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Oriole Beach Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Oriole Beach vacation rentals

Coffee/tea maker, fridge, microwave, oven

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 ￥35,870
￥85,609 total
includes taxes & fees
Aug 19 - Aug 20
Pensacola Backyard Oasis January 2026 Pool Renovation
House (3 Bedrooms) | Interior

2. 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 ￥23,913
￥61,346 total
includes taxes & fees
Aug 20 - Aug 21
Pensacola Beach Home: 1 Block to Beach Access
Indoor pool, outdoor pool

3. Gulf facing, modern 2 bedroom condo! Pools, hot tubs, restaurants & many extras!

Gulf facing, modern 2 bedroom condo! Pools, hot tubs, restaurants & many extras!
Pensacola Beach
10.0 out of 10, Exceptional, (123 reviews)
"Wonderful stay, easy to find, beautiful view!"
United States
ashley r.
The price is ￥24,965
￥92,253 total
includes taxes & fees
Aug 19 - Aug 20
Gulf facing, modern 2 bedroom condo! Pools, hot tubs, restaurants & many extras!
Coffee/tea maker, fridge, microwave, oven

4. 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.
The price is ￥24,039
￥60,323 total
includes taxes & fees
Aug 20 - Aug 21
Remodeled beachside townhome w/ Gulf views and pools - snowbirds welcome
On the beach

5. 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 ￥18,413
￥87,911 total
includes taxes & fees
Aug 28 - Aug 29
Regency Towers 406W | Pensacola Beachfront | Pool | My Beach Getaways
Indoor pool, 3 outdoor pools, open 9:00 AM to 10:00 PM, sun loungers

6. 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 ￥26,623
￥143,837 total
includes taxes & fees
Sep 3 - Sep 4
1 Portofino 1005
Outdoor dining

7. Cozy condo steps from the Gulf

Cozy condo steps from the Gulf
Pensacola Beach
9.8 out of 10, Exceptional, (153 reviews)
"Nice stay at a calmer place and beach away from the crowds. "
United States
Amy R.
The price is ￥35,622
￥77,360 total
includes taxes & fees
Aug 19 - Aug 20
Cozy condo steps from the Gulf
Beach nearby, beach towels

8. 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
9.4 out of 10, Exceptional, (29 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 ￥14,778
￥61,955 total
includes taxes & fees
Aug 19 - Aug 20
Peaceful 3-2 Home w/ Pool, 4min to beach, RV P-king, BBQ, Firepit, Fast Internet
Smart TV, DVD player

9. 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 ￥20,230
￥56,935 total
includes taxes & fees
Aug 19 - Aug 20
Enjoy the white sands of the Pan Handle of Fl, on the quiet side of Pensacola.
Interior

10. Emerald Dolphin 530 | Gym, Pool, Beachfront | Beach Getaways

Emerald Dolphin 530 | Gym, Pool, Beachfront | Beach Getaways
Pensacola Beach
9.4 out of 10, Exceptional, (108 reviews)
"Beautiful property! Soo close to the beach. Pool was amazing! Will definitely be returning for future vacations."
United States
Brittany E.
The price is ￥22,797
￥120,191 total
includes taxes & fees
Aug 23 - Aug 24
Emerald Dolphin 530 | Gym, Pool, Beachfront | Beach Getaways
Lobby

11. 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, (25 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 ￥26,304
￥107,594 total
includes taxes & fees
Sep 7 - Sep 8
Regency Towers 102W | Oceanfront | Dog Friendly | Pensacola Beach | My Beach Getaways
On the beach

12. Waterfront condo in Pensacola Beach with breathtaking balcony views, W/D & AC

Waterfront condo in Pensacola Beach with breathtaking balcony views, W/D & AC
Villa Sabine
9.8 out of 10, Exceptional, (21 reviews)
"Great location and easy to check in & out of. "
United States
Natalie L.
The price is ￥15,583
￥43,867 total
includes taxes & fees
Aug 19 - Aug 20
Waterfront condo in Pensacola Beach with breathtaking balcony views, W/D & AC
Private beach, white sand, sun loungers, kayaking

13. Navarre Beach Camping Resort

Navarre Beach Camping Resort
2.0 star property
Navarre
9.2 out of 10, Wonderful, (443 reviews)
"I liked the security rounds the staff performs; it feels very safe and has everything you need for a long stay—a nearby supermarket, restaurants, and beaches, plus easy access to enjoy it all."
United States
René
The price is ￥12,003
￥21,384 total
includes taxes & fees
Aug 19 - Aug 20
Navarre Beach Camping Resort
Exterior

14. 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, (347 reviews)
"Great place to stay, room very clean. Bed was very comfortable. Loved my stay"
United States
Wanda
The price is ￥15,629
￥17,583 total
includes taxes & fees
Aug 31 - Sep 1
stayAPT Suites Pensacola-UWF/West Florida Hospital Area
Beach nearby

15. 2 Portofino 1602

2 Portofino 1602
4.0 star property
Pensacola Beach
The price is ￥48,783
￥168,767 total
includes taxes & fees
Aug 20 - Aug 21
2 Portofino 1602
Front of property

16. 5 Portofino 1106

5 Portofino 1106
4.0 star property
Pensacola Beach
8.4 out of 10, Very Good, (7 reviews)
"Nice clean unit with view of the bay. The master bed was firm and pillows were too flat. The master didn’t have a lamp and alarm clock but they remedied that by having it delivered. Elevators are lightning fast however noisy and was able to hear them from the unit. Staff was extremely friendly. "
United States
Leslie
The price is ￥30,290
￥147,963 total
includes taxes & fees
Sep 3 - Sep 4
5 Portofino 1106
Smart TV

17. Portofino Penthouse with Breath-Taking Views of the Gulf along with Beach Access

Portofino Penthouse with Breath-Taking Views of the Gulf along with Beach Access
Pensacola Beach
10.0 out of 10, Exceptional, (77 reviews)
"The room and view was fantastic"
United States
Scott S.
The price is ￥40,604
￥80,773 total
includes taxes & fees
Aug 19 - Aug 20
Portofino Penthouse with Breath-Taking Views of the Gulf along with Beach Access
Interior

18. Pineapple Paradise: EPH, Close to Downtown, Beach!

Pineapple Paradise: EPH, Close to Downtown, Beach!
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 ￥6,532
￥25,668 total
includes taxes & fees
Aug 31 - Sep 1
Pineapple Paradise: EPH, Close to Downtown, Beach!
1 bedroom, iron/ironing board, WiFi (free), bed sheets

19. Charming cottage in Pensacola

Charming cottage in Pensacola
Southeast Pensacola
9.8 out of 10, Exceptional, (31 reviews)
"Great spot right off the Bay bridge to get you quickly to Gulf Breeze and Pensacola beach! Also just minutes away from Palafox St. and downtown dining. Highly recommended and one I plan to re-book next year!"
United States
Nate
The price is ￥13,478
￥26,415 total
includes taxes & fees
Aug 23 - Aug 24
Charming cottage in Pensacola
Property grounds

20. Regency Towers 805W | Beachfront | Pool | Pensacola Beach | Blue Angels Show | My Beach Getaways

Regency Towers 805W | Beachfront | Pool | Pensacola Beach | Blue Angels Show | My Beach Getaways
Pensacola Beach
9.6 out of 10, Exceptional, (24 reviews)
"Clean, great views!"
United States
Michael D.
The price is ￥22,797
￥102,815 total
includes taxes & fees
Aug 24 - Aug 25
Regency Towers 805W | Beachfront | Pool | Pensacola Beach | Blue Angels Show | My Beach Getaways
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

Holiday Inn Express Pensacola Beach by IHG

Holiday Inn Express Pensacola Beach by IHG

10/10 Excellent
"Clean and large rooms with a balcony. Great breakfast Right on Pensacola Beach"
James 2-night trip
Posted 1 hour ago
Holiday Inn Express Pensacola Beach by IHG

Find out more about Oriole Beach

Search for holiday rentals in Oriole Beach on Expedia! You can easily find your home rentals, villas, holiday apartments in Oriole Beach using one of the methods below:

  • View our selection of featured holiday rentals in Oriole Beach
  • Use the map to find apartments and other holiday homes in the Oriole Beach neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oriole Beach while they last

Look no further and take a look at our great range of rental properties in Oriole Beach!

Frequently asked questions

Are there vacation rentals in Oriole Beach?

Yes, we have vacation rentals near top sights in Oriole Beach, or you can go with a more remote option if you're looking for a relaxing stay.

What are some of the best vacation rentals in Oriole Beach?

Emerald Shores: Steps from the Gulf, Navarre Beach: This vacation home rental near Oriole Beach is located on the beach and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Oriole Beach?

With 12 Expedia vacation rentals, you're sure 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 larger area, you’ll find popular places like Navarre Beach and Pensacola Naval Air Station.

What are vacation rentals like in Oriole Beach?

Vacation rentals are privately owned accommodations you can reserve for a short or long stay in Oriole Beach. Vacation rentals provide amenities like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from public hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for a family trip or a small group gathering.