House holiday rentals in Pensacola Bay

4.98 out of 5 average rating, 278 reviews

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.

Superhost

4.81 out of 5 average rating, 104 reviews

Navypoint Beauty 2/2 Whole House

Kick back and relax in this calm, stylish bungalow. Very close to NAS Pensacola 2 blocks to beautiful bayou (many times full of dolphins) anda park with walking trails. Bring your kayak! You may very well get to see the Blue Angels practice in this clean and stylish home filled with lots of little amenities! Beds are super comfy Neighborhood is peaceful and safe Perdido Key Beach is only 15/20 minutes away! White sugar sand beaches. Fully stocked and supplied kitchen, lovely sunroom, large deck

4.99 out of 5 average rating, 169 reviews

Estella’s Place-your piece of Florida paradise

Beautifully renovated one bedroom, one bath 1956 home in the East Hill neighborhood of beautiful Pensacola. Come enjoy all the comforts of home while exploring Pensacola. Relax in the completely private backyard. Perfect for couples, solo adventurers, and business travelers. Conveniently located to the airport, restaurants, downtown, Gulf Breeze, and Pensacola Beach Please no children, pets, parties, smoking or vaping. Estella’s Place...where the past meets the present impacting the future.

4.96 out of 5 average rating, 162 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

4.95 out of 5 average rating, 105 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.

4.89 out of 5 average rating, 238 reviews

Tropical Boho Style Home Near Downtown Pensacola

Great historical Pensacola home with vintage charm & modern comfort. Our favorite part is the Beautiful Kitchen and private Backyard! Enjoy the gas BBQ grill out on the deck or chill in the hammock underneath the palm trees. A welcoming space to spend time with family & loved ones. Enjoy a fun unique atmosphere with a mix of new & vintage furniture & art. Convenient location close to Downtown Palafox Pier, Pensacola Bay Center, NAS Navy Base, local area hospitals, 15 mins from Pensacola Beach.

4.99 out of 5 average rating, 169 reviews

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.

4.95 out of 5 average rating, 184 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!!

4.99 out of 5 average rating, 207 reviews

✨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!

4.96 out of 5 average rating, 134 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

4.89 out of 5 average rating, 161 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.