Guesthouse holiday rentals in Pensacola

A comfortable living area showcases a leather couch accompanied by two light-colored armchairs. A ceiling fan provides airflow, while a simple art piece and a small plant add aesthetic interest. Soft lighting illuminates the warm wood flooring, enhancing the open layout.

4.98 out of 5 average rating, 166 reviews

Luxury East Hill Apt. Near Downtown Pensacola

Located in Pensacola's historic East Hill neighborhood, our luxury modern apartment is minutes away from the airport, beaches, hospitals, breakfast/coffee shops, restaurants, historic downtown, and shopping! Perfect for business trips, visiting family, budget-friendly beach vacations, or just passing through. W/Dryer, King Bed, Full Kitchen, Gas Fire Pit, and Private Parking. Enjoy your stay in America's first settlement and be sure to check out VisitPensacola.com for events while you're here!

A cozy outdoor space is showcased, featuring a patio with a light pink cottage, surrounded by lush greenery. A grill and seating area invite relaxation, with an umbrella providing shade. A small table stands alongside, enhancing the inviting outdoor setting.

4.9 out of 5 average rating, 330 reviews

Cozy Garden Cottage

Nestled in private quiet garden behind main house. Off street parking and own entrance. Safe and friendly neighborhood of East Hill. Can walk to a bakery and pub. Between downtown Pensacola and airport. 15 minute drive to beaches. Wireless internet strong signal. T.V. with antenna. Amish "fireplace" heater. Kitchenette with medium refrigerator, sink, microwave, toaster oven, George Foreman grill, griddle designed to cook anything, and eating utensils. Grill on patio. Beach gear.

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.

4.98 out of 5 average rating, 179 reviews

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!

4.99 out of 5 average rating, 195 reviews

A light-filled living area features a comfortable white sofa and a glass coffee table on a round woven rug. Two large windows allow natural light to illuminate the space, complemented by soft curtains. A decorative piece hangs on the wall above the sofa, adding interest.

Guesthouse in East Hill

EAST HILL - Bayview Park Private Carriage House

Maggie's Carriage House is a professionally decorated carriage house in the historic East Hill neighborhood. We are one block from Bayview Park - you can enjoy walks, paddle boarding and kayaking. The carriage house has a private entrance at the back of the property. At 700sf, it has a full kitchen, dining room, living room, king bedroom with second TV, and a full bath with washer/dryer. 1 mile to Publix 10 min. to the airport 5-10 min. to downtown Pensacola 10-15 min. to the beach

Guesthouse in East Pensacola Heights

A charming courtyard area features a brick patio surrounded by lush greenery and flowering plants. Two comfortable seating arrangements with woven furniture and bright blue planters create an inviting space for relaxation. Access to the guesthouse is provided through double doors adorned with turquoise accents.

4.94 out of 5 average rating, 236 reviews

Charming Guesthouse @ Live Oaks on the Bayou

Live Oaks on the Bayou is perfect for those on vacation, business or coming to the area for a beach getaway, wedding or graduation. The guesthouse is nestled behind our home with your own driveway and parking . Enjoy a private meal, coffee or a cocktail in the quiet serene courtyard-fountain area immediately out your front door. A wide variety of dining is a 3-10 minute walk. There is always some vegetation in bloom here and throughout one of Pensacola's most treasured neighborhoods.

5 out of 5 average rating, 174 reviews

A private pool area is surrounded by a wooden fence, featuring clear blue water and colorful floats. A shaded seating area with vibrant umbrellas and lounge chairs is visible nearby, offering options for relaxation. The atmosphere is bright and inviting, with a glimpse of the bungalow in the background.

Guesthouse in East Hill

Funky Flamingo~ Guest House~ Pool & Kitchenette

This charming East Hill bungalow is owner managed/cleaned. Steps from Publix, 1 mile to downtown/Bayfront and just 12 minutes to Beach! Enjoy the private pool & patio. Luxury comforts and amenities, with the highest speed Wi-Fi/streaming services. Casper mattress and pillows with (700 thread count Egyptian Cotton sheets), for an amazing nights rest, Beach chairs, cooler, umbrella and towels provided. Enjoy the new walk-in shower w/ tankless hot water heater. LBGTQIA2S+ friendly!

A modern studio features a light grey sectional sofa facing a television mounted on the wall. Large glass doors lead to a private outdoor area. Blue curtains frame the windows, while decorative mirrors adorn the wall above the sofa, enhancing the overall ambiance.

4.93 out of 5 average rating, 146 reviews

Studio 54 - a modern beach-town studio

You’ll love this modern, stylish studio (open floorplan), completely separate from main house, in a quiet neighborhood, with: -private entrance - private, covered patio -double driveway 4 blocks from the water (Bayou Chico) & a big park w/ frisbee golf. Close to everything Pensacola and Perdido Key have to offer: -Airport (PNS) - 8miles -Downtown Pensacola - 3mi -Beaches: -Bruce Beach: 3mi -Pensacola - 12mi -Perdido Keys - 12mi -Naval Air Station (NAS) - 4mi

4.97 out of 5 average rating, 716 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 North Hill

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 modern kitchenette features sleek cabinetry and a white countertop. Essential appliances include a refrigerator, a microwave, and an electric kettle. Two wooden stools are positioned at the countertop, and a wall-mounted shelf displays decorative items and kitchenware.

4.96 out of 5 average rating, 194 reviews

1950’s East Hill Carriage House

Welcome to our renovated 1950s carriage house, tucked privately behind our home in East Hill. Steps from scenic Bayview Park with paddle boards, canoes, and bikes for rent, and a short ride to bars, breweries, and restaurants on 12th Avenue. Historic downtown Pensacola offers shopping, dining, and live music at Vinyl Music Hall and performances at The Saengar Theater. Plus, the stunning white sands of Pensacola Beach are a short and stunning drive away.

A bright living area features a comfortable sofa adorned with decorative pillows and a textured throw. Two abstract art pieces are displayed on the wall above the sofa. A round table with stylish chairs sits beside a large window, allowing natural light to fill the space.

4.99 out of 5 average rating, 134 reviews

Walkable + Luxe ~ 1BR Guesthouse w/ Fire Pit+Grill

At this modern 1BR guesthouse in the heart of East Hill, you’ll enjoy a walkable neighborhood with plenty of quiet. Inside, soaring ceilings and high-end furnishings make for an upscale but comfortable space. Outside, you're steps from Alga Brewery, local food trucks, and popular morning spots like Jitterbug. Fire up the BBQ and wind down with a glass in hand—and when you’re ready for adventure, downtown and the beach are just 10 minutes away.

The spacious sleeping area features a large bed with soft bedding, complemented by a neutral-toned blanket. A comfortable couch is positioned nearby, while sliding glass doors provide natural light and access to the outdoor space.

4.87 out of 5 average rating, 250 reviews

The Carriageway Cottage -Close to Pensacola Beach!

Whether you’re visiting Pensacola for business or pleasure, thank you for your interest in our guest house. We’re located in the heart of East Hill, which is a very charming and established neighborhood. The area is peaceful and quiet, yet only about a 5-10 minute drive downtown Pensacola. We will do everything we can to make your stay great! The guest house is located directly off of our private carriageway behind the house.

Guesthouse in Gulf Breeze

The guesthouse is shown from above, highlighting its spacious layout and pitched roof. A covered porch is visible in the front, along with outdoor seating. Surrounding greenery and tall trees create a natural backdrop, complementing the tranquil setting.

4.99 out of 5 average rating, 111 reviews

Snowbird Paradise-Gulf Breeze Hidden Gem

Built in 2020, this guesthouse is located in quite and safe neighborhood. 8 miles to Pensacola beach and 17 miles to Navarre Beach. Completely private with your own driveway and parking area, plus the use of the main house pool, patio and BBQ. Beautiful view of the forest. On a case by case basis we will entertain 6 guest. Please inquire before booking. Please be sure to review the House Rules section.

Popular amenities for Pensacola guesthouses

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

A cozy studio apartment showcases a spacious bed against a white brick wall, accentuated by two pendant lights. A gray sofa is positioned nearby, accompanied by a textured throw pillow. A colorful rug adds warmth, while a framed artwork of a cow provides decorative interest.

4.85 out of 5 average rating, 55 reviews

Poolside Cabana

5 out of 5 average rating, 41 reviews

A cozy living space features a comfortable sofa adorned with decorative pillows. A wooden table with bar stools provides dining options. A flat-screen TV is mounted on the wall, and light enters through a window, brightening the room's earthy tones.

Guesthouse in Navy Point

Guest house on the Bayou

A cozy seating area features a spacious brown sectional couch adorned with decorative pillows in yellow and gray. A small side table is positioned next to the couch. Natural light streams in through a window, illuminating the tiled floor and nearby wall-mounted TV.

4.88 out of 5 average rating, 17 reviews

Sweet Comfort Cottage Close to I-10 & Navy Federal

4.94 out of 5 average rating, 69 reviews

A cozy living area features a dark blue sofa and a contemporary TV stand. Light wood flooring complements the white walls. A colorful piece of wall art and a unique lamp add charm. A door leads to the exterior, while a kitchen area is visible.

Guesthouse in North Hill

The Dragonfly House -

Superhost

A vibrant blue exterior of the Parrot House Nest is showcased. The inviting front porch features two comfortable chairs and a small table. A fully fenced yard surrounds the property, with greenery visible in the background, providing a sense of privacy and outdoor space.

4.91 out of 5 average rating, 35 reviews

Stylish Studio* Military Discount

4.92 out of 5 average rating, 25 reviews

A modern kitchen area is visible, featuring light wood cabinetry and dark appliances. A comfortable, brown sofa is positioned on a circular rug, with natural light filtering through the windows. An entrance leads to an outside area, enhancing the sense of openness.

Guesthouse in East Hill

Cozy Loft Near Downtown

5 out of 5 average rating, 16 reviews

Perdido Surf Shack-tiny house near Perdido Key

A gravel pathway leads to a charming orange-colored guest house, framed by lush greenery and palm trees. A blue hammock is suspended nearby, inviting relaxation under the shade. The fenced area ensures privacy, creating a serene retreat in the outdoors.

5 out of 5 average rating, 15 reviews

Downtown Pensacola Cottage

Guesthouses with a patio

A small outdoor seating area is shown with two blue chairs and a black table against a light-colored wall. The space is shaded by the overhang of the building, with steps leading to the upper level visible in the background.

4.87 out of 5 average rating, 142 reviews

Sonoran Mermaid’s Guest Suite

A spacious bedroom features a comfortable white bed, accented with navy blue pillows. Two bedside tables with lamps are positioned beside the bed. A large mirror and decorative wall art add a touch of style, while natural light streams in through the window.

5 out of 5 average rating, 14 reviews

Brand New Guest house 8 min. to Pensacola Beach

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.

5 out of 5 average rating, 48 reviews

The Rosales serenity suite

The living area features a comfortable seating arrangement with a dark gray sofa and a patterned area rug. Natural light enters through multiple windows, illuminating the space. A dining table with stools is present, along with a partial view of the kitchen in the background.

4.97 out of 5 average rating, 60 reviews

Newly Renovated one bedroom home

4.99 out of 5 average rating, 141 reviews

The entrance of the property is marked by a gated driveway, leading to a welcoming guest house surrounded by lush trees. The pathway is bordered by well-maintained landscaping, providing an inviting approach to the home.

Guesthouse in Milton

Siesta Cottage on the Blackwater

A cozy living room features a comfortable grey sofa adorned with decorative pillows. A recliner chair is positioned nearby, and a small ottoman rests on a patterned rug. Natural light pours in through two large windows, enhancing the room's welcoming ambiance.

5 out of 5 average rating, 45 reviews

Hummingbird Cottage

Guesthouse in Downtown Pensacola

A spacious living area features a comfortable sofa and two armchairs, complemented by a round coffee table. Natural light fills the space through multiple windows. A dining table with seating for four is situated nearby, while decorative plants enhance the welcoming environment.

5 out of 5 average rating, 49 reviews

The perfect Aragon guest retreat

The open living space features a modern design with light wood flooring. A comfortable sofa is positioned near large sliding doors that lead to the outdoor area. A dining table with white chairs is set against a backdrop of stylish decor, including a wall-mounted TV.

4.87 out of 5 average rating, 85 reviews

Lovely- Pensacola-Guesthouse

Guest house rentals with a washing machine and dryer

A screened-in pool area features a swimming pool with two white lounge chairs positioned on the deck. A hammock sits nearby in the shaded grass, surrounded by a fenced backyard, creating a relaxing outdoor space for guests.

4.98 out of 5 average rating, 263 reviews

Pet Friendly, Pool, Hot Tub, Fenced yard.

Guesthouse in Downtown Pensacola

A spacious tan sectional sofa is positioned in a bright living area, accompanied by decorative pillows. A unique wooden coffee table sits in front, while a colorful area rug adds warmth. In the background, a modern kitchen features light wood cabinets and white appliances.

4.93 out of 5 average rating, 111 reviews

Chic Studio in Historic Downtown Pensacola

Guesthouse in Navarre Beach

A private deck features a turquoise table surrounded by white adirondack chairs and a sofa. The view extends over the landscape, highlighting the gentle waters of the Santa Rosa Sound and clouds drifting across a bright sky.

4.96 out of 5 average rating, 267 reviews

S.K.I. Beach House (Spending our Kids Inheritance)

The entrance features a welcoming black door with a 'Welcome' sign. Flanking the door are two hanging flower baskets and a window box filled with greenery. A small round table is accompanied by two chairs on the porch, inviting guests to sit and relax.

4.98 out of 5 average rating, 131 reviews

The Paradise Cottage-clean+gated

Guesthouse in Gulf Breeze

A bright living area features a combination of modern and cozy furnishings. A light gray armchair is paired with a comfortable black couch. A wooden coffee table sits in the center, surrounded by two framed artworks and a large wall clock, creating a welcoming space.

4.95 out of 5 average rating, 130 reviews

Beautiful Get-Away Cottage

The entrance features a black door adorned with a decorative wreath. A small table holds a decorative item, while potted plants add greenery. Natural light filters through the window, which is flanked by soft window treatments, enhancing the welcoming feel of the entrance area.

4.96 out of 5 average rating, 112 reviews

East Hill Retreat/15 minutes to Pensacola Beach

A spacious sleeping area features a king-size bed with a light-colored comforter. Two bedside tables with lamps are positioned on either side. A colorful mural depicting Pensacola, Florida, is featured on the wall above the bed, complemented by a patterned rug beneath.

4.97 out of 5 average rating, 178 reviews

East Hill Chillin'