Guesthouse holiday rentals in 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, 191 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!

ValueLocationAccuracy

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, 191 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!

LocationFamilyCondition

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, 353 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.

LocationValueHospitality

A private patio area is surrounded by greenery, featuring a wooden deck and a large tree. Natural light filters through the large windows of the apartment. A fire pit is positioned on the deck, creating an inviting outdoor space for relaxation.

4.9 out of 5 average rating, 226 reviews

Private Apartment! Spring Street Retreat

This cozy retreat is a detached private apartment in a quiet neighborhood just minutes from downtown. The space has its own private entrance with a patio, queen bed, Roku TV, Alexa, kitchenette, and a private bathroom. The kitchenette features a mini-fridge, 2-burner stovetop, microwave, toaster, and coffee maker. Whether you are here for a quick weekend getaway, extended vacation, or visiting as a traveling professional, you will find that this space will enhance your Pensacola experience.

ValueFamilyNearby

4.99 out of 5 average rating, 240 reviews

Guesthouse in East Hill

Cozy Traveller's Cottage Close to Downtown

This cozy guest cottage has shiplap walls and a warm and inviting interior. It's perfect for a quiet getaway for 1 or 2 people. Located in Pensacola's eclectic East Hill neighborhood and close to downtown, restaurants and shopping. The cottage is best suited for guests over the age of 18 and is not equipped for small children. Please note for your comfort the standard weight capacity for the bedframe is approx 500 lbs. I have two sweet pups (Lily, Hildey) and an outdoor cat (Skipper-Doo).

ValueLocationKitchen

4.99 out of 5 average rating, 229 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

FamilyValueBeach

The exterior of the cottage is showcased, featuring a vibrant blue facade with white trim. Two yellow Adirondack chairs sit on the front porch, inviting relaxation. A bright yellow door stands out, complementing the cheerful ambiance, while greenery and blue skies complete the peaceful setting.

4.93 out of 5 average rating, 117 reviews

Downtown Pensacola Cozy Cottage

Experience beautiful Pensacola in the Gregory House, a sweet cottage tucked away in a quiet downtown neighborhood. Close to Pensacola Beach, this cozy bungalow guesthouse is located in the Westside Garden District, blocks from street fairs and festivals and a quick drive from the beach. Newly constructed adorable one bedroom cottage has one queen bed and queen sleeper sofa. The property shares a wood deck with outdoor shower, grill and firepit. Complimentary beach chairs provided.

FamilyValueAmenities

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.

4.97 out of 5 average rating, 783 reviews

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.

LocationFamilyIndoor spaces

Superhost

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.

4.86 out of 5 average rating, 111 reviews

Lovely- Pensacola-Guesthouse

Clean, and modern designed guest house, nestled in a cozy but convenient Pensacola neighborhood with easy access to Historic Downtown Pensacola, University of West Pensacola, and Beautiful Pensacola Beach. Gorgeous, peaceful space, perfect for rest and recharging. 2 smart TVs with internet, private back patio with fire pit, outdoor shower and outdoor seating. The place is great for two, but a baby or a toddler would fit as well. NOTE: It is not on Pensacola Beach!

FamilyLocationLong stay

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.

4.97 out of 5 average rating, 219 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.

ValueFamilyCondition

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.

4.92 out of 5 average rating, 251 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. 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.

FamilyValueOutdoor spaces

A red door with multiple panes is framed by a light-colored wall. A decorative metal sign reading 'WELCOME' hangs above the door, while a small warning sign indicates 'Watch Your Step' near the entrance.

4.98 out of 5 average rating, 128 reviews

The Tropical Hideaway

Located in the heart of the Seville Historic District! Walking distance to 30 different restaurants in Downtown Pensacola, the Pensacola Bay Center, Saenger Theater and Pensacola Little Theater. This carriage house sits behind an 1885 historic home that was used as a catholic nunnery. Visitors will enjoy private off street gated parking. No children under the age of 12 years old.

ValueFamilyTV

Popular amenities for Pensacola guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

The exterior of the cottage features a small outdoor seating area with blue chairs and a table surrounded by trees. A decorative fence outlines the yard, complemented by potted plants and seasonal flowers near the entrance. The door is painted blue, adding a pop of color.

4.91 out of 5 average rating, 693 reviews

Cottage Under the Trees

LocationValueGetting around

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, 101 reviews

Adorable private studio style guesthouse!

FamilyValueCleanliness

A cozy studio space features a spacious bed with light-colored bedding, complemented by a decorative throw pillow. A comfortable lounge chair is positioned next to a small table under a large window, which is covered with blinds allowing soft light to filter in.

4.97 out of 5 average rating, 120 reviews

*New* Vacation Rental in East Hill

FamilyValueWi-Fi

4.89 out of 5 average rating, 287 reviews

Sunflower Inn * Private Cozy Cottage Near beaches

LocationValueCleanliness

4.96 out of 5 average rating, 101 reviews

La Casita: studio near Downtown and NAS

LocationValueWalkability

5.0 out of 5 average rating, 151 reviews

A cozy guest cottage is framed by a pebble garden, featuring a small seating area with a green chair and a round table. The entrance is adorned with flowering plants, while a screened porch enhances the outdoor space. The structure's bright green exterior is complemented by a wooden fence.

Guesthouse in Navarre

Heart of Navarre Tiny House Guest Cottage

FamilyValueBackyard

Guesthouse in Gulf Breeze

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.

4.96 out of 5 average rating, 210 reviews

Cute Carriage House Apartment with View

FamilyLocationPool

A cozy studio guest suite features a spacious bed covered with a white quilt. A colorful rug adds vibrancy to the space, complemented by a small dining table and a kitchenette equipped with modern appliances. Natural light enters through the window, while a ceiling fan enhances airflow.

5.0 out of 5 average rating, 149 reviews

Sun-kissed Getaway by the Pensacola Bay

ValueFamilyComfort

Guesthouses with a patio

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.

4.88 out of 5 average rating, 295 reviews

The Carriageway Cottage -Close to Pensacola Beach!

FamilyLocationComfort

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.

4.97 out of 5 average rating, 224 reviews

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

FamilyValueAccuracy

4.99 out of 5 average rating, 172 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

ValueFamilyCheckout

Superhost

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.

4.89 out of 5 average rating, 196 reviews

Studio 54 - a modern beach-town studio

LocationValueDecor

4.98 out of 5 average rating, 104 reviews

Cozy & Private Guest Cottage - Perfect for Two

FamilyValueAccess

4.99 out of 5 average rating, 170 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!

ValueFamilyWalkability

5.0 out of 5 average rating, 201 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

FamilyLocationBackyard

4.98 out of 5 average rating, 126 reviews

The exterior of the coastal cottage is showcased, featuring a welcoming front porch with two chairs and potted plants. A paved pathway leads to the entrance, flanked by a natural landscape of trees and pine needles, creating a peaceful and inviting approach.

Guesthouse in Navarre

Never Navarre From Home Cottage

FamilyValueHospitality

Guest house rentals with a washing machine and dryer

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, 229 reviews

East Hill Chillin'

FamilyValueQuiet

4.99 out of 5 average rating, 156 reviews

The Paradise Cottage-clean+gated

FamilyValueWi-Fi

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, 126 reviews

East Hill Retreat/15 minutes to Pensacola Beach

LocationFamilyCheckout

Guesthouse in Gulf Breeze

4.99 out of 5 average rating, 117 reviews

Pool:Relaxing Summer Cottage - Gulf Breeze

FamilyLocationSleep quality

Guesthouse in Pensacola Beach

4.98 out of 5 average rating, 156 reviews

The Cedarwood 2 @Navarre Beach.

ValueLocationGetting around

Guesthouse in Pensacola 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.

4.95 out of 5 average rating, 289 reviews

S.K.I. BEACH•Walk to Gulf • Sound Views •1BR Suite

LocationValueOutdoor spaces

The cottage exterior displays a charming yellow facade with white trim. A front porch is visible, featuring white railing and a welcome mat. Surrounding greenery and trees provide a sense of privacy and tranquility.

5.0 out of 5 average rating, 74 reviews

Adorable cottage, hidden in downtown Pensacola!

LocationValueOutdoor spaces

An aerial view captures the surrounding area of the guest house, featuring open green spaces, a pond, and a nearby fountain. The bay is visible in the distance, with industrial structures alongside the water. The layout includes streets and designated areas for recreation.