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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!

Pineapple House! Clean/cozy/urban.

No Cleaning Fee and We Cover the Guest's Service Fee! The home is close to everything, which makes it easy to plan your next visit. Only 5 minutes to downtown Pcola and ~15 to Pcola Beach. Gentrification is occurring and you'll see a mix of homes (new to updated to those not yet revitalized), but it is quiet and safe. Contactless check-in/out via electronic front door lock. Garbage/recycle cans on location. Free WiFi. Older construction, but clean home! Park on driveway. No smoking/vaping!

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

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

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.

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!!

Azalea House: Stylish Family Retreat Near Downtown

Whole home located minutes from Downtown Pensacola. Escape with friends or family to the beautifully decorated, 2 story- 3 bed, 2.5 bath home. Guests can retreat to the first-floor master with an ensuite and walk-in closet. Master and Queen bedroom come equipped with dedicated workspaces, with high-speed WiFi. The children's bunk room is stocked with toys and books to enjoy, as well as a pack and play and toddler cot for extra little ones. Each bedroom features a smart tv.

'Coral Reef Cottage' 3BR/2BA w/ Hot Tub!

Centrally located with quick access to the interstate. This cozy space is fully furnished to be your 'home away from home'. Rest and relax with a Smart TV in every room, full kitchen, XBox with games for the kids, washer/dryer, propane grill and a Hot Tub to unwind in. Located 15 minutes from Pensacola Beach and 10 minutes from historic downtown and Palafox St. Enjoy easy access to bars, white sand beaches, art galleries, boutiques, music, unique restaurants, 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

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!

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.