Holiday houses in Pensacola Bay

BAY HOUSE-Private Beach & Sunsets on Pensacola Bay

Bay breezes 1.4 mi. to Pensacola's famous Palafox St. 9.7 mi. to Pensacola Beach. 3K sq. ft. mid-century property with private 110 ft sand beach on Pensacola Bay! The optional Bay Cottage has an adjacent 30 ft. beach. Close to restaurants & attractions. BAY VIEWS! 2 min. Watch the Blue Angels & America's Cup boat practice & dolphins play. 3 Kayaks, 2 bikes, beach toys, & life jackets are provided for fun in the bay. Watch fireworks from the beach many Friday nights. Close to EVERYTHING!

Family · Value · Accuracy

COCO RO Downtown! Outdoor Shower, Hammock +Parking

Welcome to good vibes at Coco Ro “Surf Shack!” Your cozy retreat in downtown Pensacola. This thoughtfully designed 2BR coastal cottage blends laid-back comfort w/ 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 stunning, iconic white-sand beaches! • Outdoor shower! • XL hammock • Smart TV • Washer/Dryer • Private yard • Free driveway parking *Tap ❤ to save for later

Value · Family · Long stay

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!

Value · Location · Kitchen

Upstairs on Palafox - Downtown Pensacola

This large, family-friendly downtown Pensacola loft sits right in the heart of the rich downtown historical district. Over 100 years old (but recently renovated on the inside) this space will bring you back to the time when everything was made of brick and wood. The location could not be more perfect, as you are right downtown but also just 10min away from the beach - expect normal city noises. Large Palafox balcony right on Palafox St; Great for large parties and entertaining/nightlife.

Location · Family · Parks

East Hill Haven | 2BR | Mins to Beach & Downtown

Nestled in Pensacola's beloved East Hill neighborhood, you'll be in close walking distance of local coffee shops, restaurants, breweries, and parks while staying just minutes from downtown and the white sand beaches of the Gulf Coast . Whether you're here to explore, dine, or just enjoy the local scene, this property is the perfect spot to kick off your adventures as you're just a short stroll from all the major attractions. For short or long stays, make this your home away from home.

Value · Family · Wi-Fi

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 · Kitchen

North Hill Guesthouse

This small but cute guesthouse, repainted and its floors refinished in December 2024, is a five-minute drive from downtown Pensacola, the double A baseball stadium on Pensacola Bay, and a host of restaurants and bars. It is also 20 minutes from Pensacola Beach and the beautiful Gulf Coast. The guesthouse is a separate structure, located in a semi-tropical garden, that affords lots of privacy and quiet in the historical North Hill neighborhood that is ideal for long walks.

Location · Family · Barbecue

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 · Sleep quality

Pensacola Pelican Retreat

Beautifully remodeled and updated in the summer of 2017, this vintage 1943, one bedroom, one bath, full kitchen cottage home is located in classic East Pensacola Heights. This 570 sq foot home is located in a safe, family oriented, quiet neighborhood. Its palm tree shaded yard with large deck, gas grill, seating and hammock is conveniently located only minutes to interstate 10, Pensacola's Airport, downtown and beautiful, sugar white beaches and turquoise water.

Family · Location · Layout

The Backyard Cottage

Escape to our cozy, one-of-a kind rustic cottage at the Gulf of Mexico! Centrally located, we are just 6 miles from Pensacola Beach, 17 miles from Navarre Beach, and 10 miles from Downtown Pensacola. We offer a quiet, chill environment while being just minutes from shops, restaurants, beaches, nature trails and the zoo. The Backyard Cottage is lovingly placed in our shared yard, so please be respectful of our space that we have chosen to share.

Family · Location · Access

Palafox Balcony | Staycations/Events | Posh A 2BR

Treat yourself to an unforgettable experience at our second floor Palafox St apartment with a balcony overlooking the action in the heart of our beautiful city. Our spacious 2/2 apartment sleeps up to 10 people comfortably and is the perfect destination for a weeknight concert crash pad, a downtown weekend staycation, wedding parties, family vacation, or an extended executive stay. Enjoy the luxury of a home away from home. Reserve today!

Location · Family · Condition

Casa Catrina • A Vibrant Mexican Art Retreat!

Welcome to Casa Catrina, a colorful, art-filled retreat inspired by Mexico’s joyful traditions of life, remembrance, and creativity. Designed by award-winning photographer and world traveler Ron Jordan. The home blends authentic folk art, vibrant color, and modern comfort into a warm, inspiring space. Enjoy handcrafted décor, a quiet backyard, and morning espresso before exploring downtown Pensacola.

Family · Location · Getting around