
Guesthouse holiday rentals in Pensacola
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Quick stats about guesthouse rentals in Pensacola

Total holiday rentals
Explore 60 holiday rentals in Pensacola

Nightly prices starting at
Pensacola holiday rentals start at $103 NZD per night before taxes and fees

Verified guest reviews
Over 7,860 verified reviews to help you choose

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
60 of Pensacola holiday 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 Palafox Market, Pensacola Museum of Art, and Bruce Beach
Top-rated Guesthouses in Pensacola
Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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!

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!

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.

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!

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

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.

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.

East Hill Retreat/15 minutes to Pensacola Beach
Centrally located in historic East Hill, this serene, cozy, 750 sq foot garage apartment is a quick 15 minute drive to Pensacola Beach. It features an open floor plan with a private entrance and marked guest parking. Downtown Pensacola is a short five minute drive with many local restaurants and night life. Our apartment features a keyless and private entry. Whether you are a business traveler, solo adventurist or just looking to relax, this East Hill Retreat is ideal.

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!

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

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.
Popular amenities for Pensacola guesthouses
Family-Friendly guesthouses

*New* Vacation Rental in East Hill

Charming Guesthouse @ Live Oaks on the Bayou

Adorable private studio style guesthouse!

Sun-kissed Getaway by the Pensacola Bay

Relaxing Retreat of East Hill

Gulf Breeze Bungalow

La Casita: studio near Downtown and NAS

Heart of Navarre Tiny House Guest Cottage
Guesthouses with a patio

Sonoran Mermaid’s Guest Suite

The Dragonfly House -

Siesta Cottage on the Blackwater

Willock's Rest

Charming Bayou Bungalow near downtown Milton!

Cozy 1 bedroom East Hill Garage Apartment

Quaint Tiny Home by the Bay (Mini Cottage)

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

Lilah’s Pensacola House-Downtown Apartment

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

Navy Point Pensacola Studio

Pause, go refreshed! Gulf Breeze

Cozy in-law unit fully updated!

Pool:Relaxing Summer Cottage - Gulf Breeze

Adorable cottage, hidden in downtown Pensacola!

North Hill Guesthouse
When is the best time to visit Pensacola?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $144 NZD | $144 NZD | $155 NZD | $155 NZD | $165 NZD | $184 NZD | $189 NZD | $161 NZD | $155 NZD | $144 NZD | $146 NZD | $146 NZD |
| 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 |
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