A waterfall cascading over a rocky cliff surrounded by lush green ferns and foliage.

Chipley Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Chipley vacation rentals

An indoor swimming pool with a long, narrow shape, surrounded by walls with large windows.

1. Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery

Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery
Chipley
10.0 out of 10, Exceptional, (1 review)
"Very nice place to stay. Host was very helpful and accommodating. Enjoyed being way out in the country."
United States
Gwen S.
The price is ￥13,070
￥23,704 total
includes taxes & fees
Oct 20 - Oct 21
Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery
An indoor swimming pool with a view of the outside.

2. Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful

Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful
Chipley
9.6 out of 10, Exceptional, (7 reviews)
"Great place to stay!"
United States
Carrie P.
The price is ￥21,310
￥40,542 total
includes taxes & fees
Oct 8 - Oct 9
Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful
Property grounds

3. Cozy Lakefront Airstream

Cozy Lakefront Airstream
Chipley
9.8 out of 10, Exceptional, (14 reviews)
"We loved the property, enjoyed all the amenities and relaxed comfortably."
United States
Lesley H.
The price is ￥19,731
￥28,449 total
includes taxes & fees
Nov 4 - Nov 5
Cozy Lakefront Airstream
A wooden staircase leading to a house with a deck, surrounded by trees and a lawn.

4. Charming waterfront barndominium on the beautiful spring-fed Chipola River.

Charming waterfront barndominium on the beautiful spring-fed Chipola River.
Altha
9.8 out of 10, Exceptional, (36 reviews)
"Amazing place"
United States
Alex R.
The price is ￥23,678
￥41,378 total
includes taxes & fees
Oct 5 - Oct 6
Charming waterfront barndominium on the beautiful spring-fed Chipola River.
A beach with clear turquoise water, a sandy shore, and buildings in the background.

5. ~ La Conchita ~ w private pool & Firepit

~ La Conchita ~ w private pool & Firepit
Panama City
9.8 out of 10, Exceptional, (56 reviews)
"Great location!Kids loved the pool even if it was cold. The owners were amazing, and quick to respond."
United States
Ellen D.
The price is ￥14,207
￥56,203 total
includes taxes & fees
Oct 16 - Oct 17
~ La Conchita ~ w private pool & Firepit
A beach view with a pier extending into the ocean, clear skies, and a balcony overlooking the scene.

6. Calypso Beach Resort Tower 2 by Panhandle Getaways

Calypso Beach Resort Tower 2 by Panhandle Getaways
3.5 star property
Panama City Beach
8.8 out of 10, Excellent, (193 reviews)
"Gorgeous view of the ocean. The condo was really nice and modern. This was our first time staying at the Calypso. We will definitely be back!"
United States
Cheryl
The price is ￥20,589
￥97,401 total
includes taxes & fees
Oct 12 - Oct 13
Calypso Beach Resort Tower 2 by Panhandle Getaways
A beach with rows of blue umbrellas and white beach chairs, a sandy shore, and the ocean in the background.

7. Calypso Tower 3 by Panhandle Getaways

Calypso Tower 3 by Panhandle Getaways
3.5 star property
Panama City Beach
9.2 out of 10, Wonderful, (41 reviews)
"The property was very clean and in an excellent location . We weren’t on the beach , but we had a great view of the ocean and the pools I would highly recommend"
United States
Thomas
The price is ￥19,446
￥94,320 total
includes taxes & fees
Oct 6 - Oct 7
Calypso Tower 3 by Panhandle Getaways
A beach with clear blue water, a pier, and rows of blue beach umbrellas.

8. Calypso Beach Resort Tower 1

Calypso Beach Resort Tower 1
4.5 star property
Panama City Beach
9.2 out of 10, Wonderful, (14 reviews)
"My wife and I loved that everything was close by. Qill definitely stay again 10/10"
United States
shawn
The price is ￥23,520
￥91,424 total
includes taxes & fees
Oct 7 - Oct 8
Calypso Beach Resort Tower 1
A wooden boardwalk leading to a beach with a pier extending into the ocean.

9. Private - Waterfront Cottage - Panama City, FL

Private - Waterfront Cottage - Panama City, FL
Drummond And Ware
10.0 out of 10, Exceptional, (21 reviews)
"Very clean and unique hidden gem of panama city, it may be in the city but you cant tell while at the house. Its extremely private and secluded, wildlife was everywhere, we watch herons and ducks in the bayou behind the house, a fox and a family of possums in the back yard after dusk. Its dog friendly and close to a lot of dog friendly restaurants, it also has a kayak launch and the fishing is incredible in the bayou. We caught multiple trout and reddish. Ill be posting a video on youtube @...
United States
William
The price is ￥18,468
￥48,104 total
includes taxes & fees
Oct 5 - Oct 6
Private - Waterfront Cottage - Panama City, FL
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10. Origin 1402 - Studio - Direct Beach View

Origin 1402 - Studio - Direct Beach View
Panama City Beach
9.0 out of 10, Wonderful, (14 reviews)
"It was exactly like the photos and had a great view of the ocean. I was very pleased!"
United States
Kelsie T.
Origin 1402 - Studio - Direct Beach View
A bedroom with a bed, a framed sign on the wall, and a door.

11. Octa Collection on Front Beach

Octa Collection on Front Beach
4.5 star property
Long Beach
The price is ￥35,674
￥69,819 total
includes taxes & fees
Oct 5 - Oct 6
Octa Collection on Front Beach
A wide sandy beach with footprints, a clear blue sky, and a distant pier.

12. Beachwalk 10B by Avantstay PCB Condo Across From the Beach + Pool & Tennis Court

Beachwalk 10B by Avantstay PCB Condo Across From the Beach + Pool & Tennis Court
4.0 star property
Panama City Beach
10.0 out of 10, Exceptional, (1 review)
"Great area !!"
United States
Diana
The price is ￥13,586
￥61,977 total
includes taxes & fees
Oct 7 - Oct 8
Beachwalk 10B by Avantstay PCB Condo Across From the Beach + Pool & Tennis Court
A beach with clear turquoise water, a sandy shore, and a few buildings in the distance.

13. Dog-Friendly Studio Just 500 Feet from the Sand! Walk to Beach + Free Fun!

Dog-Friendly Studio Just 500 Feet from the Sand! Walk to Beach + Free Fun!
Laguna Beach
8.8 out of 10, Excellent, (30 reviews)
"Great place to stay especially if you have your puppy. It was a really great location "
United States
Christina
The price is ￥14,049
￥57,237 total
includes taxes & fees
Oct 8 - Oct 9
Dog-Friendly Studio Just 500 Feet from the Sand! Walk to Beach + Free Fun!
A balcony with a view of the beach and ocean, featuring a table and chairs.

14. Calypso Resort and Towers by Book That Condo

Calypso Resort and Towers by Book That Condo
4.0 star property
Panama City Beach
9.4 out of 10, Exceptional, (9 reviews)
"My stay was excellent however I think we needed linen replacements for the duration of the stay"
United States
andre
The price is ￥53,337
￥132,555 total
includes taxes & fees
Oct 9 - Oct 10
Calypso Resort and Towers by Book That Condo
A balcony with a view of a beach, a palm tree, and a 'No Smoking' sign.

15. Newly renovated studio on the beach # 304

Newly renovated studio on the beach # 304
Panama City Beach
9.2 out of 10, Wonderful, (22 reviews)
"Great location! Right in the beach! Kinda in the middle of everything so you don’t have to travel very far either way you go!"
United States
Brandon t.
The price is ￥17,048
￥61,309 total
includes taxes & fees
Nov 2 - Nov 3
Newly renovated studio on the beach # 304
A balcony with wicker furniture and a view of the ocean.

16. Aqua Beach Resort by Panhandle Getaways

Aqua Beach Resort by Panhandle Getaways
3.5 star property
Panama City Beach
9.4 out of 10, Exceptional, (15 reviews)
"Great stay"
United States
Justin
The price is ￥24,940
￥95,709 total
includes taxes & fees
Oct 14 - Oct 15
Aqua Beach Resort by Panhandle Getaways
A beach with a long pier extending into the ocean, white sand, and clear blue water.

17. Pier Serenity **Beachfront Corner End Balcony** Sleeps 2

Pier Serenity **Beachfront Corner End Balcony** Sleeps 2
Panama City Beach
9.4 out of 10, Exceptional, (136 reviews)
"Great little place to stay and the views were nice!"
United States
Andres
The price is ￥13,417
￥31,128 total
includes taxes & fees
Oct 25 - Oct 26
Pier Serenity **Beachfront Corner End Balcony** Sleeps 2
A beach with a clear sky, palm trees, and a boardwalk leading to the water.

18. Sea Glass Villa! Gulf front! Pool! Dog friendly! Near Pier Park! Beach loungers!

Sea Glass Villa! Gulf front! Pool! Dog friendly! Near Pier Park! Beach loungers!
Panama City Beach
9.8 out of 10, Exceptional, (166 reviews)
"We had a great time! The view was great and the place was very clean! "
United States
Chloe G.
The price is ￥21,168
￥45,643 total
includes taxes & fees
Oct 12 - Oct 13
Sea Glass Villa! Gulf front! Pool! Dog friendly! Near Pier Park! Beach loungers!
A balcony with a view of the ocean, two lounge chairs, and a small table.

19. Gorgeous View! Spacious Beachfront Condo@Emerald Beach Resort.

Gorgeous View! Spacious Beachfront Condo@Emerald Beach Resort.
Panama City Beach
9.8 out of 10, Exceptional, (153 reviews)
"Everything was perfect from check in to check out. We can’t wait to return!"
United States
Renee H.
The price is ￥22,257
￥55,645 total
includes taxes & fees
Oct 18 - Oct 19
Gorgeous View! Spacious Beachfront Condo@Emerald Beach Resort.
A balcony with a view of a beach and ocean.

20. Romantic Condo DIRECTLY ON BEACH! - 2BR/2BA - Sky bar, Starbucks, 2 pools, pizza

Romantic Condo DIRECTLY ON BEACH! - 2BR/2BA - Sky bar, Starbucks, 2 pools, pizza
Panama City Beach
9.4 out of 10, Exceptional, (159 reviews)
"We absolutely loved staying here. The condo was very nice and all the amenities on the property were amazing. The host was very responsive."
United States
Kelsey C.
The price is ￥20,363
￥84,810 total
includes taxes & fees
Oct 18 - Oct 19
Romantic Condo DIRECTLY ON BEACH! - 2BR/2BA - Sky bar, Starbucks, 2 pools, pizza
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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Top Chipley Hotel Reviews

SpringHill Suites by Marriott Panama City Beach Beachfront

SpringHill Suites by Marriott Panama City Beach Beachfront

10/10 Excellent
"Excelente servicio y limpio"
Jesus 1-night trip
Posted 6 hours ago
SpringHill Suites by Marriott Panama City Beach Beachfront

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

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?

Beach House - Sunset Paradise by PHG: You might want to consider this Chipley vacation home rental for your stay. It is located by the ocean and offers a private balcony, air-conditioning, and Netflix to help you feel perfectly comfortable in your new surroundings. Amenities like a coffee maker and free parking are also available for your convenience.

How many vacation rentals are there in Chipley?

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

What can I see and do in Chipley?

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

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.