Cottage holiday 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.

Coco Ro Downtown! 2 BR w/Hammock + Outdoor Shower!

Welcome to good vibes at Coco Ro "Surf Shack" – your cozy, beachy retreat in downtown Pensacola! This inviting 2 bedroom cottage offers laid-back comfort - just a stone's throw from the heart of downtown. You'll be 1 mile from trendy Palafox St, 12 blocks from the bay & a short drive to stunning beaches. Your coastal escape awaits! Enjoy: ・Outdoor shower! ・King size hammock ・Smart TV ・Washer/Dryer ・Fenced yard ・Free onsite driveway parking *Tap the ❤ in the top right to save to your wishlist!

Seas the Day, Perdido Key, Florida, Purple Parrot

SNOWBIRD SPECIAL! 50% off 30 days or more Dec, Jan, Feb ,Mar! Kick back and relax in Paradise. Seas the Day is located in the gated Purple Parrot Resort. Totally updated , upscale, immaculate villa is less than 1/4 mile to the white sands of the Gulf. It's perfect for couples, solo adventurers and active military. The tropical pool and hot tub feature a rock waterfall. A new king bed in master and queen sofa sleeper in living area waits your arrival. New and updated kitchen is magazine worthy!

Pensacola Cottage Downtown & Quick Drive to Beach

My wife and I built this cottage in late 2021 in quiet downtown Pensacola with our guest in mind. Our one bedroom one bath cottage is outfitted so you will have most everything you need. This includes a full working outfitted kitchen, cleaning & paper supplies plus more. Our cottage is located near Ever'man Coop Grocery & cafe, Joe Pattis Seafood Market , Maritime Park (Wahoo Stadium) , Pensacola's popular Palafox Street and other downtown favorites. Only 9 miles away from beautiful beaches.

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!

Hibiscus Sunrise Cottage - Walk to local dining!

Enjoy our quaint cottage centrally located in East Pensacola Heights and within walking distance to local restaurants and Bayou Texar! In this family-friendly neighborhood you're sure to see folks out for a run, an evening stroll, a bike ride, or walking their dogs. You'll enjoy an amazing tree canopy on a short walk to the Bayou for fishing or boating! Popular downtown Pensacola is only 3 miles away, the airport is 4.5 miles, and our beautiful white sand beaches are a quick 15 minute drive!

Navy Point Home & game room, near NAS & downtown

*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.

"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!)

Two blocks to the beach! Bikes included!

Newly remodeled ⭐️Private beach bungalow in Crystal Beach! ⭐️This property is a private guest house two blocks from the beach! You will have your own entrance and parking for one car. Downstairs you will find living area, full kitchen, washer/dryer, and bathroom. The loft has 2 queen beds. Small courtyard for outdoor seating & outdoor shower. Wonderful neighborhood with sidewalks for biking or walking! I have a driver as well for airport pickup. Just send me a message!

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.

Tiny House for 2-4, close to beach and activities

30 minutes away from Destin FL, voted for it’s Beautiful Beaches. Tiny house for 2-4 has all your essential needs for a cozy getaway. Start your day off drinking your morning coffee on the front deck. Grab those beach towels that we provide for you…and Go Enjoy! Back porch with privately fenced back yard. NEAR BY ACTIVITIES: Emerald Coast Zoo, Hunting, Golfing, Charter fishing, Parasailing, Snorkeling, Canoeing, Tubing down river, Hiking and Amusement Parks.

Plum Orchid Cottage - New Floors!

Plum Orchid Cottage is a tiny hideaway, ideal for your visit to Pensacola! After a day at the beach (20 min to Perdido or Pensacola Beach) or visiting family at NAS Pensacola (5 min) you come home to a fully equipped kitchen, private back yard, washer/dryer, and luxury amenities. Head out to the fantastic restaurants and night life of downtown Pensacola just 10 minutes away. You will feel right at home during your vacation when staying with us!