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
Perla Blanca – 4 BR, 5 BA Oasis w/ Pool, hot tub, dock, kayaks near beach.

Perla Blanca – 4 BR, 5 BA Oasis w/ Pool, hot tub, dock, kayaks near beach.

Marathon
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 BR, 5 BA Oasis w/ Pool, hot tub, dock, kayaks near beach.
✨️ Ocean access w/Dock, 4 bed/4 bath. Inquire for any special requests ✨️

✨️ Ocean access w/Dock, 4 bed/4 bath. Inquire for any special requests ✨️

Summerland Key, FL
With a stay at this vacation home in Summerland Key (Cutthroat Harbor Estates), you'll be within a 15-minute drive of Upper Sugarloaf Key and National Key Deer ...
Opens in a new window✨️ Ocean access w/Dock, 4 bed/4 bath. Inquire for any special requests ✨️
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Finest location in Coral Lagoon.  End unit with bay views and boat slip!

Finest location in Coral Lagoon. End unit with bay views and boat slip!

Marathon
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 windowFinest location in Coral Lagoon. End unit with bay views and boat slip!
Tarpon Lagoon 5 Bedroom 4 Bath with heated pool on crystal clear deep Lagoon

Tarpon Lagoon 5 Bedroom 4 Bath with heated pool on crystal clear deep Lagoon

Marathon
With a stay at this vacation home in Marathon, you'll be within a 15-minute drive of Sombrero Beach and Marathon Air Museum.
Opens in a new windowTarpon Lagoon 5 Bedroom 4 Bath with heated pool on crystal clear deep Lagoon
Sandal Escape: 6BR Canal Front Oasis w/ Heated Pool, Dog-Friendly, Dockage & Fast Atlantic Access

Sandal Escape: 6BR Canal Front Oasis w/ Heated Pool, Dog-Friendly, Dockage & Fast Atlantic Access

Marathon
With a stay at this vacation home in Marathon, you'll be on the waterfront, within a 10-minute drive of Sombrero Beach and Marathon Air Museum.
Opens in a new windowSandal Escape: 6BR Canal Front Oasis w/ Heated Pool, Dog-Friendly, Dockage & Fast Atlantic Access
TJ1 Beach, Pool, Kitchen, Sleep 6, HotTub, W&D, Dock, BBQ, WiFi, Parking, Tennis

TJ1 Beach, Pool, Kitchen, Sleep 6, HotTub, W&D, Dock, BBQ, WiFi, Parking, Tennis

Marathon
With a stay at this vacation home in Marathon, you'll be on the beach, within a 15-minute drive of Sombrero Beach and Coco Plum Beach.
Opens in a new windowTJ1 Beach, Pool, Kitchen, Sleep 6, HotTub, W&D, Dock, BBQ, WiFi, Parking, Tennis
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts

KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts

key colony Beach
With a stay at this vacation home in Key Colony Beach, you'll be on the beach, within a 15-minute drive of Sombrero Beach and Sunset Park Beach.
Opens in a new windowKCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts
Waterfront Oasis with Boat Dock & Pool!

Waterfront Oasis with Boat Dock & Pool!

Key Colony Beach
With a stay at this vacation home in Key Colony Beach (Coury), you'll be within a 15-minute drive of Sombrero Beach and Sunset Park Beach.
Opens in a new windowWaterfront Oasis with Boat Dock & Pool!
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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
1724 Holiday Homes
Lowest Price
AU$336
Highest Price
AU$492
Popular accommodation
The Hammocks at Marathon, Perla Blanca – 4 BR, 5 BA Oasis w/ Pool, hot tub, dock, kayaks near beach., ✨️ Ocean access w/Dock, 4 bed/4 bath. Inquire for any special requests ✨️ , Finest location in Coral Lagoon. End unit with bay views and boat slip! , Tarpon Lagoon 5 Bedroom 4 Bath with heated pool on crystal clear deep Lagoon, Sandal Escape: 6BR Canal Front Oasis w/ Heated Pool, Dog-Friendly, Dockage & Fast Atlantic Access, TJ1 Beach, Pool, Kitchen, Sleep 6, HotTub, W&D, Dock, BBQ, WiFi, Parking, Tennis, KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts, Waterfront Oasis with Boat Dock & Pool!

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
The price is AU$336 per night from 30 Sept to 1 Oct
AU$336
30 Sept - 1 Oct
includes taxes & fees
With a stay at Old Wooden Bridge Resort and Marina in Big Pine Key (Punta Brisa), you'll be within a 10-minute drive of Blue Hole and National Key Deer Refuge ...
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
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
Sunshine Key RV Resort & Marina

Sunshine Key RV Resort & Marina

2 out of 5
38801 Overseas Highway, Big Pine Key, FL
With a stay at Sunshine Key RV Resort & Marina in Big Pine Key, you'll be just steps from Loggerhead Beach and Sandspur Beach.
Opens in a new windowSunshine Key RV Resort & Marina
Save an average of 15% on thousands of hotels when you're signed in
Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

5 out of 5
1 Knights Key Boulevard, MM 47, Marathon, FL
Fully refundableReserve now, pay when you stay
The price is AU$492 per night from 29 Sept to 30 Sept
AU$492
29 Sept - 30 Sept
includes taxes & fees
With a stay at Isla Bella Beach Resort & Spa in Marathon, you'll be on the beach, just steps from Vaca Key and a 2-minute drive from The Turtle Hospital.
Opens in a new windowIsla Bella Beach Resort & Spa
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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.