Cottage vacation rentals in Crestview

Charming Cottage, 2+BR (entire home, self checkin)

Orange Tree Cottage is your home away from home, a cozy place to unwind and relax within 30 minutes of sugar-sand shores of Pensacola Beach. This hidden gem is in the center of greater Pensacola, around the corner from Pensacola Christian Academy and a short drive from Pensacola International Airport. Whether you're on a business trip, vacation, or visiting family and friends, this clean, pristine, private house features lounging space, full kitchen, bonus room, and rustic (non-fenced) backyard.

Beautiful cottage nestled in the country

Relax with the whole family at this peaceful and serene place to stay. Surrounded by mature trees and beautiful foliage. Quiet and majestic, spend the days at the beach or springs and the nights listening to nature as you star gaze away from the bright lights of the city. Take a nice nature walk down the trails or relax reading a book. A country escape to recharge and just a few miles from town and close to the beach, so you can have the best of both worlds. Your little piece of heaven awaits!

It’s Just Darling

Welcome to "Just Darling" beach cottage off HWY 30A in Blue Mountain Beach. Closest Beach access is a 10 minute walk via a short cut path or 2 minute drive. Enjoy restaurants, shops, bike trail etc... close to "Watercolor and Seaside” communities. Home is sun filled and cozy with everything you would need for your stay, including a community pool up the street. Best of all, relax on the charming wrap around front porch or barbeque off the private porch off main floor back bedroom. ENJOY!

East Hill Studio

Experience a clean, comfortable getaway minutes from downtown Pensacola and a short drive to the beach. We treat our guests like family and make sure you have everything you need to experience a fantastic stay. We are always updating to ensure our guests have the best experience. Perfect for a couple’s retreat, the space features a cozy living room opening to the bedroom with pocket doors, a small kitchen, and a full bath. Kitchen was totally remodeled with new appliances in March 2026.

Cozy Bayou Home & game room near NAS Dtown Beaches

*No Pets or children under 10* No Parties $500 fine Bayou Grande Casita is a block from the water with chef's kitchen, lush beds and sofa, & game room w/ ping pong & darts. Take the kayaks to the bayou for a nice paddle where dolphins play. Screened porch for coffee, drinks or a meal outside. Miles of walking paths along the water where we watch the Blue Angels practice. Navy Point has great fishing, a boat ramp, 20 min to beaches, & 10 min to downtown. See our guidebook for local spots.

Seaside 30A "Hemingway Cottage" Close to Beach

Enjoy an inspirational artist colorful beach cottage lined with palm trees. Walk to beach / Gulf of America. Located on the beach side of 30A at the end of a no drive through street. Marble floors w/ 10 ft. ceilings & original artwork. Rosemary Beach & Seaside 5 mins away for fabulous food and shopping. Rent bikes for a perfect day out. MAXIMUM 2 car parking. **Backyard studio is also rented with private entrance. Main cottage area has own door and is separate and private.

"Quirky Cottage"

Our "Quirky" Cottage is just that!! If you want to experience "old Florida" come and stay with us in our quirky cottage nestled in old oak trees! It was originally built in 1960 as a camping cabin, it came in a box as a do it yourself kit! There are a few left around town - really unique and private space! Located just 5-10 minutes from the Okaloosa Island beaches and everything downtown Fort Walton Beach has to offer and just 15 minutes to Destin. (all depending on traffic!)

Pensacola Pelican Retreat

Beautifully remodeled and updated in the summer of 2017, this vintage 1943, one bedroom, one bath, full kitchen cottage home is located in classic East Pensacola Heights. This 570 sq foot home is located in a safe, family oriented, quiet neighborhood. Its palm tree shaded yard with large deck, gas grill, seating and hammock is conveniently located only minutes to interstate 10, Pensacola's Airport, downtown and beautiful, sugar white beaches and turquoise water.

1br/1ba Cozy Cottage - Downtown/Museum of Commerce

An experience you do not want to miss and a location that is close to the action but still tucked away. Less than one block from iconic Seville Square, where you will be centrally located in the heart of downtown Pensacola's historic district and within walking distance to dining, shopping, museums and other attractions. Find yourself enjoying sunsets on the back porch or take a easy 15 minute drive to enjoy the sugar white sands of Pensacola Beach.

Beach Vibes on Downtown’s Side

This eco-friendly cottage hosts a peaceful Gulf Coast theme on a quiet street, just blocks away from all the action. Located on the edge of downtown, you're never too far away from all Pensacola has to offer, and a quick jaunt to Pensacola or Perdido Beach. This home offers Excellent access to Wahoos Stadium, Sanders Beach, The Oar House, Pensacola Yacht Club, Pensacola Country Club, Joe Patti's, and Pensacola's Naval Air Station.

Modernized 2BR Historic Home w/ King bed

Recently renovated - this is the perfect home base for whatever brings you to Pensacola. Located in a safe and convenient neighborhood, guests are walking distance to a local grocery store, coffee shop, restaurants, parks, and water access at Bayou Texar. It is only a short drive to the airport, shopping, downtown, and the beach. There is also ample parking for you and your guests in a large unfenced yard.

Navarre Hide-a-Way #4

The whole group will enjoy easy access to everything from this centrally located place. Private location, seperate from our house! This is a 2 queen bed private cabin. Enjoy the private back porch shower when returning from the beach! Enjoy the deer that visit our yard! You might even catch a glimpse of our secretive black bears! This listing is strictly Transient Occupant!