Holiday rentals in Chipley

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Top-rated holiday rentals in Chipley

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Cottage in Laguna Beach on the Gulf of Mexico

4.93 out of 5 average rating, 124 reviews

💦LagunaBeachCottage w/fire pit! 1 min walk to 🏖

Relax and have fun with the whole family at our recently renovated cottage: Beach supplies Ping pong table Late night patio w/fire pit Outdoor shower Perfect location: 1 min walk to white sandy beach 2 min walk to the Carousel supermarket 5 min walk to the famous Thomas’s Donuts 7 min drive to Pier Park (stores & restaurants) and 30a (upscale dining & shopping) 10 min drive to Gulfworld - swim with dolphins and watch shows 7-25 min drive to State Parks 30-45 min drive to Outlet Mall and more

Top guest favourite

Home in Inlet Beach

4.97 out of 5 average rating, 38 reviews

Destination Relaxation is the perfect family getaway.

Peace and tranquility await you at this lovely vacation rental. Located a half mile from beautiful Inlet Beach, this fully equipped 3 bed/3 bath/3 story home has everything you need for the perfect family getaway. Enjoy nature from the serene back yard or any of the 4 decks. Take advantage of the private community pool that leads out to the secluded dock on Powell Lake. When you're ready to explore, you have access to food, shopping, entertainment, hiking, and all the best 30A has to offer.

Superhost

Home in Santa Rosa Beach

4.64 out of 5 average rating, 11 reviews

WaterColor! NEW 6-Seater LSV, Bikes, Steps 2 Pool!

Welcome to 'Sweet Memory Lane' in the heart of 30A's exclusive WaterColor neighborhood! This house has everything you could want in a vacation home - from the complimentary NEW 6-seater LSV + 4 YOLO bikes and 2 master bedrooms, to the screened-in porch with views of the WC Dragonfly Pool to the chef's kitchen and the multiple open-concept living spaces, it is a serene, coastal, comfortable home for a family or multiple families! Passes for Camp WaterColor & The Beach Club access included!

Superhost

Flat in Panama City Beach

4.82 out of 5 average rating, 33 reviews

Resort Community, Hot Tub, Pool, No Stairs, Golf

-Freshly remodeled and super clean - Located in the heart of Panama City Beach near food and attractions - Less than a 10 minute walk to get your toes on the beach! - Golf Cart Service to the beach included (5 minute or less ride) - Shared pool, hot tub and splash pad available in the resort - TV in each room - Blackout Curtains in each room - Fully Stocked Kitchen - Outdoor living space - Located on a golf course with a pond in the backyard with tons of turtles who love to say hello

Guest favourite

Home in Seacrest

4.95 out of 5 average rating, 63 reviews

Blue Haven 30A - Gulf View | Private Beach Access

Discover the ultimate seaside retreat in this charming beachfront condo. With panoramic ocean views, direct access to the beach, and a stylish interior, this is your perfect coastal escape. Enjoy sunsets from the private balcony, unwind in the tastefully decorated living space, and relish the convenience of nearby attractions and dining options. With modern amenities and coastal charm, this beachfront haven is the perfect escape for those seeking sun, surf, and ultimate relaxation.

Top guest favourite

Guest house in Santa Rosa Beach

5 out of 5 average rating, 184 reviews

"Watercolor-Getaway Bungalow” Beach/6 Pools/Camp

The "Getaway Bungalow" is a carriage house located in Watercolor FL across from Seaside. This ideal vacation rental is separate from the private home in a spacious studio-like room. The cozy carriage house is located on a quiet cul-de-sac overlooking a beautiful pond steps away from the beach, Camp Watercolor, and Seaside, FL. Amenities •Elevator (Lift) •Smart TV/Internet •2 Bikes/Beach Chairs/Umbrella •Parking at Carriage House Kitchen •Refrigerator •Microwave •Coffee Maker •Dishwasher

Guest favourite

Apartment in Santa Rosa Beach

4.94 out of 5 average rating, 50 reviews

Cozy updated Condo on 30A!

Check out our reviews on VRBO. Search VRBO and 1943128 Just a few steps from the Most Beautiful Beaches in America, Living the Dream is directly across the street from the Gulf of Mexico in the special beach community of Seagrove and in walking distance to restaurants and unique shops! One of our guests, Brandon B., said it best: “The location was amazing with easy access to the beach, short bike rides to The Hub and Seaside, and walking distance to other fun restaurants and shops.”

Top guest favourite

Home in Panama City Beach

5 out of 5 average rating, 22 reviews

Penthouse Living at its best!

Kick back and relax in this calm, stylish space. Two story unit with both bedrooms and two bathrooms upstairs. Two balconies, both with water views! Pinnacle Port is in the perfect location between Panama City and Destin. Minutes from Alyss Beach and Seaside. There’s a great functioning kitchen and relaxing living area downstairs. Dedicated workspace in living room. Wi-Fi is great and tv’s are in both bedrooms and large 75” tv on living area. Pool and facilities are amazing.

Superhost

Flat in Panama City

4.91 out of 5 average rating, 11 reviews

gulfsidecondo4

PET FREINDLY LOCATION LOCATION 2 bedroom 2 bath with sofa sleeper.. 2nd floor condo in small 4 unit condo building with huge pool and beach access right out the front door. 400 feet walk to world famous schooners restaurant. huge pool BBQ put area front balcony has gulf views rear porch has pool views. walk from pool or front door to beach in under 30 seconds. gulf views from living room and front balcony. More units avaialble in this building if needed rent up to 4 units if needed

Guest favourite

Townhouse in Biltmore Beach

4.84 out of 5 average rating, 227 reviews

Gulf coast vacation townhome

Nestled in the heart of Thomas Drive, minutes from Schooners (#1 beach location with a cannon blast sunset celebration every evening) marinas, state park and of course the beach is just a brief walk (about 90 yards)right across the street with crosswalk. Private backyard with grill and outdoor tiki hut shower. Three full showers and beach shower out front. TV’s all rooms (streaming only), internet “A short time change in latitudes can help improve your attitudes “

Top guest favourite

Home in Biltmore Beach

5 out of 5 average rating, 14 reviews

Next to the Beach~2BR~Walking

Welcome to Our Cozy 2BR Apartment ★ Sleeps 8 ★High-Speed WiFi ★Newly renovated ★Smart TV’s ★ Best Location ★ Free Parking ★ 0.3mil to the Beach ★Outdoor Grill+Dining ★1.3mil to St.Andrews ★No chores check-out State Park ★Host available 24/7 ★4-5min EASY WALK to the beach !!

Guest favourite

Apartment in Panama City Beach

4.94 out of 5 average rating, 69 reviews

Sunset Paradise Hideout Beach Front *Gulfgate*

THE EXTERIOR PART OF THE BUILDING WILL BE GOING UNDER A REMODEL. STARTING THE FIRST WEEK OF MARCH. SO PLEASE ASK QUESTIONS BEFORE REQUESTING TO BOOK. PLEASE READ OTHER NOTES IN THE DESCRIPTION ABOUT THE EXTERIOR CONSTRUCTION GOING ON BEFORE REQUESTING TO BOOK Located on the third floor at the east end of PCB in a quiet 5 floor complex.