Family-friendly holiday rentals in Downtown Pensacola

Apartment in Downtown Pensacola

A modern living area features a brown leather sofa adorned with decorative pillows. A wooden dresser and a television are positioned against the wall, while a small table offers additional storage. Natural light enters through several windows with light-colored shades.

Downtown Intimate Light-Filled Getaway

Explore downtown Pensacola and visit the world-class white sand beaches of Pensacola from this cozy carriage house abode located within walking distance from restaurants, shopping, museums, and nightlife. Stone floors, lots of natural light, and high ceilings. Relax on a private balcony while you sip your morning coffee after a restful night's sleep in a comfy bed with high quality linens. HD TV and a wireless JBL speaker to play your tunes. Full kitchen with everything you need to cook a meal. Ample closet space for all your things and a full size washer & dryer.

5.0 out of 5 average rating, 270 reviews

Apartment in Downtown Pensacola

A cozy living room features a dark leather sectional sofa with colorful cushions, centered around a coffee table. A gas fireplace is visible, with wood flooring and a patterned area rug. Natural light enters through large windows, adorned with sheer curtains.

Classic Coastal Getaway in Downtown + Free Parking

Looking for a cool place to stay while visiting Pensacola? Look no further! Our classic coastal getaway is the perfect home base for all your adventures! This one bedroom apartment has a full kitchen, super comfy queen size bed & pull down full size murphy bed, plus a cozy gas fireplace. This apartment is on the second floor of a beautiful historic home in downtown and within walking distance to restaurants, shopping, nightlife, etc. Only 10 miles to the beautiful white sands of Pensacola Beach!

4.98 out of 5 average rating, 122 reviews

5.0 out of 5 average rating, 109 reviews

“Sea La Vie” Luxury Downtown Home; Mins to Beaches

This new construction home is in a thriving downtown neighborhood. A perfect blend of location and safety, it's just a 17-minute drive to the beautiful Pensacola Beach, and only 3 minutes away from both Sanders Beach and Bruce Beach. One minute to Supposey Weddings. With close proximity to the renowned Joe Patti Seafood market, Wahoo stadium, the Navy base, Palafox Market, hospitals as well as a variety of restaurants, coffee shops, and grocery stores, this home offers unparalleled convenience.

Apartment in Downtown Pensacola

The Kelley House | Cozy Fall Suite 3 w/Balcony

Step into the past with a stay in our beautifully restored suite, located in the historic Kelley House, 1 of 4, located on the 2nd floor. This unique property blends the timeless charm of its original architecture with modern comforts and stylish updates, is perfect for those looking to relax and unwind in a space full of character and elegance. Whether you're here for a romantic getaway or a quiet solo retreat, the Kelley House is an unforgettable place to relax, recharge, and experience the c

4.97 out of 5 average rating, 292 reviews

Loft in Downtown Pensacola

A spacious sleeping area features a large, upholstered headboard and comfortable bedding. Two bedside lamps provide soft lighting alongside a small circular table. Decorative accents include a teal throw blanket and a modern wall art piece, enhancing the room's welcoming atmosphere.

Perfect Secret Downtown Suite | Multiday Discounts

You're going to love the style and convenience of this studio suite apartment with kitchenette and full bath located in the heart of downtown just off Palafox St and Garden St. This is the perfect spot for staying downtown after a show at Vinyl Music Hall or a night of dancing at Seville Quarter. Comfortable and well-appointed for longer stays! Walk to all downtown destinations. Parking $12 daily at the Jefferson St Garage. 1 King/1 Queen Sleeps 4. **No Palafox Balcony access from this unit.**

4.92 out of 5 average rating, 274 reviews

Guesthouse in Downtown Pensacola

A modern two-story garage studio apartment is displayed with a clean white exterior. Shaded seating areas are provided by a red shade sail, and large planters filled with greenery are positioned in front. The entrance features decorative outdoor lighting and a wooden gate.

Why pay downtown hotel prices?

Friendly, safe downtown location. New & clean 2nd story garage studio apartment with full kitchen & washer/dryer. Five blocks from downtown Pensacola’s main corridor. Palafox Street, restaurants, bars & shopping are a walkable 12 minutes(1/2 mile). Both NAS Pensacola & Pensacola Beach are a 15 min drive. This location offers quick access to festivals, parades, Blue Angel shows, Pensacon & the Blue Wahoo’s Stadium. Rest up for the McGuire’s or Double Bridge runs. Free parking. NO SMOKING!

5.0 out of 5 average rating, 206 reviews

4.97 out of 5 average rating, 135 reviews

La Petite Pineapple~Walkable to downtown Pensacola

Welcome to La Petite Pineapple located downtown Pensacola in the historic neighborhood of Old East Hill! Perfectly located 1/2 a mile to Palafox St and 8 miles to beautiful Pensacola Beach (10 minute drive). This luxury tropical retreat offers everything you need for your perfect Pensacola getaway! Owner cleaned and operated, I take great pride in providing my guests with an excellent vacation experience with as much guidance about the area such as things to do/dining options. Ask me questions!

This historical Victorian home features a pale green exterior with white trim and an inviting porch that wraps around the front. Tall trees provide shade, while the structured stairs lead to the main entrance, which is adorned with decorative elements.

4.95 out of 5 average rating, 118 reviews

Large Historical Home for Groups Walk to Downtown!

Travel back in time with your lords & ladies in this fantastic historical home! Wine & dine your guests in good old fashioned style right in the heart of historical downtown Pensacola just one block off Palafox St. This beautiful historical Pensacola home boasts many of its original features such as soaring 11 foot ceilings, huge stained glass art windows and a stunning ornate grand wood staircase. Perfect space for a tasteful Bachelor or Bachelorette Weekend! Walk to Palafox Market & Downtown!

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, 333 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!

Loft in Downtown Pensacola

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.

4.96 out of 5 average rating, 348 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.

Guesthouse 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.

A two-story building features a welcoming façade adorned with festive wreaths on each balcony. Two white chairs are positioned on the front porch, surrounded by vibrant greenery and flowering plants. A concrete driveway leads to the entrance, enhancing accessibility to the front of the home.

4.95 out of 5 average rating, 192 reviews

Stylish Downtown Home- Short drive to the beach

Experience Downtown Pensacola at Maison de la Mer "House by the Sea" where you are within walking distance of the best restaurants, coffee shops and nightlife Pensacola has to offer. You are also in walking distance to Pensacola Bay, Corrine Jones Park, and a short 15 minute drive to the beautiful white sands of Pensacola Beach. Bring the whole family, recruit some friends, stay and play at this home away from home. Your enjoyment has been considered in every preparation.

Popular amenities for Downtown Pensacola family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 150 reviews

Downtown, Hot Tub, 2 Fire Pits, Sleeps 9

A spacious living area features a large black leather sectional sofa, accented by a bright yellow pillow. A round coffee table sits atop a vibrant, multi-colored rug. Large windows allow natural light to illuminate the room, while modern curtains frame the windows.

4.95 out of 5 average rating, 188 reviews

Beautiful Historic Downtown Pensacola Charmer

4.96 out of 5 average rating, 230 reviews

The Gray Lady - Chic Downtown Pensacola Getaway

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, 187 reviews

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

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, 120 reviews

Hot tub/ Pool Relaxing Getaway

A spacious two-story home is seen from the pool area, featuring a fenced yard. Red lounge chairs are arranged around the heated pool, with a dining table set nearby. A grill is positioned on the patio, enhancing the outdoor living environment.

4.94 out of 5 average rating, 113 reviews

Pensacola Near It All-4BR, Heated Pool, Hot Tub

4.99 out of 5 average rating, 157 reviews

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.

Condo in Pensacola Beach

Beachfront Condo • Pool & Resort Perks

4.98 out of 5 average rating, 231 reviews

The exterior of a two-story home is showcased, featuring a driveway in front, surrounded by well-maintained lawns and tropical palm trees. The house has a combination of wood and shingle siding, with multiple windows and an inviting front porch.

Home in Gulf Breeze

4 BR 3 BTH w/hot tub 4 KING BEDS 2twin beds

Family- and pet-friendly home rentals

Cottage in West Pensacola

A charming cottage exterior is presented, featuring a light-colored facade and a gabled roof. A welcoming covered porch is visible, framed by tall trees. Two beach cruiser bicycles are parked on the concrete driveway, inviting exploration of the nearby downtown area.

Eclectic Eco- Friendly Luxe City Cottage

4.99 out of 5 average rating, 616 reviews

4.99 out of 5 average rating, 221 reviews

Casa del Sole • Downtown • 3 Ensuites • Pets OK

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

Cottage in Downtown Pensacola

Downtown Pensacola Cottage - Romantic!

4.97 out of 5 average rating, 184 reviews

A welcoming living space is framed by lush green leaves from a large potted plant. Classic hardwood flooring is complemented by a light area rug. A decorative fireplace and a wooden table with a lamp add a cozy touch. Archways lead to additional rooms, enhancing the home's flow.

4.98 out of 5 average rating, 107 reviews

A Romantic Downtown Get Away! The Gregory House

4.97 out of 5 average rating, 100 reviews

The charming cottage features a light blue exterior with decorative flower boxes beneath the windows. A white picket fence encloses the front yard, which is neatly landscaped with green grass. A bright red door serves as a welcoming entryway, framed by lush greenery.

Cottage in Pensacola

Octopus Cottage

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, 213 reviews

Walk To Downtown, Fenced Yard, Games, Fire Pit

4.88 out of 5 average rating, 111 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

Family-friendly home rentals with a pool

A well-furnished living area is depicted, featuring two patterned armchairs and a sectional sofa. A coffee table is centered on a vibrant area rug, while a large flat-screen television is mounted on the wall. Natural light fills the space through a glass door leading to the outside.

4.94 out of 5 average rating, 125 reviews

Downtown Oasis - Pool & Parking

A two-story home features a light blue exterior and a symmetrical design, framed by white columns on the porch. The landscaped front yard is neatly manicured, with low shrubbery and a brick pathway leading to the front door.

4.9 out of 5 average rating, 227 reviews

Historic Downtown Bayfront Home Pool Mins to Beach

5.0 out of 5 average rating, 227 reviews

A comfortable living area is shown with a large sectional sofa and a patterned chair. A round coffee table is centered in the space, complemented by a potted plant. Natural light enters through a window, while a wall-mounted TV displays a scenic beach image.

Townhouse in Pensacola

Stylish Modern Retreat in Downtown + Pool

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

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

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.

4.95 out of 5 average rating, 152 reviews

Historic Pool Cottage! Dog Friendly

4.86 out of 5 average rating, 121 reviews

A serene backyard features a refreshing pool surrounded by lush greenery. Comfortable lounge chairs are positioned under an umbrella, while potted plants add a touch of nature. A patterned outdoor rug connects the seating area to the pool, creating an inviting space for relaxation.

Home in West Pensacola

Pool House at Indigo Cove, Close to NAS!