Guesthouse vacation rentals in Pensacola Bay

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Top-rated guesthouse rentals in Pensacola Bay

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Guest favorite

Guesthouse in Pensacola

4.95 out of 5 average rating, 146 reviews

1950’s East Hill Carriage House

1950's newly renovated carriage house nestled privately behind our home, in the desirable neighborhood of EastHill. Located close to beautiful Bayview Park with bikes, paddle boards and canoe rentals as well as a short bike ride to local bars, brewery’s and restaurants on 12th Ave. Downtown Pensacola includes shopping, local bars, restaurants even enjoy a show at The Saenger Theater, Vinyl Music Hall or The Handlebar. The breathtaking white sands of Pensacola Beach are just a short drive away...

Sep 5 – 12

R2,122 ZAR per night

Guest favorite

Guesthouse in Pensacola

4.93 out of 5 average rating, 163 reviews

Blue Skies Cottage travel oasis

Blue Skies Cottage, Dog friendly, 6 miles to beautiful beaches, 8 miles to historic downtown with thriving restaurants, minutes from access to I-10 and I-110 and convenient shopping at Cordova or University Malls; nestled in a quiet neighborhood to take friendly walks any time of day. This adorable, newly renovated 1 bedroom, 1 bath with queen sleeper sofa (4 Guests), in-house laundry and full kitchen, in/out dining; would love to serve as your gateway to fun and sunshine. Great for longer stays

Aug 24 – 31

R1,866 ZAR per night

Guest favorite

Guesthouse in Pensacola

4.9 out of 5 average rating, 275 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.

Apr 11 – 18

R1,335 ZAR per night

Guest favorite

Guesthouse in Pensacola

4.9 out of 5 average rating, 177 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.

Jun 15 – 22

R2,334 ZAR per night

Guest favorite

Guesthouse in Pensacola

4.95 out of 5 average rating, 185 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.

Dec 3 – 10

R2,663 ZAR per night

Guest favorite

Guesthouse in Pensacola

5.0 out of 5 average rating, 125 reviews

EAST HILL - Bayview Park Private Carriage House

Maggie's is a professionally decorated carriage house in the historic East Hill neighborhood. We are one block over 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

Aug 30 – Sep 6

R2,625 ZAR per night

Superhost

Guesthouse in Pensacola

4.9 out of 5 average rating, 132 reviews

Vintage Charm in the Historic Heart of Pensacola

Welcome to our charming carriage house apt, where historic charm meets modern comfort! Just a 15-minute drive from Pensacola Beach, our cozy haven offers a perfect blend of relaxation & exploration. Immerse yourself in Pensacola's vibrant culture. Indulge in a delightful Sunday Jazz Brunch at Five Sister Blues Cafe or savor the renowned prime rib at McGuires Irish Pub. For beer enthusiasts, countless breweries await your discovery. Come uncover the allure of Pensacola!

Jan 20 – 27

R1,924 ZAR per night

Guest favorite

Guesthouse in Pensacola

4.91 out of 5 average rating, 601 reviews

Cottage Under the Trees

Quiet, private, secure cottage with kitchen. For sleeping: full bed, twin bed, & sofa (not a sleeper sofa). Will accommodate 3 persons comfortably. Small outside seating area is provided. Few miles from downtown Pensacola. Naval Air Station (NAS), Naval Hospital & Pensacola State College Warrington Campus are within one mile. Fast food is readily available. Walmart is 2 blocks away. Ruby T's, Sonny's BBQ and Waffle House are a few of the nearby restaurants.

Aug 17 – 24

R1,949 ZAR per night

Guest favorite

Guesthouse in Pensacola

4.84 out of 5 average rating, 139 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.

Jul 29 – Aug 5

R2,068 ZAR per night

Guest favorite

Guesthouse in Pensacola

5.0 out of 5 average rating, 154 reviews

Hidden Garden Cottage in Historic North Hill

This is not your generic Airbnb. Regardless of why you are visiting, we would like our guests to have a PENSACOLA EXPERIENCE! From downtown restaurants, breweries, and museums, to sailboat races in the bay, Blue Angels passovers, beautiful white sand beaches, to deep history around every corner, this Cottage inhabits PENSACOLA CHARACTER and is your relaxing and unique jumping off place in Northwest Florida.

Feb 15 – 22

R1,665 ZAR per night

Guest favorite

Guesthouse in Pensacola

4.96 out of 5 average rating, 109 reviews

Adorable carriage house with private entrance

Keep it simple at this peaceful and centrally-located cottage. Private access and parking, near all downtown restaurants, historical sites, and nightlife but far enough away to relax; This unique spot is only miles from Pensacola Beach and the home of the Blue Angels! Newly remodeled and ready to accommodate, we look forward to hosting you in the heart of East Hill!

Sep 8 – 15

R1,721 ZAR per night

Guest favorite

Guesthouse in Pensacola

4.97 out of 5 average rating, 599 reviews

North Hill Guesthouse

This small but cute guesthouse is a five minute drive from downtown Pensacola, the new 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 that affords lots of privacy and quiet in the historical North Hill neighborhood.

Oct 20 – 27

R1,433 ZAR per night