Pensacola Vacation Rentals

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Check prices for these dates

Tonight
Dec 24 - Dec 25
Tomorrow
Dec 25 - Dec 26
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Pensacola vacation rentals

Fridge, microwave, oven, stovetop
Monkey Island Bungalow ~ Pool ~ Golf~ Dogs welcome

Monkey Island Bungalow ~ Pool ~ Golf~ Dogs welcome

Monkey Island Bungalow ~ Pool ~ Golf~ Dogs welcome
2.0 star property
Monkey Island
9.4 out of 10, Exceptional, (8)
"Good place to stay and was peaceful"
United States
Luke F.
The price is ￥15,765
￥41,019 total
includes taxes & fees
Dec 29 - Dec 30
Monkey Island Bungalow ~ Pool ~ Golf~ Dogs welcome
Exterior
Vista Condo 2BR/2BA on Shangri-La Heritage Course

Vista Condo 2BR/2BA on Shangri-La Heritage Course

Vista Condo 2BR/2BA on Shangri-La Heritage Course
Monkey Island
10.0 out of 10, Exceptional, (10)
"Enjoyed our stay and communication was great with Lindsey!"
United States
Courtney M.
The price is ￥15,147
￥50,667 total
includes taxes & fees
Dec 30 - Dec 31
Vista Condo 2BR/2BA on Shangri-La Heritage Course
Exterior
Studio Cabin on Grand Lake near Bernice State Park 53996 E 270RD, Afton OK 74331

Studio Cabin on Grand Lake near Bernice State Park 53996 E 270RD, Afton OK 74331

Studio Cabin on Grand Lake near Bernice State Park 53996 E 270RD, Afton OK 74331
Afton
10.0 out of 10, Exceptional, (44)
"Nice cabin very clean"
United States
James H.
The price is ￥14,831
￥22,190 total
includes taxes & fees
Dec 25 - Dec 26
Studio Cabin on Grand Lake near Bernice State Park 53996 E 270RD, Afton OK 74331
Property grounds
Leaning Tree Woods Glampsite. Isolated area near Grand Lake.

Leaning Tree Woods Glampsite. Isolated area near Grand Lake.

Leaning Tree Woods Glampsite. Isolated area near Grand Lake.
Jay
9.6 out of 10, Exceptional, (5)
"My family had an amazing stay at this property! If you're looking for a secluded area with a few perks during camping this is it!! Host is very accommodating and very responsive to messages if we needed anything! "
United States
Savannah
The price is ￥9,133
￥16,137 total
includes taxes & fees
Dec 29 - Dec 30
Leaning Tree Woods Glampsite. Isolated area near Grand Lake.
Fridge, microwave, stovetop, coffee/tea maker
Cozy Lakeview Cabin, Boat Parking, Breathtaking Lake View, One Hour from Tulsa

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

Cozy Lakeview Cabin, Boat Parking, Breathtaking Lake View, One Hour from Tulsa
Afton
9.4 out of 10, Exceptional, (34)
"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."
United States
Jessica G.
The price is ￥11,241
￥30,968 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cozy Lakeview Cabin, Boat Parking, Breathtaking Lake View, One Hour from Tulsa
TV
Captains Cottage w/cozy wood burning fireplace

Captains Cottage w/cozy wood burning fireplace

Captains Cottage w/cozy wood burning fireplace
2.0 star property
Afton
10.0 out of 10, Exceptional, (1)
"The he cabin was clean, cute, and perfect for coming in for our 20th class reunion. It was walking distance to The Drunken Rooster. Thank you for such an easy transaction and a clean and cozy place to sleep."
United States
Kristina E.
The price is ￥23,418
￥44,038 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Captains Cottage w/cozy wood burning fireplace
Exterior
Romantic Getaway for 2 with Hot tub

Romantic Getaway for 2 with Hot tub

Romantic Getaway for 2 with Hot tub
Eucha
9.6 out of 10, Exceptional, (11)
"Cute cabin "
United States
Lori
The price is ￥12,958
￥25,174 total
includes taxes & fees
Dec 28 - Dec 29
Romantic Getaway for 2 with Hot tub
Smart TV, fireplace, DVD player, books
“Spectacular Waterfront Luxury w/ dock Grand Lake!!!

“Spectacular Waterfront Luxury w/ dock Grand Lake!!!

“Spectacular Waterfront Luxury w/ dock Grand Lake!!!
Eucha
10.0 out of 10, Exceptional, (23)
"Beautiful property. Very quiet and peaceful area."
United States
Jeff T.
The price is ￥20,452
￥52,836 total
includes taxes & fees
Dec 29 - Dec 30
“Spectacular Waterfront Luxury w/ dock Grand Lake!!!
Fridge, microwave, oven, stovetop
The Loft on Main. Cozy 2-bedroom apartment in Chelsea with all the amenities.

The Loft on Main. Cozy 2-bedroom apartment in Chelsea with all the amenities.

The Loft on Main. Cozy 2-bedroom apartment in Chelsea with all the amenities.
Chelsea
10.0 out of 10, Exceptional, (4)
"Super cute, clean and neat location! We loved the donut shop and coffee/bakery! "
United States
Sarah P.
The price is ￥13,415
￥27,851 total
includes taxes & fees
Dec 25 - Dec 26
The Loft on Main. Cozy 2-bedroom apartment in Chelsea with all the amenities.
Exterior
Twin Retreat Cabin 1: Hot Tub, Fire Pit, Golf Shangri La, Boat Grand Lake

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

Twin Retreat Cabin 1: Hot Tub, Fire Pit, Golf Shangri La, Boat Grand Lake
Afton
10.0 out of 10, Exceptional, (34)
"Cabin was absolutely perfect!! It had everything we needed. "
United States
Sherry A.
The price is ￥21,214
￥56,599 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Twin Retreat Cabin 1: Hot Tub, Fire Pit, Golf Shangri La, Boat Grand Lake
Terrace/patio
Romantic Stary Night Getaway

Romantic Stary Night Getaway

Romantic Stary Night Getaway
Big Cabin
10.0 out of 10, Exceptional, (1)
"Cute and peaceful setting. Would stay again."
United States
Katie C.
The price is ￥15,612
￥33,489 total
includes taxes & fees
Dec 28 - Dec 29
Romantic Stary Night Getaway
Fridge, stovetop, dishwasher, toaster
Shadow Ridge Tiny Home

Shadow Ridge Tiny Home

Shadow Ridge Tiny Home
Big Cabin
10.0 out of 10, Exceptional, (3)
"Nice place. Private and close to lake. Will be staying again soon. "
United States
Joel W.
The price is ￥15,690
￥33,657 total
includes taxes & fees
Dec 25 - Dec 26
Shadow Ridge Tiny Home
Terrace/patio
Harvest Hill Silo - Home on Route 66, 5 acre Fishing Pond

Harvest Hill Silo - Home on Route 66, 5 acre Fishing Pond

Harvest Hill Silo - Home on Route 66, 5 acre Fishing Pond
Vinita
10.0 out of 10, Exceptional, (8)
"Very nice! Very impressed with the setting. Beautiful stay for the evening!"
United States
Krysti M.
The price is ￥21,076
￥38,975 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Harvest Hill Silo - Home on Route 66, 5 acre Fishing Pond
Terrace/patio
Tranquil Cottage at Redbud Tiny Home Resort

Tranquil Cottage at Redbud Tiny Home Resort

Tranquil Cottage at Redbud Tiny Home Resort
Big Cabin
9.2 out of 10, Wonderful, (5)
"Nice and quiet and close to town. Very satisfied with my stay there. "
United States
Joel W.
The price is ￥15,612
￥32,553 total
includes taxes & fees
Dec 25 - Dec 26
Tranquil Cottage at Redbud Tiny Home Resort
Fridge, microwave, oven, stovetop
Golf Getaway with Golf Cart on Grand Lake in Shangri-La

Golf Getaway with Golf Cart on Grand Lake in Shangri-La

Golf Getaway with Golf Cart on Grand Lake in Shangri-La
Afton
9.6 out of 10, Exceptional, (21)
"This property was great and presented just as it did in the pictures. We loved that it was in a gated area and it was very quiet at night. The little extras provided by the host made the stay even better! We will definitely stay here again! "
United States
Heather M.
The price is ￥18,969
￥45,865 total
includes taxes & fees
Dec 25 - Dec 26
Golf Getaway with Golf Cart on Grand Lake in Shangri-La
Dining
Monkey Island Lodge - 4B/2BA Log Cabin - Lake View

Monkey Island Lodge - 4B/2BA Log Cabin - Lake View

Monkey Island Lodge - 4B/2BA Log Cabin - Lake View
2.0 star property
Afton
10.0 out of 10, Exceptional, (2)
"Lake was up and boat ramps in the area were flooded but once we found an opening it was all great"
United States
Marilu B.
The price is ￥33,539
￥99,144 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Monkey Island Lodge - 4B/2BA Log Cabin - Lake View
Exterior detail
Lake View Family Retreat - Arcade • Fire Pit • BBQ

Lake View Family Retreat - Arcade • Fire Pit • BBQ

Lake View Family Retreat - Arcade • Fire Pit • BBQ
Vinita
10.0 out of 10, Exceptional, (1)
"Fantastic property on the south end of the lake. Had a group of friends in that was a little large for my house. Put overflow people here. Everything was great. Property owners were amazing. Can’t go wrong here. "
United States
Eddie F.
The price is ￥22,876
￥88,983 total
includes taxes & fees
Dec 25 - Dec 26
Lake View Family Retreat - Arcade • Fire Pit • BBQ
Terrace/patio
Bring your boat Afton Grand Lake FREE Private Boat Ramp, Slips available to rent

Bring your boat Afton Grand Lake FREE Private Boat Ramp, Slips available to rent

Bring your boat Afton Grand Lake FREE Private Boat Ramp, Slips available to rent
2.0 star property
Afton
The price is ￥13,348
￥22,272 total
includes taxes & fees
Dec 29 - Dec 30
Bring your boat Afton Grand Lake FREE Private Boat Ramp, Slips available to rent
Interior
Spring Pond Cabin at White Buffalo Lodge; Family-sized with lake access

Spring Pond Cabin at White Buffalo Lodge; Family-sized with lake access

Spring Pond Cabin at White Buffalo Lodge; Family-sized with lake access
Grove
10.0 out of 10, Exceptional, (6)
"Very clean and nice cabin"
United States
Alisha
The price is ￥31,614
￥39,935 total
includes taxes & fees
Dec 28 - Dec 29
Spring Pond Cabin at White Buffalo Lodge; Family-sized with lake access
Property grounds
Cozy Cabin feel & picturesque views of Grand Lake!

Cozy Cabin feel & picturesque views of Grand Lake!

Cozy Cabin feel & picturesque views of Grand Lake!
2.0 star property
Afton
The price is ￥12,490
￥18,045 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cozy Cabin feel & picturesque views of Grand Lake!
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

South Grand Lakefront w/ Hot Tub, Dock & Game Room

South Grand Lakefront w/ Hot Tub, Dock & Game Room

10/10 Excellent
"Fantastic place, beautiful and well kept. Perfect for our large family. "
Tom P. 3-night trip
Posted 2 days ago
South Grand Lakefront w/ Hot Tub, Dock & Game Room

Find out more about Pensacola

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

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Frequently asked questions

Are there vacation rentals in Pensacola?

Yes, we offer vacation rentals near well known attractions in Pensacola, or you can go with a more remote option if you're looking for relaxation.

What are some of the best vacation rentals in Pensacola?

South Grand Lakefront w/ Hot Tub, Dock & Game Room: This vacation home rental outside of Pensacola is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a 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 larger area, you’ll find Little Blue State Park and Lake Hudson.

What are vacation rentals like in Pensacola?

Vacation rentals are private accommodations you can stay in for a couple days or more in Pensacola. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for families.