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 vacation home in Marathon. Enjoy a marina, a fitness center, and a 24-hour front desk. Popular attractions Sombrero Beach and Shady Palm Art Gallery ...
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
Stay at this vacation home in Marathon. Enjoy private pools, a garden, and laundry facilities. Popular attractions Sombrero Beach and Marathon Air Museum are ...
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
Stay at this vacation home in Summerland Key. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Florida Keys Beaches and Out Key are located ...
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
Stay at this vacation home in Marathon. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Sombrero Beach and Captain Hooks Marina and Dive ...
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
Stay at this vacation home in Marathon. Enjoy free WiFi, private pools, and laundry facilities. Popular attractions Sombrero Beach and Marathon Air Museum are ...
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
Stay at this vacation home in Marathon. Enjoy private pools, laundry facilities, and patios. Popular attractions Sombrero Beach and Marathon Air Museum are located ...
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
Book a stay at this beach vacation home in Marathon. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Sombrero Beach and Coco Plum Beach are ...
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
Book a stay at this beach vacation home in Key Colony Beach. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Sombrero Beach and Sunset ...
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
Stay at this vacation home in Key Colony Beach. Enjoy private pools, a fitness center, and a garden. Popular attractions 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
1731 Holiday Homes
Lowest Price
NZ$381
Highest Price
NZ$558
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 NZ$381 per night from 30 Sept to 1 Oct
NZ$381
30 Sept - 1 Oct
includes taxes & fees
Stay at this cottage in Big Pine Key. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff in our reviews. Popular attractions Blue ...
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 3-star beach B&B in Big Pine Key. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Coupon Bight Aquatic Preserve and Cook ...
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
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
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 NZ$558 per night from 29 Sept to 30 Sept
NZ$558
29 Sept - 30 Sept
includes taxes & fees
Stay at this 5-star luxury hotel in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Opens in a new windowIsla Bella Beach Resort & Spa
Don't see what you're looking for?
See all available properties in Big Pine Key
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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.