Guesthouse vacation rentals in Santa Rosa Island

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.

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

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.

Carriage House 1.5 bed/1 bath located off 30A

You’ll love our place because of the ambiance, the neighborhood, the people and the location. This guest house is located in a gated community just steps from the beach with a community pool across from the home. Beach is 700 steps from front door along a paved sidewalk to private beach access for the neighborhood. The Carriage House is perfect for couples, families (with kids), and solo adventurers. Need more room? We have a larger home on property that sleeps 11.

S.K.I. Beach House (Spending our Kids Inheritance)

Scan QR code for video of property- One of the new houses on the beach. Where you have beautiful views of the sunrise over the Gulf from your front deck and the sunset over the Santa Rosa Sound from your back deck. 3 min walk to amazing shelling, swimming, paddle boarding, kayaking, boogie boarding or just plain relaxing on the "Most Relaxing Place in Florida." All on the sugar white sand beaches of the Emerald Coast.suite full of amenities.

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.

The Cedarwood 2 @Navarre Beach.

Newest studio on Navarre Beach. Steps away from the powdery white sand beaches and crystal clear waters. From your room, overlook the Santa Rosa Sound while enjoying the extraordinary sunsets. You are just a short walk to amazing shelling, swimming, paddle boarding, boogie boarding, kayaking , or just plain relaxing at "The Most Relaxing Place in Florida."