Guesthouse holiday rentals in Pensacola

Why pay downtown hotel prices?

Friendly, safe downtown location. New & clean 2nd story garage studio apartment with full kitchen & washer/dryer. Five blocks from downtown Pensacola’s main corridor. Palafox Street, restaurants, bars & shopping are a walkable 12 minutes(1/2 mile). Both NAS Pensacola & Pensacola Beach are a 15 min drive. This location offers quick access to festivals, parades, Blue Angel shows, Pensacon & the Blue Wahoo’s Stadium. Rest up for the McGuire’s or Double Bridge runs. Free parking. NO SMOKING!

Location · Value · Beach

Luxury East Hill Apt. Near Downtown Pensacola

Located in Pensacola's historic East Hill neighborhood, our luxury modern apartment is minutes away from the airport, beaches, hospitals, breakfast/coffee shops, restaurants, historic downtown, and shopping! Perfect for business trips, visiting family, budget-friendly beach vacations, or just passing through. W/Dryer, King Bed, Full Kitchen, Gas Fire Pit, and Private Parking. Enjoy your stay in America's first settlement and be sure to check out VisitPensacola.com for events while you're here!

Family · Location · Long stay

Studio 54 - a modern beach-town studio

You’ll love this modern, stylish studio (open floorplan), completely separate from main house, in a quiet neighborhood, with: -private entrance - private patio -double, extra-long driveway (trailer,rv,etc) 4 blocks from water (Bayou Chico) & a big park w/ frisbee golf. Close to everything Pensacola and Perdido Key have to offer: -Airport (PNS) - 8miles -Downtown Pensacola - 3mi -Beaches: --Bruce Beach: 3mi --Pensacola - 12mi --Perdido Keys - 12mi -Naval Air Station (NAS) - 4mi

Location · Value · Condition

EAST HILL - Bayview Park Private Carriage House

Maggie's Carriage House is a professionally decorated carriage house in the historic East Hill neighborhood. We are one block 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

Family · Value · Bathroom

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.

Value · Family · Laundry

North Hill Guesthouse

This small but cute guesthouse, repainted and its floors refinished in December 2024, is a five-minute drive from downtown Pensacola, the double A 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, located in a semi-tropical garden, that affords lots of privacy and quiet in the historical North Hill neighborhood that is ideal for long walks.

Location · Family · Parks

Siesta Cottage on the Blackwater

Looking for convenience to all of the Gulf Coast's treasures without breaking the bank? Have a boat or jet skis? Coastal guest house on 3 acre waterfront estate on Ward Basin/Blackwater Bay. Close to beaches, downtown Pensacola, and all of the natural wonders of NW FL. Nearby boat ramp, space for boat trailer, and ability to tie up to the dock on site. Sleeps four (queen bed and queen sleeper). No Pets - 2 min to I-10 -20 min to Navarre Beach -30 min to Downtown Pensacola

Family · Value · Accuracy

Lovely- Pensacola-Guesthouse

Clean, and modern designed guest house, nestled in a cozy but convenient Pensacola neighborhood with easy access to Historic Downtown Pensacola, University of West Pensacola, and Beautiful Pensacola Beach. Gorgeous, peaceful space, perfect for rest and recharging. 2 smart TVs with internet, private back patio with fire pit, outdoor shower and outdoor seating. The place is great for two, but a baby or a toddler would fit as well. NOTE: It is not on Pensacola Beach!

Family · Value · Accuracy

1950’s East Hill Carriage House

Welcome to our renovated 1950s carriage house, tucked privately behind our home in East Hill. Steps from scenic Bayview Park with paddle boards, canoes, and bikes for rent, and a short ride to bars, breweries, and restaurants on 12th Avenue. Historic downtown Pensacola offers shopping, dining, and live music at Vinyl Music Hall and performances at The Saengar Theater. Plus, the stunning white sands of Pensacola Beach are a short and stunning drive away.

Family · Location · Kitchen

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. 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.

Family · Value · Beach

*New* Vacation Rental in East Hill

Beautiful newly built studio apartment, only minutes from downtown. Located in the desirable East Hill of Pensacola. Enjoy restaurants and craft breweries within biking distance. Spend a relaxing day at our amazing white sand beaches only a 15 minute drive. The studio has luxury flooring throughout and quartz countertops in its full-sized kitchen. Guests will have their own private driveway fenced separately away from homeowners.

Value · Family · Parking

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.

Location · Family · Condition