Holiday rentals with outdoor seating in Downtown Pensacola

Downtown Intimate Light-Filled Getaway

Explore downtown Pensacola and visit the world-class white sand beaches of Pensacola from this cozy carriage house abode located within walking distance from restaurants, shopping, museums, and nightlife. Stone floors, lots of natural light, and high ceilings. Relax on a private balcony while you sip your morning coffee after a restful night's sleep in a comfy bed with high quality linens. HD TV and a wireless JBL speaker to play your tunes. Full kitchen with everything you need to cook a meal. Ample closet space for all your things and a full size washer & dryer.

Walk To Downtown, Fenced Yard, Games, Fire Pit

Welcome to Cooper's Cottage a beautifully renovated 1933 home in the Garden District of Pensacola less than one mile from downtowns historic Seville Square and Palafox St. where you will enjoy bars, restaurants , shopping, art galleries and more. Just 15 min to Pensacola beach and close to NAS home of the Blue Angels. Relax in our fully fenced, pet friendly back yard with gas grill, outdoor dining, lounge seating with fire pit. There are 2 bikes, outdoor games and more. Smart TVs in each room

Coco Ro Downtown! 2 BR w/Hammock + Outdoor Shower

Welcome to good vibes @ Coco Ro "Surf Shack" – your cozy, beachy retreat in downtown Pensacola! This inviting 2 bedroom cottage offers laid-back comfort - just a stone's throw from the heart of downtown. You'll be 1 mile from trendy Palafox St, 12 blocks from the bay & a short drive to pristine beaches. Your coastal escape awaits! Enjoy: ・Outdoor shower! ・King size hammock ・Smart TV ・Washer/Dryer ・Fenced yard ・Free onsite driveway parking *Tap the ❤ in the top right to save to your wishlist

Historic Downtown Bayfront Home Pool Mins to Beach

The Bayfront Manor brings the best of both worlds to your vacation or business stay in Pensacola. Located 5 min walk from historic downtown, Seville Square, and Palafox Street, the location is ideal for all dining, nightlife, and events. The home is positioned on the corner of Bayfront Dr allowing for great water views of Pensacola Bay. The best beaches on the Gulf are only a 10 min drive. The location is also great for wedding parties as the Barkley House and Christ Church are walkable.

Spacious Downtown Flat w/ free parking

You will not soon forget your stay in this beautiful, historic home in downtown Pensacola where you can enjoy all the comforts of home with the charm of the past. This charming 3 bedroom home is has everything you need for your stay, featuring an outdoor patio and garden space, a cozy living room, full kitchen and dining room. We also provide beach accessories, coffee and tea, as well as a Roku smart tv. Just a few blocks away you’ll find cafes, popular restaurants and Pensacola nightlife.

Luxe Downtown Studio Apartment

Curated style within walking distance to bars and restaurants downtown, and only a 15 minute drive to Pensacola Beach! This apartment features a a fully equipped kitchen, separate private entrance, fast high speed internet, in unit washer and dryer, a heated bathroom floor, and commercially rated sound proof insulation. The apartment boasts 11ft ceilings, 100%cotton luxury bedding and pillows, rain shower, and a private dedicated parking space just steps from the entrance.

Stylish Modern Retreat in Downtown + Pool

It's all about the location! This comfortable, spacious townhome is the perfect home base for all your Pensacola adventures. Enjoy the many activities close by: Pensacola Beach (10 miles), Perdido Beach & Johnson's Beach (15 miles), boat charters and fishing, fine dining and pubs, museums, Blue Angel air shows, festivals, Wahoo baseball etc. Or spend the day relaxing at the beautiful pool. Book now to enjoy all the amenities and comforts this home offers.

Casa Catrina-North Downtown with unique art theme!

Beautiful, themed artist home located just 7 minutes from Downtown Palafox. 20 minutes from NAS Pensacola, quick access to the route to Pensacola Beach. This property is located in an old, diverse downtown neighborhood that is rapidly changing with new homes and remodeled ones appearing everywhere. This is a clean and comfortable, pet friendly house with fully equipped kitchen, WIFI, smart TVs with Netflix, Amazon, and commercial free YouTube, and more.

Palafox Balcony | Staycations/Events | Posh A 2BR

Treat yourself to an unforgettable experience at our second floor Palafox St apartment with a balcony overlooking the action in the heart of our beautiful city. Our spacious 2/2 apartment sleeps up to 10 people comfortably and is the perfect destination for a weeknight concert crash pad, a downtown weekend staycation, wedding parties, family vacation, or an extended executive stay. Enjoy the luxury of a home away from home. Reserve today!

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.

The RED DOOR: Explore Downtown Pensacola & Venues!

Step into history at The Hawkins House — a meticulously preserved 1880s gem in downtown Pensacola. This 2,000-sq-ft retreat blends vintage charm with modern comfort, offering a Southern ambiance on a peaceful side street. Sunlit and elegantly furnished, it highlights authentic 19th-century details. Sleeps six comfortably and welcomes screened pets (fee). Your perfect downtown getaway awaits!

Relaxing Historic Suite Downtown | 12 min to Beach

Experience the perfect blend of historic charm and modern luxury in our beautifully renovated Kelley House Suite 1 of 4, located on the first floor. Just blocks from the heart of downtown Pensacola, a comfortable retreat where classic architecture meets contemporary design. Whether you're here for a romantic retreat or a solo escape, this Suite offers an unforgettable Pensacola experience.