Holiday homes in Pensacola

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Top-rated holiday homes in Pensacola

Guests agree: These condos are highly rated for location, cleanliness and more.

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Guest favourite

Condo in Mary Esther

4.87 out of 5 average rating, 131 reviews

Waterfront Condo with FREE Kayaks

* Right on the waterfront ! *Free Kayaks ($300-$400 value as the same kayaks rent for $ 100/day /kayak) down the road at the rental place. The place is right in front of the water with amazing views of the Santa Rosa sound and Okaloosa island, the pool is 5 steps away. *Large and airy one bedroom, one living room, kitchen and bath, TV in both rooms. Endless summer days at its best. *Kayaks are free to use. *We are 4 miles to the Gulf beach on Okaloosa Island and 9 miles to Destin Harbor.

14 – 21 Jan

$1,322 AUD total

Guest favourite

Condo in Pensacola Beach

4.97 out of 5 average rating, 131 reviews

The Flamingo Flat @ Villas on the Gulf

🦩Welcome to the Flamingo Flat! PLEASE READ FULL LISTING. This airy, Palm Beach style condo is the perfect place to relax on a quiet stretch of Pensacola Beach. For great shopping, dining and entertainment you can drive ( less than 3 miles West) to the main hub of P’Cola Beach. Trolley service available during summer months. The beautiful Portofino Island Resort is just 1 mile to the East. MUST BE 25 TO RENT. NO CHILDREN UNDER 12. NO PETS. EARLY CHECK IN MAY BE AVAILABLE FOR AN ADDITIONAL $50.

14 – 21 Dec

$1,919 AUD total

Superhost

Condo in Orange Beach

4.87 out of 5 average rating, 182 reviews

Phoenix 3 3052-BEACHFRONT, NEWLY REMODELED!

WELCOME TO PARADISE! Located in the center of Orange Beach! A 5th floor BEACHFRONT unit in Phoenix III with a million dollar view of the beach. Decorated beautifully with beach decor and furnishings. Sleeps 5. One bedroom condos are only allowed one parking space. So only one pass at front desk. Wolf Bay restaurant , Doc's Seafood, Live Bait and Ruby Slipper are within walking distance. a zoo, shopping and Owa park near by at Foley. 65+5 star reviews with VRBO, started AIRBNB 8/24/18

18 – 25 Dec

$1,688 AUD total

Guest favourite

Condo in Orange Beach

4.91 out of 5 average rating, 274 reviews

PHX 3143 On Beach, Pools and Spas

NOTE>>One Elevator out 11.2023 thru 5.2024. BEACH REFURB PROJECT IS COMPLETE! You’ll love this GULF FACING NEST for your beach stay. 1BR/1BA, King Bed, Queen sofa sleeper, Spa bath, slip covered furniture, 55" Samsung TV with FREE cable, & FREE internet. Amenities include: outdoor and indoor pool, hot tubs, sauna, racquetball and tennis court, shuffle board, fitness center, and arcade. Across from Live Bait - Bar& Live entertainment, Ruby Slipper best brunch place. Parking/ stay is $55.

9 – 16 Dec

$1,895 AUD total

Guest favourite

Condo in Pensacola

4.98 out of 5 average rating, 117 reviews

This is the one! Perfect Getaway near the beach.

Welcome to a place you will want to return to time and again. Fresh renovations, all the amenities! Steps away from a Tiki bar and huge outdoor pool/hot tub! Live music almost nightly! Parking right out front! Johnson and Orange Beach are minutes away. Our goal is to make sure you have the best possible time! You deserve a break. The couch pulls out to a queen bed. Enjoy full kitchen, large shower, fitness center, indoor and outdoor pool and if something feels like it’s missing, let us know!

2 – 9 Apr

$2,611 AUD total

Guest favourite

Condo in Pensacola

4.99 out of 5 average rating, 116 reviews

MELODY OF THE SEA - ON THE BEACH- INCREDIBLE VIEWS

WHAT A VIEW! DIRECTLY ON THE BEACH...GULF SIDE!!! No roads to cross. Stunning panoramic sunset views! Guests love the option of an indoor heated pool and outdoor pool and hot tub overlooking the ocean. A contemporary electric fireplace in the living room & bedroom is perfect for those cozy mild winters for your stay on the beach. Enjoy a king size bed in the master... nautical bunkbeds with port holes and queen sleeper sofa in the main living areas. Reserve Your Time Away Today!

23 – 30 Mar

$2,373 AUD total

Guest favourite

Condo in Pensacola

4.96 out of 5 average rating, 148 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!

27 Sept – 4 Oct

$1,098 AUD total

Guest favourite

Condo in Pensacola

4.95 out of 5 average rating, 172 reviews

Updated Coastal Chic Villa @ Purple Parrot Resort

Relax and enjoy your stay in this newly renovated 1BR/1BH, decorated with a bright color scheme and located in an island paradise. The Purple Parrot is a gated vacation resort that embodies the care-free lifestyle of the islands. The resort is just minutes away from the beaches, marinas and restaurants that make this barrier island a must visit! Our unit is just a few steps from the giant outdoor pool, complete with a grotto waterfall and an island hot tub.

28 Mar – 4 Apr

$1,822 AUD total

Guest favourite

Condo in Gulf Breeze

4.88 out of 5 average rating, 128 reviews

Beachy-N-B Getaway | close to Pensacola Beach

Enjoy a cozy getaway in a private 2nd floor apartment 10 minutes from Pensacola beach. Light, airy, beach-themed decor gives you the feeling of being on island time. Fully stocked kitchen with quartz countertops provide an at-home experience while away on vacation! Private bedroom with queen sized bed, and a full size pull out couch. Close to shopping, dining, and more! We are a pet-free home. Enjoy a quiet vacation at our beachy-n-b :)

15 – 22 July

$1,563 AUD total

Guest favourite

Condo in Pensacola Beach

4.93 out of 5 average rating, 368 reviews

Bay View Condo on Pensacola Beach Great Location!

Lovely 1 bed/1 bath, water view condo located on Little Sabine Bay in Pensacola Beach, FL! Relax on the patio as you look out at the tranquil water with the salty breeze blowing in your hair. The white sandy beaches of the Gulf of Mexico are right across the street, the nearest public access less than a 5 minute walk away! You can also easily walk/drive to the bustling boardwalk with shopping and plenty of great restaurants.

5 – 12 Sept

$2,311 AUD total

Guest favourite

Condo in Pensacola

4.86 out of 5 average rating, 164 reviews

Island Resort Cottage in Perdido Key

My unit is in The Purple Parrot. There is a huge outdoor pool with an island hot tub. There is also an indoor pool, hot tub, and sauna. It is about half a mile to Johnson Beach National Seashore. my unit has its own washer and dryer. My unit is on the second floor and there is no elevator. Gorgeous beaches, fabulous restaurants, two golf courses, and grocery stores are all less then one mile away.

10 – 17 Mar

$1,723 AUD total

Guest favourite

Condo in Pensacola

4.96 out of 5 average rating, 103 reviews

Perdido Skye 34 luxury beach vacation rental

Perdido Skye condo is located directly on the beach with breathtaking views from your balcony of the emerald green ocean, white sandy beach as well as this 4th floor unit overlooks the pool. Condo was extensively renovated throughout. Condo is decorated with bright beach decor and colors.

8 – 15 Dec

$1,947 AUD total