Guesthouse vacation rentals in Pensacola Beach

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.

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

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

Our 2 story Guest house is the definition of cozy and inviting. Located on our spacious and gated property. We strive to make your stay feel as if you were at home. We are 5 min from Navy Federal Headquarters. 10 min from the Equestrian Center. A quick 30 min (mostly interstate travel) to Pensacola Beach. Perfect location to visit your family if located in Beulah/cantonment/9mile area. When you choose to stay with us you are getting a host that cares 100% about the quality of your stay.

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, 235 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.

Guesthouse in Gulf Shores

Colorful adirondack chairs in vibrant shades of red, green, and blue are positioned on white sand, overlooking calm waters. A wooden pier extends into the lagoon, with clear skies and sunshine creating a serene atmosphere.

4.97 out of 5 average rating, 101 reviews

Waters’ Edge Cottage Gulf Shores

"Water's Edge Cottage" is a completely updated and furnished one bedroom, 450 sq ft cottage that is literally just steps away from all that Little Lagoon has to offer. A charcoal grill is available to cook your catch or anything else. Try kayaking (that we provide) in the Lagoon or just sit and relax. We are just 5 minutes from the beach, secluded yet convenient. If you have questions or need help with anything we (Ebie and Steve) live right next door to provide answers or help.

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, 145 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 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.

A serene canal view showcases calm waters lined with docks and boats. Lush greenery frames the waterway, and buildings are visible in the distance against a clear blue sky. The scene is tranquil, inviting a sense of peace and relaxation.

4.95 out of 5 average rating, 193 reviews

Cute Carriage House Apartment with View

Situated just east of Pensacola and just north of Pensacola Beach, our place is located in a quiet neighborhood, just a short drive from amazing restaurants and the most beautiful, snow white beaches in Florida. Our private suite has one bedroom, one bathroom and an open living/kitchen area. Sleep up to four guests with a queen bed in the bedroom and a new queen size pull out sofa in the living area.

Popular amenities for Pensacola Beach guesthouses

Kitchen

Wifi

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, 59 reviews

The open-concept kitchen features modern stainless steel appliances, including a side-by-side refrigerator and oven. A dining table with a light-colored tablecloth is positioned beside the kitchen, and a comfortable reclining sofa is visible in the living area, creating a welcoming space for relaxation.

Guesthouse in Foley

The Yellow Door

Guesthouse in Spanish Fort

A cozy detached guest house is presented, featuring a dark brown door and two windows adorned with white curtains. The exterior is painted in neutral tones, complemented by a small table and two blue chairs placed outside. An American flag is displayed on the front, and a wooden fence provides privacy.

4.98 out of 5 average rating, 149 reviews

Adorable 1-Bedroom Guesthouse in Spanish Fort

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

5 out of 5 average rating, 20 reviews

A well-constructed carriage house features a spacious front porch with black railings and rocking chairs. The overhang creates a shaded area, while the driveway leads to the garage beneath. Lush trees surround the house, complementing the gravel pathway and landscaped areas.

Guesthouse in Milton

Rainbow Land Carriage House

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 -

4.78 out of 5 average rating, 145 reviews

A wooden gazebo is set on a grassy area, surrounded by tall trees. The structure features an open design with a slatted roof for shade, wooden railings, and steps leading up to its spacious deck. Sunlight filters through the leaves, creating a serene atmosphere.

Guesthouse in Fairhope

Historic Home Away from Home

Guesthouse in Gulf Breeze

The entrance features a welcoming porch with a set of white railings and steps leading to a door. A small wooden dog figure is placed on the porch, accompanied by a flower pot with colorful blooms. The cottage exterior is painted in a vibrant red, contrasting with the gray flooring.

4.99 out of 5 average rating, 85 reviews

Adorable private studio style guesthouse!

Guesthouses with a patio

Superhost

A cozy guest room features a spacious bed dressed in soft linens, complemented by decorative pillows. Nearby, a small table and two chairs provide a seating area. Natural light is filtered through a window with blinds, enhancing the room's tranquil ambiance.

Guesthouse in Fort Walton Beach

4.87 out of 5 average rating, 109 reviews

Cozy 1-bedroom Guest House

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

5 out of 5 average rating, 9 reviews

Gulf Breeze Bungalow

A private balcony features two turquoise lounge chairs positioned to offer unobstructed views of the bay. Lush greenery frames the scene, which includes a fishing pier extending into the water. A clear sky and distant land contribute to the peaceful atmosphere.

5 out of 5 average rating, 57 reviews

Pensacola Beach Waterfront Condo

4.99 out of 5 average rating, 140 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

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

4.99 out of 5 average rating, 151 reviews

A front porch is framed by white columns, providing a welcoming approach to the cottage. Neatly landscaped gardens with various plants and shrubs create a lush atmosphere, while a wooden porch adorned with a small table and chairs invites relaxation and enjoyment of the outdoor setting.

Guesthouse in Milton

Charming Bayou Bungalow near downtown Milton!

Guesthouse rentals with a washer and dryer

Guesthouse in Gulf Shores

A serene view of Little Lagoon at sunrise, reflecting soft hues of orange and purple across the water's surface. Wooden docks extend into the lagoon, offering a tranquil foreground, while city buildings can be seen in the distance under an early morning sky.

4.97 out of 5 average rating, 181 reviews

Escape relax & enjoy Lagoon Life

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.

4.97 out of 5 average rating, 389 reviews

An outdoor area features a private pool surrounded by a patio with lounge chairs and a dining table. Two surfboards are positioned near the pool, alongside palm trees and residential buildings in the background, creating a relaxed, tropical setting.

Guesthouse in Destin

Carriage House by the Beach

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, 110 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)

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

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.