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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

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 pristine, iconic white sand beaches! • Outdoor shower! • XL hammock • Smart TV • Washer/Dryer • Private yard • Free driveway parking *Tap ❤ to save for later

Summer House! Beach & Downtown!

Welcome to Henry’s Hideaway! Whether your visit is to enjoy the beaches or downtown Pensacola, we want to welcome you and ensure you have a fantastic stay with us. The home is a 3 bed, 2.5 bath and beautifully decorated. The home is only about a 15 minute drive to the sugar sand beaches in Pensacola, 2 minutes to get onto I-110, and 5 minutes from vibrant downtown Pensacola where you can enjoy amazing restaurants and local shops! The house is fully equipped, so please make yourselves at home

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.

A Romantic Downtown Get Away! The Gregory House

Welcome to The Gregory House, circa 1908, your Southern tropical downtown getaway! This gem of a single-family home is centrally located in the Downtown-Seville Historic District in Pensacola, Florida. Perfect for weddings, family, or couples' vacations, the home features high-end antiques, two gas fireplaces, & plenty of wonder and charm in an Old West Indies-inspired backdrop. The house can host up to 6 guests. We are family dog friendly (screening + $90 fee). We look forward to your stay!

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)

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 Wright Place: Your Perfect Beach Escape

Relax in this chic beach-style haven with modern amenities and Pensacola's tropical allure. This 3BR/2.5BA retreat is steps from downtown's vibrant nightlife—lively bars, events at Pensacola Bay Center, and top restaurants—yet minutes from Pensacola Beach's sugar-white sands and emerald waves. Dine al fresco on your patio or sip coffee on the upper deck for ultimate unwind vibes. *Government-issued ID and signed rental agreement required to book and must be submitted post-reservation.

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