
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.

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!

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.

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

Sunflower Inn * Private Cozy Cottage Near beaches
Fully equipped 1-bedroom guesthouse attached to main house with a private entrance, full kitchen, and everything you need to feel at home. Guests love the cozy atmosphere, peaceful location, and easy access to I-10, downtown Pensacola, beaches, military bases and hospitals. Many guests return again and again for the comfort, safety, and convenience this space offers. Small pets allowed (potty trained and non destructive only). 1 queen bed, 1 full size futon in living area. Non smokers only.

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).

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

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.

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.

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.

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

*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.

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
Family-friendly guest house rentals

Poolside Cabana

Heron’s Hideaway near NAS/Downtown

The Lantern

The Dragonfly House -

Brand New Guest house 8 min. to Pensacola Beach

Cozy Loft Near Downtown

Relaxing Retreat of East Hill

"Jerry's Drive In" Blue Angels
Guest house rentals with a patio

Sonoran Mermaid’s Guest Suite

The Rosales serenity suite

Newly Renovated one bedroom home

Siesta Cottage on the Blackwater

Lovely- Pensacola-Guesthouse

Charming Bayou Bungalow near downtown Milton!

Cozy & Private Guest Cottage - Perfect for Two

Never Navarre From Home Cottage
Guest house rentals with a washer and dryer

Pet Friendly, Pool, Hot Tub, Fenced yard.

Chic Studio in Historic Downtown Pensacola

Walk to Gulf • Sound Views • 1BR Suite • 2 Decks

Olive Cove Studio

Spring Break Oasis-Gulf Breeze Hidden Gem

The Paradise Cottage-clean+gated

Beautiful Get-Away Cottage

East Hill Retreat/15 minutes to Pensacola Beach
When is the best time to visit Pensacola?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$17,778 GYD | G$16,942 GYD | G$18,615 GYD | G$18,824 GYD | G$20,079 GYD | G$22,380 GYD | G$23,007 GYD | G$19,661 GYD | G$18,824 GYD | G$17,569 GYD | G$17,778 GYD | G$17,778 GYD |
| Avg. temp | 12°C | 14°C | 17°C | 20°C | 24°C | 28°C | 29°C | 28°C | 27°C | 22°C | 16°C | 13°C |
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
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