property
9.0 out of 10, Wonderful, 1,034 reviews
"Friendly staff and easy to use. Loved it there, would recommend to others. "
The price is AU$199
per night
24 June - 25 June
Knight's Key Suites
Cabins at Bonefish Bay
3.0 star property
10.0 out of 10, Exceptional, 10 reviews
"Cabin was very clean and nice. "
Cabins at Bonefish Bay
34’ Catamaran Sailboat
9.4 out of 10, Exceptional, 25 reviews
"Friendly, easy access and close to desired destination "
34’ Catamaran Sailboat
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, 206 reviews
"Location was great to Key West as well as access to grocery stores. The view from the dock was spectacular. The pool was a bit small but it was not a problem as there were not alot of guests in the pool at one time. The door handle to the oven was quite loose but Melanie got it fixed quickly. Some other minor problems were the following: the clicker to open the gate didn't work, the door lock worked for 2 days but then stopped working, the can opener didn't work which was an issue because we...
The price is AU$669
per night
11 July - 12 July
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
9.8 out of 10, Exceptional, 189 reviews
"This place was awesome. Location was great. The only real problem I had was that "my" bed did not make the trip with us. No matter where I stay, my bed at home is always more comfortable. There is no way to fix this. It is my own personal demon. Everything was as described. The manager was easy to communicate with. I give it a 6 out of 5 stars."
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Old Florida Style, wrap around porch, boat basin for dockage, open water
9.8 out of 10, Exceptional, 47 reviews
"So glad we found this location. Nice and peaceful but close to anything we needed. Sitting on the porch was so relaxing, watching boats go by. The house was very comfortable. Only wish the 2nd bedroom had a working TV. Our host was quick to answer any issue we had and left some great suggestions on places to eat. I would definitely return to enjoy this beautiful location"
Old Florida Style, wrap around porch, boat basin for dockage, open water
Life in Paradise w/ Boat Slip at #1 Rated Resort in Marathon - Coral Lagoon
10.0 out of 10, Exceptional, 191 reviews
"We just wanted a short vacation getaway. It was great. We rented a boat and spent our time in the water. Great time with friends."
Life in Paradise w/ Boat Slip at #1 Rated Resort in Marathon - Coral Lagoon
Authentic And Charming Little Cottage 60 Ft From The Ocean
9.8 out of 10, Exceptional, 170 reviews
"The description was very accurate, price was very fair and accommodations served our needs and purpose!"
Authentic And Charming Little Cottage 60 Ft From The Ocean
Southern Diversion Estate-see our reduced rates
10.0 out of 10, Exceptional, 82 reviews
"We were celebrating my wife’s 40th birthday. There were 17 people in our group. Adults and children. Something for everyone to do. We enjoyed relaxing at the property by the pools, fishing from the dock, kayaking and paddle boarding. We went scuba diving with better than most scuba, deep sea fishing on the tail walker. We hired chef Heather for several dinners. It was an amazing trip."
Southern Diversion Estate-see our reduced rates
No Name Cottage- Close to everything you need in Marathon
10.0 out of 10, Exceptional, 14 reviews
"The house was beautiful and everything we needed was right there. If I could have changed anything about the house, it would be to add a dresser in each bedroom. I'm not a live out of a suitcase kind of girl. So having a place to put my clothes that don't hang up would be nice. But, it had very large closets in each bedroom. Thank you for everything. God Bless! Teresa G."
No Name Cottage- Close to everything you need in Marathon
Comfortable Waterfront Vacation Rental
9.4 out of 10, Exceptional, 140 reviews
"Lynn was an excellent host. Very quick to respond to any questions you may have. The check in process with the resort leaves a lot to be desired. Security is not friendly nor very helpful. The neighbors we interacted with were very friendly. "
Comfortable Waterfront Vacation Rental
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
9.6 out of 10, Exceptional, 39 reviews
"Ww stayed for 6 nights as our first time in the Keys. The property is very well manicured with everything you'll need. We had a small issue with one cottage that was quickly rectified by the owners. Hope Nd Glenn were terrific! Not sure if we'll ever return to the Keys, but we highly recommend The Hidden Hammick to anyone visiting the area."
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!
10.0 out of 10, Exceptional, 181 reviews
"We found your place on Vrbo and It was fantastic! The place we stayed was everything we needed. Relaxing , beautiful the view was beautiful and the beach is very nice and great chairs to relax, and take in the beauty! Micheal was amazing host and very helpful to help with ideas where to eat, get groceries, and just so Grateful he alllowed us to stay and enjoy 30 years. Loved just a short walk to sunset park to watch the beautiful view of sunset !!! If looking for a place to relax and enjoy a...
One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!
Don't see what you're looking for?
See all available properties in Big Pine Key
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Big Pine Key you may be interested in

Old Wooden Bridge Resort and Marina
2.5 star property
8.6 out of 10, Excellent, 133 reviews
"We enjoyed our stay at Old Wooden Bridge. "
The price is AU$235
per night
23 June - 24 June
Old Wooden Bridge Resort and Marina
Barnacle Bed and Breakfast
2.0 star property
8.0 out of 10, Very good, 15 reviews
"The location of the property was great and we saw the key deer on property and nearby. The room and bathroom were very nicely decorated and clean. The bed was comfortable. The beach front area had some trash that needed to be picked up and the home could use some landscaping. We did not stay for the continental breakfast so can not speak to that. Check in was a little challenging; I did not receive the e-mail day before check-in that I was expecting but did receive a phone call. However,...
The price is AU$351
per night
9 July - 10 July
Barnacle Bed and Breakfast
Tropical Caribbean Wonderland
9.2 out of 10, Wonderful, 75 reviews
"Property was excellent and host was very responsive. Rained for most of our trip and this place was our safe haven for the week. The restaurant next door also had great food and friendly staff and was within walking distance. Would definitely stay here again."
Tropical Caribbean Wonderland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Big Pine Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Big Pine Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Big Pine Key holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Big Pine Key holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Big Pine Key. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Big Pine Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Big Pine Key holiday rentals we have selected for you start as low as AU$199 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Big Pine Key rentals

At Expedia, we put the best Big Pine Key holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Big Pine Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Big Pine Key holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Big Pine Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Big Pine Key?

Yes, there are holiday rentals in Big Pine Key close to Key West Visitors Center, or you can select a more secluded option if you're looking for a relaxing stay. Big Pine Key is known for its beaches.

What are some of the best holiday rentals that Big Pine Key has to offer?

Aqua Lodge Rentals At Coconut Cay: This holiday home rental outside of Big Pine Key is located near the beach, and offers an outdoor pool, air conditioning and daily housekeeping to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave.

How many holiday rentals are there in Big Pine Key?

With 148 Expedia holiday rentals, you're guaranteed to find just the right place for your Big Pine Key stay.

What can I see and do in Big Pine Key?

Family-friendly attractions include Key West Visitors Center and Blue Hole, whereas Calusa Beach and Bahia Honda State Park are a couple of great spots to enjoy the outdoors. Other places in town to visit include Florida Keys Beaches and Cook Island.

What are holiday rentals like in Big Pine Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Big Pine Key. Holiday rentals feature extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy reception areas while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family trip.

Recent reviews of Big Pine Key properties
Expedia verified reviews