House holiday rentals in Pensacola

The living area features a light-colored sofa and two armchairs, complemented by decorative pillows. A coffee table is centrally placed, with a woven tray on top. Soft lighting is provided by multiple lamps, and large windows are adorned with sheer curtains, allowing natural light to enter.

4.96 out of 5 average rating, 113 reviews

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!

A spacious backyard is featured, surrounded by a wooden privacy fence. A circular seating area with gravel and fire pit is highlighted, complemented by two hammocks. A well-maintained grassy lawn offers ample space for outdoor activities, while string lights add a warm touch to the evening ambiance.

4.97 out of 5 average rating, 116 reviews

The Lantana Leisure - A Lavish Central Vibe!

Welcome to the Lantana Leisure! 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 cook out. 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 that actively record audio and visual.

A charming cottage is set within a lush yard, featuring a welcoming front porch adorned with potted plants. A brick pathway leads to the entrance, framed by vibrant greenery and shaded by mature trees in the background.

4.96 out of 5 average rating, 166 reviews

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

4.92 out of 5 average rating, 110 reviews

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.

4.99 out of 5 average rating, 138 reviews

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!

A covered patio area is depicted, featuring a private hot tub with bubbling water. A cozy hanging chair adds a relaxed touch next to a large window. An outdoor dining table is visible, surrounded by wooden decking and a privacy fence in the background.

4.95 out of 5 average rating, 192 reviews

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!!

4.96 out of 5 average rating, 198 reviews

The stilt house features a wooden deck with seating options and overlooks the tranquil Blackwater River. Surrounding trees provide a natural setting, while the calm water reflects the structure and landscape. A boat dock is visible, enhancing the waterfront experience.

Home in Milton

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.

A bright living area features two orange armchairs and a brown leather couch, arranged around a circular area rug. A blue kitchen with modern appliances is visible in the background, with bar seating for three. Natural light fills the space through large windows.

4.97 out of 5 average rating, 211 reviews

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.

An outdoor patio area is showcased with a spacious dining set and two lounge chairs, all positioned on a paved surface. A large striped umbrella provides shade, while the fenced backyard features green grass and palm trees, creating a suitable environment for relaxation.

4.96 out of 5 average rating, 139 reviews

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 exterior of a charming white cottage features colorful accents on the front door and window shutters. A welcoming porch is adorned with two blue chairs overlooking a vibrant painted staircase. Lush greenery surrounds the property, enhancing its friendly neighborhood appeal.

4.88 out of 5 average rating, 162 reviews

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.

Home in East Pensacola Heights

A spacious bedroom features a comfortable bed dressed in white linens, flanked by large windows with sheer curtains. An inviting lounge area is seen nearby, offering plush seating. The well-equipped kitchen showcases modern appliances and ample counter space. The outdoor pool area is visible, providing a relaxing retreat.

4.98 out of 5 average rating, 112 reviews

Perry Cottage * POOL*Historic Charm*Dog Friendly

The Perry Pool Cottage is nestled in one of the most desirable neighborhoods in Pensacola, with quick access to downtown and Pensacola Beach just 7 miles away. This charming 2 bedroom 1 bathroom cottage is ready for your visit. This home has a new 12ft x 20ft pool with a 6 foot deep end and two outdoor patios/deck as well as a separate fenced area perfect for children and pets.