Photo by Official flight chick

Chipley Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Chipley vacation rentals

Terrace/patio
Cozy Lakefront Airstream

Mobile Home in Chipley

Cozy Lakefront Airstream
9.8 out of 10, Exceptional, (14)
"We loved the property, enjoyed all the amenities and relaxed comfortably."
United States
Lesley H.
The price is ￥17,593
￥26,025 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Cozy Lakefront Airstream
Outdoor spa tub
Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful

Mobile Home in Chipley

Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful
10.0 out of 10, Exceptional, (3)
"Easy check in. Breakfast was delicious. Quite county setting. "
United States
Deborah H.
The price is ￥21,056
￥40,059 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful
Property grounds
Charming waterfront barndominium on the beautiful spring-fed Chipola River.

Cabin in Altha

Charming waterfront barndominium on the beautiful spring-fed Chipola River.
2.0 star property
9.6 out of 10, Exceptional, (23)
"Great stay! Very peaceful river setting! Great host! "
United States
Mike A.
The price is ￥23,396
￥39,169 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Charming waterfront barndominium on the beautiful spring-fed Chipola River.
Property grounds
Private Cozy bedroom with on suite living room

Vacation Home in Panama City

Private Cozy bedroom with on suite living room
10.0 out of 10, Exceptional, (27)
"According to our friends the stay was very peaceful and very relaxing for them."
United States
Ken N.
The price is ￥12,322
￥19,642 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Private Cozy bedroom with on suite living room
Apartment (Four bedroom Gulf View) | Individually decorated, individually furnished, iron/ironing board
Origin At Seahaven

Aparthotel in Panama City Beach

Origin At Seahaven
3.5 star property
7.0 out of 10, Good, (2171)
"Room was great loved the contactless "
United States
Avontay
The price is ￥9,670
￥34,087 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Origin At Seahaven
Exterior
Beach Guest House Cottage Pier Park, Frank Brown Park, & 30a, private driveway

Cottage in Sunnyside

Beach Guest House Cottage Pier Park, Frank Brown Park, & 30a, private driveway
9.6 out of 10, Exceptional, (11)
"Enough room for 2 and wonderful bed"
United States
Angel C.
The price is ￥17,202
￥22,394 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Beach Guest House Cottage Pier Park, Frank Brown Park, & 30a, private driveway
Marina
Dog-Friendly Retreat with Private Dock & Water Views - Great for Fishing & Boating

Vacation Home in Bayside Park

Dog-Friendly Retreat with Private Dock & Water Views - Great for Fishing & Boating
9.0 out of 10, Wonderful, (64)
"I loved being able to walk out the door down the deck and straight to dock to boat. It was very clean on the inside, I will stay here again"
United States
Allen G.
The price is ￥12,946
￥50,521 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Dog-Friendly Retreat with Private Dock & Water Views - Great for Fishing & Boating
Beach nearby, sun loungers
~ La Conchita 🐚 ~ w private pool!

Vacation Home in Panama City

~ La Conchita 🐚 ~ w private pool!
9.8 out of 10, Exceptional, (49)
"Very clean and comfortable. Would definitely recommend for a family."
United States
Neil L.
The price is ￥8,422
￥49,806 total
includes taxes & fees
Jan 4 - Jan 5, 2026
~ La Conchita 🐚 ~ w private pool!
Pool
Grand Panama Beach Resort

Condo in Panama City Beach

Grand Panama Beach Resort
4.0 star property
6.4 out of 10, (5)
"Nice!"
United States
Erik
The price is ￥15,032
￥64,698 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Grand Panama Beach Resort
Beach nearby
Private Pool Private Yard "Golf Cart Rentals Available locally"

Vacation Home in Sunnyside

Private Pool Private Yard "Golf Cart Rentals Available locally"
9.6 out of 10, Exceptional, (62)
"Great place to stay. Parking for 2 vehicles . Three vehicles kinda sketchy. Overall excellent stay"
United States
John F.
The price is ￥13,292
￥63,959 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Private Pool Private Yard "Golf Cart Rentals Available locally"
On the beach, white sand
Landmark Holiday Beach

Aparthotel in Panama City Beach

Landmark Holiday Beach
3.5 star property
8.6 out of 10, Excellent, (222)
"Kitchen has everything you need along with washer and dryer.. Beautiful beachfront view ."
United States
Judy
Landmark Holiday Beach
Outdoor dining
The Banana, A Peaceful Getaway

Vacation Home in Panama City

The Banana, A Peaceful Getaway
9.6 out of 10, Exceptional, (24)
"Excellent stay! Will be back!"
United States
Nathan T.
The price is ￥21,111
￥33,715 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Banana, A Peaceful Getaway
On the beach
Pier Serenity **Beachfront Corner End Balcony** Sleeps 2

Condo in Panama City Beach

Pier Serenity **Beachfront Corner End Balcony** Sleeps 2
9.4 out of 10, Exceptional, (108)
"Covered parking, nice location, clean comfortable room, close to the Pier. Great Sunset views!..... "
United States
Gerald L.
The price is ￥10,165
￥27,101 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Pier Serenity **Beachfront Corner End Balcony** Sleeps 2
Beach nearby
Origin 0538- Studio - Breath Taking Gulf Views

Condo in Panama City Beach

Origin 0538- Studio - Breath Taking Gulf Views
9.2 out of 10, Wonderful, (32)
"In the middle of everything. Easy to get around and to get to beach. "
United States
Suzy V.
The price is ￥10,138
￥37,999 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Origin 0538- Studio - Breath Taking Gulf Views
On the beach, sun loungers, beach towels
Newly renovated studio on the beach # 304

Apartment in Panama City Beach

Newly renovated studio on the beach # 304
2.0 star property
9.4 out of 10, Exceptional, (9)
"Everything was as promised and the communication with the property manager was perfect as well!!"
United States
Christy T.
The price is ￥4,691
￥34,969 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Newly renovated studio on the beach # 304
On the beach
Oceanfront studio with shared pool & washer/dryer - steps from the beach

Apartment in Panama City Beach

Oceanfront studio with shared pool & washer/dryer - steps from the beach
9.2 out of 10, Wonderful, (68)
"Amazing find. Very clean updated room . Comfortable bed . On the beach ,close walk to water . Near Sharkey's restaurant. I would love to stay here again on my next visit. "
United States
Kimberly C.
The price is ￥13,881
￥44,225 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Oceanfront studio with shared pool & washer/dryer - steps from the beach
A heated pool
BEACHFRONT CONDO NOW ACCEPTING RENTALS!!

Condo in Panama City Beach

BEACHFRONT CONDO NOW ACCEPTING RENTALS!!
9.2 out of 10, Wonderful, (123)
"Beautiful view somewhat dated interior. Only stayed one night as we had a week planned in Seacrest and needed one additional night. Parking was full when we arrived very late ( peak season). "
United States
George Z.
The price is ￥14,074
￥67,629 total
includes taxes & fees
Jan 5 - Jan 6, 2026
BEACHFRONT CONDO NOW ACCEPTING RENTALS!!
A heated pool
Sea Breeze-PCB-Deluxe Beachfront King Main Suite-2 baths-Sea Breezes Await!

Condo in Panama City Beach

Sea Breeze-PCB-Deluxe Beachfront King Main Suite-2 baths-Sea Breezes Await!
9.4 out of 10, Exceptional, (79)
"Condo was very comfortable and beautiful view of the ocean. "
United States
Anonymous traveler
The price is ￥17,029
￥81,591 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Sea Breeze-PCB-Deluxe Beachfront King Main Suite-2 baths-Sea Breezes Await!
On the beach
Oceanfront Paradise! with Beach Chairs, and Free Activities Each Day +More

Condo in Panama City Beach

Oceanfront Paradise! with Beach Chairs, and Free Activities Each Day +More
9.2 out of 10, Wonderful, (52)
"Pool,condo , beach& the Whole property was wonderful & had everything we wanted & needed."
United States
Linda T.
The price is ￥13,881
￥89,656 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Oceanfront Paradise! with Beach Chairs, and Free Activities Each Day +More
A heated pool
Free Beach Chair Service + Free Activities! Summer Deals! 17th Floor!

Condo in Panama City Beach

Free Beach Chair Service + Free Activities! Summer Deals! 17th Floor!
9.0 out of 10, Wonderful, (126)
"This was an awesome place stay. We will keep on our favorites list. "
United States
Kenneth W.
Free Beach Chair Service + Free Activities! Summer Deals! 17th Floor!
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.
View all properties
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

Beachcomber Beachfront Hotel, a By The Sea Resort

Beachcomber Beachfront Hotel, a By The Sea Resort

10/10 Excellent
"Everything was good, only thing but minor was the tv remote control don’t have batteries but nothing big! Was the best stay of my life!"
Isaac 4-night trip
Posted 1 day ago
Beachcomber Beachfront Hotel, a By The Sea Resort

Find out more about Chipley

Search for holiday rentals in Chipley on Expedia! You can easily find your home rentals, villas, holiday apartments in Chipley using one of the methods below:

  • View our selection of featured holiday rentals in Chipley
  • Use the map to find apartments and other holiday homes in the Chipley neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chipley while they last

Look no further and take a look at our great range of rental properties in Chipley!

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Chipley?

Yes, there are vacation rentals close to popular points of interest in Chipley, or you can go with a secluded option if you'd like a relaxing place to 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's the top vacation rental that Chipley has to offer?

"Tide Life" - Perfect Sized Family Beach House: You might want to consider this vacation home rental near Chipley, which is located on the beach and has an outdoor pool, a private balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Chipley?

Choose from 8 Expedia vacation rentals in Chipley for a memorable vacation.

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. In the larger area, you’ll find Pal's Park and Moss Hill Methodist Church.

What are vacation rentals like in Chipley?

Vacation rentals are private accommodations you can book for a couple days or more in Chipley. Vacation rentals feature amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for families.