Photo by Anthony Creamer

Chipley Holiday Rentals

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Holiday Rentals in Chipley

Condo, 2 Bedrooms | Beach
Origin at Seahaven
4.5 star property
8.8 out of 10, Excellent, (16)
"The property was nice and pleasant "
The price is AU$378
includes taxes & fees
28 May - 29 May
Origin at Seahaven
Condo, Multiple Beds, Balcony, Ocean View (1131)
Emerald Beach Resort by Southern Vacation Rentals
3.5 star property
7.6 out of 10, Good, (752)
"Everything is clos"
Emerald Beach Resort by Southern Vacation Rentals
Condo, 3 Bedrooms, Beachfront (817) | Balcony view
Tidewater Beach Resort by Panhandle Getaways
3.5 star property
7.2 out of 10, Good, (118)
"I just didn’t like elevator it takes too long of waiting "
The price is AU$1,002
includes taxes & fees
28 May - 29 May
Tidewater Beach Resort by Panhandle Getaways
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Aerial view
Newly Remodeled!! 500 Feet to Beach!!
9.6 out of 10, Exceptional, (4)
"We chose this property because our son was participating in the Iron Man competition. After studying the route on the IRONMAN website, I felt like this was in close proximity to the course. Little did I know, the running portion of the race goes directly in front of the house! It worked out perfectly! The property was clean and comfortable. A little bit small, but worked very well for us. It was myself, my husband, one adult child and one grandchild. Definitely recommend this spot! Convenience...
Newly Remodeled!! 500 Feet to Beach!!
Pool
Edgewater Beach and Golf Resort by Southern Vacation Rentals
4.0 star property
7.4 out of 10, Good, (2162)
"The condo was perfect for our stay. 2 bathrooms is awesome. The balcony with ocean and beach view made for the perfect perch when not down by the water. The main pool area had some policies that I did not care for. Specifically, are not permitted to be turned to face the sun. Of course if you want to rent a cabana then there are perks. 🙄 Great stay and I look forward to a return trip."
Edgewater Beach and Golf Resort by Southern Vacation Rentals
Pool
Edgewater Beach and Golf Resort by Southern Vacation Rentals VI
4.0 star property
8.2 out of 10, Very good, (19)
"Great resort!"
Edgewater Beach and Golf Resort by Southern Vacation Rentals VI
Aerial view
Newly Remodeled Two bedroom Two bath! 500 Feet to Beach!
9.2 out of 10, Wonderful, (10)
"We loved the place, it was very clean and really close to the beach. The checking in and checking out process was very easy. Also, the place is very close to many restaurants and stores, we didn’t have to drive very far. You can even walk to the stores and restaurants if you want to. The only thing I would recommend changing it would be the beds, they were not very comfortable. Other then that everything was great 👍"
Newly Remodeled Two bedroom Two bath! 500 Feet to Beach!
Exterior
Gulf Front condo PRIVATE JACUZZI BATH and almost a mile of private gated beach.
8.6 out of 10, Excellent, (41)
"Nice room with a nice view! The weather and the waves were perfect. The laundry was right by us which was handy so no dirty clothes to bring home!"
The price is AU$355
includes taxes & fees
22 May - 23 May
Gulf Front condo PRIVATE JACUZZI BATH and almost a mile of private gated beach.
Condo, 1 Bedroom, Sea View (403E) | View from room
Splash Beach Resort by Panhandle Getaways
3.5 star property
7.2 out of 10, Good, (163)
"Everything was as good as it could be. "
The price is AU$1,018
includes taxes & fees
28 May - 29 May
Splash Beach Resort by Panhandle Getaways
On the beach, white sand
Continental Condominiums by Southern Vacation Rentals II
3.5 star property
6.8 out of 10, (448)
"It was a good trip. The room was nice. People were nice with the exception of not being able to use the patio because someone was smoking pot the whole time we were there."
Continental Condominiums by Southern Vacation Rentals II
Condo, 2 Bedrooms, Sea View (1-307) | View from room
Grand Panama Beach Resort by Panhandle Getaways
3.5 star property
8.2 out of 10, Very good, (67)
"Really great location and property. Pool for kids was great. Super close to the beach. Room was clean and easy to settle into. The main issue we ran into was the lack of complete elevator access in the first tower. Only two of three were working at any one time. When checkout at 10a rolled around, elevators were packed! Cleaners were also using the elevators (to tightly do their job!), but they had no utility elevator for them. So, ask for a late checkout if you do stay in tower 1"
The price is AU$1,047
includes taxes & fees
28 May - 29 May
Grand Panama Beach Resort by Panhandle Getaways
A heated pool
Gulf-front condo with balcony, beach access, hot tub, pool & gym
9.2 out of 10, Wonderful, (27)
"We enjoyed everything about this place."
Gulf-front condo with balcony, beach access, hot tub, pool & gym
On the beach
High-rise condo with pool, hot tub, central AC, & free WiFi
9.4 out of 10, Exceptional, (64)
"Absolutely love the Emerald Isle Resort. Staff is friendly and the beach is gorgeous. This is our second year there and we will be back next year!!"
High-rise condo with pool, hot tub, central AC, & free WiFi
Beach nearby
Steps to the beach! 2 br/1 bath Sleeps 6, ground floor Condo
9.6 out of 10, Exceptional, (40)
"The unit was exactly as pictured. Everything was clean and well appointed. We had return home sooner than expected due to unforeseen issues, so we weren't able to explore the whole area like we had planned."
Steps to the beach! 2 br/1 bath Sleeps 6, ground floor Condo
Interior
2-Bed Condo Just Steps from the Sand!
7.6 out of 10, Good, (7)
"Great all but owners wouldn't contact me back"
2-Bed Condo Just Steps from the Sand!
Fridge, microwave, oven, stovetop
Calypso 902 West - 3 Bedroom, 2 Bathroom Beach Front Condominium
6.4 out of 10, (26)
"I have been stuck at home for six months and this was my first time out since my health crisis. We have stayed at the Calypso in many different units over the years, we have been coming to the Calypso for going on 13 years always a great time staying here have not had a problem at any other units. I would say that there is very little deck furniture only one chair. And the beds are hard but other than that it’s all good. PS the dryer takes forever to dry your clothes."
Calypso 902 West - 3 Bedroom, 2 Bathroom Beach Front Condominium
Property grounds
TIDEWATER 8th Fl 2BR/3BA + Bunk Beachfront near Pier Park & Beach Chairs too!
9.0 out of 10, Wonderful, (163)
"Quiet, wonderful place to be at the beach. Easy check in and out also parking a breeze."
TIDEWATER 8th Fl 2BR/3BA + Bunk Beachfront near Pier Park & Beach Chairs too!
On the beach, sun-loungers
Beachfront Condo With Free Beach Chairs & Umbrella Set Up
9.8 out of 10, Exceptional, (62)
"The propriety was close to the event we attended. Beach access was very good. I would book it again."
Beachfront Condo With Free Beach Chairs & Umbrella Set Up
Beach nearby
Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!
9.6 out of 10, Exceptional, (195)
"Love this place perfect location. Quite location but we have stayed here twice and both times we have had cleaning issues. Not owner fault. The owners are amazing people. We will definitely stay again and again"
The price is AU$578
includes taxes & fees
27 May - 28 May
Gorgeous beachfront 2BR Condo Steps from the beach with a pool!!!
On the beach
Beachfront!! Free Beach Chairs!! Over 241 Five Star Reviews!
10.0 out of 10, Exceptional, (252)
"The place was as advertised, couple of minor issues that were addressed immediately. Properly manager was in continuous cotact just making sure everything was perfect. Would stay again, thanks."
The price is AU$708
includes taxes & fees
22 May - 23 May
Beachfront!! Free Beach Chairs!! Over 241 Five Star Reviews!
Don't see what you're looking for?
See all available properties in Chipley
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.

Other types of properties in Chipley you may be interested in

Iron/ironing board, free WiFi, bed sheets
Palmetto Beachfront Hotel, a By the Sea Resort
2.0 star property
8.8 out of 10, Excellent, (1012)
"Everything was great other than at checkout they over charge for the stay. We booked through the hotel app which was one price. At checkout they charged $90.00 more on my card through hotel. "
The price is AU$174
includes taxes & fees
23 May - 24 May
Palmetto Beachfront Hotel, a By the Sea Resort
View from room
Radisson Panama City Beach - Oceanfront
3.0 star property
7.4 out of 10, Good, (1514)
"Shower was leaking, suspect the room has painted over mold. Allergies were off the chart for us both."
The price is AU$254
includes taxes & fees
22 May - 23 May
Radisson Panama City Beach - Oceanfront
Outdoor pool, pool loungers
Seahaven Beach Hotel
2.0 star property
5.4 out of 10, (1338)
"Good stay for the cost, beach front balcony and the elevator worked! :-) room needed some upgrades, exhaust fan in bathroom sounded like a broken helicopter and the AC ran like a diesel truck but would still stay again. "
The price is AU$199
includes taxes & fees
29 May - 30 May
Seahaven Beach Hotel
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.

Everything you need to know about Chipley holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chipley holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chipley holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chipley holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chipley. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chipley holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chipley holiday rentals we have selected for you start as low as AU$355 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chipley rentals

At Expedia, we put the best Chipley holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chipley rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chipley holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chipley. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

2000.00 a month Winter Rental! Newly Remodeled!! 500 Feet to Beach!!: This holiday home rental outside of Chipley is located near the beach, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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.

Recent reviews of Chipley properties
Expedia verified reviews

The Flamingo Hotel and Tower

The Flamingo Hotel and Tower

5/5 Excellent
"This is the first time we stayed here, and we loved it. It was clean, balcony was great, and location spot on"
A verified traveller stayed at The Flamingo Hotel and Tower
Posted 1 day ago
The Flamingo Hotel and Tower