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.

5.0 out of 5 average rating, 262 reviews

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.

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.

4.98 out of 5 average rating, 110 reviews

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!

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.

5.0 out of 5 average rating, 181 reviews

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!

A vibrant living room is adorned with bold palm leaf wallpaper in pink and green. A tufted pink sofa is paired with black and beige accent chairs, while a circular coffee table sits at the center. Natural light filters through sheer curtains, adding warmth to the space.

4.97 out of 5 average rating, 128 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!

The living area includes a modern entertainment setup with a large flat-screen TV mounted on the wall. A cozy white sofa is complemented by a textured blue rug, while surfboards are displayed as wall decor, enhancing the coastal theme.

4.98 out of 5 average rating, 320 reviews

COCO RO Downtown! Outdoor Shower, Hammock+Parking!

Welcome to good vibes @ 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

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, 225 reviews

Historic Downtown Bayfront Home Pool Mins to Beach

The Bayfront Manor brings the best of both worlds to your vacation or business stay in Pensacola. Located 5 min walk from historic downtown, Seville Square, and Palafox Street, the location is ideal for all dining, nightlife, and events. The home is positioned on the corner of Bayfront Dr allowing for great water views of Pensacola Bay. The best beaches on the Gulf are only a 10 min drive. The location is also great for wedding parties as the Barkley House and Christ Church are walkable.

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, 190 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.

A modern exterior view of the white one-story building is presented, featuring large windows framed by minimalistic planters. A pathway leads from the road to the entrance, and a wooden fence provides privacy, complemented by surrounding green landscaping.

4.99 out of 5 average rating, 253 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!

An outdoor patio area is showcased with a spacious dining set and two lounge chairs, all positioned on a paved surface. A large striped umbrella provides shade, while the fenced backyard features green grass and palm trees, creating a suitable environment for relaxation.

4.97 out of 5 average rating, 178 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

Loft in Downtown Pensacola

A spacious bedroom features exposed brick walls and large windows allowing natural light. The king-sized bed is dressed in soft linens with decorative pillows. Nightstands with warm lamps flank each side, while a small vase holds flowers on the bed, enhancing the inviting atmosphere.

4.95 out of 5 average rating, 275 reviews

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!

4.99 out of 5 average rating, 214 reviews

Casa del Sole • Downtown • 3 Ensuites • Pets OK

Welcome to Casa del Sole — the House of Sunshine. A sun-yellow designer cottage in the heart of Downtown Pensacola, with a private ensuite bath for every bedroom. Stroll 4 blocks to Palafox Street dining; NAS and IWTC Corry Station are 10 minutes, sugar-white beaches 15. Guests call it "the cleanest Airbnb we've ever stayed in." Dog-friendly, EV charging, private parking, 🇺🇸 TDY & PCS friendly.

4.99 out of 5 average rating, 135 reviews

The RED DOOR: Historic Seville & Downtown Venues

Step into history at The Hawkins House — a meticulously preserved 1880s gem in downtown Pensacola. This 2,000-sq-ft retreat blends vintage charm with modern comfort, offering a Southern ambiance on a peaceful side street. Sunlit and elegantly furnished, it highlights authentic 19th-century details. Sleeps six comfortably and welcomes screened pets (fee). Your perfect downtown getaway awaits!

Popular amenities for Downtown 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, 146 reviews

Historic 1944 Cottage | Hot Tub + Spa Bath | Beach

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, 184 reviews

Beautiful Historic Downtown Pensacola Charmer

A charming cottage exterior is presented, featuring a welcoming front porch with two chairs. A stone pathway leads to the entrance, surrounded by a landscaped yard with greenery. The building is framed by trees, creating a serene atmosphere during twilight.

4.96 out of 5 average rating, 224 reviews

The Gray Lady - A Beautiful Cottage in Pensacola!

Superhost

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.

4.89 out of 5 average rating, 176 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, 117 reviews

Hot tub/ Pool Relaxing Getaway

4.94 out of 5 average rating, 140 reviews

Poolside Family Retreat w/ Hot Tub & Game Room

4.93 out of 5 average rating, 384 reviews

Townhouse in East Hill

Townhome A w/Private Hottub, mins to the beach

A serene backyard space features a clear blue pool surrounded by lush greenery. Sunlight filters through the trees, and a variety of plants decorate the perimeter. Lounge chairs are positioned near the pool, providing a comfortable area to relax and enjoy the outdoors.

4.94 out of 5 average rating, 219 reviews

Flamingo On Fisher In The Heart Of Pensacola

Family- and pet-friendly home rentals

Bungalow in Downtown Pensacola

The exterior of a charming 1920's cottage is featured, showcasing a white façade with dark trim accents. A brick wall surrounds the front yard, and a spacious driveway is visible. Lush green trees provide shade in the background, and inviting steps lead to the front porch.

4.8 out of 5 average rating, 141 reviews

Bear's Bungalow in the Historic Heart of Pensacola

A private backyard space features a circular firepit surrounded by brightly colored adirondack chairs in red and blue. A hammock is suspended between two posts, with sandy areas and low landscaping visible. The yard is enclosed by a wooden fence for added privacy.

4.96 out of 5 average rating, 182 reviews

NEW BUILD Near Downtown! Stars Stripes & Salt Life

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, 105 reviews

A Romantic Downtown Get Away! The Gregory House

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, 205 reviews

Walk To Downtown, Fenced Yard, Games, Fire Pit

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.

4.99 out of 5 average rating, 600 reviews

Eclectic Eco- Friendly Luxe City Cottage

A bright dining area is furnished with a glass-top table and stylish black metal chairs, accented by greenery in a vase. The space features large windows that provide ample natural light, with wooden beams enhancing the ceiling's height. A modern kitchen area is visible in the background.

4.88 out of 5 average rating, 252 reviews

Vintage Charmer with Tiny Pool Close to Downtown

4.93 out of 5 average rating, 138 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 Getaway | 12 minutes to Beach

The two-story home features a vibrant turquoise exterior, complemented by crisp white columns and railings. A small porch with two white chairs is visible, framed by green plants. The driveway is spacious, offering plenty of room for parking.

4.99 out of 5 average rating, 233 reviews

Downtown Oasis - Sunsets and Nightlife

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, 117 reviews

Downtown Oasis - Pool & Parking

5.0 out of 5 average rating, 223 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

4.89 out of 5 average rating, 107 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

4.93 out of 5 average rating, 106 reviews

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

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.

4.94 out of 5 average rating, 141 reviews

Historic Pool Cottage! Dog Friendly

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, 101 reviews

Beautiful 1-bedroom cottage with pool

4.96 out of 5 average rating, 146 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.

Guesthouse in Bellview

The Rosales serenity suite