Guest house holiday rentals in Santa Rosa Island, Florida

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!

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!

Dune Villa - Santa Rosa Beach / 30-A

Dune Villa is located on the west end of 30-A. Our stand alone guest house has a private entrance with guest parking, full kitchen, laundry, queen size bed, bathroom and outdoor shower. Beach chairs/umbrella, beach towels, cooler, and two bicycles are provided. Just around the corner from Stinky’s Fish Camp, Santa Rosa Golf Club, Topsail State Park, Coastal Dune Lakes and Gulf Place Town Center. The perfect vacation rental for quick trips to the beach, business trips, or an extended vacation.

Never Navarre From Home Cottage

Escape to Florida's best-kept secret, Navarre Beach, just a 5-minute drive from this charming 330 sq. ft. coastal cottage. Perfect for solo travelers or couples, it features airy gabled ceilings, a King-size Murphy bed that converts into a dining/work table, and unforgettable shower experiences!! Conveniently located near restaurants and grocery stores within walking distance, this cozy retreat has everything you need for a relaxing getaway, all just minutes from stunning white sand beaches!!

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

Southern Wind Guest Cottage

Private guest cottage 100 feet from main house. Very quiet; parking 5 steps to entrance. Queen-size bed with mattress topper, sleeps 2. Full bathroom. Full refrigerator with ice maker, microwave, coffee maker, dining table with 2 chairs, new large screen TV receives 300 channels, WiFi, and Netflix. Heating and Air Conditioning controlled by guests. Keyless entry. Excellent location minutes from beach, 5 minutes from Wal-Mart Supercenter, and a few minutes from restaurants.

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

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!

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.

Pool:Relaxing Summer Cottage - Gulf Breeze

Built in 2020, this guesthouse is located in quite and safe neighborhood. 8 miles to Pensacola beach and 17 miles to Navarre Beach. Completely private with your own driveway and parking area, plus the use of the main house pool, patio and BBQ. Beautiful view of the forest. On a case by case basis we will entertain 6 guest. Please inquire before booking. Please be sure to review the House Rules section.