Book Holiday Homes in Chipley

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Featured Holiday Homes in Chipley

Sands of Time! Private Pool! Dog Friendly! 600ft to Beach! Sleeps 18

Sands of Time! Private Pool! Dog Friendly! 600ft to Beach! Sleeps 18

Panama City Beach FL
Stay at this holiday home in Panama City Beach. Enjoy free Wi-Fi, private pools and a water park. Popular attractions Pier Park and Frank Brown Park are located ...
Opens in a new windowSands of Time! Private Pool! Dog Friendly! 600ft to Beach! Sleeps 18
Newly Listed! Beach House w/ Salt Water Pool; Steps from the Beach and Pier Park

Newly Listed! Beach House w/ Salt Water Pool; Steps from the Beach and Pier Park

Panama City Beach FL
Stay at this holiday home in Panama City Beach. Enjoy free Wi-Fi, private pools and a garden. Our guests praise the pool in their reviews. Popular attractions ...
Opens in a new windowNewly Listed! Beach House w/ Salt Water Pool; Steps from the Beach and Pier Park
⭐Beach Across the Street-Pool+Hot Tub-The Palms A6⭐

⭐Beach Across the Street-Pool+Hot Tub-The Palms A6⭐

Panama City Beach FL
Stay at this holiday home in Panama City Beach. Enjoy free Wi-Fi, a beach locale and laundry facilities. Popular attractions Pier Park and Frank Brown Park are ...
Opens in a new window⭐Beach Across the Street-Pool+Hot Tub-The Palms A6⭐
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Beachfront Luxury! 4BR Townhouse w/Pool & Stunning Gulf Views! Sleeps 10!

Beachfront Luxury! 4BR Townhouse w/Pool & Stunning Gulf Views! Sleeps 10!

Panama City Beach FL
Stay at this holiday home in Panama City Beach. Enjoy free Wi-Fi, a water park and a fitness centre. Popular attractions Pier Park and Frank Brown Park are located ...
Opens in a new windowBeachfront Luxury! 4BR Townhouse w/Pool & Stunning Gulf Views! Sleeps 10!
 Sandpiper Cottage • Private Pool • 1 Block to Beach • FREE 6‑Person Golf Cart

Sandpiper Cottage • Private Pool • 1 Block to Beach • FREE 6‑Person Golf Cart

Panama City Beach FL
Stay at this holiday home in Panama City Beach. Enjoy free Wi-Fi, private pools and a garden. Our guests praise the pool in their reviews. Popular attractions ...
Opens in a new window Sandpiper Cottage • Private Pool • 1 Block to Beach • FREE 6‑Person Golf Cart
☀️Stunning Beachfront Views-Great Location-Ocean Bliss☀️

☀️Stunning Beachfront Views-Great Location-Ocean Bliss☀️

Panama City Beach FL
Stay at this beach holiday home in Panama City Beach. Enjoy free Wi-Fi, a beach locale and a water park. Popular attractions Pier Park and Frank Brown Park are ...
Opens in a new window☀️Stunning Beachfront Views-Great Location-Ocean Bliss☀️
Stunning Three Story PCB House - Pool - Pet Friendly - Gulf Views - Awarded 2026

Stunning Three Story PCB House - Pool - Pet Friendly - Gulf Views - Awarded 2026

Panama City Beach FL
Stay at this beach holiday home in Panama City Beach. Enjoy free Wi-Fi, a beach locale and a fitness centre. Popular attractions Pier Park and Frank Brown Park ...
Opens in a new windowStunning Three Story PCB House - Pool - Pet Friendly - Gulf Views - Awarded 2026
Fantastic Beachfront Townhome in Panama City Beach

Fantastic Beachfront Townhome in Panama City Beach

Panama City Beach FL
Stay at this holiday home in Panama City Beach. Enjoy laundry facilities, patios and air conditioning. Popular attractions Pier Park and Frank Brown Park are ...
Opens in a new windowFantastic Beachfront Townhome in Panama City Beach
Sunset Cove: Charming 3BR/3BA Beach House Sleeps 8 with Sunsets & Serenity

Sunset Cove: Charming 3BR/3BA Beach House Sleeps 8 with Sunsets & Serenity

Panama City Beach FL
Stay at this holiday home in Panama City Beach. Enjoy free Wi-Fi, a water park and a fitness centre. Popular attractions Pier Park and Frank Brown Park are located ...
Opens in a new windowSunset Cove: Charming 3BR/3BA Beach House Sleeps 8 with Sunsets & Serenity
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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.

Chipley 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 Chipley vacation homes are the perfect way for you to wing it.

Holiday houses in Chipley 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 Chipley 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 Chipley adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chipley 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 Chipley 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.

Chipley Holiday Homes essential information

Accommodation
1884 Holiday Homes
Lowest Price
NZ$128
Highest Price
NZ$324
Popular accommodation
Sands of Time! Private Pool! Dog Friendly! 600ft to Beach! Sleeps 18, Newly Listed! Beach House w/ Salt Water Pool; Steps from the Beach and Pier Park, ⭐Beach Across the Street-Pool+Hot Tub-The Palms A6⭐, Beachfront Luxury! 4BR Townhouse w/Pool & Stunning Gulf Views! Sleeps 10!, Sandpiper Cottage • Private Pool • 1 Block to Beach • FREE 6‑Person Golf Cart, ☀️Stunning Beachfront Views-Great Location-Ocean Bliss☀️, Stunning Three Story PCB House - Pool - Pet Friendly - Gulf Views - Awarded 2026, Fantastic Beachfront Townhome in Panama City Beach, Sunset Cove: Charming 3BR/3BA Beach House Sleeps 8 with Sunsets & Serenity

Top trending hotels in Chipley

Palmetto Beachfront Hotel, a By the Sea Resort

Palmetto Beachfront Hotel, a By the Sea Resort

2 out of 5
17255 Front Beach Road Panama City Beach FL
Fully refundableReserve now, pay when you stay
The price is NZ$128 per night from 10 May to 11 May
NZ$128
10 May - 11 May
includes taxes & fees
Stay at this beach hotel in Panama City Beach. Enjoy free Wi-Fi, free parking and a beach locale. Our guests praise the pool and the helpful staff in their reviews. ...
Opens in a new windowPalmetto Beachfront Hotel, a By the Sea Resort
Radisson Beachfront Hotel - Panama City Beach

Radisson Beachfront Hotel - Panama City Beach

3 out of 5
15325 Front Beach Road Panama City Beach FL
Fully refundable
The price is NZ$181 per night from 10 May to 11 May
NZ$181
10 May - 11 May
includes taxes & fees
Stay at this beach hotel in Panama City Beach. Enjoy free Wi-Fi, free parking and a beach locale. Our guests praise the helpful staff and the clean rooms in ...
Opens in a new windowRadisson Beachfront Hotel - Panama City Beach
Chateau Beachfront Hotel, A By The Sea Resort

Chateau Beachfront Hotel, A By The Sea Resort

2.5 out of 5
12525 Front Beach Rd Panama City Beach FL
The price is NZ$183 per night from 12 May to 13 May
NZ$183
12 May - 13 May
includes taxes & fees
Stay at this beach hotel in Panama City Beach. Enjoy free Wi-Fi, free parking and a beach locale. Our guests praise the pool and the helpful staff in their reviews. ...
Opens in a new windowChateau Beachfront Hotel, A By The Sea Resort
Save an average of 15% on thousands of hotels when you're signed in
Sandpiper Beacon Beach Resort

Sandpiper Beacon Beach Resort

3 out of 5
17403 Front Beach Rd Panama City Beach FL
The price is NZ$324 per night from 10 May to 11 May
NZ$324
10 May - 11 May
includes taxes & fees
Stay at this beach hotel in Panama City Beach. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Popular attractions Pier Park and Frank Brown Park are located ...
Opens in a new windowSandpiper Beacon Beach Resort
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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.