Holiday rentals in Pensacola

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Top-rated holiday rentals in Pensacola

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Guest favourite

Guest house in Pensacola

4.95 out of 5 average rating, 145 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...

5–12 Sep

$156 SGD per night

Guest favourite

Guest house in Pensacola

4.9 out of 5 average rating, 273 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.

28 Jan – 4 Feb

$67 SGD per night

Guest favourite

Home in Pensacola

4.95 out of 5 average rating, 112 reviews

Renovated Bungalow near Downtown with King Bed!

Completely renovated historic 1940s shotgun-style home with 2 bedrooms and 2 baths. Located just 1 mile from downtown Pensacola, this home is the perfect balance of original character and modern amenities. Walking distance to the Pensacola Yacht Club, several bars and restaurants, and the world-famous Joe Patti's fishmarket. 15 minute drive to Pensacola Beach. This home includes 2 smart TV, wifi, covered porches, firepit, fenced-in yard, and plenty of additional parking. Well-stocked kitchen.

4–11 Jan

$166 SGD per night

Guest favourite

Guest suite in Pensacola

4.98 out of 5 average rating, 249 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.

14–21 Aug

$129 SGD per night

Guest favourite

Home in Pensacola

4.97 out of 5 average rating, 507 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.

16–23 Oct

$175 SGD per night

Guest favourite

Apartment in Pensacola

4.96 out of 5 average rating, 145 reviews

Comfy Bayou Cottage - 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 Cottage 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!

11–18 Sep

$124 SGD per night

Guest favourite

Guest suite in Gulf Breeze

4.98 out of 5 average rating, 129 reviews

Starlight Ste, near Pensacola Beach & Downtown!

Unique private suite for two, Pensacola Beach is 6-7 min away. Speedy wifi, fenced pergola, patio, grill, & garden. This suite includes a minisplit for air/heat and a tankless water heater. Attached to the main house, separated with a privacy fence, hear the rain drops on the tin roof. Queen memory foam bed, 70" Samsung TV w/Roku, thermal blinds. Must be willing to stay regardless of rain drops on the tin roof, or lightning and torrential rain on a tin roof in a room of glass. Enjoy!

22–29 Sep

$136 SGD per night

Guest favourite

Apartment in Orange Beach

4.91 out of 5 average rating, 289 reviews

Beachfront - PENTHOUSE - Breathtaking Views!

In the heart of Orange Beach is this luxury condo with gorgeous views of the sugar white beaches & emerald waters. From the balcony you can watch the majestic sunrise or marvel at the dolphins playing. When a break from the beach is needed you can enjoy the many amenities onsite. Orange Beach offers activities for the whole family including restaurants & shopping. After a fun day prepare to make dinner in the well appointed kitchen, relax with the cheerful decor & comfortable sitting.

20–27 Jan

$163 SGD per night

Guest favourite

Loft in Pensacola

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.

4–11 Aug

$151 SGD per night

Guest favourite

Guest suite in East Hill

4.98 out of 5 average rating, 404 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.

16–23 Jul

$180 SGD per night

Guest favourite

Cottage in Pensacola

4.98 out of 5 average rating, 408 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.

17–24 Dec

$175 SGD per night

Guest favourite

Cottage in Sanders Beach

4.99 out of 5 average rating, 143 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.

2–9 Oct

$156 SGD per night