Family-friendly holiday rentals in Pensacola

A spacious outdoor deck is set with a long table, accommodating multiple guests. Chairs and glassware are arranged neatly for dining. Lush green trees surround the area, offering a relaxed atmosphere, while a glimpse of water can be seen in the distance.

4.89 out of 5 average rating, 279 reviews

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.

A serene backyard is illuminated at night, featuring a sparkling pool surrounded by a deck and lush greenery. A hot tub, positioned under a wooden pergola, adds to the relaxation area, with soft lighting creating a calm atmosphere. Lounge seating and a dining table are visible nearby.

4.93 out of 5 average rating, 119 reviews

Hot tub/ Pool Relaxing Getaway

Picture your family enjoying the pool & hot tub while you grill out in the large private backyard, or lounge in the comfy screened in porch seating area of this peaceful getaway! Located b/t the bayou & scenic bluffs overlooking the bay, our home is close to all the area has to offer! Relax on the beach, visit the fishing pier or historic downtown's upscale dining/shopping. 1 block from Exchange Park which has baseball/softball fields, a playground, free wifi, walking path/trails & picnic areas!

4.96 out of 5 average rating, 101 reviews

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

A bright living area is highlighted by large windows allowing natural light to fill the space. A white couch adorned with textured cushions sits on a vibrant blue area rug. A small round table with a plant stands beside the couch, while wall art features a motivational phrase.

4.98 out of 5 average rating, 332 reviews

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!

5.0 out of 5 average rating, 154 reviews

Quiet Family Pool Home! Airbnb's Favorite! TOP 1%!

Welcome to your quiet Pensacola getaway! The perfect home base for beach days, Blue Angels excitement, and relaxing evenings. Located in a peaceful neighborhood just minutes from Pensacola Beach, NAS Pensacola, and downtown, this clean and comfortable home is ideal for families, couples, military visitors, quick visits or longer stays. Whether you’re here for the sugar-white beaches, aviation events, or a laid-back escape, this home offers space, convenience, and comfort without the crowds.

4.89 out of 5 average rating, 110 reviews

A spacious living room is furnished with a large sectional sofa and a matching ottoman, set atop a decorative area rug. Natural light is provided by windows, with ceiling fans enhancing the comfortable atmosphere.

Home in Sanders Beach

Private Pool / Two living rooms /Downtown

This 3000sqft home features a private pool, two living rooms, four bedrooms, two bathrooms, a kitchen, and a beautiful sunroom overlooking a private pool! Two families traveling together?? This is the ideal home for you! This home sleeps 10 comfortably but can accommodate more with the use of an air mattress or crib if traveling with a toddler. Located just a few blocks from Joe Patti's, the Blue Wahoo Stadium, and Palafox Street! YOU AGREE TO ALL HOUSE RULES WHEN YOU BOOK. READ THEM.

4.92 out of 5 average rating, 133 reviews

Lemmington Retreat House

Welcome to Lemmington retreat home located beside Pensacola Scenic Bluffs ✦Close to park by 1 min walk ✦3 mins to Bay Bluffs Park, 42-acre natural preserve ✦7 mins to Pensacola International Airport ✦9 mins to Cordova Mall, shopping and restaurants ✦18 mins to Pensacola beach ✦12 mins to downtown with restaurants, museums ✦26 mins to Naval Air Station Pensacola ✦9 mins to Pensacola State College ✦14 mins to Pensacola Christian College ✦12 mins to University of West Florida

Apartment in Pensacola Beach

A vibrant sunset casts warm hues of orange and gold across the sky, reflecting on the water's surface. The shoreline is framed by gentle waves lapping against the soft, sandy beach. A pier extends into the ocean, while nearby properties provide a coastal backdrop.

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.

4.99 out of 5 average rating, 156 reviews

4.97 out of 5 average rating, 783 reviews

A patio area is visible, surrounded by lush greenery and vibrant flowers. A red table and chairs sit under a green umbrella, providing a shaded spot for relaxation. An enormous live oak tree offers additional coverage, enhancing the secluded garden feel.

Guest house in Pensacola

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.

4.98 out of 5 average rating, 552 reviews

A vintage cottage features a light blue exterior surrounded by a white picket fence. A gravel driveway leads to the entrance, complemented by tropical landscaping including palm trees.

Cottage in Pensacola

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.

4.91 out of 5 average rating, 698 reviews

The exterior of the cottage features a small outdoor seating area with blue chairs and a table surrounded by trees. A decorative fence outlines the yard, complemented by potted plants and seasonal flowers near the entrance. The door is painted blue, adding a pop of color.

Guest house in Pensacola

Cottage Under the Trees

Quiet, private, secure cottage with kitchen. For sleeping: full bed, twin bed, & sofa (not a sleeper sofa). Will accommodate 3 persons comfortably. Small outside seating area is provided. Few miles from downtown Pensacola. Naval Air Station (NAS), Naval Hospital & Pensacola State College Warrington Campus are within one mile. Fast food is readily available. Walmart is 2 blocks away. Ruby T's, Sonny's BBQ and Waffle House are a few of the nearby restaurants.

4.98 out of 5 average rating, 168 reviews

A three-story beach house is set against a clear blue sky, featuring a light-colored exterior and large windows. Palm trees line the entrance, leading to a stairway that connects to the main door. A private beach area is visible in the background.

Home in Pensacola Beach

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!

Popular amenities for Pensacola family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 149 reviews

Downtown, Hot Tub, 2 Fire Pits, Sleeps 9

4.95 out of 5 average rating, 100 reviews

A spacious tropical pool is surrounded by lush palm trees and a charming thatched-roof structure. The inviting water reflects the clear blue sky, while rock formations and gentle waterfalls enhance the natural beauty of the area. Lounge chairs are visible along the pool's edge.

Apartment in Perdido Key

Sea La Vie, Perdido Key, Florida Fall Sale!

4.88 out of 5 average rating, 153 reviews

An aerial view of the property reveals a spacious deck with outdoor seating, overlooking sandy terrain and palm trees. The large upper deck includes a dining area and the entrance to a staircase leading to additional outdoor spaces.

Home in Pensacola Beach

Hot Tub! Game Room! Balconies Views! Steps 2 Beach

Apartment in Pensacola Beach

A private balcony overlooks the Gulf, featuring a pair of wicker chairs with blue cushions. The railing provides safety while maximizing views of the beach and ocean waves under a clear blue sky.

Island Oasis, 3Bed/2Bath, Pool, & Beach Gear

4.98 out of 5 average rating, 101 reviews

4.97 out of 5 average rating, 196 reviews

The outdoor pool is framed by a screened enclosure, providing clear views of the tranquil bay waters. Comfortable lounge chairs are positioned beside the pool, and potted plants add a touch of greenery. A wooden dock extends into the bay, enhancing the serene ambiance.

Home in Navarre

East Bay Hideaway — A Private Waterfront Escape

A welcoming living space features a large wall-mounted television displaying aquatic life. Light-colored walls complement the chic decor, including framed art and a decorative plant. A comfortable seating area is arranged with a small accent table and an ottoman, creating an inviting atmosphere for relaxation.

4.9 out of 5 average rating, 186 reviews

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

4.9 out of 5 average rating, 169 reviews

A lagoon pool is surrounded by tropical palm trees and thatched-roof cabanas. Natural rock formations complement the pool area, which features a gradual entry for easy access. Lounge chairs are arranged around the pool, inviting relaxation in a sunny environment.

Townhouse in Perdido Key

Poolside @ Resort + Two Pools, near Johnson Beach

4.97 out of 5 average rating, 149 reviews

Home in Perdido Key

Arcade Beach Retreat| Firepit | King Bds| Hot Tub!

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 167 reviews

A wooden deck is featured at the front of a small cabin, outlined by a sturdy railing. Comfortable seating is seen on the deck, shaded by a canopy. A circular firepit made of stone is located on the ground nearby, surrounded by gravel.

Guest house in Bellview

The Rosales serenity suite

Loft in Downtown Pensacola

Upstairs on Palafox - Downtown Pensacola

4.96 out of 5 average rating, 348 reviews

The kitchen features white cabinetry and stainless steel appliances, complemented by a wooden island with teal accents. Pendant lights hang above the island, which is set with decorative placemats. A large window provides natural light, enhancing the functional layout.

4.99 out of 5 average rating, 200 reviews

Surrey Escape

4.91 out of 5 average rating, 127 reviews

Townhouse in East Hill

Townhome B w/hottub in downtown/mins to the beach

4.87 out of 5 average rating, 151 reviews

Lookout Nest 20 min from Pensacola beach

An expansive living area is showcased with large windows that allow natural light to brighten the space. A sectional sofa is arranged around a central area rug, complemented by a decorative fireplace and a large television mounted on the wall, providing a cozy gathering spot.

4.88 out of 5 average rating, 109 reviews

Luxury Home Near Marina | Pool, Pickleball, Arcade

4.93 out of 5 average rating, 146 reviews

A modern living area is highlighted by large windows draped with sheer curtains, allowing natural light to filter in. A comfortable sofa with decorative pillows faces a wooden coffee table, complemented by a TV mounted on the wall. Light wood floors enhance the bright atmosphere.

Cottage in Pensacola

Charming Cozy Fall Getaway | 12 min from beach

Superhost

An outdoor deck is featured with a spacious dining area, black chairs arranged around a large table, and a built-in grill nearby. Lush plants add greenery, and an area rug provides warmth. Solar panels are visible on the roof, enhancing sustainability.

Home in Gulf Breeze

Charming home, 10 min drive to Pensacola Beach

4.89 out of 5 average rating, 288 reviews

Family-friendly home rentals with a pool

Superhost

A spacious saltwater pool is framed by a grassy yard, with clear blue water reflecting the sunlight. Surrounding the pool area are simple landscaping features, and nearby structures provide a glimpse of the home’s inviting layout. Trees provide partial shade in the background.

Home in Bellview

Fam Fun-Spacious Home-BOHO Vibes-Game Room & Pool

4.92 out of 5 average rating, 112 reviews

4.96 out of 5 average rating, 108 reviews

An inviting screened area features a heated saltwater pool surrounded by comfortable loungers and a dining set. A large umbrella provides shade for relaxation, while lush greenery offers a tranquil backdrop. Clear blue skies enhance the bright and airy environment.

Home in Navarre

Heated Salt Pool, 3 Kings, Near Beach.

Superhost

A community pool area features a rectangular swimming pool surrounded by a spacious deck. Lounge chairs are arranged neatly along the edge, and two pavilions with covered seating are visible. Lush greenery and a clear blue sky create a serene setting.

4.87 out of 5 average rating, 149 reviews

Beautiful Paradise Home - 1 Mile From Beach - POOL

4.89 out of 5 average rating, 103 reviews

A well-lit bedroom features a spacious bed dressed in neutral linens, complemented by warm-toned throw pillows. Two bedside tables with lamps flank the bed, and a piece of artwork depicting a coastal scene hangs above. Natural light filters through the window adorned with sheer curtains.

Home in Gulf Breeze

Modern Dream Home | Heated Pool and a Fire Pit!

4.99 out of 5 average rating, 142 reviews

Private Pool-Near NAS-Grills-Game Room FamilySetUp

An inviting above ground pool is surrounded by a wooden deck, featuring a circular shape and clear blue water. Comfortable lounge chairs are positioned nearby, offering a relaxing spot to enjoy the sun. Tall trees and a privacy screen add a sense of seclusion to the area.

5.0 out of 5 average rating, 107 reviews

Beautiful 1-bedroom cottage with pool

4.91 out of 5 average rating, 148 reviews

A serene pool area is framed by lush tropical plants and flowering hibiscus. A lounge chair is positioned by the inviting blue water, surrounded by vibrant greenery and palm trees, offering a tranquil outdoor space for relaxation.

Home in Pensacola Beach

Backyard Oasis Family friendly Pensacola Beach, FL