Guesthouse holiday rentals in Santa Rosa County

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!

Pet Friendly, Pool, Hot Tub, Fenced yard.

This cozy one bedroom one bathroom guest house is waiting for you! The guest house is tucked away in a quiet neighborhood in our backyard and includes a kitchenette with washer and dryer. Stay a little while or a while! We have a big fenced in backyard for your pet to play in, a pool to swim in, a grill to cook on, a hot tub to soak in, a firepit to sit by and a hammock to nap in. It's time to Relax! We are just a 16 mile drive to the beach. We would love for you to come and visit!

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.

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

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. You are just a short 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. During your stay here you will find yourself in a suite full of amenities.

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

Spacious Guesthouse by Alga Brewery & Waterfront

The Hatton Guesthouse is a spacious modern retreat in Pensacola's most historic and influential neighborhood, next to Alga Brewery and local eateries. Walkable to everything! Built in 2022, the space boasts soaring ceilings and a professionally design interior with luxurious linens, bedding, and a full kitchen. A fire pit and BBQ are also located on the property, with firewood provided, and are highly encouraged to be used to enjoy evenings with family or friends.

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.

Summer Paradise Getaway

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.