Cottage vacation rentals in Santa Rosa Island

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Top-rated cottage rentals in Santa Rosa Island

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Superhost

Cottage in Pensacola

4.89 out of 5 average rating, 223 reviews

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.

Top guest favorite

Cottage in Santa Rosa Beach

4.99 out of 5 average rating, 102 reviews

2-bdrm coastal cottage: Close to all 30A!

Welcome to our stylish coastal cottage. Nestled in the salt pines of Pt. Washington and loaded with modern amenities, it's the perfect blend of relaxation and convenience—just minutes from the best 30A offers! KEY FEATURES: • SmartLock self check-in • Fully-equipped kitchen with Keurig • Lighting fast WiFI • Private pool access • 5 mins to Grayton Beach & world famous Red Bar • 10 mins to Seaside, Seagrove & Blue Mountain beaches • Stress-Free Checkout: No long chore list, just two quick favors!

Top guest favorite

Cottage in Pensacola

4.99 out of 5 average rating, 211 reviews

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

Welcome to good vibes at Coco Ro "Surf Shack" – your cozy, beachy retreat in downtown Pensacola! This charming 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 pristine 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

Guest favorite

Cottage in Pensacola

4.97 out of 5 average rating, 117 reviews

The Bee Cottage-Downtown Pensacola Home Near Beach

The Bee Cottage is a cozy 2 bedroom, 2 bathroom 1150 sq foot home in downtown Pensacola that offers a fully equipped kitchen, living room, dining area, laundry room, and side yard. This private home is ideal for individuals, couples, or families of up to 4 people. Sleeping arrangements include an en-suite bedroom with a queen bed and a separate bedroom with a full bed. The cottage is just a few blocks from the heart of downtown, a 15 minute drive to the beach, and 20 minutes to NAS Pensacola!

Guest favorite

Cottage in Gulf Breeze

4.76 out of 5 average rating, 243 reviews

Cozy Treetop Cabin Near East Bay & Beaches

Looking for a beach vacation while staying away from crowds? Enjoy the shady trees at our cozy cabin, across the street from East Bay. Sleep peacefully on a queen sized bed, have your morning coffee on the deck, or relax outside by the fire pit after a day at the beach. Our street features miles of sidewalks if you'd like to walk, run or bike. We are 9 miles from the beautiful white beaches of the Gulf of Mexico. Need a little extra room? Check out Laura's Loft, our twin cabin next door.

Top guest favorite

Cottage in Pensacola

5 out of 5 average rating, 225 reviews

Magical Cottage * Couples & Solo * Near Airport

🌴 Your Perfect Pensacola Getaway! In the heart of Pensacola, this cozy, private cottage is perfect for solo travelers or couples. *Vacationing *Visiting family *College visit * Medical stays * Military travel * Work You’ll love the peaceful privacy Your own parking and fenced area Centrally located ~20-30 minute drive to beaches ~5 minutes - Airport ~2 minutes - Shopping mall ~2 Blocks - Best Bistro/food/drink This charming retreat is ready to welcome you with open arms!

Top guest favorite

Cottage in Destin

4.95 out of 5 average rating, 279 reviews

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!

Top guest favorite

Cottage in Pensacola

4.98 out of 5 average rating, 479 reviews

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.

Superhost

Cottage in Pensacola

4.78 out of 5 average rating, 161 reviews

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!

Guest favorite

Cottage in Pensacola

4.8 out of 5 average rating, 302 reviews

Cute Cottage Getaway Downtown!

Wonderful cottage within walking distance to enjoy everything downtown Pensacola has to offer- gallery night, festivals, concerts, market days, parades, Ice flyers games, and Pensacon are all within walking distance! Very cute 1 bedroom 1 bath, light and bright though out. Front porch for relaxing afternoons. A few blocks away from the convention center!!! We charge a pet fee of $75+tax that will be charged per pet. Collected separately.

Superhost

Cottage in Mary Esther

4.84 out of 5 average rating, 141 reviews

Nature's Nest Cottage on the Sound - Pets Welcome!

Come spend a magical vacation with us and enjoy our comfortable cottage on Santa Rosa Sound. Close enough to town, shopping, and beaches, but off the beaten track away from the heavy tourist traffic. Our nest is a private home with a shallow beach and small dock where you can relax along Santa Rosa Sound. The cottage has a complete kitchen, laundry, covered parking, fenced yard, grill, and patio. Life is easy at the ShipAhoy Nest!

Top guest favorite

Cottage in Pensacola

4.99 out of 5 average rating, 155 reviews

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.