Photo by Anthony Creamer

Chipley Holiday Rentals

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Holiday Rentals in Chipley

Origin at Seahaven

4.0 star property
8.8 out of 10, Excellent, (45)
"We have extended our stay we love it so much and the staff is amazing ."
The price is AU$382
includes taxes & fees
30 Nov - 1 Dec
Origin at Seahaven

Tidewater Beach Resort by Panhandle Getaways

3.5 star property
7.2 out of 10, Good, (149)
"Excellent! We will be back for sure! "
The price is AU$1,598
includes taxes & fees
30 Nov - 1 Dec
Tidewater Beach Resort by Panhandle Getaways

Beachfront Condo With Free Beach Chairs & Umbrella Set Up Tidewater 2416

9.8 out of 10, Exceptional, (86)
"We had a wonderful time in the Condo - It was just what we needed to decompress and relax after some stressful times. Lois Pitt was very helpful and went out of her way to make our stay everything that it should be! Thanks - I think we would like to stay here again for a longer term!"
Beachfront Condo With Free Beach Chairs & Umbrella Set Up Tidewater 2416

Newly Remodeled!! 500 Feet to Beach!!

9.8 out of 10, Exceptional, (10)
"👍👍"
Newly Remodeled!! 500 Feet to Beach!!

Gulf-front condo with balcony, beach access, hot tub, pool & gym

9.2 out of 10, Wonderful, (35)
"We had a great time. Condo and building is as described. The lady at the front desk is awesome. The only issue was the shower in the hall bathroom does not drain that was not an issue for us because we did not need to use it. Also the sales service and Wi-Fi were not great but that is literally all I have negative to say and neither one of those were a big deal"
Gulf-front condo with balcony, beach access, hot tub, pool & gym

High-rise condo with pool, hot tub, central AC, & free WiFi

9.4 out of 10, Exceptional, (76)
"Plenty of room and great views. "
High-rise condo with pool, hot tub, central AC, & free WiFi

Edgewater Beach and Golf Resort by Southern Vacation Rentals

4.0 star property
7.4 out of 10, Good, (2181)
"I liked the beach view and it was across the street from the Panhandle Power Washing event I was attending."
Edgewater Beach and Golf Resort by Southern Vacation Rentals

BeachFront~Large Balcony~Pool~Fitness Center~Spa~Sterling Breeze 1204

9.4 out of 10, Exceptional, (10)
"My family had the most relaxing vacation.upon arrival to condo we had a beautiful flower arrangement and card for the loss of my son I was not expecting and still we are all trying to figure life out without him being here something so simple truly made a huge difference for myself his sisters and his daughter because this trip was about healing"
BeachFront~Large Balcony~Pool~Fitness Center~Spa~Sterling Breeze 1204

Edgewater Beach and Golf Resort by Southern Vacation Rentals VI

4.0 star property
8.0 out of 10, Very good, (35)
"Great place, nice golf cart "
Edgewater Beach and Golf Resort by Southern Vacation Rentals VI

Newly Remodeled Two bedroom Two bath! 500 Feet to Beach!

9.4 out of 10, Exceptional, (18)
"Property was perfect for what we needed! Close to the beach and very nice! Property manager was very helpful every time we had a question. Will definitely book again next time we come to PCB! Thanks"
Newly Remodeled Two bedroom Two bath! 500 Feet to Beach!

Emerald Beach Resort by Southern Vacation Rentals

3.5 star property
7.6 out of 10, Good, (779)
"Clean and nice a little long walk to parking is the only conplaint"
Emerald Beach Resort by Southern Vacation Rentals

Calypso 902 West - 3 Bedroom, 2 Bathroom Beach Front Condominium

6.6 out of 10, (35)
"We have stayed in the Calypso 2 other times at different condos. This condo is on the lower side as far as condition, but the price and location are great. Plan to bring some lawn chairs if you want to enjoy the view from the balcony. There is only one chair outside and it is broken. Also, there was only 1 hand towel for the kitchen, so you'll need to bring/buy additional dishcloths to do dishes and wipe the counters, etc. Overall, we got what we expected after reading previous reviews. As...
Calypso 902 West - 3 Bedroom, 2 Bathroom Beach Front Condominium

Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!

9.6 out of 10, Exceptional, (209)
"Very nice property, couldn't of been happier with the stay. Will rebook same place this summer"
The price is AU$392
includes taxes & fees
14 Dec - 15 Dec
Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!

Stunning Three Story PCB House / Pool / Pet Friendly / Gulf of Mexico Views

10.0 out of 10, Exceptional, (222)
"We loved our vacation at PCB. The house was great and as described. The location was the best we ever had at the beach. Our rescue dogs loved the house and the beach. The bedroom and beds were perfect. We were central to Frank Brown Park and Pier Park. Everyone had a great time and we will return. "
Stunning Three Story PCB House / Pool / Pet Friendly / Gulf of Mexico Views

“On the Sands” Luxury Beach front Townhouse – 4BR/4 BA (8 beds and sleeps 14)

9.6 out of 10, Exceptional, (43)
"The Townhouse was exactly as described. We enjoyed our stay very much. I would love to give 5 stars all around the only issue we had was cockroaches in the kitchen cabinets, one bed and one of the bathrooms. We just washed all the dishes before using and cleaned the cabinets before putting the dishes back in the cabinets. Other than those nasty creatures everything else was perfect!"
“On the Sands” Luxury Beach front Townhouse – 4BR/4 BA (8 beds and sleeps 14)

Waterfront condo with a balcony overlooking the Gulf, pool & a gym

8.8 out of 10, Excellent, (19)
"Was awesome was up high don’t like height but everything bwas was awesome love it hate to leave but at 7 am. I had to leave work was calling me"
Waterfront condo with a balcony overlooking the Gulf, pool & a gym

🌴 Beach Chairs Included-7th floor 2-King & Bunkroom Directly On the Beach

10.0 out of 10, Exceptional, (77)
"We were very satisfied with the property. Owner quickly responded to any questions we had. Looking forward to another visit!"
🌴 Beach Chairs Included-7th floor 2-King & Bunkroom Directly On the Beach

Gulf Front condo PRIVATE JACUZZI BATH and almost a mile of private gated beach.

8.6 out of 10, Excellent, (50)
"Quick trip to Panama City Beach to surprise my wife for her birthday. The condo was awesome! Clean, great decor, kitchen. This condo is right on the beach!! Pool was awesome too! Security was excellent! We will definitely be back! Loved it!"
The price is AU$390
includes taxes & fees
9 Dec - 10 Dec
Gulf Front condo PRIVATE JACUZZI BATH and almost a mile of private gated beach.

Lovely Oceanfront Studio w/Shared Pool, Free WiFi, Firepit, Balcony, Patio, Deck

7.8 out of 10, Good, (14)
"When you rent this condo, it goes through Vacasa. They were terrible as property managers. we were told days in advance we could get an early check in if the room was clean. Upon arrival, we were told no early check in was allowed. So we waited hours to check in. After checking in we had an issue with the cold water not turning on in the shower our first night. I contacted vacasa as they requested and no one showed up for two of the four days we stayed. The condo itself was clean and the...
Lovely Oceanfront Studio w/Shared Pool, Free WiFi, Firepit, Balcony, Patio, Deck

2-Bed Condo Just Steps from the Sand!

8.0 out of 10, Very good, (10)
"Small kitchen comfortable beds dirty carpets "stained". Over all 8/10 we just slept there."
2-Bed Condo Just Steps from the Sand!
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.
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Other types of properties in Chipley you may be interested in

Palmetto Beachfront Hotel, a By the Sea Resort

2.0 star property
8.4 out of 10, Very good, (1295)
"Great place at an exceptionally price!"
The price is AU$86
includes taxes & fees
9 Dec - 10 Dec
Palmetto Beachfront Hotel, a By the Sea Resort

Radisson Panama City Beach - Oceanfront

3.0 star property
7.4 out of 10, Good, (1905)
"The staff when I checked in was wonderful. I had to make a last minute reservation due to my father's illness. They were very accommodating and very empathetic. I didn't spend much time at the hotel given the circumstances. The property is a little dated but nothing was unsatisfactory."
The price is AU$143
includes taxes & fees
12 Dec - 13 Dec
Radisson Panama City Beach - Oceanfront

Hampton Inn & Suites Panama City Beach-Beachfront

2.5 star property
8.8 out of 10, Excellent, (1615)
"The front desk,Nan, was great to us. Breakfast was good. Only complaint was a wake-up call that never came! Have stayed there before and would again if we ever go back to PCB, Fl."
The price is AU$176
includes taxes & fees
9 Dec - 10 Dec
Hampton Inn & Suites Panama City Beach-Beachfront
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.
Beautiful view of the beach with palm trees

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Frequently asked questions

Can I find holiday rentals in Chipley?

Yes, there are holiday rentals close to the most popular sights in Chipley, or you can select a more secluded option if you're looking for a relaxing stay. Chipley is known for its churches and lake views. Make sure you have time to check out the forests while you're in the area.

What are some of the best holiday rentals that Chipley has to offer?

Stunning Three Story PCB House / Pool / Pet Friendly / Gulf of Mexico Views: This holiday home rental outside of Chipley is located on the beach, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many holiday rentals are there in Chipley?

Choose from 6 Expedia holiday rentals in Chipley for a memorable holiday.

What can I see and do in Chipley?

Falling Waters State Park and Lucas Lake are a couple of lovely local spots to get outside and enjoy nature. Pal's Park and Moss Hill Methodist Church are other places to visit while you're in town.

What are holiday rentals like in Chipley?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chipley. Holiday rentals feature extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.