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

Holiday Homes in Chipley

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Chipley holiday homes

A living room with a television, a sofa, a coffee table, and a bookshelf.

1. The Cozy Farmhouse Retreat

The Cozy Farmhouse Retreat
Chipley
The price is €437
includes taxes & fees
8 Nov - 9 Nov
The Cozy Farmhouse Retreat
A single-story building with a gabled roof, a front porch with a bench, and a large planter with flowers.

2. Charming In-town Bungalow

Charming In-town Bungalow
Marianna
10.0 out of 10, Exceptional, (13 reviews)
"The home was so beautiful and cozy. The kitchen was well equipped and the home was impeccably decorated. The owners texted often to make sure we were comfortable and enjoying our stay."
United States
Jennifer
The price is €311
includes taxes & fees
23 Nov - 24 Nov
Charming In-town Bungalow
A modern kitchen with a large island, wooden cabinets, and pendant lighting.

3. Spacious 5-bedroom house in lovely Ponce de Leon with AC

Spacious 5-bedroom house in lovely Ponce de Leon with AC
Ponce de Leon
10.0 out of 10, Exceptional, (1 review)
The price is €410
includes taxes & fees
24 Oct - 25 Oct
Spacious 5-bedroom house in lovely Ponce de Leon with AC
A laundry room with a washing machine and a sign above the door that reads "Lost Socks Seeking Sole Mates".

4. Sparrow

Sparrow
3.0 star property
Lynn Haven
8.6 out of 10, Excellent, (4 reviews)
"Great neighborhood. I didn’t know what to expect with it being a converted garage area but it was great! Had everything we needed for our weekend stay."
United States
Cateria
The price is €117
includes taxes & fees
2 Nov - 3 Nov
Sparrow
A modern kitchen with wooden cabinets, a refrigerator, stove, microwave, and a dining area with a sofa and coffee table.

5. Reel Bayou Private Staycation / Extended Stay

Reel Bayou Private Staycation / Extended Stay
Bay County
Reel Bayou Private Staycation / Extended Stay
A bedroom with a bed, bedside tables, a hanging light fixture, a closet, and a painting on the wall.

6. Adorable 1 BDR with Full Kitchen Deck Washer Dryer

Adorable 1 BDR with Full Kitchen Deck Washer Dryer
Lynn Haven
8.8 out of 10, Excellent, (6 reviews)
"Clean and convenient. Served our purpose quite nicely."
United States
Jerry C.
The price is €168
includes taxes & fees
27 Oct - 28 Oct
Adorable 1 BDR with Full Kitchen Deck Washer Dryer
A modern kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and a breakfast bar with metal chairs.

7. Escape to Paradise w Saltwater Pool 25 Min to PCB

Escape to Paradise w Saltwater Pool 25 Min to PCB
Lynn Haven
The price is €349
includes taxes & fees
27 Oct - 28 Oct
Escape to Paradise w Saltwater Pool 25 Min to PCB
A hallway with white doors, a wooden floor, and a console table with decorative items.

8. Loaded House and Guest House w Game Room Gym

Loaded House and Guest House w Game Room Gym
Lynn Haven
9.2 out of 10, Wonderful, (10 reviews)
"This property was the perfect setup for my large family group."
United States
Teresa M.
The price is €481
includes taxes & fees
17 Nov - 18 Nov
Loaded House and Guest House w Game Room Gym
A beach with clear turquoise water, a sandy shore, and buildings in the background.

9. ~ La Conchita ~ w private pool & Firepit

~ La Conchita ~ w private pool & Firepit
Panama City
9.8 out of 10, Exceptional, (56 reviews)
"The house was amazing. We really enjoyed our stay and it was in a great location. Would definitely stay again."
United States
Jordan B.
The price is €358
includes taxes & fees
28 Oct - 29 Oct
~ La Conchita ~ w private pool & Firepit
A covered outdoor seating area with a wicker chair and a table, a wooden staircase, and string lights.

10. La Casita POOL & GAME ROOM Fenced Yard!

La Casita POOL & GAME ROOM Fenced Yard!
Panama City
8.8 out of 10, Excellent, (5 reviews)
"We had a very good time,Host left eggs "
United States
Rebecca E.
The price is €374
includes taxes & fees
27 Oct - 28 Oct
La Casita POOL & GAME ROOM Fenced Yard!
Private kitchen

11. Coastal Drift: 3BR, Fenced Yard + Pets

Coastal Drift: 3BR, Fenced Yard + Pets
Panama City
10.0 out of 10, Exceptional, (2 reviews)
"We loved the house! Very clean and had everything we needed!"
United States
Sye M.
The price is €293
includes taxes & fees
23 Nov - 24 Nov
Coastal Drift: 3BR, Fenced Yard + Pets
Private kitchen

12. Turtle Cove: Sleeps 7, Pets + Arcade

Turtle Cove: Sleeps 7, Pets + Arcade
Panama City
10.0 out of 10, Exceptional, (13 reviews)
"We enjoyed our stay so much. Lovely place!"
United States
Kristyne G.
The price is €292
includes taxes & fees
23 Nov - 24 Nov
Turtle Cove: Sleeps 7, Pets + Arcade
A beach with clear turquoise water, a sandy shore, and a few buildings in the background.

13. "The Wine Cellar" Will be no longer available. Family is moving back to FL

"The Wine Cellar" Will be no longer available. Family is moving back to FL
Panama City
9.6 out of 10, Exceptional, (8 reviews)
"Amazing property!! Chuck is a wonderful host and is SO accommodating!! This was our first time in PCB and we will definitely be back just to stay at The Hideaway!!!"
United States
Chelsea M.
The price is €182
includes taxes & fees
26 Oct - 27 Oct
"The Wine Cellar" Will be no longer available. Family is moving back to FL
A beach with clear turquoise water, a sandy shore, and a few buildings in the background.

14. The Bungalow - Quiet and Relaxing Oasis

The Bungalow - Quiet and Relaxing Oasis
Panama City
10.0 out of 10, Exceptional, (7 reviews)
"We received excellent service while there. The owner is a very nice person! We had a new boat, first time in ocean and he was very helpful! We had a wonderful time! The place was clean and supplied with dishes, pots, utensils, towels, and bedding. The place was quiet especially at night. We eat at the Golden Coral for breakfast every morning. "
United States
Louis H.
The price is €244
includes taxes & fees
25 Oct - 26 Oct
The Bungalow - Quiet and Relaxing Oasis
A greenhouse with various plants, a wooden table, chairs, and a hanging chair.

15. Heron Cottage - Private & Quaint

Heron Cottage - Private & Quaint
Panama City
10.0 out of 10, Exceptional, (11 reviews)
"Great stay"
United States
Mecca K.
Heron Cottage - Private & Quaint
A beach with a clear sky and calm sea.

16. Coastal Breeze Perfect Family Getaway/ Sleep 9

Coastal Breeze Perfect Family Getaway/ Sleep 9
Laguna Beach
9.4 out of 10, Exceptional, (79 reviews)
"Property was easy to find. Very spacious. Plenty of room for our family. Great location in proximity to the beach, food, and shopping."
United States
Brittany K.
Coastal Breeze Perfect Family Getaway/ Sleep 9
A beach with palm trees and a sandy shore.

17. Waterfront short walk- Do summer right in Panama City Florida Boat Launch too

Waterfront short walk- Do summer right in Panama City Florida Boat Launch too
St. Andrews
9.8 out of 10, Exceptional, (10 reviews)
"Clean and nicely decorated. Great value in a great location! "
United States
JC W.
The price is €314
includes taxes & fees
25 Oct - 26 Oct
Waterfront short walk- Do summer right in Panama City Florida Boat Launch too
A sandy beach path leading to the ocean, surrounded by beach vegetation and wooden railings.

18. Vintage Waves

Vintage Waves
4.0 star property
Laguna Beach
The price is €480
includes taxes & fees
25 Oct - 26 Oct
Vintage Waves
A spacious kitchen with white cabinetry, a black stove, and a dining area with a table and chairs.

19. Beach House - Baby Blue Heron by PHG

Beach House - Baby Blue Heron by PHG
3.5 star property
Sunnyside
The price is €901
includes taxes & fees
25 Oct - 26 Oct
Beach House - Baby Blue Heron by PHG
A modern kitchen with a central island, stainless steel appliances, and decorative wall art.

20. The Coral Casa, 2B/2B, Pet friendly

The Coral Casa, 2B/2B, Pet friendly
Laguna Beach
10.0 out of 10, Exceptional, (33 reviews)
"This is the 2nd time we have stayed at Coral Casa and am positive it won't be the last. The property is close to a quiet area of PCB and is a perfect house to relax after a day in the sun. Both times we have stayed we wonder how they seemed to think of everything! From pet friendly items like water bowls and mats to beach friendly items for when you forget the beach towels and wagon, they have it covered. The cleanliness is superb and makes you know they really care about your stay!"
United States
Suzette S.
The price is €423
includes taxes & fees
15 Nov - 16 Nov
The Coral Casa, 2B/2B, Pet friendly
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

The Flamingo Hotel and Tower

The Flamingo Hotel and Tower

8/10 Good
"our stays at the Flamingo are always great!!! very friendly staff, clean rooms, and all areas well maintained. only a minor glitch this time, we put our used towels and wash rags outside our room door as in times past, but never received replacements, even after going to office and requesting them. desk attendant did give us the last two she had in her handout cabinet, but that's all we ever got. other than that , another great stay!!!"
terry 10-night trip
Posted 5 hours ago
The Flamingo Hotel and Tower

Find out more about Chipley

Chipley Holiday Homes information

Number of reviews
239
Accommodation
1892 Holiday Homes
Lowest Price
€117
Highest Price
€901