Family-friendly holiday rentals in Downtown Pensacola

Downtown Intimate Light-Filled Getaway

Explore downtown Pensacola and visit the world-class white sand beaches of Pensacola from this cozy carriage house abode located within walking distance from restaurants, shopping, museums, and nightlife. Stone floors, lots of natural light, and high ceilings. Relax on a private balcony while you sip your morning coffee after a restful night's sleep in a comfy bed with high quality linens. HD TV and a wireless JBL speaker to play your tunes. Full kitchen with everything you need to cook a meal. Ample closet space for all your things and a full size washer & dryer.

GOOD VIBES @ COCO RO! Outdoor Shower + XL Hammock!

Welcome to good vibes at Coco Ro Surf Shack - your cozy, beachy retreat in downtown Pensacola! This coastal 2-bedroom cottage offers laid-back comfort just a stone’s throw from the heart of downtown. Only 1 mile to trendy Palafox St, 12 blocks from the bay & a short drive to pristine white sand beaches. Your escape awaits! ・Outdoor shower ・XL hammock ・Smart TV ・Washer/Dryer ・Private yard ・Free driveway parking *Seasonal outdoor shower closed in cold months *Tap the ❤ in the top right to save!

The Kelley House | Suite 3 w/Balcony

Step into the past with a stay in our beautifully restored suite, located in the historic Kelley House, 1 of 4, located on the 2nd floor. This unique property blends the timeless charm of its original architecture with modern comforts and stylish updates, is perfect for those looking to relax and unwind in a space full of character and elegance. Whether you're here for a romantic getaway or a quiet solo retreat, the Kelley House is an unforgettable place to relax, recharge, and experience the c

La Petite Pineapple~Walkable to downtown Pensacola

Welcome to La Petite Pineapple located downtown Pensacola in the historic neighborhood of Old East Hill! Perfectly located 1/2 a mile to Palafox St and 8 miles to beautiful Pensacola Beach (10 minute drive). This luxury tropical retreat offers everything you need for your perfect Pensacola getaway! Owner cleaned and operated, I take great pride in providing my guests with an excellent vacation experience with as much guidance about the area such as things to do/dining options. Ask me questions!

Bear's Bungalow in the Historic Heart of Pensacola

PETS WELCOME $0 deposit!!!! Charming 1920's Historic Cottage with large backyard & outdoor kitchen w/ TV perfect for entertaining and the inner BBQ in you! This centrally located 2/1.5 home in the heart of Olde East Hill is a stones throw from the Civic Center, a 10 minute walk downtown, just over a mile to the Blue Wahoos Stadium, and 8 blocks to Krispy Kreme. Desirable 10' ceilings w/ elevated 16' in the living room, original windows, upgrades throughout. Driveway and ample street parking!

Walk To Eat & Shop, Downtown Tropical Hideaway

Lovely private hideaway, securely located on the 2nd floor of an 1890's Victorian home & only a 15 minute drive to the world's most beautiful beaches. An easy walk to restaurants, bars & museums of downtown Pensacola, named one of "10 Best Streets in America". Tropical art adorns the walls & an antique claw foot tub has treetop views. WiFi, Roku TV, fridge, microwave, toaster oven & coffee maker along with beach gear & bicycles are provided. Check in anytime with the combination lock box.

Upstairs on Palafox - Downtown Pensacola

This large, family-friendly downtown Pensacola loft sits right in the heart of the rich downtown historical district. Over 100 years old (but recently renovated on the inside) this space will bring you back to the time when everything was made of brick and wood. The location could not be more perfect, as you are right downtown but also just 10min away from the beach - expect normal city noises. Large Palafox balcony right on Palafox St; Great for large parties and entertaining/nightlife.

The Wright Place: Your Perfect Beach Escape

Relax in this chic beach-style haven with modern amenities and Pensacola's tropical allure. This 3BR/2.5BA retreat is steps from downtown's vibrant nightlife—lively bars, events at Pensacola Bay Center, and top restaurants—yet minutes from Pensacola Beach's sugar-white sands and emerald waves. Dine al fresco on your patio or sip coffee on the upper deck for ultimate unwind vibes. *Government-issued ID and signed rental agreement required to book and must be submitted post-reservation.

The Gray Lady - A Beautiful Cottage in Pensacola!

The Gray Lady is a luxurious cottage in downtown Pensacola. It combines two pieces of paradise - named after Nantucket and located in Pensacola. This home sleeps 9. Relax in the backyard oasis, equipped with a private hot tub! A park, brewery, and restaurants are all within walking distance. Just a mile from downtown, be sure to checkout the restaurants, shops, and nightlife! Pensacola Beach, NAS, Fort Pickens, the mall and airport are all 15 mins away. We hope you enjoy your stay!!

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.

✨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!

1br/1ba Cozy Cottage - Downtown/Museum of Commerce

An experience you do not want to miss and a location that is close to the action but still tucked away. Less than one block from iconic Seville Square, where you will be centrally located in the heart of downtown Pensacola's historic district and within walking distance to dining, shopping, museums and other attractions. Find yourself enjoying sunsets on the back porch or take a easy 15 minute drive to enjoy the sugar white sands of Pensacola Beach.