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

Chipley Vacation Rentals

  • 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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Chipley vacation rentals

Indoor pool, a heated pool

1. 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 AED 496
AED 943 total
includes taxes & fees
26 Sep - 27 Sep
Outdoorsmen Retreat: Indoor pool, Spa, fire pits, Bed& Breakfast, Peaceful
Property grounds

2. 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.
Cozy Lakefront Airstream
Pool

3. 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 AED 317
AED 566 total
includes taxes & fees
19 Oct - 20 Oct
Romantic Country Escape Indoor Heated Pool Hot Tub Breakfast Art Studio Bakery
Property grounds

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, (35 reviews)
"Amazing place"
United States
Alex R.
The price is AED 551
AED 937 total
includes taxes & fees
22 Sep - 23 Sep
Charming waterfront barndominium on the beautiful spring-fed Chipola River.
Beach nearby, sun loungers

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 AED 331
AED 1,297 total
includes taxes & fees
16 Oct - 17 Oct
~ La Conchita ~ w private pool & Firepit
Beach

6. Private - Waterfront Cottage - Panama City, FL

Private - Waterfront Cottage - Panama City, FL
Drummond And Ware
10.0 out of 10, Exceptional, (20 reviews)
"Perfect stay "
United States
Jess C.
The price is AED 413
AED 1,071 total
includes taxes & fees
3 Oct - 4 Oct
Private - Waterfront Cottage - Panama City, FL
On the beach

7. Beach Haven-Pets/11 Pools/Pickleball/Mini-Golf/Walk to Beach!

Beach Haven-Pets/11 Pools/Pickleball/Mini-Golf/Walk to Beach!
Panama City Beach
9.8 out of 10, Exceptional, (17 reviews)
"We enjoyed our stay. Everything was as advertised. The weather was perfect. "
United States
Anonymous traveler
The price is AED 350
AED 1,342 total
includes taxes & fees
24 Sep - 25 Sep
Beach Haven-Pets/11 Pools/Pickleball/Mini-Golf/Walk to Beach!
Exterior

8. Prime Gulf Highlands Property: 0.4 Mile to Private Beach & 11 Pools!

Prime Gulf Highlands Property: 0.4 Mile to Private Beach & 11 Pools!
Panama City Beach
9.0 out of 10, Wonderful, (28 reviews)
"Great place "
United States
Lynn O.
The price is AED 246
AED 1,004 total
includes taxes & fees
20 Oct - 21 Oct
Prime Gulf Highlands Property: 0.4 Mile to Private Beach & 11 Pools!
Superior Apartment, 1 Bedroom, Kitchen, City View | Living area | 55-inch Smart TV with digital channels

9. Octa Collection on Front Beach

Octa Collection on Front Beach
4.5 star property
Long Beach
The price is AED 808
AED 1,600 total
includes taxes & fees
22 Sep - 23 Sep
Octa Collection on Front Beach
Outdoor pool, a heated pool

10. Sea La Vie - NEWLY RENOVATED - On the Beach at First Class Edgewater Resort

Sea La Vie - NEWLY RENOVATED - On the Beach at First Class Edgewater Resort
Panama City Beach
9.6 out of 10, Exceptional, (177 reviews)
"INCREDIBLE place to stay. Everything was exactly as described and everything about this place is perfect!!!"
United States
Gray M.
The price is AED 511
AED 1,142 total
includes taxes & fees
17 Oct - 18 Oct
Sea La Vie - NEWLY RENOVATED - On the Beach at First Class Edgewater Resort
Outdoor pool, a heated pool

11. Premier Partner Oceanfront Edgewater Condo With Full Amenities

Premier Partner Oceanfront Edgewater Condo With Full Amenities
Panama City
10.0 out of 10, Exceptional, (118 reviews)
"Great location on the 2nd floor. Host was awesome and we would definitely stay here again."
United States
John R.
The price is AED 771
AED 2,006 total
includes taxes & fees
2 Oct - 3 Oct
Premier Partner Oceanfront Edgewater Condo With Full Amenities
A heated pool

12. Edgewater T3 #802- Amazing Gulf Views!

Edgewater T3 #802- Amazing Gulf Views!
Panama City
9.8 out of 10, Exceptional, (71 reviews)
"Great location, easy access to beach, pools and restaurants!/"
United States
Jim M.
The price is AED 1,400
AED 2,842 total
includes taxes & fees
22 Sep - 23 Sep
Edgewater T3 #802- Amazing Gulf Views!
Outdoor pool, a heated pool

13. [5 O'Clock Somewhere] Gorgeous Edgewater Beach Resort Panama City Beach, Florida

[5 O'Clock Somewhere] Gorgeous Edgewater Beach Resort Panama City Beach, Florida
Panama City Beach
9.6 out of 10, Exceptional, (145 reviews)
"Great location. Short walk to the beach, and beautiful pool area."
United States
Caralyn H.
The price is AED 400
AED 1,142 total
includes taxes & fees
5 Oct - 6 Oct
[5 O'Clock Somewhere] Gorgeous Edgewater Beach Resort Panama City Beach, Florida
A heated pool

14. Red Sky Nights 🌊 Deluxe 2-Bedroom Condo @ Edgewater Beach & Golf Resort Tower 1

Red Sky Nights 🌊 Deluxe 2-Bedroom Condo @ Edgewater Beach & Golf Resort Tower 1
Panama City Beach
10.0 out of 10, Exceptional, (78 reviews)
"Excellent vacation"
United States
Brittany H.
Red Sky Nights 🌊 Deluxe 2-Bedroom Condo @ Edgewater Beach & Golf Resort Tower 1
A heated pool

15. Edgewater T1 #609 - Lagoon Pool Tower

Edgewater T1 #609 - Lagoon Pool Tower
Panama City Beach
9.6 out of 10, Exceptional, (131 reviews)
"Great place to stay with kids."
United States
Andy W.
Edgewater T1 #609 - Lagoon Pool Tower
Fitness facility

16. Edgewater Beach & Golf Resort by Panhandle Getaways

Edgewater Beach & Golf Resort by Panhandle Getaways
3.5 star property
Panama City Beach
7.8 out of 10, Good, (42 reviews)
"Balcony overlooking pool was amazing! Spacious, clean and perfect for our group!"
United States
Kara
The price is AED 673
AED 2,224 total
includes taxes & fees
22 Sep - 23 Sep
Edgewater Beach & Golf Resort by Panhandle Getaways
Outdoor pool, a heated pool

17. GORGEOUS AMAZING BEACH VIEWS CONDO DIRECTLY ON THE BEACH! Edgewater Beach Resort

GORGEOUS AMAZING BEACH VIEWS CONDO DIRECTLY ON THE BEACH! Edgewater Beach Resort
Panama City Beach
9.8 out of 10, Exceptional, (96 reviews)
"Great location, building amenities were amazing. Host was great. "
United States
Monica P.
The price is AED 664
AED 2,000 total
includes taxes & fees
22 Sep - 23 Sep
GORGEOUS AMAZING BEACH VIEWS CONDO DIRECTLY ON THE BEACH! Edgewater Beach Resort
A heated pool

18. Sandcastle Dreams PCB Edgewater 104T2-Beachfront King Main with Jetted Garden Tub! 1Bd/2Ba

Sandcastle Dreams PCB Edgewater 104T2-Beachfront King Main with Jetted Garden Tub! 1Bd/2Ba
Panama City Beach
9.4 out of 10, Exceptional, (113 reviews)
"Room was clean. Host was easy to communicate with. View was nice. Being in the first floor made it super easy to access!"
United States
Jana G.
The price is AED 568
AED 2,123 total
includes taxes & fees
18 Oct - 19 Oct
Sandcastle Dreams PCB Edgewater 104T2-Beachfront King Main with Jetted Garden Tub! 1Bd/2Ba
Property grounds

19. Edgewater Windward 104- Amazing Views!

Edgewater Windward 104- Amazing Views!
Panama City Beach
9.2 out of 10, Wonderful, (48 reviews)
"The condo was clean at check in and the view is fabulous..just steps from the beach. The amenities were adequate and met our needs. We have stayed at the Edgewater a number of times and never disappointed. Good location for restaurants and shopping."
United States
Vicki P.
Edgewater Windward 104- Amazing Views!
A rooftop pool, a heated pool

20. **Shore 2 Please** 3/3 Luxury Condo**5 ⭐️ Reviews**Sleeps 8

**Shore 2 Please** 3/3 Luxury Condo**5 ⭐️ Reviews**Sleeps 8
Panama City Beach
9.8 out of 10, Exceptional, (99 reviews)
"House was very easy to work with. We really enjoyed our stay."
United States
Alyce H.
The price is AED 533
AED 1,690 total
includes taxes & fees
22 Sep - 23 Sep
**Shore 2 Please** 3/3 Luxury Condo**5 ⭐️ Reviews**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.
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

La Quinta by Wyndham PCB Coastal Palms

La Quinta by Wyndham PCB Coastal Palms

8/10 Good
"Loved the room, very clean."
Austin 3-night trip
Posted 3 hours ago
La Quinta by Wyndham PCB Coastal Palms

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 7 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.