Book Holiday Homes in Big Pine Key

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Featured Holiday Homes in Big Pine Key

The Hammocks at Marathon

The Hammocks at Marathon

2.5 out of 5
1688 Overseas Hwy Marathon FL
Stay at this holiday home in Marathon. Enjoy a marina, a fitness centre and a 24-hour front desk. Popular attractions Sombrero Beach and Shady Palm Art Gallery ...
Opens in a new windowThe Hammocks at Marathon
Charming 3-bedroom house in 
Big Pine Key near Beach and Key West

Charming 3-bedroom house in Big Pine Key near Beach and Key West

Big Pine Key FL
The price is NZ$1,103 per night from 5 Jan to 6 Jan
NZ$1,103
5 Jan - 6 Jan 2026
includes taxes & fees
Stay at this holiday home in Big Pine Key. Enjoy free Wi-Fi, laundry facilities and balconies. Popular attractions Bahia Honda State Park and Big Pine Key Flea ...
Opens in a new windowCharming 3-bedroom house in Big Pine Key near Beach and Key West
Perla Blanca 4 Bed 5 Bath kayaks pool boat dock

Perla Blanca 4 Bed 5 Bath kayaks pool boat dock

Marathon FL
Stay at this holiday home in Marathon. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Sombrero Beach and Marathon Air Museum are located ...
Opens in a new windowPerla Blanca 4 Bed 5 Bath kayaks pool boat dock
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Outstanding pool and outdoor area 5 minute walk to beach!

Outstanding pool and outdoor area 5 minute walk to beach!

Marathon FL
Stay at this family-friendly holiday home in Marathon. Enjoy free Wi-Fi, private pools and laundry facilities. Popular attractions Sombrero Beach and Coco Plum ...
Opens in a new windowOutstanding pool and outdoor area 5 minute walk to beach!
Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water

Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water

Marathon FL
Stay at this golf holiday home in Marathon. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Sombrero Beach and Captain Hooks Marina and ...
Opens in a new windowCoral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water
Waterfront 2BR w/ Dock, Hot Tub & Easy Ocean Access – Boaters Welcome!

Waterfront 2BR w/ Dock, Hot Tub & Easy Ocean Access – Boaters Welcome!

Marathon FL
Stay at this holiday home in Marathon. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Sombrero Beach and Coco Plum Beach are located ...
Opens in a new windowWaterfront 2BR w/ Dock, Hot Tub & Easy Ocean Access – Boaters Welcome!
Private Secluded Ocean View & Pool Near Key West

Private Secluded Ocean View & Pool Near Key West

Summerland Key FL
Stay at this holiday home in Summerland Key. Enjoy free Wi-Fi, private pools and a fitness centre. Our guests praise the helpful staff in their reviews. Popular ...
Opens in a new windowPrivate Secluded Ocean View & Pool Near Key West
FALL 2025~399/NT~NO HLDY Wk~Fish, Swim, Relax! Pool & Dock – Perfect 4 Families~

FALL 2025~399/NT~NO HLDY Wk~Fish, Swim, Relax! Pool & Dock – Perfect 4 Families~

Marathon FL
Stay at this family-friendly holiday home in Marathon. Enjoy free Wi-Fi, private pools and laundry facilities. Our guests praise the helpful staff in their reviews. ...
Opens in a new windowFALL 2025~399/NT~NO HLDY Wk~Fish, Swim, Relax! Pool & Dock – Perfect 4 Families~
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Key FL
The price is NZ$1,240 per night from 2 Jan to 3 Jan
NZ$1,240
2 Jan - 3 Jan 2026
includes taxes & fees
Stay at this holiday home in Summerland Key. Enjoy a garden, laundry facilities and patios. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key ...
Opens in a new windowCudjoe Cottages, swimming pool, just 20 miles from Key West
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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.

Big Pine Key Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Big Pine Key vacation homes are the perfect way for you to wing it.

Holiday houses in Big Pine Key let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Big Pine Key in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Big Pine Key adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Big Pine Key with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Big Pine Key vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Big Pine Key Holiday Homes essential information

Accommodation
1759 Holiday Homes
Lowest Price
NZ$588
Highest Price
NZ$1,240
Popular accommodation
The Hammocks at Marathon, Charming 3-bedroom house in Big Pine Key near Beach and Key West, Perla Blanca 4 Bed 5 Bath kayaks pool boat dock, Outstanding pool and outdoor area 5 minute walk to beach!, Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water, Waterfront 2BR w/ Dock, Hot Tub & Easy Ocean Access – Boaters Welcome!, Private Secluded Ocean View & Pool Near Key West, FALL 2025~399/NT~NO HLDY Wk~Fish, Swim, Relax! Pool & Dock – Perfect 4 Families~, Cudjoe Cottages, swimming pool, just 20 miles from Key West

Top trending hotels in Big Pine Key

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

2.5 out of 5
1791 Bogie Drive Big Pine Key FL
Stay at this cottage in Big Pine Key. Enjoy free Wi-Fi, free parking and a marina. Our guests praise the helpful staff in their reviews. Popular attractions ...
Opens in a new windowOld Wooden Bridge Resort and Marina
Barnacle Resort

Barnacle Resort

3 out of 5
1557 Long Beach Dr Big Pine Key FL
Stay at this beach B&B in Big Pine Key. Enjoy free Wi-Fi, free parking and a beach locale. Popular attractions Bahia Honda State Park and Coupon Bight Aquatic ...
Opens in a new windowBarnacle Resort
Sunshine Key RV Resort & Marina

Sunshine Key RV Resort & Marina

2 out of 5
38801 Overseas Highway Big Pine Key FL
Fully refundableReserve now, pay when you stay
The price is NZ$588 per night from 4 Jan to 5 Jan
NZ$588
4 Jan - 5 Jan 2026
includes taxes & fees
Enjoy a private beach, a marina and laundry facilities. Popular attractions Bahia Honda State Park and Sandspur Beach are located nearby.
Opens in a new windowSunshine Key RV Resort & Marina
Save an average of 15% on thousands of hotels when you're signed in
🌴 TROPICAL RETREAT 🌴 RV in the Keys

🌴 TROPICAL RETREAT 🌴 RV in the Keys

Big Pine Key FL
The price is NZ$613 per night from 3 Jan to 4 Jan
NZ$613
3 Jan - 4 Jan 2026
includes taxes & fees
Stay at this campsite in Big Pine Key. Enjoy laundry facilities, cable/satellite TV service and air conditioning. Popular attractions Big Pine Key Flea Market ...
Opens in a new window🌴 TROPICAL RETREAT 🌴 RV in the Keys
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.