Caribbean Isle Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • Bayside at Sandestin One Bedroom | In-room dining
    Jul 2 - Jul 6

    Sandestin Golf and Beach Resort + Flight

    Miramar Beach
    4 nights
    4.0 star property
    7.8/10 - Good (3,899 reviews)
    "We have stayed at this property in the past and always have a great experience. We used the pool a few times and enjoyed it. The room was very clean and everything was in good working order. The location is great! Very close to down town Destin area and also 30a beaches and restaurants."
    Reviewed May 26, 2026
    Roundtrip • Toronto (YYZ) - Fort Walton Beach (VPS)
    YYZ - VPS • 1 stop VPS - YYZ • 1 stop
    CA $1,689
    CA $1,322
    per traveller
    found 1 day ago
    Sandestin Golf and Beach Resort
  • Interior
    Jul 2 - Jul 6

    Spyglass by Avantstay 5BR + 3 Balconies + Community Pool Walk to Beach + Minutes to Harborwalk Village & Henderson Beach State Park + Flight

    Destin
    4 nights
    3.0 star property
    Roundtrip • Toronto (YYZ) - Fort Walton Beach (VPS)
    YYZ - VPS • 1 stop VPS - YYZ • 1 stop
    CA $5,287
    CA $3,989
    per traveller
    found 1 day ago
    Spyglass by Avantstay 5BR + 3 Balconies + Community Pool Walk to Beach + Minutes to Harborwalk Village & Henderson Beach State Park
  • Outdoor pool, free cabanas
    Aug 3 - Aug 10

    Landing Apartments Santa Rosa Beach + Flight

    Santa Rosa Beach
    7 nights
    4.0 star property
    9.2/10 - Wonderful (12 reviews)
    Roundtrip • Toronto (YYZ) - Fort Walton Beach (VPS)
    YYZ - VPS • 1 stop VPS - YYZ • 1 stop
    CA $2,444
    CA $1,849
    per traveller
    found 18 hours ago
    Landing Apartments Santa Rosa Beach
  • House (3 Bedrooms) | Front of property
    Jul 16 - Jul 21

    Beachfront Townhome With Instant Access to Beach Beachside Kisses by Avantstay + Flight

    Okaloosa Island
    5 nights
    3.0 star property
    Roundtrip • Toronto (YYZ) - Fort Walton Beach (VPS)
    YYZ - VPS • 1 stop VPS - YYZ • 1 stop
    CA $6,097
    CA $4,615
    per traveller
    found 1 day ago
    Beachfront Townhome With Instant Access to Beach Beachside Kisses by Avantstay
  • Beach/ocean view
    Jul 2 - Jul 6

    Hampton Inn & Suites Destin + Flight

    Destin
    4 nights
    2.5 star property
    8.6/10 - Excellent (1,005 reviews)
    "Nice large room"
    Reviewed May 26, 2026
    Roundtrip • Toronto (YYZ) - Fort Walton Beach (VPS)
    YYZ - VPS • 1 stop VPS - YYZ • 1 stop
    CA $2,378
    CA $1,881
    per traveller
    found 1 day ago
    Hampton Inn & Suites Destin

Caribbean Isle Hotel Deals

The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
165 Fort Pickens Road Pensacola Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $434 per night from May 31 to Jun 1
CA $434
per night
May 31 - Jun 1
9.6/10 Exceptional! (3,180 reviews)
"Outdoor pool was closed for most of our stay. The Rose was closed to us as well for a private event. This is the second time staying the rose has been closed. The restaurant needs upgrading. The bar is way too small especially when weather is not great. They need more one TV in the restaurant. The ..."

Reviewed on May 26, 2026

The Pensacola Beach Resort
Wyndham Garden Fort Walton Beach Destin

Wyndham Garden Fort Walton Beach Destin

3 out of 5
573 Santa Rosa Blvd Fort Walton Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $358 per night from May 31 to Jun 1
CA $358
per night
May 31 - Jun 1
8.2/10 Very Good! (2,337 reviews)
"Honestly, the place is very rundown and falling apart. The main lobby looked nice, but as soon as we started heading towards our room, we knew we got tricked. Roaches everywhere, stains and water damage everywhere. Honestly would have rather stayed at a cheap motel it was so bad. Now we're having ..."

Reviewed on May 27, 2026

Wyndham Garden Fort Walton Beach Destin
Surf & Sand Hotel

Surf & Sand Hotel

2 out of 5
40 Fort Pickens Road Pensacola Beach FL
The price is CA $245 per night from May 31 to Jun 1
CA $245
per night
May 31 - Jun 1
8.8/10 Excellent! (3,163 reviews)
"We had a mixed experience during our 5-day stay. Elizabet, who was there every morning at breakfast except for our last day (May 26), was absolutely amazing. She always greeted us warmly, checked on us, asked if we needed anything, and genuinely made us feel welcome. She was one of the highlights ..."

Reviewed on May 26, 2026

Surf & Sand Hotel
See all 7,153 properties in Caribbean Isle
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.
All Inclusive Vacations
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Frequently asked questions

How much does a Caribbean Isle vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Caribbean Isle from just . And the more you bundle, the more money you save. The getaway of your dreams has never been more affordable.
How do I get a cheap travel package to Caribbean Isle?
Bundle your hotel and flight bookings, toss in extras such as activities or a rental car, and save with a Caribbean Isle vacation package. You won't just walk away with amazing discounts on your adventure — you'll have loads of choice too. When you book with Expedia, you can choose from more than 550 partner airlines and 1,000,000 hotels around the world. Your unforgettable vacation starts right here, right now!
Where should I stay in Caribbean Isle?
If you hope to check out Navarre Beach Marine Park, forget about commuting and find someplace to stay close by. It's one of the best attractions in this neighborhood.
What are the top hotels in Caribbean Isle?
If it's your first visit to Caribbean Isle, reserve a room at Gorgeous Large, Recently Renovated Private Home In Gated Beach Community or Beach Home With Ocean View, High Speed Wifi. Both have good amenities and are top options with lots of travelers.
How far in advance should I book my Caribbean Isle vacation?
While not all airlines advertise tickets early, you can normally compare international fares on Expedia up to a year in advance. This is the time you'll nab some fantastic bargains. If you've left things to the last minute, you might still get lucky. Sometimes the lowest prices appear only weeks prior to departure.
What does an Expedia Caribbean Isle travel package include?
It comes down to what type of trip you're contemplating. Caribbean Isle travel deals can include flights, car rentals and hotels. You can mix and match to find the travel package that suits your budget and style. You can also add on activities and experiences after you've booked to score even bigger discounts.
What should I know before booking a Caribbean Isle travel package?
You'll land terrific savings when you bundle your hotels, flights and rental cars into a travel package. Plus, booking everything in one place makes trip planning much easier. So why waste time or money? Whether you're organizing a fancy romantic getaway or an affordable family break, browse our package deals today.
Can I choose my airline with a Caribbean Isle Expedia vacation package?
Expedia offers access to more than 550 airline partners globally, so you sure can! Just select your preferred carrier and craft the perfect Caribbean Isle escape.
If I'm not able to travel, can I cancel my Caribbean Isle vacation package?
Because we understand life can be unpredictable, the answer is yes. For more information, visit our Customer Service Portal. But generally speaking, if you've booked your Caribbean Isle vacation package in the last 24 hours, you may be able to cancel or change it for free. Your airline, hotel or car rental company may impose a fee if your booking is older than that.

Things to do

Destin: Buccaneer Pirate Cruise

Destin: Buccaneer Pirate Cruise

CA $76
per adult
100% of travellers recommend
Destin: Buccaneer Pirate Cruise
Sandestin: Fireworks Cruise

Sandestin: Fireworks Cruise

CA $55
per adult
Sandestin: Fireworks Cruise
Clear Kayak Ecotour Destin Ft. Walton Beach

Clear Kayak Ecotour Destin Ft. Walton Beach

CA $123
per adult
Clear Kayak Ecotour Destin Ft. Walton Beach
See all activities in Navarre
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.