Photo by Anthony Creamer

Holiday Homes in Chipley

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Chipley

OCEAN FRONT / ON THE BEACH Charming Townhome at West Side of PCB- LAGUNA BEACH
On the beach, sun-loungers, beach towels

OCEAN FRONT / ON THE BEACH Charming Townhome at West Side of PCB- LAGUNA BEACH

9.8 out of 10, Exceptional, (78)
"The location was perfect for relaxing on a white sand beach with easy swimming in the Gulf. The host provided beach chairs, umbrella, and beach towels for a perfect beach vacation. We truly enjoyed this stay and do recommend for those wanting a beach right outside your back door!"
OCEAN FRONT / ON THE BEACH Charming Townhome at West Side of PCB- LAGUNA BEACH
#215 Polynesian Village RIGHT BY PIER PARK
Interior

#215 Polynesian Village RIGHT BY PIER PARK

8.0 out of 10, Very good, (12)
"Location this place has it . Access to the Beach got that too . Price excellent ."
#215 Polynesian Village RIGHT BY PIER PARK
The Yard - Walking distance to Sharkys - Steps to the beach!
Fridge, microwave, oven, stovetop

The Yard - Walking distance to Sharkys - Steps to the beach!

8.0 out of 10, Very good, (23)
"The property was adorable, clean and accurately described. The check in and out was seamless. Will look to book again. "
The Yard - Walking distance to Sharkys - Steps to the beach!
Fully Fenced, Single level, pet friendly, golf cart,bikes,large patio and grill
Beach nearby, sun-loungers, beach towels

Fully Fenced, Single level, pet friendly, golf cart,bikes,large patio and grill

10.0 out of 10, Exceptional, (11)
"We loved everything about this rental! Quiet neighborhood, close to popular attractions, plenty of space and parking and every amenity we could possibly need. The Warrens were excellent hosts and super helpful when we decided to extended our stay. We will definitely stay again! "
Fully Fenced, Single level, pet friendly, golf cart,bikes,large patio and grill
5-Bed Beach House with Private Pool
Property grounds

5-Bed Beach House with Private Pool

8.0 out of 10, Very good, (1)
"was in great location pool was alittle smaller than expected but all in all was a beautiful place."
5-Bed Beach House with Private Pool
Celadon Beach Resort
On the beach, white sand, sun-loungers, beach umbrellas

Celadon Beach Resort

3.0 star property
8.4 out of 10, Very good, (165)
"The condo was clean and comfortable. The property is well maintained. The elevators were a hassle. They stopped at every floor and one was not working. Overall our stay was enjoyable. "
Celadon Beach Resort
Coastal Breeze BRAND NEW Luxury Home Steps 2 Beach, INCLUDED Golf Cart!
Beach nearby

Coastal Breeze BRAND NEW Luxury Home Steps 2 Beach, INCLUDED Golf Cart!

8.4 out of 10, Very good, (5)
Coastal Breeze BRAND NEW Luxury Home Steps 2 Beach, INCLUDED Golf Cart!
AWESOME BEACHFRONT townhouse! RENOVATED, Spectacular VIEWS! Pet Friendly!
On the beach, sun-loungers, beach towels

AWESOME BEACHFRONT townhouse! RENOVATED, Spectacular VIEWS! Pet Friendly!

10.0 out of 10, Exceptional, (40)
"My family had a wonderful stay at the Three Dolphins for spring break this year! All the information in the listening is accurate and you really can't beat the view from the deck or the master bedroom."
AWESOME BEACHFRONT townhouse! RENOVATED, Spectacular VIEWS! Pet Friendly!
PCB Townhome w/ Resort Amenities - Walk to Ocean!
Beach nearby

PCB Townhome w/ Resort Amenities - Walk to Ocean!

10.0 out of 10, Exceptional, (14)
"Nice little place close to the beach owner was nice and would answer you if you have any questions clean unit and a very nice gated community we really enjoyed our stay"
PCB Townhome w/ Resort Amenities - Walk to Ocean!
Entire Home with GOLF CART & just 0.2 miles from the beach! Pet-Friendly!
Beach

Entire Home with GOLF CART & just 0.2 miles from the beach! Pet-Friendly!

10.0 out of 10, Exceptional, (5)
"we had a amazing time at house."
Entire Home with GOLF CART & just 0.2 miles from the beach! Pet-Friendly!
20% off 4+ days -Big dog-friendly steps to beach, 2 kitchens, game & dressing Rm
Terrace/patio

20% off 4+ days -Big dog-friendly steps to beach, 2 kitchens, game & dressing Rm

9.2 out of 10, Wonderful, (21)
"We had a great time! Sandy was very helpful and responsive, and the house was spacious and as advertised."
20% off 4+ days -Big dog-friendly steps to beach, 2 kitchens, game & dressing Rm
1 Block to the Beach, Private POOL and FREE 6-Person golf cart!!
Beach

1 Block to the Beach, Private POOL and FREE 6-Person golf cart!!

10.0 out of 10, Exceptional, (170)
"The house is perfect! The house is super nice and well supplied with towels,beach towel and beach toys for the kids. The pool and golf cart really make your vacation even better! Thank you so much ! We will book again!"
1 Block to the Beach, Private POOL and FREE 6-Person golf cart!!
Beachside Bungalow 3 Blocks from Private Beach! Just 3 miles to Pier Park!
Dining

Beachside Bungalow 3 Blocks from Private Beach! Just 3 miles to Pier Park!

10.0 out of 10, Exceptional, (34)
"The house was beautiful and very clean! Super close to the beach with emerald green waters 💚. Host was very commutative and sweet, we will definitely use this home again! "
Beachside Bungalow 3 Blocks from Private Beach! Just 3 miles to Pier Park!
Margaritaville Resort | 6BR Beach Villa | Pool
A heated pool

Margaritaville Resort | 6BR Beach Villa | Pool

9.8 out of 10, Exceptional, (6)
"Everyone loved the location and the Beach Villa. Overall best place we have stayed at in Panama City."
Margaritaville Resort | 6BR Beach Villa | Pool
Pool in Backyard and steps to beach
Outdoor pool, a heated pool

Pool in Backyard and steps to beach

10.0 out of 10, Exceptional, (8)
"Beautiful area. Close to everything. House was clean and beautiful. Very spacious. Host replied always within minutes. Great option for a family vacation "
Pool in Backyard and steps to beach
Beachfront Bliss: Spacious Deck, Grill & Unmatched Gulf Views!
Smart TV

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

9.4 out of 10, Exceptional, (19)
"If you're looking for a great on the beach location, this is it. I had a wonderful experience. Communication was great. Hosts flexible. Access to the Gulf of Mexico at your leisure. "
Beachfront Bliss: Spacious Deck, Grill & Unmatched Gulf Views!
Private Luxury Ocean Front 4BR/4BA Home PCB - Walk to Pier Park - Pet Friendly!
On the beach, sun-loungers, beach towels

Private Luxury Ocean Front 4BR/4BA Home PCB - Walk to Pier Park - Pet Friendly!

10.0 out of 10, Exceptional, (24)
"Beautiful location directly on beach and very short distance to Pier Park."
The price is AU$2,743
includes taxes & fees
2 Sept - 3 Sept
Private Luxury Ocean Front 4BR/4BA Home PCB - Walk to Pier Park - Pet Friendly!
Directly on the Beach~Private Sun Deck~Outdoor Shower~Jetted Tub~Covered Balcony
Pool

Directly on the Beach~Private Sun Deck~Outdoor Shower~Jetted Tub~Covered Balcony

8.6 out of 10, Excellent, (73)
"best time"
Directly on the Beach~Private Sun Deck~Outdoor Shower~Jetted Tub~Covered Balcony
🌴ALOHA BEACH HOUSE RETREAT🌴Hot tub,SAUNA, Cold plunge,GAME ROOM,Putting green.
Terrace/patio

🌴ALOHA BEACH HOUSE RETREAT🌴Hot tub,SAUNA, Cold plunge,GAME ROOM,Putting green.

10.0 out of 10, Exceptional, (49)
"My husband & I came to Celebrate his Birthday & ride our Harley with Friends for Bike week - However we never rode the Harley once because the Beach, Fishing, and Spa Amenities kept us busy - It was a relaxing experience and Comfortable house - We will be back soon! "
🌴ALOHA BEACH HOUSE RETREAT🌴Hot tub,SAUNA, Cold plunge,GAME ROOM,Putting green.
Pet friendly beach front home next to PCB dog beach. Walk to Pier Park! Sleeps 8!
Outdoor dining

Pet friendly beach front home next to PCB dog beach. Walk to Pier Park! Sleeps 8!

9.4 out of 10, Exceptional, (41)
"3rd time staying here. Best location, always nice to stay at"
Pet friendly beach front home next to PCB dog beach. Walk to Pier Park! Sleeps 8!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chipley Hotel Reviews

Embassy Suites by Hilton Panama City Beach Resort

Embassy Suites by Hilton Panama City Beach Resort

10/10 Excellent
"Great place!!!"
Dainiel 3-night trip
Posted 10 hours ago
Embassy Suites by Hilton Panama City Beach Resort