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Jay Vacation Rentals

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Our top choices for Jay vacation rentals

1. ADORABLE COTTAGE ON A FARM

ADORABLE COTTAGE ON A FARM
Milton
10.0 out of 10, Exceptional, (75 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 CA $139
CA $277 total
includes taxes & fees
Nov 8 - Nov 9
ADORABLE COTTAGE ON A FARM

2. 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, (419 reviews)
"Very convenient and comfortable stay in Pensacola."
United States
Blaise
The price is CA $167
CA $188 total
includes taxes & fees
Nov 8 - Nov 9
stayAPT Suites Pensacola-UWF/West Florida Hospital Area

3. 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, (55 reviews)
"Perfect, convenient pet friendly stay"
United States
Melisa D.
The price is CA $158
CA $265 total
includes taxes & fees
Nov 8 - Nov 9
Cozy Private Room-Queen&Full Bed, Hot Tub Pool Pets Welcome!

4. 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, (21 reviews)
"Great place to stay looking forward to booking again on our next trip."
United States
David B.
The price is CA $182
CA $346 total
includes taxes & fees
Nov 8 - Nov 9
The Cottage at Steve’s Farm in Walnut Hill Fl

5. 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, (12 reviews)
"Very well kept and cozy. Would definitely stay again if we are in the area. Thanks for sharing your tiny house with us."
United States
Kelly D.
The price is CA $131
CA $259 total
includes taxes & fees
Nov 8 - Nov 9
Charming Tiny Home in Pace Near Downtown and Pensacola Beach, 2 min from Walmart

6. 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, (28 reviews)
"Great place to land while visiting the area! Comfy beds, very nicely equipped. Thanks so much for having us!"
United States
Rhonda F.
The price is CA $214
CA $512 total
includes taxes & fees
Nov 8 - Nov 9
Milton's Remodeled Cozy Retreat- 30min to Beaches and 4 min to Blackwater River

7. Private Studio Oasis

Private Studio Oasis
North Northwest Pensacola
10.0 out of 10, Exceptional, (5 reviews)
"We loved the room. It was quiet and private. We enjoyed it."
United States
Heather P.
The price is CA $123
CA $227 total
includes taxes & fees
Nov 8 - Nov 9
Private Studio Oasis

8. 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 CA $360
CA $604 total
includes taxes & fees
Nov 10 - Nov 11
Sowell Farm's Retreat

9. Serene Studio Near Downtown Milton & Water!

Serene Studio Near Downtown Milton & Water!
Milton
9.4 out of 10, Exceptional, (6 reviews)
"The owners were super friendly, the cottage was super cute and clean, they were super fast with responses to any questions I had and it was just over all a great stay!!"
United States
Diana D.
The price is CA $101
CA $249 total
includes taxes & fees
Nov 8 - Nov 9
Serene Studio Near Downtown Milton & Water!

10. 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 CA $223
CA $523 total
includes taxes & fees
Nov 8 - Nov 9
Perfect 3-bedroom house with AC in serene Milton

11. Sowell’s Cozy Cottage

Sowell’s Cozy Cottage
Milton
The price is CA $353
CA $595 total
includes taxes & fees
Nov 15 - Nov 16
Sowell’s Cozy Cottage

12. Quiet Milton Retreat Close to Downtown & Water!

Quiet Milton Retreat Close to Downtown & Water!
Milton
10.0 out of 10, Exceptional, (2 reviews)
"From the Host, to the property, to the stay; All exception. Great communication with the Host. Property is great, off the busy path, in a quiet neighborhood. Will definitely stay again. Thank you!"
United States
Jason W.
The price is CA $125
CA $405 total
includes taxes & fees
Nov 8 - Nov 9
Quiet Milton Retreat Close to Downtown & Water!

13. 30 Minutes to Beaches and Entertainment

30 Minutes to Beaches and Entertainment
Milton
10.0 out of 10, Exceptional, (43 reviews)
"Excellent property, everything you could ask for and nice little extras, near to shops very clean"
United States
Julie B.
The price is CA $223
CA $558 total
includes taxes & fees
Nov 15 - Nov 16
30 Minutes to Beaches and Entertainment

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

Luxury Cabin At Blackwater Getaway, Short Walk Downhill To The River!
Wing
9.2 out of 10, Wonderful, (5 reviews)
"This was our 2nd time staying, cabin was perfect and we had a great trip."
United States
David H.
The price is CA $214
CA $294 total
includes taxes & fees
Nov 9 - Nov 10
Luxury Cabin At Blackwater Getaway, Short Walk Downhill To The River!

15. Spacious 3BR Pace Home — King Bed + Screened Porch — Pet Friendly

Spacious 3BR Pace Home — King Bed + Screened Porch — Pet Friendly
Pace
9.2 out of 10, Wonderful, (15 reviews)
"Quick communication on short notice. Good backyard for our dogs, Super close to grocery store. Quick overnight stay for us while traveling and house worked out great. Would stay again for longer if opportunity presents."
United States
Bradford B.
The price is CA $154
CA $482 total
includes taxes & fees
Dec 6 - Dec 7
Spacious 3BR Pace Home — King Bed + Screened Porch — Pet Friendly

16. 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, (17 reviews)
"Lovely home and clean and our stay was great!"
United States
Dina S.
The price is CA $189
CA $330 total
includes taxes & fees
Nov 9 - Nov 10
W Milton 15 min to downtown PCola and beaches

17. Three bedroom Home in Milton Near NAS

Three bedroom Home in Milton Near NAS
Milton
4.0 out of 10, (1 review)
The price is CA $265
CA $724 total
includes taxes & fees
Nov 17 - Nov 18
Three bedroom Home in Milton Near NAS

18. Stocked Fishing Pond On-site: Quiet Pensacola Home

Stocked Fishing Pond On-site: Quiet Pensacola Home
3.0 star property
Pensacola
The price is CA $171
CA $620 total
includes taxes & fees
Dec 8 - Dec 9
Stocked Fishing Pond On-site: Quiet Pensacola Home

19. Pensacola FL | 2 Full Bed

Pensacola FL | 2 Full Bed
Northwest Pensacola
10.0 out of 10, Exceptional, (65 reviews)
"Friendly staff and good amenities kept us smiling."
United States
Anonymous traveller
The price is CA $85
CA $117 total
includes taxes & fees
Dec 2 - Dec 3
Pensacola FL | 2 Full Bed

20. Luxury Executive Home • Perfect for Groups

Luxury Executive Home • Perfect for Groups
Pace
9.8 out of 10, Exceptional, (16 reviews)
"How was super clean and we had enough room to spread out and have our own space after working 12 hour night shifts."
United States
George M.
The price is CA $421
CA $928 total
includes taxes & fees
Nov 30 - Dec 1
Luxury Executive Home • Perfect for Groups
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Jay?

Yes, we offer vacation rentals close to the most popular sights in Jay, or you can choose a more remote option if you're looking for relaxation.

What are some of the best vacation home rentals that Jay has to offer?

W Milton 15 min to downtown PCola and beaches: This vacation home near Jay offers a garden, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of books.

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 larger area, you’ll find Adventures Unlimited Outdoor Center and Country Club of Brewton.

What’s a vacation rental in Jay like?

Vacation rentals are privately owned properties you can book for short or long periods in Jay. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for a small group gathering.