House holiday rentals in Pensacola

Large Mid-Century Home w/Bay View & Ancient Trees

Large nicely furnished 4/4 home located high on a hill overlooking Escambia Bay in Pensacola. This unique home features a large yard & relaxing views of the bay & towering trees, interesting artwork, 2 huge decks, 2 balconies, 70" big screen 4K TV, large open living & huge master suite. Great location short drive from beaches parks & trails. 10 mins from historical downtown, bars and restaurants. 10 mins to Pensacola Airport 25 mins to Pensacola Beach 28 mins to NAS 1 hour to Fort Walton/Destin.

Pensacola Lighthouse Retreat

The Pensacola Lighthouse Retreat is our second Airbnb in Pensacola. We enjoyed hosting so much that we bought a 1927 Tudor cottage in the East Hill area of Pensacola, renovated and decorated it with lighthouses from around the US featuring the Pensacola Lighthouse. The cottage is 1000 square feet with a modern floor plan in the living space with enough room for larger families or two families. Two bedrooms, one bath, and lots of outdoor space, including a shower will accommodate larger groups.

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!

La Petite Pineapple~Walkable to downtown Pensacola

Welcome to La Petite Pineapple located downtown Pensacola in the historic neighborhood of Old East Hill! Perfectly located 1/2 a mile to Palafox St and 8 miles to beautiful Pensacola Beach (10 minute drive). This luxury tropical retreat offers everything you need for your perfect Pensacola getaway! Owner cleaned and operated, I take great pride in providing my guests with an excellent vacation experience with as much guidance about the area such as things to do/dining options. Ask me questions!

COCO RO DownTown! Outdoor Shower + Hammock+Parking

Welcome to good vibes at Coco Ro "Surf Shack" - your cozy retreat in downtown Pensacola! This thoughtfully styled 2BR coastal cottage blends laid-back comfort with curated nautical details, creating the perfect space to unwind after a day of exploring. Just 1 mile to vibrant Palafox St, 12 blocks to the bay & a short drive to the Gulf’s stunning, iconic white sand beaches! • Outdoor shower! • XL hammock • Smart TV • Washer/Dryer • Private yard • Free driveway parking *Tap ❤ to save for later!

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

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.

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.

Historic Pensacola, a new warehouse inspired home.

Stay at this brand-new Industrial style home walking distance to all Historic Downtown Pensacola has to offer. Don't like walking, ride one of the included beach cruisers to Museums, Restaurants, Breweries or shopping. Featuring 3 comfortable bedrooms, a fully stocked kitchen and laundry. Only a 15-minute drive to Pensacola Beach, this location gives you the best of both worlds. After a long day of seeing the sights relax in the private courtyard. You are sure to love this unique home.

✨Olivia Downtown✨ Industrial chic/ Sleeps 4

Welcome to Olivia Downtown, your new home away from home! This gem is an 860 sq ft one bedroom one bathroom home equipped with a full kitchen and laundry room. Whether you’re working from the designated office space, snuggled up on the comfiest couch watching some Netflix or cozied up around the fire pit on a chilly night Olivia will make you never want to leave! However, if you do decide to venture out we are minutes away from Pensacola’s best of the best!

Summer House - Beach & Downtown

Enjoy all downtown Pensacola has to offer in this stylish 2 BR, 2.5 BA Vacation Home! Perfect for families or couples. Comfortable, open floorplan with beautiful interior touches & furnishings. With all the essential comforts combined and easy access to shopping/dining, as well as close proximity to Florida's best beaches & outdoor adventures, this Pensacola home promises an ideal Florida gateway for friends and family, no matter the season

Waterfront Sunsets

Come enjoy our beautiful newly renovated spacious home and let your worries melt away. You’ve never seen sunsets like this. Dolphins are frequent visitors and the peace and tranquility here is unmatched. Enjoy the water if you want or just sit and watch, either way you’ll never want to leave. We know you’ll love being here as much as we do.