Caribbean Isle Holidays
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- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Price found within the past 48 hours. Click for updated prices.
Landing Apartments - Northwest Pensacola
Northwest Pensacola
€678
per person
9 Oct - 11 Oct
found 1 day ago
Return flight included
Chicago (ORD) to Pensacola (PNS)
9.2/10 Wonderful! (27 reviews)
Property was beautiful clean. Just hated I was there for six days and the pool was only open 1 day. That was my reason for choosing this place. I most likely will not stay again for that reason. Spoke to on site staff and none could tell us why pool was closed or when it would reopen huge inconvenience. Drove all the way from Michigan 15 hours for that amenities to enjoy the week with my child in the Navy just overall a not so great experience. Be prepared to park far away from your designated spot as people had guest all week and the spot in front of our residence was always occupied at front door and in the rear.
Reviewed on 22 Aug 2026
Surf & Sand Hotel
€727
per person
9 Oct - 11 Oct
found 1 day ago
Return flight included
Chicago (ORD) to Pensacola (PNS)
8.8/10 Excellent! (3,262 reviews)
It isnt for the boujie type. Room was everything it needs to be though. Clean, with a mini fridge, microwave, and coffee pot all in working manner. Pool was open and maintained, regular tub and shower with unlimited hot water supply. Free breakfast every morning. If you're looking for simple an necessity this is the place for you and worth the price
Reviewed on 26 Aug 2026
Landing Apartments - North Central Pensacola
€688
per person
9 Oct - 11 Oct
found 1 day ago
Return flight included
Chicago (ORD) to Pensacola (PNS)
10/10 Exceptional! (12 reviews)
Amenities were solid (gym, swimming pool, filtered water machine, clubhouse). Nice apartment overall, able to cook and WFH with no issue. Parking was ample, residents were friendly. Will definitely be staying here again.
Reviewed on 16 Aug 2026
Top hotels in Caribbean Isle
The Pensacola Beach Resort
165 Fort Pickens Road Pensacola Beach FL
Fully refundableReserve now, pay when you stay
€202
30 Aug - 31 Aug
includes taxes & fees
Wyndham Garden Fort Walton Beach Destin
573 Santa Rosa Blvd Fort Walton Beach FL
Fully refundableReserve now, pay when you stay
€122
27 Sept - 28 Sept
includes taxes & fees
8.2/10 Very good! (2,548 reviews)
"The staff was amazing very responsive when you ask questions very attentive with fixing things like TV won’t come on our back door was stuck. They did send maintenance to open it, but never fixed it. Several ice machines were down so hard to find ice but all in all a great experience."
Reviewed on 27 Aug 2026
Wavecrest Lodge
540 Santa Rosa Blvd Fort Walton Beach FL
€172
7 Sept - 8 Sept
includes taxes & fees
9.2/10 Wonderful! (1,073 reviews)
"Beach view is amazing, not to many places to each within walking distance. Overall experience was amazing."
Reviewed on 24 Aug 2026
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.
Frequently asked questions
How much does a Caribbean Isle holiday package cost?
Choose from any combination of hotels, flights and car rentals, and you can be holidaying in Caribbean Isle from just €678. 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 holiday 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 holiday 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 neighbourhood.
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 travellers.
How far in advance should I book my Caribbean Isle holiday?
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 organising a fancy romantic getaway or an affordable family break, browse our package deals today.
Can I choose my airline with a Caribbean Isle Expedia holiday 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 holiday 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 holiday 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
€52
per adult
94% of travellers recommend
Fort Walton: Dolphin Discovery and Snorkeling Cruise
€58
per adult
100% of travellers recommend
Fort Walton Beach: Jet Ski Rental
€97
per traveller
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.