Holiday houses in Pensacola

4.99 out of 5 average rating, 216 reviews

Cottage in Pensacola

Coco Ro Downtown! 2 BR w/Hammock + Outdoor Shower!

Welcome to good vibes @ Coco Ro "Surf Shack" – your cozy, beachy retreat in downtown Pensacola! This charming 2 bedroom cottage offers laid-back comfort - just a stone's throw from the heart of downtown. You'll be 1 mile from trendy Palafox St, 12 blocks from the bay & a short drive to stunning beaches! Your coastal escape awaits! Enjoy: ・Outdoor shower! ・King size hammock ・Smart TV ・Washer/Dryer ・Fenced yard ・Free onsite driveway parking *Tap the ❤ in the top right to save to your wishlist.

5 out of 5 average rating, 140 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!

4.99 out of 5 average rating, 147 reviews

Condo in Pensacola

Cozy Bayou Bungalow - just steps from the water

Are you looking for a comfortable, clean place to relax in an established and desirable area of town while visiting beautiful Pensacola? Then look no further! The Bayou Bungalow is located just steps from the water along Bayou Texar and only minutes from the downtown entertainment district and our pristine beaches. Enjoy a morning walk along the waters edge under the oak trees, check out the neighborhood beach or let this location serve as your hub while enjoying all Pensacola has to offer!

4.99 out of 5 average rating, 176 reviews

Guesthouse in East Hill

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

Apartment in Downtown Pensacola

4.99 out of 5 average rating, 123 reviews

Luxe Downtown Studio Apartment

Curated style within walking distance to bars and restaurants downtown, and only a 15 minute drive to Pensacola Beach! This apartment features a a fully equipped kitchen, separate private entrance, fast high speed internet, in unit washer and dryer, a heated bathroom floor, and commercially rated sound proof insulation. The apartment boasts 11ft ceilings, 100%cotton luxury bedding and pillows, rain shower, and a private dedicated parking space just steps from the entrance.

Home in Downtown Pensacola

4.98 out of 5 average rating, 197 reviews

✨Olivia Downtown✨ Industrial chic/ Sleeps 4

Welcome to Olivia Downtown, your new home away from home! This gem is an 860 sq ft one bedroom one bathroom home equipped with a full kitchen and laundry room. Whether you’re working from the designated office space, snuggled up on the comfiest couch watching some Netflix or cozied up around the fire pit on a chilly night Olivia will make you never want to leave! However, if you do decide to venture out we are minutes away from Pensacola’s best of the best!

4.97 out of 5 average rating, 155 reviews

Guest suite in Pensacola

Tiny Home Pool View 25 Mins to Beacha

Welcome to our cozy tiny home located in my secured backyard, where a queen-sized bed promises a peaceful night’s sleep and our well-equipped kitchenette simplifies meal preparation. You will have free parking in the backyard located just steps away from the tiny home. Additionally, you’ll have the opportunity to gather around the outdoor fire pit for cozy evenings under the stars. Inside, unwind with a smart TV and stay connected with complimentary Wi-Fi.

4.96 out of 5 average rating, 180 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.

4.87 out of 5 average rating, 222 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.

Superhost

Tiny home in Pensacola

4.84 out of 5 average rating, 169 reviews

Tiny Cabin in the Heart of Pcola! Free WIFI

Welcome to Aspen at The Oasis! The greenery surrounding this tiny cabin makes it feel like it's in the country yet it's only minutes to downtown, shopping, dining, the mall, and PNS airport. Pensacola beach is only 20 minutes away. Amenities include a full kitchen, large deck, WiFi, Roku TV with Netflix, Washer/Dryer, and Keurig coffee maker. Enjoy a peaceful stay with reasonable cleaning fees and no chore lists!

4.96 out of 5 average rating, 136 reviews

Apartment in Pensacola

Entire studio space is private, clean & relaxing.

This is an attached apartment connected to the garage’s ours house with three exit/entrances. One is the main entry with your specific code. The second door is dead bolted from your side that leads to the garage you see in the picture. The third is dead bolted on your side and gives you access to the back yard. The security and privacy is much like a hotel room. Note we rarely meet or interact with our guests.

4.98 out of 5 average rating, 519 reviews

Cottage in Pensacola

Eclectic Eco- Friendly Luxe City Cottage

New eco chic cottage features high end touches and appliances in a cozy luxe setting. Sitting on the edge of the downtown jurisdiction, you're never too far away from the action on Palafox Street and a quick jaunt over to the beach. Excellent access to Wahoos Stadium, Sanders Beach, The Oar House, Pensacola Yacht Club, Pensacola Country Club, Joe Patti's, and Pensacola's Naval Air Station.

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Cottages

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Popular amenities for Pensacola holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Pensacola

4.91 out of 5 average rating, 43 reviews

Home in Pensacola

Tiny House Retreat~Hot Tub~Cozy

SonyaRating, 5 stars3 days ago

This tiny home is so cute!!! I came on a solo trip and I was just fine. Any time I had a question, the host responded in a matter of minutes. Had a little trouble with the gate but the maid came right out and helped me get in…I learned to just lift the latch and push🤓 I would definitely stay again when I return✌🏾

4.98 out of 5 average rating, 498 reviews

Guest suite in East Hill

Beautiful, Peaceful East Hill Guesthouse

Mary EllenRating, 5 stars2 weeks ago

My boyfriend and I just returned from a 4 day visit at Whitney’s property. It was everything and more. We were hoping for one more day but it was already booked. We enjoyed ourselves so much that we’re returning in October. The neighborhood is extremely safe and while quiet and away from the crowds, there is much to do close by and within walking distance. There’s a barbecue spot , which we weren’t able to make but will next time, a grocery store and several cafes. You need a car to get to the downtown area but it’s within 5 minutes and the beach is about a 15 minute drive. Whitney was very friendly and offered many tips to avoid the heavy surf and their favorite restaurants. She brought out a yoga mat when she saw me stretching on the patio and cut some bay leaf for me from her tree. I could go on. Best place and people ever! Thank you Whitney and Captain Kirk! Looking forward to next time!

4.98 out of 5 average rating, 482 reviews

Cottage in Pensacola

Pensacola Pelican Retreat

KaitlynRating, 5 stars2 weeks ago

What a wonderful stay! From the moment we got to the house- delicious cookies were made for us when we arrived- to the moment we left- very easy checkout. Vicki was responsive to any questions we had. Vicki truly thought of everything. My sister and I were in such a rush to get to Florida- traveling from Tennessee- that we forgot beach towels and a beach bag. It was a lifesaver that those were provided for use at the house. I could not recommend this home enough. I hope to visit again.

4.96 out of 5 average rating, 165 reviews

Guesthouse in East Hill

Adorable carriage house with private entrance

RobbRating, 5 stars1 week ago

perfect little carriage house! great location!

4.98 out of 5 average rating, 347 reviews

Guest suite in Pensacola

Luxe Studio in Gardener's Cottage above the Bay

BrookeRating, 5 stars4 weeks ago

Joan is a very accommodating and warm hostess. She went above and beyond to make our stay amazing. The studio was the perfect size for us and a cozy place to come home to. Great location and quaint neighborhood. Can't say enough good things about this sweet little spot.

4.93 out of 5 average rating, 109 reviews

Studio 54 - a modern beach-town studio

LaceeRating, 5 stars1 week ago

Very calm and peaceful weekend we had. Easy access to the property no noisy neighbors. Cozy living space. Overall would highly recommend to a couple who just wants to get away for a wknd!!

4.99 out of 5 average rating, 155 reviews

Home in Pensacola

East Pensacola Heights Casita

ClaraRating, 5 stars6 days ago

Very communicative host, and helpful. Quiet neighborhood and easily found. Would stay again!