Guesthouse vacation rentals in Pensacola

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Top-rated guesthouse rentals in Pensacola

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Top guest favorite
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.
Guesthouse in Pensacola
4.98 out of 5 average rating, 171 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!

Top guest favorite
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.
Guesthouse in Pensacola
4.9 out of 5 average rating, 335 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.

Top guest favorite
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.
Guesthouse in North Hill
4.9 out of 5 average rating, 208 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

Guest favorite
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.
Guesthouse in Pensacola
4.97 out of 5 average rating, 186 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!

Top guest favorite
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
4.99 out of 5 average rating, 199 reviews

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

Guest favorite
Guesthouse in East Pensacola Heights
4.93 out of 5 average rating, 240 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.

Top guest favorite
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.
Guesthouse in Downtown Pensacola
5 out of 5 average rating, 124 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.

Top guest favorite
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
4.97 out of 5 average rating, 735 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.

Top guest favorite
A bright and airy living space showcases a spacious white sofa and a light green accent chair. Artwork adorns the walls, adding color to the room. A wooden table sits nearby, and a modern light fixture provides illumination. The open kitchen is visible in the background, enhancing the inviting atmosphere.
Guesthouse in Downtown Pensacola
4.96 out of 5 average rating, 106 reviews

Modern Carriage House in Downtown Pensacola

Discount for last minute bookings 10%. Immerse yourself in history. Located in the heart of the Pensacola historic district, walking everywhere is a breeze. The carriage house has 2 bedrooms/2 baths, living room and a full size kitchen w/washer and dryer. The perfect location if you are here for a wedding, graduation, work or vacation. Close to wedding venues, restaurants, breweries, pubs, galleries & shopping. Beaches & Pensacola Airport are just minutes away by car.

Guest favorite
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.
Guesthouse in Pensacola
4.92 out of 5 average rating, 156 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 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

Top guest favorite
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.
Guesthouse in Pensacola
5 out of 5 average rating, 100 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.

Guest favorite
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.
Guesthouse in Pensacola
4.87 out of 5 average rating, 263 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.

Popular amenities for Pensacola guesthouse rentals

When is the best time to visit Pensacola?

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Avg. priceG$17,778 GYDG$16,942 GYDG$18,615 GYDG$18,824 GYDG$20,079 GYDG$22,380 GYDG$23,007 GYDG$19,661 GYDG$18,824 GYDG$17,569 GYDG$17,778 GYDG$17,778 GYD
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Quick stats about guesthouse rentals in Pensacola

  • Total vacation rentals

    Explore 60 vacation rentals in Pensacola

  • Nightly prices starting at

    Pensacola vacation rentals start at G$8,366 GYD per night before taxes and fees

  • Verified guest reviews

    Over 7,600 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Pensacola vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Pensacola rentals

  • 4.9 Average rating

    Pensacola stays are highly rated by guests—averaging 4.9 out of 5!

  • Nearby attractions

    Pensacola's top spots, include Pensacola Museum of Art, Palafox Market, and Bruce Beach

Destinations to explore