Guesthouse vacation rentals in Pensacola

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.

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!

ValueLocationParking

5.0 out of 5 average rating, 206 reviews

5.0 out of 5 average rating, 206 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 pool bungalow is owner managed/cleaned. Steps from Publix, 1 mile to downtown/Bayfront and just 12 minutes to Beach! Enjoy the private pool & entire back yard. 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!

ValueFamilyLayout

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, 193 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!

FamilyLocationLong stay

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.

4.9 out of 5 average rating, 202 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 patio -double, extra-long driveway (trailer,rv,etc) 4 blocks from 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

LocationValueNearby

4.99 out of 5 average rating, 233 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

LocationValueBathroom

4.97 out of 5 average rating, 99 reviews

Waterfront Haven | King Studio | Hot Tub | UWF I10

Welcome to Mackey Haven! This Superhost designed & managed coastal escape features luxe amenities, stylish décor, beautiful waterfront views, a plush king bed, fully stocked kitchen, and relaxing outdoor spaces. Our peaceful, boutique retreat is perfect for couples or solo travelers. You’ll want to stay for days! ⭐️ Hot Tub / Kayak / Boat Dock ⭐️ Coffee Bar & Breakfast to go ⭐️ Organic Cotton Bed Sheets ⭐️ 75” Roku TV & Fast WiFi ⭐️ Massaging Waterfall Shower ⭐️ Easy UWF & Freeway Acces

FamilyLocationAmenities

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.

ValueFamilyAccuracy

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, 112 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!

LocationFamilySleep quality

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, 222 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.

LocationFamilyHeating

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, 252 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.

LocationFamilyLaundry

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, 124 reviews

*New* Vacation Rental in East Hill

Beautiful newly built studio apartment, only minutes from downtown. Located in the desirable East Hill of Pensacola. Enjoy restaurants and craft breweries within biking distance. Spend a relaxing day at our amazing white sand beaches only a 15 minute drive. The studio has luxury flooring throughout and quartz countertops in its full-sized kitchen. Guests will have their own private driveway fenced separately away from homeowners.

LocationValueAmenities

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, 298 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.

ValueLocationBathroom

Popular amenities for Pensacola guesthouse rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

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, 698 reviews

Cottage Under the Trees

FamilyValueNearby

4.96 out of 5 average rating, 102 reviews

La Casita: studio near Downtown and NAS

LocationValueSleep quality

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.

Adorable private studio style guesthouse!

ValueLocationWifi

4.99 out of 5 average rating, 102 reviews

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, 227 reviews

Private Apartment! Spring Street Retreat

ValueLocationView

5.0 out of 5 average rating, 155 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

ValueLocationNearby

4.99 out of 5 average rating, 173 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!

FamilyValueGetting around

4.97 out of 5 average rating, 104 reviews

Relaxing Retreat of East Hill

FamilyLocationCheckout

4.89 out of 5 average rating, 292 reviews

Sunflower Inn * Private Cozy Cottage Near beaches

LocationValueLayout

Guest house rentals with a patio

4.99 out of 5 average rating, 175 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

LocationFamilyParks

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, 229 reviews

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

LocationFamilyDecor

4.98 out of 5 average rating, 111 reviews

Cozy & Private Guest Cottage - Perfect for Two

FamilyValueAir conditioning

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

FamilyValueNearby

Guesthouse in Pensacola Beach

Sonoran Mermaid’s Guest Suite

ValueLocationIndoor spaces

4.89 out of 5 average rating, 167 reviews

4.98 out of 5 average rating, 130 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

ValueFamilyCheckout

4.95 out of 5 average rating, 214 reviews

A functional living space features a cozy sofa facing a light wood coffee table. The kitchen, equipped with blue cabinetry and modern appliances, is positioned in the background. A ceiling fan provides ventilation, while a welcoming entry door allows natural light to brighten the area.

Guesthouse in Elberta

Quaint Tiny Home by the Bay (Mini Cottage)

FamilyValueParking

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.

The perfect Aragon guest retreat

ValueLocationAmenities

5.0 out of 5 average rating, 72 reviews

Guest house rentals with a washer and dryer

4.99 out of 5 average rating, 241 reviews

Guesthouse in East Hill

Cozy Traveller's Cottage Close to Downtown

ValueLocationSleep quality

4.99 out of 5 average rating, 160 reviews

The Paradise Cottage-clean+gated

LocationValueCheckout

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, 129 reviews

East Hill Retreat/15 minutes to Pensacola Beach

FamilyValueWalkability

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, 357 reviews

Cozy Garden Cottage

LocationValueIndoor spaces

Guesthouse in Pensacola Beach

The Cedarwood 2 @Navarre Beach.

FamilyLocationComfort

4.98 out of 5 average rating, 162 reviews

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, 239 reviews

East Hill Chillin'

ValueLocationAccess

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.

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

FamilyLocationCondition

4.95 out of 5 average rating, 293 reviews