Guesthouse vacation rentals in Pensacola

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Top-rated guesthouse rentals in Pensacola

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Pensacola

4.93 out of 5 average rating, 203 reviews

Blue Skies Cottage - Travel Oasis

Private, Dog friendly, work space, 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 Mall;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, 289 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

4.98 out of 5 average rating, 103 reviews

The Paradise Cottage-clean+gated

Our 2 story Guest house is the definition of cozy and inviting. Located on our spacious and gated property. We strive to make your stay feel as if you were at home. We are 5 min from Navy Federal Headquarters. 10 min from the Equestrian Center. A quick 30 min (mostly interstate travel) to Pensacola Beach. Perfect location to visit your family if located in Beulah/cantonment/9mile area. When you choose to stay with us you are getting a host that cares 100% about the quality of your stay.

Guest favorite

Guesthouse in Pensacola

4.95 out of 5 average rating, 208 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, 150 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, 125 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 Pensacola

4.88 out of 5 average rating, 178 reviews

The Carriageway Cottage -Close to Pensacola Beach!

Whether you’re visiting Pensacola for business or pleasure, thank you for your interest in our guest house. We’re located in the heart of East Hill, which is a very charming and established neighborhood. The area is peaceful and quiet, yet only about a 5-10 minute drive downtown Pensacola. We will do everything we can to make your stay great! The guest house is located directly off of our private carriageway behind the house.

Guest favorite

Guesthouse in East Hill

4.96 out of 5 average rating, 145 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!

Guest favorite

Guesthouse in Pensacola

4.96 out of 5 average rating, 629 reviews

North Hill Guesthouse

This small but cute guesthouse is a five minute drive from downtown Pensacola, the new baseball stadium on Pensacola Bay, and a host of restaurants and bars. It is also 20 minutes from Pensacola Beach and the beautiful Gulf Coast. The guesthouse is a separate structure that affords lots of privacy and quiet in the historical North Hill neighborhood.

Guest favorite

Guesthouse in Pensacola

4.99 out of 5 average rating, 181 reviews

Beautiful Guesthouse right off the I-10 Interstate

Welcome to our private guest house off I-10, just 16 miles from Pensacola Beach and 8.5 miles from downtown. Enjoy a cozy stay with a well-equipped kitchenette, plush bed, and modern bathroom. A private patio is under construction, but you can use the main house's patio. Book now for a memorable stay in Pensacola, Florida!

Guest favorite

Guesthouse in East Hill

4.94 out of 5 average rating, 159 reviews

Cozy 1 bedroom East Hill Garage Apartment

Keep it simple at this peaceful and centrally-located garage apartment. Just blocks away from the peaceful bayou, a 6 minute drive from the extraordinary downtown district, and a 15 minute drive to our beautiful white sand beaches. Our neighborhood stands as one of the safest and most centrally located areas in Pensacola.

Guest favorite

Guesthouse in Pensacola

5 out of 5 average rating, 171 reviews

The Winston

Escape and unwind in this quiet coastal theme Guesthouse just minutes away from the breathtaking white sands of the Gulf of Mexico and all of the hip & trendy spots Pensacola has to offer! Enjoy a relaxing time in this quiet neighborhood, whether you spend your days on Pensacola Beach, or a business stay.