Book Holiday Homes in Chipley

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Featured Holiday Homes in Chipley

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
When you stay at this vacation home in Panama City Beach, you'll be by the sea, within a 15-minute walk of Pier Park and Panama City Beaches.
Newly Listed! Beach House w/ Salt Water Pool; Steps from the Beach and Pier Park
CoCo Beach at Premier!  New to VRBO!  Pet Friendly Beachfront Townhome

CoCo Beach at Premier! New to VRBO! Pet Friendly Beachfront Townhome

Panama City Beach
With a stay at this vacation home in Panama City Beach, you'll be on the beach, within a 5-minute drive of Pier Park and Panama City Beaches.
CoCo Beach at Premier! New to VRBO! Pet Friendly Beachfront Townhome
Private Home | New Construction / Quiet West End | FLPCB63

Private Home | New Construction / Quiet West End | FLPCB63

Panama City Beach
With a stay at this vacation home in Panama City Beach (Miramar Heights), you'll be a 2-minute drive from Panama City Beaches and 6 minutes from Pier Park.
Private Home | New Construction / Quiet West End | FLPCB63
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Spring Break and Summer deals are heating up!

Spring Break and Summer deals are heating up!

Panama City Beach
With a stay at this vacation home in Panama City Beach (Laguna Beach Estates), you'll be within a 15-minute drive of Pier Park and Alys Beach.
Spring Break and Summer deals are heating up!
Surf-N-Santa, 6 BR/4 BA, Private Pool with Hot Tub, West End PCB, Sleeps 18

Surf-N-Santa, 6 BR/4 BA, Private Pool with Hot Tub, West End PCB, Sleeps 18

Panama City Beach
With a stay at this vacation home in Panama City Beach (Laguna Beach Estates), you'll be within a 15-minute drive of Pier Park and Alys Beach.
Surf-N-Santa, 6 BR/4 BA, Private Pool with Hot Tub, West End PCB, Sleeps 18
Panama City Sea Ease Beach House Spring & Summer Deals - Pets & Ages 18-25 OK

Panama City Sea Ease Beach House Spring & Summer Deals - Pets & Ages 18-25 OK

Panama City Beach
When you stay at this vacation home in Panama City Beach, you'll be on the beach, within a 5-minute walk of Panama City Beaches and Pier Park.
Panama City Sea Ease Beach House Spring & Summer Deals - Pets & Ages 18-25 OK
Beachfront Bliss: Spacious Deck, Grill & Unmatched Gulf Views!

Beachfront Bliss: Spacious Deck, Grill & Unmatched Gulf Views!

Panama City Beach
With a stay at this vacation home in Panama City Beach (Miramar Beach), you'll be a 1-minute drive from Panama City Beaches and 5 minutes from Pier Park.
Beachfront Bliss: Spacious Deck, Grill & Unmatched Gulf Views!
Private Pool, Tanning Ledge / Pet-Friendly / Golf Cart Friendly / FLPCB8

Private Pool, Tanning Ledge / Pet-Friendly / Golf Cart Friendly / FLPCB8

Panama City Beach
The price is AU$865 per night from 28 Jan to 29 Jan
AU$865
includes taxes & fees
28 Jan - 29 Jan
With a stay at this vacation home in Panama City Beach (Riviera Beach), you'll be within a 10-minute drive of Pier Park and Alys Beach.
Private Pool, Tanning Ledge / Pet-Friendly / Golf Cart Friendly / FLPCB8
Beachside Joy! Adorable, Cozy, and Beachfront -- Not a Condo!!!

Beachside Joy! Adorable, Cozy, and Beachfront -- Not a Condo!!!

Panama City Beach
The price is AU$700 per night from 28 Jan to 29 Jan
AU$700
includes taxes & fees
28 Jan - 29 Jan
With a stay at this vacation home in Panama City Beach, you'll be on the beach, within a 5-minute drive of Pier Park and Panama City Beaches.
Beachside Joy! Adorable, Cozy, and Beachfront -- Not a Condo!!!
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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
1573 Holiday Homes
Lowest Price
AU$110
Highest Price
AU$865
Popular accommodation
Newly Listed! Beach House w/ Salt Water Pool; Steps from the Beach and Pier Park, CoCo Beach at Premier! New to VRBO! Pet Friendly Beachfront Townhome, Private Home | New Construction / Quiet West End | FLPCB63, Spring Break and Summer deals are heating up! , Surf-N-Santa, 6 BR/4 BA, Private Pool with Hot Tub, West End PCB, Sleeps 18, Panama City Sea Ease Beach House Spring & Summer Deals - Pets & Ages 18-25 OK, Beachfront Bliss: Spacious Deck, Grill & Unmatched Gulf Views!, Private Pool, Tanning Ledge / Pet-Friendly / Golf Cart Friendly / FLPCB8, Beachside Joy! Adorable, Cozy, and Beachfront -- Not a Condo!!!

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 AU$112 per night from 28 Jan to 29 Jan
AU$112
includes taxes & fees
28 Jan - 29 Jan
Located in Panama City Beach, Palmetto Beachfront Hotel, a By the Sea Resort is by the ocean, within a 5-minute drive of Museum of Man in the Sea and Russell-Fields ...
Palmetto Beachfront Hotel, a By the Sea Resort
Radisson Panama City Beach - Oceanfront

Radisson Panama City Beach - Oceanfront

3 out of 5
15325 Front Beach Road, Panama City Beach, FL
Fully refundable
The price is AU$151 per night from 30 Jan to 31 Jan
AU$151
includes taxes & fees
30 Jan - 31 Jan
With a stay at Radisson Panama City Beach - Oceanfront in Panama City Beach, you'll be on the beach, within a 5-minute drive of Pier Park and Panama City ...
Radisson Panama City Beach - Oceanfront
La Quinta by Wyndham PCB Coastal Palms

La Quinta by Wyndham PCB Coastal Palms

2.5 out of 5
7115 Coastal Palms Blvd., Panama City Beach, FL
Fully refundableReserve now, pay when you stay
The price is AU$110 per night from 28 Jan to 29 Jan
AU$110
includes taxes & fees
28 Jan - 29 Jan
Located in Panama City Beach, La Quinta by Wyndham PCB Coastal Palms is a 1-minute drive from Naval Support Activity Panama City and 6 minutes from Florida State ...
La Quinta by Wyndham PCB Coastal Palms
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Holiday Inn Express & Suites Panama City Beach - Beachfront, an IHG Hotel

Holiday Inn Express & Suites Panama City Beach - Beachfront, an IHG Hotel

3 out of 5
12907 Front Beach Rd, Panama City Beach, FL
Fully refundable
The price is AU$267 per night from 28 Jan to 29 Jan
AU$267
includes taxes & fees
28 Jan - 29 Jan
A stay at Holiday Inn Express & Suites Panama City Beach - Beachfront, an IHG Hotel places you in the heart of Panama City Beach, within a 5-minute drive of ...
Holiday Inn Express & Suites Panama City Beach - Beachfront, an IHG Hotel
Don't see what you're looking for?
See all available properties in Chipley
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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.