Holiday houses in Pensacola Beach

Large Mid-Century Home w/Bay View & Ancient Trees

Large nicely furnished 4/4 home located high on a hill overlooking Escambia Bay in Pensacola. This unique home features a large yard & relaxing views of the bay & towering trees, interesting artwork, 2 huge decks, 2 balconies, 70" big screen 4K TV, large open living & huge master suite. Great location short drive from beaches parks & trails. 10 mins from historical downtown, bars and restaurants. 10 mins to Pensacola Airport 25 mins to Pensacola Beach 28 mins to NAS 1 hour to Fort Walton/Destin.

Location · Family · Beach

Our Shangrila: Waterfront Home with Kayaks & More

Welcome to Our Shangrila! This home sits directly on a calm, shallow cove of Perdido Bay, providing the perfect place for families to relax, play, swim, & paddle safely. Come enjoy gorgeous views, coffee on the balconies, & serene waters. This 2 bed/2.5 bath sleeps up to 7 & includes a full kitchen, laundry, 2 kayaks, 2 SUPs, & more! Spend all day right here, isolated from the hustle & bustle. Or take a very short drive to the beaches, dining & more along Perdido Key. Continue for more Details

Location · Family · Parking

Bayou Breeze - Pool, Views & 8 Min to Downtown

BAYOU BREEZE The Blue Angels are scheduled to fly overhead on September 9, 15, & 22 and Oct 14, 20, & 28! Bayou Breeze offers a private pool, waterfront views of Bayou Davenport, and a peaceful coastal setting just 8 minutes from downtown Pensacola. This 3-bedroom, 2.5-bath cottage sleeps up to 7 and sits directly across from a waterfront park with a fishing dock, kayak launch, playground, gazebo, and walking path. During Blue Angels practice season, guests may enjoy watching them overhead.

Family · Location · Backyard

Newly renovated condo with amazing water views!

Experience the clear blue water and white sand of Pensacola Beach. Enjoy spectacular views of Pensacola Bay from a private 3rd floor balcony. This newly renovated condo offers solid surface floors throughout, a fully stocked kitchen and calming beach decor. The master has a queen size bed, flat screen TV, and ensuite bathroom. The 2nd bedroom offers 2 full size bunk beds. The main living room has another flat screen TV, comfortable couch and is a perfect place for your group to gather.

Location · Family · Accuracy

Cozy Bayou Home & game room near NAS Dtown Beaches

*No Pets or children under 10* No Parties $500 fine Bayou Grande Casita is a block from the water with chef's kitchen, lush beds and sofa, & game room w/ ping pong & darts. Take the kayaks to the bayou for a nice paddle where dolphins play. Screened porch for coffee, drinks or a meal outside. Miles of walking paths along the water where we watch the Blue Angels practice. Navy Point has great fishing, a boat ramp, 20 min to beaches, & 10 min to downtown. See our guidebook for local spots.

Family · Value · Sleep quality

The Pensacola Retreat-Luxurious, pet-friendly home

Welcome to The Pensacola Retreat! This spacious 3-bedroom, 2.5-bath home features plush queen beds, an open living area, and a fully equipped kitchen. Located within walking distance of downtown Pensacola, you’ll enjoy easy access to local breweries, the Blue Wahoos Stadium, and Veo scooters for effortless transport. Steps away, a charming park offers a playground, water fountain, and nearby basketball area. Perfect for families or groups, this retreat blends comfort, convenience, and fun!

Location · Value · Access

Beachfront Condo • Pool & Resort Perks

Welcome to Pensacola Perch, an 8th‑floor beachfront condo offering expansive views of Pensacola Beach—perfect for dolphin watching and catching the Blue Angels airshow. This modern 2BR/2BA condo sits in the highly sought‑after Emerald Isle gated resort, where guests enjoy premium amenities including direct beach access, two swimming pools, a hot tub, sauna, and a beachfront fitness center. From March–October, enjoy complimentary beach chairs and an umbrella from La Dolce Vita.

Location · Value · Air conditioning

Shady Oaks Cottage

This charming home offers the ideal combination of comfort, convenience, and coastal charm, making it the perfect base for exploring everything this vibrant Gulf Coast city has to offer. Whether you’re here for a relaxing beach vacation or cultural escape, our centrally located home is just minutes from Pensacola’s best attractions. There is a breakfast nook and a large patio table, or relax under the sunshade and charming cafe lights while lounging on the sectional sofa.

Family · Location · Checkout

Coastal Family Retreat | Pool, Fire Pit & Playset

Private Pool, Fire Pit & Kids’ Playset — A Coastal Retreat for Family & Friends! This inviting Gulf Breeze home features 4 bedrooms, a fully equipped kitchen, and a spacious backyard. Publix, Walmart, and a Tesla Supercharger are less than a mile away. Pensacola Beach is about 15 minutes away, and Navarre Beach is about 20 minutes away. Gulf Breeze Zoo and Tiger Point Golf Club are also nearby, while Woodlawn Beach Boat Ramp is approximately a 5–7 minute drive away.

Location · Family · Condition

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.

Family · Location · Parks

Soundside Paradise

Private waterfront home with boat dock, private beach, community pool and tennis courts. Relax, unwind, and enjoy the views at this private tropical retreat. Paddle or kayak the sound or drop a line in the water to catch and cook some of the best fish Florida has to offer... all right from your backyard! Home features an open floor plan with breathtaking views of the water seen throughout. This one of a kind experience is sure to create lasting memories!

Value · Family · Pool

Island Life Beach House! 300ft to water!

The entire vibe of this home is "Island Life". If you're looking for a cozy spot on the beach that will make you feel more like you're at home than a tourist on vacation, this is the place for it. Our cute beach house is located on Pensacola Beach, and the water is within sight from the roomy outdoor deck. There are 2 bedrooms and 1 bathroom, kitchen, living space, outdoor space, and everything you need to enjoy life on the beach! FREE PARKING

Location · Value · Accuracy