Guesthouse vacation rentals in Pensacola Beach

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Top-rated guesthouse rentals in Pensacola Beach

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Guest favorite

Guesthouse in Pensacola

4.95 out of 5 average rating, 151 reviews

1950’s East Hill Carriage House

1950's newly renovated carriage house nestled privately behind our home, in the desirable neighborhood of EastHill. Located close to beautiful Bayview Park with bikes, paddle boards and canoe rentals as well as a short bike ride to local bars, brewery’s and restaurants on 12th Ave. Downtown Pensacola includes shopping, local bars, restaurants even enjoy a show at The Saenger Theater, Vinyl Music Hall or The Handlebar. The breathtaking white sands of Pensacola Beach are just a short drive away...

Guest favorite

Guesthouse in Pensacola

4.93 out of 5 average rating, 175 reviews

Blue Skies Cottage travel oasis

Blue Skies Cottage, Dog friendly, 6 miles to beautiful beaches, 8 miles to historic downtown with thriving restaurants, minutes from access to I-10 and I-110 and convenient shopping at Cordova or University Malls; nestled in a quiet neighborhood to take friendly walks any time of day. This adorable, newly renovated 1 bedroom, 1 bath with queen sleeper sofa (4 Guests), in-house laundry and full kitchen, in/out dining; would love to serve as your gateway to fun and sunshine. Great for longer stays

Guest favorite

Guesthouse in Pensacola

4.9 out of 5 average rating, 281 reviews

Cozy Garden Cottage

Nestled in private quiet garden behind main house. Off street parking and own entrance. Safe and friendly neighborhood of East Hill. Can walk to a bakery and pub. Between downtown Pensacola and airport. 15 minute drive to beaches. Wireless internet strong signal. T.V. with antenna. Amish "fireplace" heater. Kitchenette with medium refrigerator, sink, microwave, toaster oven, George Foreman grill, griddle designed to cook anything, and eating utensils. Grill on patio. Beach gear.

Guest favorite

Guesthouse in Pensacola

4.9 out of 5 average rating, 182 reviews

Private Apartment! Spring Street Retreat

This cozy retreat is a detached private apartment in a quiet neighborhood just minutes from downtown. The space has its own private entrance with a patio, queen bed, Roku TV, Alexa, kitchenette, and a private bathroom. The kitchenette features a mini-fridge, 2-burner stovetop, microwave, toaster, and coffee maker. Whether you are here for a quick weekend getaway, extended vacation, or visiting as a traveling professional, you will find that this space will enhance your Pensacola experience.

Guest favorite

Guesthouse in Pensacola

4.95 out of 5 average rating, 193 reviews

Charming Guesthouse @ Live Oaks on the Bayou

Live Oaks on the Bayou is perfect for those on vacation, business or coming to the area for a beach getaway, wedding or graduation. The guesthouse is nestled behind our home with your own driveway and parking . Enjoy a private meal, coffee or a cocktail in the quiet serene courtyard-fountain area immediately out your front door. A wide variety of dining is a 3-10 minute walk. There is always some vegetation in bloom here and throughout one of Pensacola's most treasured neighborhoods.

Guest favorite

Guesthouse in East Hill

5 out of 5 average rating, 133 reviews

EAST HILL - Bayview Park Private Carriage House

Maggie's is a professionally decorated carriage house in the historic East Hill neighborhood. We are one block over from Bayview Park - you can enjoy walks, paddle boarding and kayaking. The carriage house has a private entrance at the back of the property. At 700sf, it has a full kitchen, dining room, living room, king bedroom with second TV, and a full bath with washer/dryer. 1 mile to Publix 10 min. to the airport 5-10 min. to downtown Pensacola 10-15 min. to the beach

Guest favorite

Guesthouse in East Hill

5 out of 5 average rating, 102 reviews

Funky Flamingo~ Guest House~ Pool & Kitchenette

This charming East Hill bungalow is owner managed/cleaned. Steps from Publix, 1 mile to downtown/Bayfront and just 12 minutes to Beach! Enjoy the private pool & patio. Luxury comforts and amenities, with the highest speed Wi-Fi/streaming services. Casper mattress and pillows with (700 thread count Egyptian Cotton sheets), for an amazing nights rest, Beach chairs, cooler, umbrella and towels provided. Enjoy the new walk-in shower w/ tankless hot water heater. LBGTQIA2S+ friendly!

Guest favorite

Guesthouse in Loxley

4.96 out of 5 average rating, 172 reviews

Cozy Charming and Private Cottage -great location!

Welcome to our cozy private guest house in Loxley, minutes away from Daphne/Malbis. Enjoy a peaceful and quaint retreat with a comfy king-size bed. The guest house is located in a peaceful country setting, perfect for a serene getaway, yet we are also close enough to town for dining and to explore all the local attractions Baldwin County has to offer. Escape from the hustle and bustle of the city and unwind in this tranquil and comfortable home.

Guest favorite

Guesthouse in Fort Walton Beach

5 out of 5 average rating, 105 reviews

Backyard Bungalow

Come visit sunny Fort Walton Beach and stay in our cozy backyard Bungalow! It sits among old oaks, native palms, and fruit trees. There is a private outdoor space to enjoy your morning coffee and listen to the birds and other Florida wildlife. It’s located 5-10 minutes from the beautiful Okaloosa Island beaches and 2-3 minutes from downtown Fort Walton Beach, which has many restaurants, food trucks , shopping, and events.

Guest favorite

Guesthouse in Pensacola

5 out of 5 average rating, 161 reviews

Hidden Garden Cottage in Historic North Hill

This is not your generic Airbnb. Regardless of why you are visiting, we would like our guests to have a PENSACOLA EXPERIENCE! From nearby downtown restaurants, breweries, and museums, to sailboat races in the bay, Blue Angels passovers, beautiful white sand beaches, to deep history around every corner, this Cottage inhabits PENSACOLA CHARACTER and is your relaxing and unique jumping off place in Northwest Florida.

Guest favorite

Guesthouse in Gulf Breeze

4.96 out of 5 average rating, 158 reviews

Cute Carriage House Apartment with View

Situated just east of Pensacola and just north of Pensacola Beach, our place is located in a quiet neighborhood, just a short drive from amazing restaurants and the most beautiful, snow white beaches in Florida. Our private suite has one bedroom, one bathroom and an open living/kitchen area. Sleep up to four guests with a queen bed in the bedroom and a new queen size pull out sofa in the living area.

Guest favorite

Guesthouse in East Hill

4.96 out of 5 average rating, 120 reviews

Adorable carriage house with private entrance

Keep it simple at this peaceful and centrally-located cottage. Private access and parking, near all downtown restaurants, historical sites, and nightlife but far enough away to relax; This unique spot is only miles from Pensacola Beach and the home of the Blue Angels! Newly remodeled and ready to accommodate, we look forward to hosting you in the heart of East Hill!