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
Located in Marathon, The Hammocks at Marathon is by the ocean, a 1-minute drive from The Turtle Hospital and 5 minutes from Florida Keys Country Club.
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 AU$1,026 per night from 1 Feb to 2 Feb
AU$1,026
1 Feb - 2 Feb
includes taxes & fees
With a stay at this vacation home in Big Pine Key (Sands), you'll be within a 10-minute drive of Florida Keys Beaches and Coupon Bight Aquatic Preserve.
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
With a stay at this vacation home in Marathon, you'll be within a 10-minute drive of Sombrero Beach and Marathon Air Museum.
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
With a stay at this vacation home in Marathon, you'll be on the waterfront, within a 15-minute drive of Sombrero Beach and Curry Hammock State Park.
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
With a stay at this vacation home in Marathon (Coral Lagoon), you'll be within a 10-minute drive of Sombrero Beach and Marathon Visitor Center.
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
When you stay at this vacation home in Marathon, you'll be on the waterfront, within a 5-minute drive of Coco Plum Beach and Curry Hammock State Park.
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
With a stay at this vacation home in Summerland Key, you'll be by the sea, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
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
With a stay at this vacation home in Marathon, you'll be on the waterfront, just a 3-minute walk from Sombrero Beach and within a 5-minute drive of Crane Point ...
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 AU$1,046 per night from 6 Feb to 7 Feb
AU$1,046
6 Feb - 7 Feb
includes taxes & fees
With a stay at this vacation home in Summerland Key, you'll be on the waterfront, within a 10-minute drive of 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
AU$487
Highest Price
AU$1,046
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
With a stay at Old Wooden Bridge Resort and Marina in Big Pine Key (Punta Brisa), you'll be within a 15-minute drive of Florida Keys Beaches and Blue Hole.
Opens in a new windowOld Wooden Bridge Resort and Marina
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 AU$487 per night from 22 Feb to 23 Feb
AU$487
22 Feb - 23 Feb
includes taxes & fees
With a stay at Sunshine Key RV Resort & Marina in Big Pine Key, you'll be within a 10-minute drive of Florida Keys Beaches and Veterans Memorial Park & ...
Opens in a new windowSunshine Key RV Resort & Marina
Barnacle Resort

Barnacle Resort

3 out of 5
1557 Long Beach Dr Big Pine Key FL
With a stay at Barnacle Resort in Big Pine Key (Long Beach Estates), you'll be steps from Florida Keys Beaches and Coupon Bight Aquatic Preserve.
Opens in a new windowBarnacle Resort
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 AU$540 per night from 22 Feb to 23 Feb
AU$540
22 Feb - 23 Feb
includes taxes & fees
With a stay at this campground in Big Pine Key, you'll be within a 15-minute drive of Florida Keys Beaches and National Key Deer Refuge Visitor Center.
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.

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^Subject to availability and chosen travel dates.