Big Pine Key Holiday Rentals

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Holiday Rentals in Big Pine Key

Cottage in Punta Brisa

2.5 star property
8.6 out of 10, Excellent, (271)
"We will definitely stay here again. Perfect spot to relax. Clean Rooms "
United States
Gregory
Old Wooden Bridge Resort and Marina

Holiday Home in Sands

The price is AU$885
includes taxes & fees
23 Nov - 24 Nov
Charming 3-bedroom house in Big Pine Key near Beach and Key West

Houseboat in Marathon

3.5 star property
9.8 out of 10, Exceptional, (224)
"Nice Lodge nice area close to grocery store & shops, will love to stay there again."
United States
Xiomeidy
Yacht Haven Marina

Aparthotel in Marathon

3.0 star property
8.6 out of 10, Excellent, (1209)
"Had a great time in Marathon. Nice accommodations, very friendly staff."
Canada
Brenda
Skipjack Resort & Marina

Cottage in Marathon

3.0 star property
8.6 out of 10, Excellent, (903)
"Beautiful place, conveniently located "
United States
Clifton
The price is AU$165
includes taxes & fees
30 Nov - 1 Dec
Tropical Cottages

Cabin in Marathon

3.0 star property
9.6 out of 10, Exceptional, (77)
"The staff were very nice. The place was clean. We stayed in aqua 2, the view wasn’t great but by no means bad. Just be prepared for the noseeums, they could ruin your trip!"
United States
Shanna
Cabins at Bonefish Bay

Holiday Home in Marathon

2.5 star property
9.0 out of 10, Wonderful, (111)
"It was my first time staying there but it won’t be my last."
United States
Dennis
The Hammocks at Marathon

Aparthotel in Marathon

3.0 star property
9.0 out of 10, Wonderful, (1155)
"Room were clean and staff was very helpful "
United States
Leonard
The price is AU$204
includes taxes & fees
30 Nov - 1 Dec
Knight's Key Suites

Houseboat in Marathon

3.5 star property
9.6 out of 10, Exceptional, (192)
"Clean room, spacious, nice and quiet. "
United States
Douglas
Aqua Lodge Rentals At Coconut Cay

Holiday Home in Marathon

9.0 out of 10, Wonderful, (32)
"So enjoyed our stay here with a couple friends. Place has everything you need, is immaculate, fantastic view, and so close to either the beach in one direction and grocery stores in the other. Also located in a very nice residential neighborhood. Plan on returning! Thanks for the lovely stay!! "
United States
Debbie T.
Waterfront home with dock, pool table & private pool - walk to Sombrero Beach

Condo resort in Marathon

4.0 star property
Marlin Bay Resort & Marina

Villa in Marathon

9.4 out of 10, Exceptional, (121)
"Quiet and friendly "
United States
Damon J.
TF Pool Beach Kitchen Sleep 6, Hot Tub W&D Marina WiFi Parking

Holiday Home in Marathon

10.0 out of 10, Exceptional, (73)
"Loved the location and this home was the perfect place to spend a week with the family!! "
United States
Diana W.
Outstanding pool and outdoor area 5 minute walk to beach!

Holiday Home in Little Torch Key

9.6 out of 10, Exceptional, (85)
"The secluded dock is a nice feature. The driveway is tricky to exit. "
United States
drywall c.
The price is AU$1,234
includes taxes & fees
24 Nov - 25 Nov
Old Florida Style, wrap around porch, boat basin for dockage, open water

Holiday Home in Summerland Key

8.2 out of 10, Very good, (98)
"Thank you so much for the great stay! The ocean view was beautiful! The landscaping with surrounding trees and flowers was lovely! The house was comfortable and had everything that we needed. It was perfect for our family!"
United States
Deidra B.
Private Secluded Ocean View & Pool Near Key West

Holiday Home in Marathon

8.0 out of 10, Very good, (1)
"Great Home & Location & Enjoyable Stay! Thanks!"
United States
James J.
The price is AU$953
includes taxes & fees
23 Nov - 24 Nov
Charming 2-bedroom house in Marathon with pool

Holiday Home in Marathon

9.6 out of 10, Exceptional, (25)
"Very nice and spacious property. Plenty of amenities. Host is super responsive and helpful. "
United States
Brad M.
Extraordinary waterfront custom home, pool 56'dock ,ice machine,kayaks,bikes,ect

Holiday Home in Marathon

10.0 out of 10, Exceptional, (75)
"Being close to sombrero beach was our goal. The house itself was so perfect we barely left. Great stay"
United States
Timothy G.
FALL 2025~399/NT~NO HLDY Wk~Fish, Swim, Relax! Pool & Dock – Perfect 4 Families~

Cottage in Little Torch Key

8.6 out of 10, Excellent, (192)
"Great location"
United States
Kimberly W.
Direct Oceanfront Cottage-Sunrise View- #2,

Cottage in Cudjoe Key

8.8 out of 10, Excellent, (73)
"It was ok for what we needed. Needs some repairs though."
United States
Craig M.
The price is AU$513
includes taxes & fees
22 Nov - 23 Nov
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
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.

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Find out more about Big Pine Key

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$165 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 Blue Hole, 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?

The Hammocks at Marathon: This holiday home rental outside of Big Pine Key is located by the ocean, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities such as a microwave and a coffee maker can make your holiday run smoothly. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in Big Pine Key?

With 147 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 Blue Hole and Big Munson Island, whereas Calusa Beach and Florida Keys Beaches are a couple of great spots to enjoy the outdoors. Other places in town to visit include Bahia Honda State Park and Big Pine Key Flea Market.

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.