Vacations in Pensacola Beach

Vacations in Pensacola Beach

2 travellers

KAYAK searches hundreds of travel sites at once for vacation package deals in Pensacola Beach

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Bundle and saveSave money when you bundle your flight + hotel.

Search
Best Deals

Cheap Pensacola Beach package deals

Discover the best prices by selecting your travel dates on KAYAK.
Go to map

Search by stars

2+ stars3+ stars4+ stars

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by board

BreakfastHalf boardSelf cateringAll inclusiveMeals not included

Search by price

C$ 816 - C$ 1,140C$ 1,140 - C$ 1,466C$ 1,466 - C$ 1,790C$ 1,790 - C$ 2,115C$ 2,115+ per night

Search by freebies

Free breakfastFree internetFree airport shuttleFree parking

Most popular Pensacola Beach flight and hotel deals

Show all
Starboard Village 121 - Pensacola Beach - Balcony
Starboard Village 121 - Pensacola Beach - Balcony
Starboard Village 121
9.9 Wonderful
Parking
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 1,611
Turtle Hideaway - Pensacola Beach - Balcony
Turtle Hideaway - Pensacola Beach - Balcony
Turtle Hideaway
10 Wonderful
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 1,018
Aquaverde Beach House - Pensacola Beach - Patio
Aquaverde Beach House - Pensacola Beach - Patio
Aquaverde Beach House
9 Wonderful
Free Wi-Fi
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 1,514
Regency Towers Unit 701W - Pensacola Beach
Regency Towers Unit 701W - Pensacola Beach
Regency Towers Unit 701W
9 Wonderful
Free Wi-Fi
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 1,484
Portofino Island Resort - Pensacola Beach - Bedroom
Portofino Island Resort - Pensacola Beach - Bedroom
Portofino Island Resort
8.8 Very good
Parking
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 1,922
Santa Rosa Dunes by Southern Vacation Rentals - Pensacola Beach - Dining room
Santa Rosa Dunes by Southern Vacation Rentals - Pensacola Beach - Dining room
Santa Rosa Dunes by Southern Vacation Rentals
8.5 Very good
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 854
Portofino Island Resort 2-1902 - Pensacola Beach - Bedroom
Portofino Island Resort 2-1902 - Pensacola Beach - Bedroom
Portofino Island Resort 2-1902
10 Wonderful
Parking
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 1,119
Villas on the Gulf unit D2 - Pensacola Beach - Pool
Villas on the Gulf unit D2 - Pensacola Beach - Pool
Villas on the Gulf unit D2
Parking
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 1,310
Sand Dollar W-103 - Pensacola Beach - Patio
Sand Dollar W-103 - Pensacola Beach - Patio
Sand Dollar W-103
10 Wonderful
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 957
Seahorse Siesta - Pensacola Beach - Living room
Seahorse Siesta - Pensacola Beach - Living room
Seahorse Siesta
10 Wonderful
Parking
Free Wi-Fi
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 1,413
Salt Therapy - Pensacola Beach
Salt Therapy - Pensacola Beach
Salt Therapy
Free Wi-Fi
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 1,426
Villas on the Gulf by Southern Vacation Rentals - Pensacola Beach - Living room
Villas on the Gulf by Southern Vacation Rentals - Pensacola Beach - Living room
Villas on the Gulf by Southern Vacation Rentals
Free Wi-Fi
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 1,151
Santa Rosa Dunes 1063 - Pensacola Beach - Pool
Santa Rosa Dunes 1063 - Pensacola Beach - Pool
Santa Rosa Dunes 1063
9.1 Wonderful
Parking
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 1,034
1 Portofino 1005 - Pensacola Beach - Living room
1 Portofino 1005 - Pensacola Beach - Living room
1 Portofino 1005
8.9 Very good
Parking
Free Wi-Fi
Pool
Spa
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 1,335
Baywatch by Southern Vacation Rentals - Pensacola Beach - Building
Baywatch by Southern Vacation Rentals - Pensacola Beach - Building
Baywatch by Southern Vacation Rentals
Free Wi-Fi
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 1,261
Baywatch Unit F10 - Pensacola Beach
Baywatch Unit F10 - Pensacola Beach
Baywatch Unit F10
10 Wonderful
Free Wi-Fi
Chicago O'Hare Intl
Meals not included
3 nights + flight
C$ 1,251

When to book a vacation in Pensacola Beach

Price includes flights and 3 nights accommodation for 2 travellers. Prices are not fixed and may vary with time.

Where to stay in Pensacola Beach

Our map will help you find the perfect place to stay for your vacation in Pensacola Beach by showing you the exact location of each hotel.

Everything you need to know for your vacation in Pensacola Beach

Complete your trip to Pensacola Beach

Hotels in Pensacola Beach

Pensacola Beach vacation: Search Pensacola Beach vacation packages on KAYAK. KAYAK is a travel tool that searches Pensacola Beach trips on hundreds of travel sites to help you find the Pensacola Beach package that suits you best. Discover Pensacola Beach deals now and book your Pensacola Beach flight and hotel today.

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.