Cottage holiday rentals in Pensacola Bay

4.89 out of 5 average rating, 218 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.

4.99 out of 5 average rating, 152 reviews

Perdido Coastal Cottage- pets ok w/ fee-

3B/2BA Perdido Coastal Cottage w/ fenced yard, across bayou and 1.6 miles from Gulf of Mexico! High Speed Wi-Fi. Enjoy close proximity to everything on your vacation checklist as this cottage sits within walking distance to Publix Supermarket, a public boat ramp access 1.1 miles away at Galvez Landing, and just a 3 min drive to 3 of the top golf courses in NW Florida! Watch the Navy's Blue Angels. Pet friendly. *Gov't Issued ID is required to book our property & must be submitted after booking

4.94 out of 5 average rating, 122 reviews

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.

4.96 out of 5 average rating, 114 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!

4.77 out of 5 average rating, 241 reviews

Cottage in Gulf Breeze

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.

5 out of 5 average rating, 224 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!

4.92 out of 5 average rating, 118 reviews

Intracoastal Beach Cottage

Newly renovated beach cottage. Located on a 2 acre intracoastal waterfront property on beautiful Perdido Key, Florida. Walking or boating distance to any local eats and haunts. Ample space for dry boat parking, or 100 feet of semi-private beach pull up. 1/4 mile from public boat ramp. 1 mile to public beach access on Gulf of Mexico. Fully furnished with extra amenities for a good beach getaway; private grill, deck, walkway, chairs. We welcome you to our little piece of paradise!

4.97 out of 5 average rating, 156 reviews

Downtown | Families | Couples | Seafood | Beaches

Discover a chic and serene beach-inspired retreat in west Downtown Pensacola, perfect for a relaxing getaway with family, couples or friends. Indulge in the ultimate vacation experience, blending modern comfort with proximity to downtown, Pensacola Bay and Pensacola Beach! Unwind in the living area or bedrooms, equipped with 40-50" TVs offering access to Netflix, Disney+, Hulu, Max and Amazon Prime. Dive into entertainment with a variety of DVDs, CDs, and board games to enjoy!

4.98 out of 5 average rating, 473 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.

4.9 out of 5 average rating, 145 reviews

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.

4.79 out of 5 average rating, 159 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!