Holiday rentals in Pensacola
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Top-rated holiday rentals in Pensacola
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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.
Large Mid-Century Home w/Bay View & Ancient Trees
Large nicely furnished 4/4 home located high on a hill overlooking Escambia Bay in Pensacola. This unique home features a large yard & relaxing views of the bay & towering trees, interesting artwork, 2 huge decks, 2 balconies, 70" big screen 4K TV, large open living & huge master suite. Great location short drive from beaches parks & trails. 10 mins from historical downtown, bars and restaurants. 10 mins to Pensacola Airport 25 mins to Pensacola Beach 28 mins to NAS 1 hour to Fort Walton/Destin.
Downtown "SURF SHACK"! Outdoor Shower + Hammock!
Welcome to good vibes @ 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
Pensacola Lighthouse Retreat
The Pensacola Lighthouse Retreat is our second Airbnb in Pensacola. We enjoyed hosting so much that we bought a 1927 Tudor cottage in the East Hill area of Pensacola, renovated and decorated it with lighthouses from around the US featuring the Pensacola Lighthouse. The cottage is 1000 square feet with a modern floor plan in the living space with enough room for larger families or two families. Two bedrooms, one bath, and lots of outdoor space, including a shower will accommodate larger groups.
The Lantana Leisure - A Lavish Central Vibe!
Welcome to the Lantana Leisure! This modern duplex embraces a bohemian feel which creates a welcoming space of relaxation and bright engagement. Slow down and decompress in a woven hammock. Laugh with friends and family as you gather around the warm fire or relish the moments of a family cook out. However you choose to spend your time, embrace the uniqueness of this space that had the experience in mind. There are 2 cameras on the exterior of the property that actively record audio and visual.
Walk To Downtown, Fenced Yard, Games, Fire Pit
Welcome to Cooper's Cottage a beautifully renovated 1933 home in the Garden District of Pensacola less than one mile from downtowns historic Seville Square and Palafox St. where you will enjoy bars, restaurants , shopping, art galleries and more. Just 15 min to Pensacola beach and close to NAS home of the Blue Angels. Relax in our fully fenced, pet friendly back yard with gas grill, outdoor dining, lounge seating with fire pit. There are 2 bikes, outdoor games and more. Smart TVs in each room
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!
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
🌟Luxurious new build minutes from beach+downtown
Our tiny house was custom built in 2022 and is located in beautiful East Hill. Our place is centrally located just minutes from PNS airport, downtown restaurants and bars, and Pensacola Beach! It is also just a short walk to Bayou Texar and Bayview park. The tiny house is a completely private space with driveway parking for 2 cars and your own patio area! Enjoy beautiful views of the Bayou from the dining room table or the patio area. We'll do anything we can to make your stay great!
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.
Minutes from the Beach! A-Frame at The Point
Unwind at this modern home just minutes from the beach. This home is located on Innerarity Point, a locals-only spot with restaurants and grocery stores within a short drive. This home was lovingly built with exposed beams for a luxurious yet charming feel. Take an early morning stroll to Innerarity Point Park with beautiful oaks for shade, walking paths, playground equipment and pier. Enjoy the nightlife at FloraBama or The Jellyfish. A short drive to historic downtown Pensacola.
✨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!
Popular amenities for Pensacola holiday rentals
Stay near Pensacola's top sights
Other great holiday rentals in Pensacola
Gadsden Hideaway: Historic Downtown Luxury in East
Cozy Bayou Bungalow - just steps from the water
Beautiful, Peaceful East Hill Guesthouse
La Petite Pineapple~Walkable to downtown Pensacola
Luxurious East Hill Guest House w/ King Bed!
Historic SR Moreno House • Walk to Downtown
The Kelley House | Suite 1 - 1st Floor
Adorable cottage, hidden in downtown Pensacola!
When is the best time to visit Pensacola?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $127 SGD | $133 SGD | $147 SGD | $146 SGD | $159 SGD | $172 SGD | $177 SGD | $151 SGD | $137 SGD | $135 SGD | $140 SGD | $141 SGD |
| 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 |
Frequently Asked Questions
What are the best places to stay in Pensacola?
Explore Downtown Pensacola for walkable city life, the Pensacola Beach area for waterfront access, or East Hill for a relaxed residential vibe. These neighborhoods are frequently suggested for their dining, cultural sites, and unique atmosphere.
What are the best things to do in Pensacola with kids?
Families often explore the National Naval Aviation Museum for interactive exhibits, spend time at Gulf Islands National Seashore enjoying the beach, or discover city parks with play areas. The area also has mini golf and waterfront activities for kids.
What are some of the best things to do in Pensacola?
Explore white sand beaches at Gulf Islands National Seashore, stroll Downtown, or visit the National Naval Aviation Museum. Historic forts, lively local markets, and beachside trails are often recommended experiences.
How is the weather in Pensacola?
Pensacola has mild winters around 44–65°F (7–18°C) and warm, humid summers that reach 75–92°F (24–33°C), with rainfall spread throughout the year. Lightweight clothing is comfortable for most seasons, and summer brings higher humidity.
What are the best places to visit in Pensacola?
Gulf Islands National Seashore, Historic Pensacola Village, and the National Naval Aviation Museum are frequently suggested. You can also explore Fort Pickens and the lively downtown district for a mix of history, arts, and beaches.
What are some hiking trails in Pensacola?
Explore scenic trails at Gulf Islands National Seashore, Big Lagoon State Park, or Tarkiln Bayou Preserve State Park. Bricker trails in these parks feature coastal views, native plants, and diverse wildlife.
What are some family activities we can do in Pensacola?
Families can enjoy interactive displays at the National Naval Aviation Museum, play at waterfront parks, or spend the day at Gulf Islands National Seashore. Outdoor spaces and playful spots are found throughout Pensacola.
What are some of the best day trip ideas from Pensacola?
You can explore the beaches and nature trails at Gulf Islands National Seashore, visit state parks around the region, or tour local art galleries and historical sites. Barrier islands and unique coastal communities are also accessible nearby.
Are there any pet friendly accommodations available in Pensacola?
Many vacation rentals in Pensacola welcome pets, especially around East Hill, Downtown, and Pensacola Beach. Parks and outdoor spaces make it easy to enjoy time with your pet near the coast.
What are some local tips for visiting Pensacola?
Consider exploring the historic neighborhoods on foot and checking local calendars for festivals or farmers’ markets. Light clothing works well year-round, and sun protection is always helpful near the water.
What is Pensacola known for?
Pensacola is known for its white sand beaches, deep naval aviation history, and vibrant downtown filled with galleries, live music, and regional cuisine. The city’s roots blend Spanish, French, and African American cultural influences.
What are the best hidden gems to explore in Pensacola?
You can wander the trails at Tarkiln Bayou Preserve State Park, explore the murals and alleyways downtown, or visit the coastal marshes around Bay Bluffs Park. Local art spaces and small historic sites often offer a quieter experience.
What are the best foods to try in Pensacola?
Pensacola has Gulf shrimp, oysters, and grouper prepared with regional twists, as well as Creole and Southern-inspired dishes. Local food spots also highlight fresh catch sandwiches, hushpuppies, and house-made desserts.
What should I bring for a trip to Pensacola?
Pack lightweight clothing, a hat, and sun protection for most seasons, plus comfortable shoes for exploring downtown and coastal parks. Consider a light rain jacket during the summer and spring months.
What is the nightlife in Pensacola like?
Downtown Pensacola has live music venues, local pubs, and relaxed cocktail lounges, many with outdoor patios. Around the beach, you’ll find waterfront establishments, sunset spots, and casual late-night eateries.
What are the most popular events or festivals in Pensacola?
Pensacola hosts the Blue Angels air shows in the summer and fall, parades and celebrations around Mardi Gras, and lively seafood and music festivals through the year. The Foo Foo Festival and Great Gulfcoast Arts Festival are also frequently suggested.
Are there family friendly vacation rentals in Pensacola?
You can find family-friendly rentals throughout Pensacola, especially in areas like Downtown, East Hill, and near Pensacola Beach. Many offer features such as equipped kitchens, multiple bedrooms, and easy access to parks or beaches.
When is the best time to visit Pensacola?
Late spring and early fall are often recommended for warm temperatures and fewer crowds. Summer is popular for beaches and events, while winter has mild weather for historic and indoor activities.
Quick stats about holiday rentals in Pensacola
Total holiday rentals
Explore 1,230 holiday rentals in Pensacola
Nightly prices starting at
Pensacola holiday rentals start at $26 SGD per night before taxes and fees
Verified guest reviews
Over 76,130 verified reviews to help you choose
Family-friendly holiday rentals
780 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 460 rentals that welcome pets
Holiday rentals with a pool
130 properties feature pools
Rentals with dedicated workspaces
680 properties have a dedicated workspace
Wifi availability
1,220 of Pensacola holiday rentals include wifi access
Popular amenities for guests
Guests love Self check-in, Pet-friendly and Beachfront across Pensacola rentals
4.8 Average rating
Pensacola stays are highly rated by guests – averaging 4.8 out of 5!
Nearby attractions
Pensacola’s top spots include Palafox Market, Pensacola Museum of Art and Bruce Beach
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- Gulf Shores Public Beach
- Destin Beach
- Crab Island
- Destin Harbor Boardwalk
- OWA Parks & Resort
- Pensacola Beach
- Opal Beach
- Perdido Key Beach
- Navarre Beach Fishing Pier
- Johnson's Beach, Gulf Islands National Seashore
- Gulf State Park
- Waterville USA/Escape House
- Gulf Breeze Zoo
- Adventure Island
- Alabama Point Beach
- Gulfarium Marine Adventure Park
- Henderson Beach State Park
- Flora-Bama Lounge
- The Track - Destin
- The Hangout
- The Boardwalk on Okaloosa Island
- HarborWalk Village
- Alabama Gulf Coast Zoo
- Destiny East