Guesthouse vacation rentals in Santa Rosa County

Studio 54 - a modern beach-town studio

You’ll love this modern, stylish studio (open floorplan) duplex/guest house, completely separate from main house, in a quiet neighborhood, with private entrance, patio, & your own double driveway. Walking distance, 4 blocks, from the water (Bayou Chico) and big park. And 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

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!

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.

Private Guesthouse- 2 mi. downtown & 5 mi. Beach

Tucked away in the highly coveted East Hill area, this cottage has everything Pensacola has to offer. 1/1 on .5 acres. Space includes king bed & futon private driveway parking, courtyard & 2 patios with gas fire pit. Access to common spaces: wood burning fire pit, pergola dining & 2 kayaks! Close to downtown, beaches, shopping & dining. Walking distance to restaurants, coffee shops, & several parks. Whether you are in town for business or here for a vacation you will love this little charmer!

Charming Bayou Bungalow near downtown Milton!

Visit historic Milton while staying in our comfortable bungalow, which is close to everything making it easy to plan your visit. Nearby downtown boasts music, festivals, breweries, restaurants and farmers markets. Ride on site bikes on Blackwater Heritage Trail. Explore Marquis Bayou and Blackwater River in on site kayaks. Pick blueberries in season. 40 mins to Navarre Beach. 30 mins to Pensacola. Kitchen w/fridge/micro/toaster oven/dbl burner cooktop. Queen bed with comfy Serta mattress.

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

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

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.

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.

Walkable + Luxe ~ 1BR Guesthouse w/ Fire Pit+Grill

At this modern 1BR guesthouse in the heart of East Hill, you’ll enjoy a walkable neighborhood with plenty of quiet. Inside, soaring ceilings and high-end furnishings make for an upscale but comfortable space. Outside, you're steps from Alga Brewery, local food trucks, and popular morning spots like Jitterbug. Fire up the BBQ and wind down with a glass in hand—and when you’re ready for adventure, downtown and the beach are just 10 minutes away.

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.

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.