Holiday houses in Pensacola

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Top-rated holiday rentals in Pensacola

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Guest favourite

Guesthouse in Pensacola

4.95 out of 5 average rating, 144 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...

14–21 Sep

$227 NZD per night

Guest favourite

Bungalow in Pensacola

4.97 out of 5 average rating, 696 reviews

•Sanctuary of Light•

A unique space, perfect for 2, accentuating the balance between natural and modern living. A block away from the peaceful bayou, a 5 minute drive from the quaint downtown district, and a 12 minute drive to our beautiful white sand beaches. Our neighborhood stands as one of the safest and most centrally located areas in Pensacola. The Sanctuary is complete with a kitchenette, back patio and plenty of fresh sunlight. Note that we do NOT have a TV as our hope is to offer a peaceful space to unplug!

9–16 Jul

$261 NZD per night

Guest favourite

Guest suite in Pensacola

4.98 out of 5 average rating, 248 reviews

The Intendencia Suite

Private guest suite with private entrance, in the heart of Historic Downtown Pensacola. 5 minute walking distance to Palafox, Ferry, bay, Ballpark, festivals, Breweries, restaurants, art, museums and shopping! Perfectly suited for a low stress weekend getaway. I strive to keep my space clean and affordable because I know how expensive travel can be. Quiet residential street close enough to enjoy the fun but far enough away to feel like home. Not suitable for pets or children under 12.

4–11 Sep

$183 NZD per night

Guest favourite

Home in Pensacola

4.97 out of 5 average rating, 506 reviews

Ms Di's Place. Price Inclusive.

Newly renovated, spotlessly clean 2 bdrm, 1 bath house conveniently located in the heart of East Hill. Carport, bathtub/shower, oven, microwave, frig with icemaker, hardwood floors, Kuerig, WIFI and TV. 5 minutes from downtown Pensacola and Baptist Hospital, 8 minutes from Sacred Heart, 10 minutes from West Florida Hospital, and 15 minutes from beautiful Pensacola Beach.This property belongs to St. Mark UMC and all proceeds are used to fund local missions. Price is inclusive- no added fees.

3–10 Mar

$232 NZD per night

Guest favourite

Loft in East Hill

4.96 out of 5 average rating, 156 reviews

Hernandez Hideout

Cute upstairs studio apartment in the heart of East Hill in Pensacola, FL. It’s a quick 10 minute drive to downtown or across 3 mile bridge to Gulf Breeze and Pensacola Beach. Located off of 12th Avenue, it’s within walking distance to several bars and restaurants. Alga Brewery recently opened just 3 blocks away. Coming soon is Magnolia, a Pensacola restaurant staple as well as Jitterbug, a coffee/pastry shop. East Hill Pizza is also next door, and has some of the best pizza in town.

27 Jul – 3 Aug

$219 NZD per night

Guest favourite

Guest suite in East Hill

4.98 out of 5 average rating, 401 reviews

Beautiful, Peaceful East Hill Guesthouse

Beautiful, quiet, relaxing guesthouse (formerly Whitney’s ironwork studio). Private entrance. In historic East Hill, surrounded by peaceful, towering oak and pecan trees. The French doors provide lots of natural light and an open, airy feeling. Private patio. Quiet, historic neighborhood -- perfect for walks or bike rides. Only 1.2 miles from downtown. Within a few blocks are breakfast/coffee shops, restaurants, Publix Grocery, pubs. Easy 15 minute drive to the beach.

24–31 Jul

$253 NZD per night

Guest favourite

Cottage in Pensacola

4.99 out of 5 average rating, 406 reviews

Pensacola Pelican Retreat

Beautifully remodeled and updated in the summer of 2017, this vintage 1943, one bedroom, one bath, full kitchen cottage home is located in classic East Pensacola Heights. This 570 sq foot home is located in a safe, family oriented, quiet neighborhood. Its palm tree shaded yard with large deck, gas grill, seating and hammock is conveniently located only minutes to interstate 10, Pensacola's Airport, downtown and beautiful, sugar white beaches and turquoise water.

8–15 Dec

$224 NZD per night

Guest favourite

Home in Downtown Pensacola

5.0 out of 5 average rating, 136 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!

30 Aug – 6 Sep

$284 NZD per night

Guest favourite

Cottage in Sanders Beach

4.99 out of 5 average rating, 142 reviews

Beach Vibes on Downtown’s Side

This eco-friendly cottage hosts a peaceful Gulf Coast theme on a quiet street, just blocks away from all the action. Located on the edge of downtown, you're never too far away from all Pensacola has to offer, and a quick jaunt to Pensacola or Perdido Beach. This home offers 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.

16–23 Aug

$219 NZD per night

Guest favourite

Home in Pensacola

4.96 out of 5 average rating, 193 reviews

Casey's Corner

Our home features a large master suite and two guest bedrooms. The master suite includes a desk (for when work is absolutely necessary), and all bedrooms have their own tv with cable. Wireless, high-speed internet is available throughout the home. The kitchen is fully stocked with all the tools you need to cook your own delicious meals and is open to the dining and living areas. A washer and dryer are available in the garage.

28 Sep – 5 Oct

$227 NZD per night

Guest favourite

Apartment in Pensacola

4.98 out of 5 average rating, 282 reviews

Luxurious apartment walk to the Bay-2m to downtown

MUST READ our CONSTRUCTION UPDATE IN OUR DESCRIPTION BELOW BEFORE RESERVING WITH US - 1 br LUXURY apt attached to our home in Historical East Hill, Pensacola's most sought after neighborhood. EXTREMELY well furnished & supplied with more than you would expect from most AirBnb rentals. Walk or bike to many stores, restaurants, breweries, coffee shops & bakeries between .5 to 2 miles away and a 10 min walk to Pensacola Bay !

17–24 Feb

$199 NZD per night

Guest favourite

Guesthouse in Pensacola

5.0 out of 5 average rating, 151 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.

25 Mar – 1 Apr

$183 NZD per night