House holiday rentals in Downtown Pensacola

Jackson Street Retreat - Highly Acclaimed Digs!

This newly renovated, charming 1926 shotgun house is located in the historic Belmont-Devilliers district in downtown Pensacola. The home is a short walk or bike ride to Blue Wahoos stadium, Joe Patti's Seafood, and Palafox Street. The home has every convenience; new HVAC, appliances & fully equipped kitchen with Keurig/coffee, smart TVs, and Wi-Fi. Additionally, the full bath has a standard whirlpool tub/shower and the backyard has a playhouse for the kiddos. Come enjoy your home away from home.

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!

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

Comfortable Downtown Stay • Pet Friendly Yard

Charming, pet-friendly cottage in Downtown Pensacola! Just minutes to beautiful beaches, Palafox Market, breweries, coffee shops, and the Blue Angels. Enjoy a spacious fenced yard for your pups, fast, reliable Wi-Fi, and a game room for fun nights in. Perfectly stocked for military families, wedding guests, staycations, or remote work. Close to parks, shopping, and dining. Dogs welcome—with treats and bowls! Feel right at home in this comfortable, convenient, and well-located Pensacola escape.

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.

NEW BUILD Near Downtown! Stars Stripes & Salt Life

We are a new bungalow located right next to downtown Pensacola. The house is conveniently located near many restaurants, breweries, entertainment and a short 15 min drive to the world's most beautiful beaches! We offer plenty of space for your visit inside and out. There is a wonderful outdoor space complete with a firepit and a gas grill if you want to stay in and hang out! Travel nurses welcome! 🐾Pets welcome!🐾 Please specify how many you'll be bringing when you book. ($50 flat fee/stay)

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.

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.

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

Fun, Quirky, Get-a-Way for Singles or Couples.

Great place for couples or singles within just a few blocks of thriving downtown Pensacola. Only a short drive to our famous sugar white beaches. This cottage is small, but the whole place is yours, and the two original rooms, which were built in 1940, have 9 1/2 foot ceilings with magnificent crown moldings. New flooring, paint, kitchen and bath upgrades have come together to make this cottage a jewel of style, comfort, and grace.

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!

Cozy Studio

This is part of a compound with two structures ! There are 3 bedroom in the main house and the cozy studio is a beautifully converted space with private bath, cold / hot air unit , refrigerator , walk in closet ect ect . Note : you share the laundry room only which is rarely used . You have 2 door with your keys that only i have an extra set .