
Cottage holiday rentals in Santa Rosa Island, Florida
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Top-rated cottage rentals in Santa Rosa Island, Florida
Guests agree: these cottages are highly rated for location, cleanliness and more.

Tommy's Tropical Zen Garden & Cottage Oasis
Step through the gate. The photos don't capture this;tropical palms overhead, butterflies everywhere, string lights waiting for evening. Your cypress cottage with treehouse style loft. That 100-year-old clawfoot tub. The outdoor shower everyone raves about. Hot tub under stars. Hammock between palms. Covered deck with grill. Fenced yard for your pup. Walk to coffee, drive 15 minutes to white beaches. But you'll want to stay right here.Our guests say it best: magical, restorative, transformative.

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!

East Hill Studio
Closed for Jan and Feb to remodel the kitchen. Photos coming soon. 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.

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.

Historic Smith House, authentic cottage
Originally built in 1925, our renovation provides all the modern conveniences while maintaining its true southern “old Grayton” charm. Guests love the vaulted ceilings and exposed beams, wood floors, large screened porch, and the vintage Florida decor. We have a 7-night minimum during the Summer, with a Saturday check-in, and 3-night min during most of the year. The maximum number of guests is limited to four (4) persons, including infants and toddlers.

Eclectic Eco- Friendly Luxe City Cottage
New eco chic cottage features high end touches and appliances in a cozy luxe setting. Sitting on the edge of the downtown jurisdiction, you're never too far away from the action on Palafox Street and a quick jaunt over to the beach. 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.

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!

Hammock Hideaway - waterfront cabin
Backyard oasis on a deep water creek. If you are coming for travel ball, love kayaking and/or just hanging out right on the water, you will appreciate this special hideaway. A fisherman’s/nature lovers dream and truly unique rental experience at this creekside cottage with water frontage on deepwater Hammock Creek. Close to the beach but out of the congestion

Downtown Pensacola Cottage - Romantic!
Charming private cottage home in a historical neighborhood only 5 blocks from the heart of downtown Pensacola. Beautifully decorated and Meticulously clean! Kitchen equipped with refrigerator, microwave, dual hot plate to cook on, cooking utensils, pots/pans and coffee pot. Only 8.5 miles from Pensacola beach. Dog friendly $75 pet fee.
Popular amenities for cottage rentals in Santa Rosa Island, Florida
Cottage rentals with a hot tub

Surf N Sand Cottage at Purple Parrot Resort!

Walk to the Beach - Private Cottage + Resort

The cottages at Thai Win/Serenity

Vibe! Coastal living experience! Screened pool!

Just Beachin' -A Pet Friendly Beach Cottage

Hwy30A House Private Beach w/ Pool Jacuzzi Bikes

Peaceful Adult Retreat w/ Huge Pool + Bikes + Beac

Charming Beachside Cottage | Walk to Beach
Pet-friendly cottage rentals

Navy Blues Cottage

NEW LUXE Beach House -Pool -Steps to Sand -Pets OK

Coastal Home-2 min walk to beach-Pets Stay Free!

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

Modernized 2BR Historic Home w/ King bed

P’s Paradise. Close to AL. Beaches

Charming Beach Cottage- with beach service

Hibiscus Sunrise Cottage - Walk to local dining!
Private cottage rentals

Heated Pool | Walk to Beach | Designer Inspired

Bon Secour Relax on the River - Riverfront House

Sanders Beach Sanctuary - Great Location!

Beachside Escape: Movie Room+Private Backyard+Fun

Coastal Country Living

Octopus Cottage

Ocean vibes/Country living-Country Coastal Cottage

The Atlas Cottage
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