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Jay Holiday Rentals

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Our top choices for Jay holiday rentals

1. ADORABLE COTTAGE ON A FARM

ADORABLE COTTAGE ON A FARM
Milton
10.0 out of 10, Exceptional, (70 reviews)
"It was clean and nicely setup, definitely gave us some beautiful mornings despite rain but enjoyed the stay. Will definitely be back in the future when in the area!"
United States
Tyler F.
The price is NZ$344
includes taxes & fees
30 Aug - 31 Aug
ADORABLE COTTAGE ON A FARM

2. The Cottage at Steve’s Farm in Walnut Hill Fl

The Cottage at Steve’s Farm in Walnut Hill Fl
Walnut Hill
10.0 out of 10, Exceptional, (20 reviews)
The price is NZ$433
includes taxes & fees
30 Aug - 31 Aug
The Cottage at Steve’s Farm in Walnut Hill Fl

3. Charming Tiny Home in Pace Near Downtown and Pensacola Beach, 2 min from Walmart

Charming Tiny Home in Pace Near Downtown and Pensacola Beach, 2 min from Walmart
Pace
10.0 out of 10, Exceptional, (9 reviews)
"Small and simple, very clean and comfortable."
United States
Matt R.
The price is NZ$350
includes taxes & fees
31 Aug - 1 Sept
Charming Tiny Home in Pace Near Downtown and Pensacola Beach, 2 min from Walmart

4. 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, (354 reviews)
"Will be staying again very soon"
United States
India
The price is NZ$185
includes taxes & fees
30 Aug - 31 Aug
stayAPT Suites Pensacola-UWF/West Florida Hospital Area

5. Exotic Farm Stay

Exotic Farm Stay
Milton
9.8 out of 10, Exceptional, (18 reviews)
"Loved our stay! Great "
United States
JuYoung
Exotic Farm Stay

6. Cozy Private Room-Queen&Full Bed, Hot Tub Pool Pets Welcome!

Cozy Private Room-Queen&Full Bed, Hot Tub Pool Pets Welcome!
Milton
10.0 out of 10, Exceptional, (50 reviews)
The price is NZ$262
includes taxes & fees
1 Sept - 2 Sept
Cozy Private Room-Queen&Full Bed, Hot Tub Pool Pets Welcome!

7. Milton's Remodeled Cozy Retreat- 30min to Beaches and 4 min to Blackwater River

Milton's Remodeled Cozy Retreat- 30min to Beaches and 4 min to Blackwater River
Milton
9.6 out of 10, Exceptional, (26 reviews)
"Neighbor was quiet. House was clean and a good size and just as described. "
United States
Wendy A.
The price is NZ$588
includes taxes & fees
30 Aug - 31 Aug
Milton's Remodeled Cozy Retreat- 30min to Beaches and 4 min to Blackwater River

8. Luxury Cabin At Blackwater Getaway, Short Walk Downhill To The River!

Luxury Cabin At Blackwater Getaway, Short Walk Downhill To The River!
Wing
10.0 out of 10, Exceptional, (4 reviews)
"This was our 2nd time staying, cabin was perfect and we had a great trip."
United States
David H.
The price is NZ$365
includes taxes & fees
29 Aug - 30 Aug
Luxury Cabin At Blackwater Getaway, Short Walk Downhill To The River!

9. Perfect 3-bedroom house with AC in serene Milton

Perfect 3-bedroom house with AC in serene Milton
Milton
8.0 out of 10, Very good, (1 review)
"The house is nice, spacious, and quiet. The beds are really firm. One of the toilets was backed up the whole time we were there and couldn’t use it. The kitchen has the bare minimum to cook with. "
United States
Cassie W.
The price is NZ$659
includes taxes & fees
11 Sept - 12 Sept
Perfect 3-bedroom house with AC in serene Milton

10. 30 Minutes to Beaches and Entertainment

30 Minutes to Beaches and Entertainment
Milton
10.0 out of 10, Exceptional, (43 reviews)
"Home was beautiful and the host communicated very well! Would definitely come back again!"
United States
Tia S.
The price is NZ$691
includes taxes & fees
31 Aug - 1 Sept
30 Minutes to Beaches and Entertainment

11. Sowell’s Cozy Cottage

Sowell’s Cozy Cottage
Milton
The price is NZ$739
includes taxes & fees
11 Sept - 12 Sept
Sowell’s Cozy Cottage

12. No cleaning fee! Coastal Boho Townhouse central to beach-river-Whiting Field!

No cleaning fee! Coastal Boho Townhouse central to beach-river-Whiting Field!
Milton
9.2 out of 10, Wonderful, (33 reviews)
"We always love staying at this beautiful house! We’ll be back soon! "
United States
Kami M.
No cleaning fee! Coastal Boho Townhouse central to beach-river-Whiting Field!

13. Sowell Farm's Retreat

Sowell Farm's Retreat
Milton
9.0 out of 10, Wonderful, (2 reviews)
"Property was clean and wonderful. We enjoyed the set up. Not much in kitchen for food prep. Just plates cups and utensils. But the kitchen was very nice and clean. Beds were comfortable."
United States
Ashley G.
The price is NZ$750
includes taxes & fees
30 Aug - 31 Aug
Sowell Farm's Retreat

14. W Milton 15 min to downtown PCola and beaches

W Milton 15 min to downtown PCola and beaches
Milton
9.8 out of 10, Exceptional, (12 reviews)
"Absolutely beautiful home and the host is wonderful as well. "
United States
Don Don B.
The price is NZ$407
includes taxes & fees
29 Aug - 30 Aug
W Milton 15 min to downtown PCola and beaches

15. King Bed|Smoking|Pensacola FL

King Bed|Smoking|Pensacola FL
Northwest Pensacola
10.0 out of 10, Exceptional, (52 reviews)
"The surrounding area is nice, peaceful yet still close enough to attractions."
United States
Anonymous traveller
The price is NZ$121
includes taxes & fees
30 Aug - 31 Aug
King Bed|Smoking|Pensacola FL

16. A-frame Retreat in Pensacola, 10 Mi to Dtwn

A-frame Retreat in Pensacola, 10 Mi to Dtwn
3.0 star property
Northeast Pensacola
A-frame Retreat in Pensacola, 10 Mi to Dtwn

17. Welcome to Our Home - Pace/Pensacola - Pet friendly - Close to beaches!

Welcome to Our Home - Pace/Pensacola - Pet friendly - Close to beaches!
Pace
9.2 out of 10, Wonderful, (15 reviews)
"My stay at this lovely home was outstanding. I had a wonderful time. The location was superb for all of my needs. The hosts are wonderful, thoughtful. Madison and Brandon are a wonderful team. Any question that arose, they addressed, if not immediately, very shortly after."
United States
Catherine S.
The price is NZ$673
includes taxes & fees
14 Sept - 15 Sept
Welcome to Our Home - Pace/Pensacola - Pet friendly - Close to beaches!

18. Very Clean, Spacious and Comfortable Home Near Pensacola

Very Clean, Spacious and Comfortable Home Near Pensacola
Milton
The price is NZ$727
includes taxes & fees
28 Sept - 29 Sept
Very Clean, Spacious and Comfortable Home Near Pensacola

19. Pensacola FL | King Bed

Pensacola FL | King Bed
Northwest Pensacola
10.0 out of 10, Exceptional, (62 reviews)
"Prices were reasonable for good accommodations. I was pleased I chose this spot."
United States
Anonymous traveller
The price is NZ$121
includes taxes & fees
30 Aug - 31 Aug
Pensacola FL | King Bed
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 Jay Hotel Reviews

Find out more about Jay

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 Jay 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 Jay. 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 Jay. Seeing all the best attractions is bound to make you fall in love with Jay. 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 Jay short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Jay?

Yes, there are holiday rentals close to the most popular sights in Jay, 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 Jay has to offer?

"Tree House" on The Creek in Mid Town Pensacola!: This holiday home rental outside of Jay is located on the waterfront, and has a balcony, 1 hot tub and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Jay?

While you're exploring the area, Blackwater River State Forest and Secret Beach are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Adventures Unlimited Outdoor Center and Jefferson Davis Community College.

What’s a holiday rental in Jay like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Jay. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a family trip or a small group gathering.