House holiday rentals in Pensacola Bay

Midtown Luxury Stay w/Courtyard

Centrally located in Pensacola's thriving shopping district, your home base is minutes away from the airport, beaches, hospitals, breakfast/coffee shops, restaurants, historic downtown, and shopping! Full Kitchen, Washer & Dryer, Gas Grill, Garage, and Private Parking. Perfect for business trips, visiting family, budget-friendly beach vacations, or just passing through. Enjoy your stay in America's first settlement and be sure to check out the VisitPensacola website for events while you're here!

Coco Ro Downtown! Hammock, Porches & Free Parking!

Welcome to good vibes @ Coco Ro Surf Shack - your cozy, beachy retreat in downtown Pensacola! This designer 2-bedroom cottage offers laid-back comfort just a stone’s throw from the heart of downtown. Only 1 mile to trendy Palafox St, 12 blocks from the bay & a short drive to pristine beaches. Your coastal escape awaits! ・Seasonal outdoor shower ・XL hammock ・Smart TV ・Washer/Dryer ・Private yard ・Free driveway parking *Outdoor shower closed in colder months *Tap the ❤ in the top right to save!

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

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.

Charming 2BR Cottage in East Hill near cafes/shops

Relax and unwind in this cozy 2-bedroom cottage nestled in the vibrant, historic East Hill neighborhood. Ideally located, you're just a short stroll away from a dog park, local coffee shops, East Hill Pizza, Publix and Alga Brewery—everything you need for a laid-back day out or an extended stay. Plus, you’re only minutes from all the top attractions in Pensacola. Whether you're here to explore, dine, or just enjoy the local scene, this property is the perfect spot to kick off your adventures.

Modern, cozy, pet-friendly cottage w/king

Auer House (pronounced “our”) is a spacious, modern downtown Pensacola home steps from walkable restaurants and parks. Experience NAS Pensacola and the Blue Angels…sit on the front porch and hear their roar as you catch a glimpse as they practice! We are near the Blue Wahoos Stadium, Joe Patti’s and all the festivals! And Fido is welcome; there’s a dog park across the street! Unwind in this super clean retreat featuring fast WiFi, or sit outside around the fire pit, disconnect and reconnect!

The Hosta Hangout - A Luxury Central Haven!

Welcome to the Hosta Hangout! This modern duplex embraces a bohemian feel which creates a welcoming space of relaxation and bright engagement. Slow down and decompress in a woven hammock. Laugh with friends and family as you gather around the warm fire or relish the moments of a family cookout. However you choose to spend your time, embrace the uniqueness of this space that had the experience in mind. There are 2 cameras on the exterior of the property which actively record audio & visual.

The Cypress House

The Cypress House was built in 1908 & renovated in a coastal theme. It is very clean, cozy & offers the feeling of home away from home. The Oar House seafood restaurant is 1 block away & Bahia Mar Marina is directly across the street. The house is close to the downtown historical district, beaches, museums, restaurants/bars, the Wahoos Stadium & Pensacola NAS is 4 miles away. The house includes a FULL kitchen, fenced-in backyard with a shower and fish-cleaning area. All guests are welcome!

The Gray Lady - A Beautiful Cottage in Pensacola!

The Gray Lady is a luxurious cottage in downtown Pensacola. It combines two pieces of paradise - named after Nantucket and located in Pensacola. This home sleeps 9. Relax in the backyard oasis, equipped with a private hot tub! A park, brewery, and restaurants are all within walking distance. Just a mile from downtown, be sure to checkout the restaurants, shops, and nightlife! Pensacola Beach, NAS, Fort Pickens, the mall and airport are all 15 mins away. We hope you enjoy your stay!!

Waterfront with kayaks* Blackwater River Shanty

Enjoy nature in this 2 bedroom stilt house on Paradise Island surrounded by the Blackwater River- just a 30 minute drive to Gulf Beaches! Kayak around the island, enjoying the turtles & birdwatching, or boat or drive to downtown Milton to dock and dine at Blackwater Bistro or Boomerang Pizza. There is a boat ramp, boat house, 4 kayaks and life jackets for guest use. Easily visit Navarre Beach, vibrant Downtown Pensacola, Pensacola Beach, or Ponce de Leon Springs.

The Orange Bayview 🍊 Pet Friendly 🐬Studio Suite 🌴

Orange You Glad You Found This Place? Steps from Bayview Park including small and large dog parks, dog beach, tennis courts, workout area, boat ramp, Bayview Center & more. 5 minutes to downtown, 15 minutes to Pensacola Beach. While attached to the main house, the guest suite is its own private space, with a separate entrance, temperature control, driveway parking for 2 and room for a 20’ boat. We’ll do anything to make your stay great!

Mid-Century Retreat: Winter Specials

Experience the ultimate getaway in our beautiful Mid-Century decorated home. Private back yard with propane fire pit with stunning mossy oak trees. This 2 spacious 2 bedroom/2 full bath duplex home sleeps 6 with the use of sleeper sofa. Great for the kids with a special playroom off the main bedroom! Safe and walkable to kids playground, local restaurants, and Bayou Texas boat ramp. 8 miles to Pensacola Beach 3 miles to Downtown