Caribbean Isle Vacations from $1,810

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Your Caribbean Isle Vacation

Experiencing all that Caribbean Isle has to offer is simple with a Caribbean Isle vacation package. Renowned for its golfing and more, this captivating neighborhood is waiting to welcome you. When it's time to get out and explore, you'll find loads of big-name attractions nearby including Navarre Beach Fishing Pier, Navarre Beach Gulf Snorkel Reef and Navarre Beach Marine Park. Tick off one or all during your trip to Caribbean Isle. No matter what your dream Caribbean Isle vacation looks like, you can make it a reality with Expedia.

The Latest Caribbean Isle Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Oyster Bay Boutique Hotel
30A Southern Sugar by Avantstay Sleeps 26 Pool + Hot Tub + Game Room + Golf Cart + Bikes
Beachfront Hot Tub Covered Lounge Backyard Beach by Avantstay
Monarch by Avantstay Stunning Estate 1 Block to Beach, Swim Up Bar, Hot Tub, & Rooftop Views
Destin Dream by Avantstay 2-story Home, Walk to Beach

Caribbean Isle Hotel Deals

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
$152 nightly
The price is $172 total per night from May 10 to May 11
$172 total
May 10 - May 11
Total with taxes and fees
8.2/10 Very Good! (2,292 reviews)
My kids loved the pool! It was so warm. We got a room that went straight out to the pool, so it was perfect. The beach was so good! Beautiful. Easy to get to. Clean. Softest sand I’ve ever felt!

Reviewed on May 5, 2026

Wyndham Garden Fort Walton Beach Destin
 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
$336 nightly
The price is $377 total per night from May 31 to Jun 1
$377 total
May 31 - Jun 1
Total with taxes and fees
9.6/10 Exceptional! (3,098 reviews)
Everything was great- food, pool, drinks! Upscale with welcoming vibe.

Reviewed on May 7, 2026

The Pensacola Beach Resort
Surf & Sand Hotel

Surf & Sand Hotel

2 out of 5
40 Fort Pickens Road Pensacola Beach FL
Fully refundableReserve now, pay when you stay
$174 nightly
The price is $195 total per night from May 10 to May 11
$195 total
May 10 - May 11
Total with taxes and fees
8.8/10 Excellent! (3,161 reviews)
Everything was perfect. Great place to stay. I’ll be back

Reviewed on May 8, 2026

Surf & Sand Hotel
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.

Discover the most popular places to visit in Caribbean Isle

Things to do

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.