Pensacola Holiday Rentals

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Holiday Rentals in Pensacola

Lakeside, boat dock and hot tub with this snug small cabin.

2.0 star property
10.0 out of 10, Exceptional, (11)
"We stayed here for 3 nights to enjoy some riding out on the rocks with the kids!! The host was excellent with communication and helping us with anything we needed! The property was clean and had everything we needed for our stay and to be able to make our meals while there. Loved the hot tub and the lake views!! It was too cold while we were there but I want to definitely book again to take advantage of the lake access!! "
The price is NZ$367
includes taxes & fees
12 Oct - 13 Oct
Lakeside, boat dock and hot tub with this snug small cabin.

Modern Cabin on Monkey Island with Expansive Deck & Hot Tub!

10.0 out of 10, Exceptional, (14)
"Very clean, very nice, and perfect for families. 5 minutes to Shangri La marina."
Modern Cabin on Monkey Island with Expansive Deck & Hot Tub!

Cozy Lakeview Cabin, Boat Parking, Breathtaking Lake View, One Hour from Tulsa

9.4 out of 10, Exceptional, (31)
"If you enjoy coffee on the deck/porch with a view, this is the place for you! The owners have thought of it all! What a relaxing stay."
The price is NZ$320
includes taxes & fees
7 Oct - 8 Oct
Cozy Lakeview Cabin, Boat Parking, Breathtaking Lake View, One Hour from Tulsa

Calhoun Lakehouse on Monkey Island

9.8 out of 10, Exceptional, (23)
"We really enjoyed this little cabin. The cabin was very nice and close to all the things to do on Monkey Island."
Calhoun Lakehouse on Monkey Island

Romantic Getaway for 2 with Hot tub

10.0 out of 10, Exceptional, (7)
"We LOVED staying here, the property was beautiful and all of the animals are very friendly and sweet!"
The price is NZ$280
includes taxes & fees
6 Oct - 7 Oct
Romantic Getaway for 2 with Hot tub

Waterfront beauty with dock and fireplace! Check in Bay! New Hot Tub!!

10.0 out of 10, Exceptional, (166)
"We love staying here every year. Everything is great. Great communication with the owner. We will be back to stay here. "
Waterfront beauty with dock and fireplace! Check in Bay! New Hot Tub!!

Grand Lake cabin on Monkey Island minutes from Shangri-La w/Hot Tub and Fire Pit

10.0 out of 10, Exceptional, (57)
"This property was exactly what we needed!!! Clean, beautiful, and easy to get to!"
Grand Lake cabin on Monkey Island minutes from Shangri-La w/Hot Tub and Fire Pit

Lakefront, 35ft Dock , Battlefield Golf Views, New Build , Sleeps 16 Guests

9.8 out of 10, Exceptional, (27)
"All was perfect "
The price is NZ$1,177
includes taxes & fees
4 Nov - 5 Nov
Lakefront, 35ft Dock , Battlefield Golf Views, New Build , Sleeps 16 Guests

Lakeside, Boat Dock and Hot Tub with this small quaint cottage.

2.0 star property
9.8 out of 10, Exceptional, (9)
"Waterfront home very nice! Located on a quiet cove. We were able to fish and enjoy the beautiful view! We definitely plan to go again! "
The price is NZ$308
includes taxes & fees
19 Oct - 20 Oct
Lakeside, Boat Dock and Hot Tub with this small quaint cottage.

Waterfront oasis with gazebo and fire pit, crappie dock with swim deck and slide

10.0 out of 10, Exceptional, (14)
"great location, close to shopping, excellent management "
Waterfront oasis with gazebo and fire pit, crappie dock with swim deck and slide

The Lakeside Family Oasis Spacious 5-BD house Pvt dock ramp Monkey Island

10.0 out of 10, Exceptional, (3)
"There was a groups of 6 there for the world national fishing tournament for the high school! Perfect place on the water with the ramp right beside us. Only bad thing was the walkway to the boat slip was underwater but that was beyond any control of the owner! Perfect location on the water. Easy to walk down to the water and great place to stay! "
The Lakeside Family Oasis Spacious 5-BD house Pvt dock ramp Monkey Island

Fly-In Home on Monkey Island, Grand Lake OK

10.0 out of 10, Exceptional, (100)
"We really enjoyed our time on monkey Island. We were there for a family reunion and our house was our place to rest after a full day. "
Fly-In Home on Monkey Island, Grand Lake OK

Cabin 2 on Stony Point

9.8 out of 10, Exceptional, (15)
"Once we got there we did not leave"
Cabin 2 on Stony Point

Captains Hide Away

2.0 star property
2.0 out of 10, (1)
The price is NZ$609
includes taxes & fees
10 Oct - 11 Oct
Captains Hide Away

Monkey Island, Afton, OK Grand Lake, Waterfront, Boat Slip, No stairs, Pets Ok

10.0 out of 10, Exceptional, (74)
"The house is great, very clean, had everything you could need for your vacation. The outside area is top-notch. The host was available for anything you needed. Would definitely stay again "
Monkey Island, Afton, OK Grand Lake, Waterfront, Boat Slip, No stairs, Pets Ok

Twin Retreat Cabin 1: Hot Tub, Fire Pit, Golf Shangri La, Boat Grand Lake

10.0 out of 10, Exceptional, (28)
"An absolutely amazing cabin."
The price is NZ$644
includes taxes & fees
6 Oct - 7 Oct
Twin Retreat Cabin 1: Hot Tub, Fire Pit, Golf Shangri La, Boat Grand Lake

Modern Luxury Lakefront w/ Hot Tub, Unbelievable Views!

9.8 out of 10, Exceptional, (9)
"It couldn't have been nicer! Everyone loved it and can't wait to come back!"
Modern Luxury Lakefront w/ Hot Tub, Unbelievable Views!

Lakefront in Duck Creek with Private Dock, 2 Units

9.4 out of 10, Exceptional, (3)
"Excellent stay. Our teenagers loved having their own area. Very clean. "
Lakefront in Duck Creek with Private Dock, 2 Units

That Dam Cabin - Outdoor Living - Hot Tub, 65” TV, & Blackstone Griddle!

10.0 out of 10, Exceptional, (4)
"Simple little lake cabin, exactly what we were looking for "
That Dam Cabin - Outdoor Living - Hot Tub, 65” TV, & Blackstone Griddle!

Grand Lake's Newest Two Bedroom Two Bathroom Cottage Plus Full Hookup RV Spot

9.8 out of 10, Exceptional, (27)
"Was a great location and pretty house "
The price is NZ$575
includes taxes & fees
6 Oct - 7 Oct
Grand Lake's Newest Two Bedroom Two Bathroom Cottage Plus Full Hookup RV Spot
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 Pensacola Hotel Reviews

Find out more about Pensacola

Find out more about Pensacola

Everything you need to know about Pensacola holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pensacola holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pensacola holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Pensacola holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pensacola. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pensacola holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pensacola holiday rentals we have selected for you start as low as NZ$280 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pensacola rentals

At Expedia, we put the best Pensacola holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Pensacola rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pensacola holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pensacola. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Pensacola?

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

Modern Cabin on Monkey Island with Expansive Deck & Hot Tub!: This holiday home rental outside of Pensacola is located on a lake, and has a fireplace, a patio 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. You can relax into your holiday with a selection of games and 1 hot tub.

What can I see and do in Pensacola?

While exploring the area, visit family-friendly sights like Lulabelle's, or get outside and enjoy nature at Little Blue-Disney State Park. In the wider area, you’ll find Little Blue State Park and Salina State Park.

What are holiday rentals like in Pensacola?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pensacola. Holiday rentals provide amenities such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for families.