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Oriole Beach Holiday Rentals

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Our top choices for Oriole Beach holiday rentals

1. Pensacola Backyard Oasis January 2026 Pool Renovation

Pensacola Backyard Oasis January 2026 Pool Renovation
Gulf Breeze
9.8 out of 10, Exceptional, (6 reviews)
"I enjoy staying at this amazing place !! Highly recommend"
United States
Cristian A.
The price is NZ$911
includes taxes & fees
8 Sept - 9 Sept
Pensacola Backyard Oasis January 2026 Pool Renovation

2. Blue Coral Bay | Boat Dock | Waterfront | My Beach Getaways

Blue Coral Bay | Boat Dock | Waterfront | My Beach Getaways
Gulf Breeze
8.0 out of 10, Very good, (1 review)
"Overall, it was a good stay. This place could be excellent with a little tweaking. The property is super cute. The house was very clean and looked exactly as the pictures describe. The finishes in the house are nice and give it an elevated feel. We especially enjoyed the hot tub at night to wind down before bed and the screened in porches! We ate every meal on the patio. My husband and sons fished in the canal behind the house. There is a playground very close-by for the littles. Communication...
United States
Bethany C.
The price is NZ$1,344
includes taxes & fees
7 Sept - 8 Sept
Blue Coral Bay | Boat Dock | Waterfront | My Beach Getaways

3. Gorgeous coastal home with plenty of space and easy beach access

Gorgeous coastal home with plenty of space and easy beach access
Pensacola Beach
9.6 out of 10, Exceptional, (29 reviews)
"It was amazing! Perfect location quiet and very clean!"
United States
chris
Gorgeous coastal home with plenty of space and easy beach access

4. Regency Towers 406W | Pensacola Beachfront | Pool | My Beach Getaways

Regency Towers 406W | Pensacola Beachfront | Pool | My Beach Getaways
Pensacola Beach
8.8 out of 10, Excellent, (17 reviews)
"It was a wonderful room with a great location! It is older and in need of some TLC but it was a lovely stay. "
United States
Amelia N.
The price is NZ$940
includes taxes & fees
12 Sept - 13 Sept
Regency Towers 406W | Pensacola Beachfront | Pool | My Beach Getaways

5. Pensacola Beach Home: 1 Block to Beach Access

Pensacola Beach Home: 1 Block to Beach Access
3.0 star property
Toilla Segunda
10.0 out of 10, Exceptional, (3 reviews)
The price is NZ$654
includes taxes & fees
21 Sept - 22 Sept
Pensacola Beach Home: 1 Block to Beach Access

6. Cozy Coastal Gulf Condo with Shared Pool and Beach Access

Cozy Coastal Gulf Condo with Shared Pool and Beach Access
Pensacola Beach
9.2 out of 10, Wonderful, (7 reviews)
"Great location! Cozy spot with a great pool and the beach is right there. Great restaurants very close by. Can’t ask for more! Would definitely stay again!"
United States
Terry T.
The price is NZ$534
includes taxes & fees
13 Sept - 14 Sept
Cozy Coastal Gulf Condo with Shared Pool and Beach Access

7. Dog-friendly townhome with private deck, charming interior, washer&dryer & AC

Dog-friendly townhome with private deck, charming interior, washer&dryer & AC
Gulf Breeze
9.6 out of 10, Exceptional, (25 reviews)
"Great property, great location. Had everything we needed."
United States
Anonymous traveller
Dog-friendly townhome with private deck, charming interior, washer&dryer & AC

8. Remodeled beachside townhome w/ Gulf views and pools - snowbirds welcome

Remodeled beachside townhome w/ Gulf views and pools - snowbirds welcome
Pensacola Beach
9.0 out of 10, Wonderful, (66 reviews)
"The property was clean and everything was super easy with the check in/checkout process. Very close to the beach and good restaurants. "
United States
Erin M.
Remodeled beachside townhome w/ Gulf views and pools - snowbirds welcome

9. Regency Towers 102W | Oceanfront | Dog Friendly | Pensacola Beach | My Beach Getaways

Regency Towers 102W | Oceanfront | Dog Friendly | Pensacola Beach | My Beach Getaways
Pensacola Beach
9.2 out of 10, Wonderful, (28 reviews)
"My family and I stayed for several days and honestly couldn’t have asked for a more pleasant and convenient stay. We’ve traveled a lot, including many beach stays via VRBO, and this was the first time my wife and I agreed that we’d like to return to the exact place again in the future."
United States
Wes B.
The price is NZ$1,140
includes taxes & fees
7 Sept - 8 Sept
Regency Towers 102W | Oceanfront | Dog Friendly | Pensacola Beach | My Beach Getaways

10. 1 Portofino 1005

1 Portofino 1005
3.5 star property
Pensacola Beach
7.4 out of 10, Good, (8 reviews)
"Expensive for what the place offers. WiFi doesn’t exist on this particular unit, we have to use public WiFi, when I called the front desk, I was advised to reach out to either Expedia or hosteeva since they’re the once I booked with, what a disappointment. Positive feedback, it’s complete with kitchen utensils, pots & pans, clean unit. "
United States
Dale
The price is NZ$1,640
includes taxes & fees
2 Oct - 3 Oct
1 Portofino 1005

11. Lovely Oasis with private swimming pool 3,6,8 f deep

Lovely Oasis with private swimming pool 3,6,8 f deep
Gulf Breeze
9.0 out of 10, Wonderful, (26 reviews)
"Great property! We enjoyed our stay!"
United States
Tina G.
The price is NZ$905
includes taxes & fees
1 Oct - 2 Oct
Lovely Oasis with private swimming pool 3,6,8 f deep

12. Enjoy the white sands of the Pan Handle of Fl, on the quiet side of Pensacola.

Enjoy the white sands of the Pan Handle of Fl, on the quiet side of Pensacola.
Pensacola Beach
9.4 out of 10, Exceptional, (178 reviews)
"We had an excellent stay! The condo had everything we needed and the location is perfect. It’s a short walk or drive to both Pensacola beach Gulf side and Pensacola Bay. It’s also a quick drive to Gulf Islands National Seashore. Would absolutely stay here again. "
United States
Stacey L.
The price is NZ$599
includes taxes & fees
8 Sept - 9 Sept
Enjoy the white sands of the Pan Handle of Fl, on the quiet side of Pensacola.

13. stayAPT Suites Pensacola-UWF/West Florida Hospital Area

stayAPT Suites Pensacola-UWF/West Florida Hospital Area
4.0 star property
Pensacola
9.0 out of 10, Wonderful, (365 reviews)
"Will be staying again very soon"
United States
India
The price is NZ$156
includes taxes & fees
7 Sept - 8 Sept
stayAPT Suites Pensacola-UWF/West Florida Hospital Area

14. Peaceful 3-2 Home w/ Pool, 4min to beach, RV P-king, BBQ, Firepit, Fast Internet

Peaceful 3-2 Home w/ Pool, 4min to beach, RV P-king, BBQ, Firepit, Fast Internet
Gulf Breeze
9.2 out of 10, Wonderful, (30 reviews)
"Room and staff was great. Only issues we ran into was some of the guest was being rude to my kids at the swimming pool area"
United States
Hubie
The price is NZ$748
includes taxes & fees
9 Sept - 10 Sept
Peaceful 3-2 Home w/ Pool, 4min to beach, RV P-king, BBQ, Firepit, Fast Internet

15. Cozy condo steps from the Gulf

Cozy condo steps from the Gulf
Pensacola Beach
9.8 out of 10, Exceptional, (154 reviews)
"Nice stay at a calmer place and beach away from the crowds. "
United States
Amy R.
The price is NZ$864
includes taxes & fees
2 Oct - 3 Oct
Cozy condo steps from the Gulf

16. Sound side condo with pool, central AC, & washer/dryer - snowbirds welcome

Sound side condo with pool, central AC, & washer/dryer - snowbirds welcome
Pensacola Beach
9.4 out of 10, Exceptional, (80 reviews)
"The place was great and very well decorated! It was super clean as well! We would stay again…. "
United States
kelene e.
Sound side condo with pool, central AC, & washer/dryer - snowbirds welcome

17. Pineapple Paradise | Bayou Texar Water View Rental Near Downtown Pensacola

Pineapple Paradise | Bayou Texar Water View Rental Near Downtown Pensacola
Southeast Pensacola
9.2 out of 10, Wonderful, (38 reviews)
"Our host was wonderful! She was amazing to work with and helped us with any small issues we had! Would definitely stay here again anytime!"
United States
Pen S.
The price is NZ$274
includes taxes & fees
7 Sept - 8 Sept
Pineapple Paradise | Bayou Texar Water View Rental Near Downtown Pensacola

18. Pensacola FL | 2 Full Bed

Pensacola FL | 2 Full Bed
Northwest Pensacola
10.0 out of 10, Exceptional, (63 reviews)
"Friendly staff and good amenities kept us smiling."
United States
Anonymous traveller
The price is NZ$143
includes taxes & fees
29 Sept - 30 Sept
Pensacola FL | 2 Full Bed

19. Gulf front @ Emerald Ise, Pensacola Beach~HEATED pool!

Gulf front @ Emerald Ise, Pensacola Beach~HEATED pool!
Pensacola Beach
9.6 out of 10, Exceptional, (48 reviews)
"We only stayed w days but the condo was perfect. Bed was very comfortable. Views were spectacular!!"
United States
Sheila C.
The price is NZ$1,119
includes taxes & fees
8 Sept - 9 Sept
Gulf front @ Emerald Ise, Pensacola Beach~HEATED pool!

20. 5 Portofino 1106

5 Portofino 1106
4.0 star property
Pensacola Beach
8.4 out of 10, Very good, (7 reviews)
"The resort amenities and view were great. The only negative was the mattress in the master bedroom was quite hard. The kitchen could have had more dishes and a wine bottle opener and a lamp in the living room. Other than that we had a great time! The pools were fabulous!"
United States
Julie
The price is NZ$1,687
includes taxes & fees
16 Sept - 17 Sept
5 Portofino 1106
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Oriole Beach Hotel Reviews

Find out more about Oriole Beach

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Oriole Beach holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Oriole Beach. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Oriole Beach. Seeing all the best attractions is bound to make you fall in love with Oriole Beach. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Oriole Beach short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Oriole Beach?

Yes, there are holiday rentals close to the most popular sights in Oriole Beach, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Oriole Beach has to offer?

Paradise On The Beach With Crystal Clear Water & Gulf Front Complex--2 BR Suites: This holiday home rental outside of Oriole Beach is located on the beach, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Oriole Beach?

With 12 Expedia holiday rentals, you're guaranteed to find just the right place for your Oriole Beach stay.

What can I see and do in Oriole Beach?

Explore the area and family-friendly sights such as Gulf Breeze Zoo, or get out into nature at a spot like Santa Rosa Sound. In the wider area, you’ll find popular places such as Navarre Beach and Pensacola Naval Air Station.

What are holiday rentals like in Oriole Beach?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oriole Beach. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for a family trip.