Holiday rentals with outdoor seating in Pensacola

Flat 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 out of 5 average rating, 254 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.

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.

4.88 out of 5 average rating, 255 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 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, 288 reviews

Downtown "SURF SHACK"! Outdoor Shower + Hammock!

Welcome to good vibes @ Coco Ro "Surf Shack" - your cozy, beachy retreat in downtown Pensacola! This coastal 2-bedroom cottage offers laid-back comfort just a stone’s throw from the heart of downtown. Only 1 mile to trendy Palafox St, 12 blocks from the bay & a short drive to pristine white sand beaches. Your escape awaits! ・Outdoor shower ・XL hammock ・Smart TV ・Washer/Dryer ・Private yard ・Free driveway parking *Seasonal outdoor shower closed in cold months *Tap the ❤ in the top right to save

Home in East Pensacola Heights

5 out of 5 average rating, 127 reviews

Mid-Century Retreat: Spring Specials

Welcome to this stylish mid-century modern retreat! This home offers 2 bedrooms and 2 full bathrooms, blending mid century design with modern comfort. Located 1 block from the Bayou. The home sits in a safe walkable neighborhood near public playground and great local restaurants. Only 3 miles to downtown Pensacola & 8 miles to Pensacola Beach. Whether you’re visiting for a beach getaway or a weekend downtown, this home offers comfort, character, and a prime location-an ideal place to relax.

A charming cottage exterior is framed by a mixture of brick and stucco, featuring a covered front porch with seating options. Colorful flower pots are positioned beside the entrance, which is adorned with an arched doorway, large windows, and a prominent chimney.

4.98 out of 5 average rating, 283 reviews

Pensacola Lighthouse Retreat

The Pensacola Lighthouse Retreat is our second Airbnb in Pensacola. We enjoyed hosting so much that we bought a 1927 Tudor cottage in the East Hill area of Pensacola, renovated and decorated it with lighthouses from around the US featuring the Pensacola Lighthouse. The cottage is 1000 square feet with a modern floor plan in the living space with enough room for larger families or two families. Two bedrooms, one bath, and lots of outdoor space, including a shower will accommodate larger groups.

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, 181 reviews

Walk To Downtown, Fenced Yard, Games, Fire Pit

Welcome to Cooper's Cottage a beautifully renovated 1933 home in the Garden District of Pensacola less than one mile from downtowns historic Seville Square and Palafox St. where you will enjoy bars, restaurants , shopping, art galleries and more. Just 15 min to Pensacola beach and close to NAS home of the Blue Angels. Relax in our fully fenced, pet friendly back yard with gas grill, outdoor dining, lounge seating with fire pit. There are 2 bikes, outdoor games and more. Smart TVs in each room

4.97 out of 5 average rating, 188 reviews

The exterior of the cottage showcases a welcoming entrance with a decorative wreath adorning the door. A paved driveway leads up to the home, surrounded by well-maintained landscaping featuring shrubs and trees. The backdrop includes a clear blue sky highlighting the peaceful neighborhood.

Guest house in Pensacola

Private Guesthouse- 2 mi. downtown & 5 mi. Beach

Tucked away in the highly coveted East Hill area, this cottage has everything Pensacola has to offer. 1/1 on .5 acres. Space includes king bed & futon private driveway parking, courtyard & 2 patios with gas fire pit. Access to common spaces: wood burning fire pit, pergola dining & 2 kayaks! Close to downtown, beaches, shopping & dining. Walking distance to restaurants, coffee shops, & several parks. Whether you are in town for business or here for a vacation you will love this little charmer!

A spacious backyard is illuminated by soft lights, featuring a central gravel area. Woven hammocks are positioned for relaxation, surrounded by a grassy lawn and a wooden fence that provides privacy. Trees stand tall, contributing to the inviting outdoor atmosphere.

4.99 out of 5 average rating, 195 reviews

The Hosta Hangout - A Luxury Central Haven!

Welcome to the Hosta Hangout! This modern duplex embraces a bohemian feel which creates a welcoming space of relaxation and bright engagement. Slow down and decompress in a woven hammock. Laugh with friends and family as you gather around the warm fire or relish the moments of a family cookout. However you choose to spend your time, embrace the uniqueness of this space that had the experience in mind. There are 2 cameras on the exterior of the property which actively record audio & visual.

4.96 out of 5 average rating, 404 reviews

An outdoor patio area features four adirondack chairs arranged around a small table, set on a stone pathway. The modern exterior of the tiny house is visible, with large windows allowing natural light. A grassy area surrounds the patio, enhancing the tranquil environment.

Tiny home in Pensacola

🌟Luxurious new build minutes from beach+downtown

Our tiny house was custom built in 2022 and is located in beautiful East Hill. Our place is centrally located just minutes from PNS airport, downtown restaurants and bars, and Pensacola Beach! It is also just a short walk to Bayou Texar and Bayview park. The tiny house is a completely private space with driveway parking for 2 cars and your own patio area! Enjoy beautiful views of the Bayou from the dining room table or the patio area. We'll do anything we can to make your stay great!

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, 218 reviews

The Gray Lady - A Beautiful Cottage in Pensacola!

The Gray Lady is a luxurious cottage in downtown Pensacola. It combines two pieces of paradise - named after Nantucket and located in Pensacola. This home sleeps 9. Relax in the backyard oasis, equipped with a private hot tub! A park, brewery, and restaurants are all within walking distance. Just a mile from downtown, be sure to checkout the restaurants, shops, and nightlife! Pensacola Beach, NAS, Fort Pickens, the mall and airport are all 15 mins away. We hope you enjoy your stay!!

Guest house 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 out of 5 average rating, 137 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.

4.98 out of 5 average rating, 550 reviews

French doors open to reveal a bright interior space with an open floor plan, featuring a cozy sleeping area and a kitchen. A dining table with chairs is visible, alongside warm wood accents, while natural light filters in through the doors.

Guest suite in East Hill

Beautiful, Peaceful East Hill Guesthouse

Beautiful, quiet, relaxing guesthouse (formerly Whitney’s ironwork studio). Private entrance. In historic East Hill, surrounded by peaceful, towering oak and pecan trees. The French doors provide lots of natural light and an open, airy feeling. Private patio. Quiet, historic neighborhood -- perfect for walks or bike rides. Only 1.2 miles from downtown. Within a few blocks are breakfast/coffee shops, restaurants, Publix Grocery, pubs. Easy 15 minute drive to the beach.

Popular amenities for outdoor seating rentals in Pensacola

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

Home in East Pensacola Heights

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.

4.98 out of 5 average rating, 121 reviews

Historic Pool Cottage! Dog Friendly

Superhost

A charming front porch is featured, with two floral-patterned chairs positioned around a small table. A blue door offers a welcoming entrance, and a landscaped area with greenery complements the light-colored siding. A pathway leads to the porch, enhancing accessibility.

Home in Myrtle Grove

4.94 out of 5 average rating, 106 reviews

Piece of Paradise

4.87 out of 5 average rating, 171 reviews

A welcoming entryway features a decorative round mirror above a console table. A potted plant adds greenery beside the door. A wreath adorns the glass panel of the door, while natural light filters through nearby windows, illuminating the space.

Home in Gulf Breeze

Gulf Breeze getaway w/hot tub, minutes to beach

The exterior of a single-story cottage is shown, featuring a welcoming porch with planters. Lush green grass surrounds the house, and a driveway leads to a red car parked nearby. A fence provides privacy along one side, complemented by sunny blue skies.

4.99 out of 5 average rating, 177 reviews

Estella’s Place-your piece of Florida paradise

4.98 out of 5 average rating, 121 reviews

A historic house with a vibrant red exterior is surrounded by colorful flowering plants and well-maintained shrubs. A covered porch features white columns, and a gentle staircase leads up to the entrance. The sky above is partly cloudy, creating a bright and welcoming atmosphere.

Home in Old East Hill

Little Red House Book a Getaway weekend!

A spacious living area showcases comfortable leather seating arranged around a light coffee table. An open kitchen features stainless steel appliances and a dining area with bright decor. Natural light enhances the inviting atmosphere through large windows.

4.94 out of 5 average rating, 359 reviews

Best 3BR Retreat for 6 in Florida!

4.98 out of 5 average rating, 144 reviews

Home in Old East Hill

The Wright Place: Your Perfect Beach Escape

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.

4.97 out of 5 average rating, 162 reviews

NEW BUILD Near Downtown! Stars Stripes & Salt Life

Apartment rentals with outdoor seating

Superhost

A living area is shown with comfortable leather sofas arranged around a coffee table. Large glass doors provide access to an outdoor space, allowing natural light to fill the room. Framed artwork adorns the walls, adding subtle decor to the neutral-toned space.

Flat in Gulf Breeze

4.83 out of 5 average rating, 123 reviews

The Lazy Dolphin

Superhost

A vibrant kitchen area features green walls and a tiled floor. A round table with a menu and brochures is placed next to a window with natural light. A futon can be seen in the background, along with a glimpse of the organized kitchen layout.

Flat in North Hill

4.76 out of 5 average rating, 278 reviews

Shore Break: Downtown Pensacola, North Hill

4.97 out of 5 average rating, 177 reviews

An inviting entryway is seen, featuring a brick facade and large glass doors. A welcome sign is prominently displayed next to the entrance. The surrounding outdoor area includes a well-maintained garden and trees, providing a serene atmosphere.

Flat in Myrtle Grove

Entire studio space is private, clean & relaxing.

4.82 out of 5 average rating, 172 reviews

Flat in Perdido Key

Caribbean Blue steps from the beach

4.97 out of 5 average rating, 341 reviews

The bedroom features a spacious bed with a decorative headboard, topped with plush pillows and a patterned throw blanket. Two bedside tables with soft lamps provide warm lighting, and natural light streams through sheer curtains, enhancing the inviting atmosphere.

Flat in East Hill

Luxurious apartment walk to the Bay-2m to downtown

4.94 out of 5 average rating, 118 reviews

A spacious living area is arranged with a large sectional sofa adorned with colorful cushions. A round coffee table is centered on a patterned area rug. Bright artwork depicting beach scenes is displayed on the wall. A potted palm adds a touch of greenery.

Flat in Gulf Breeze

Stylish Place 7 Miles from the Beach/self-check-in

4.91 out of 5 average rating, 116 reviews

A wooden deck is featured in the backyard, furnished with four blue Adirondack chairs and a small table. A potted plant adds a touch of greenery, while a BBQ grill is positioned to the side. The fenced area provides a sense of privacy.

Flat in Pensacola

East Hill Nest~Private apt close to it all!

4.94 out of 5 average rating, 106 reviews

Flat in Pensacola Beach

Ocean Tranquility label by guest“Heaven on Earth”.

Apartment rentals with outdoor seating

4.98 out of 5 average rating, 104 reviews

Two wooden lounge chairs are positioned on the sandy beach, facing the serene Gulf waters. Light fluffy clouds scatter across the clear blue sky, while gentle waves lap at the shore, creating a peaceful coastal scene.

Apartment in Perdido Key

Marisol del Cielo/Sea Sun Of The Sky-On The Beach

4.93 out of 5 average rating, 134 reviews

A serene waterfront view at sunset features a serene bay with multiple sailboats and yachts docked. The sky is painted in soft shades of pink and purple, reflecting on the calm water. A grassy area with kayaks and canoes is visible in the foreground.

Apartment in Pensacola

Sunset on the Bayou near NAS/Downtown Pensacola

4.92 out of 5 average rating, 127 reviews

A cozy living area is furnished with a tufted navy blue sofa and two white accent chairs. A round coffee table with a marble top sits on a patterned area rug. Decorative wall art and a potted plant add visual interest, while natural light filters through the window.

Apartment in Gulf Breeze

Chic Townhouse across from Sound

A private balcony offers sweeping views of the Gulf of Mexico, showcasing the clear blue waters and soft sandy beach below. The horizon merges sky and sea, creating a serene coastal scene. Beach chairs and umbrellas are positioned along the shoreline, inviting relaxation.

4.98 out of 5 average rating, 220 reviews

Beachfront Bliss: Walk to Dine & Play on Sands

A bright waterfront scene is captured, featuring Little Sabine Bay with reflections shimmering on the water's surface. The view includes marinas with sailboats and yachts, framed by palm trees and gardens, with a pool visible in the foreground.

5 out of 5 average rating, 147 reviews

Stay at Sunshine Daydream on Pensacola Beach

4.99 out of 5 average rating, 115 reviews

A bright living space features a light-colored sofa paired with modern dining chairs around a table. Large windows frame stunning ocean views, while sheer curtains allow natural light to fill the room. A comfortable chair and a woven accent chair add to the inviting atmosphere.

Apartment in Perdido Key

Beach Front - Peaceful & Private in Perdido Key FL

The open concept living area features a cream-colored sofa and a round coffee table. A wooden loft area is visible in the background, with warm lighting illuminating the kitchen. A large television hangs on the wall, complementing the bright and welcoming space.

4.92 out of 5 average rating, 237 reviews

Amazing Condo on Bay, Steps from Gulf of America

A serene view of the bay is captured from the balcony, showcasing the calm water and sandy beach lined with outdoor furniture. In the distance, a pier extends into the water, while boats can be seen sailing peacefully, framed by the clear blue sky.