Caribbean Isle Vacation Packages for 2026

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

Top 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
27.82 km from Caribbean Isle
Book a stay at this beach hotel in Fort Walton Beach. Enjoy free WiFi, 2 outdoor pools, and a beach locale. Our guests praise the pool and the helpful staff ...
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
165 Fort Pickens Road Pensacola Beach FL
23.92 km from Caribbean Isle
Book a stay at this beach hotel in Pensacola Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our ...
Surf & Sand Hotel

Surf & Sand Hotel

2 out of 5
40 Fort Pickens Road Pensacola Beach FL
23.41 km from Caribbean Isle
Book a stay at this beach hotel in Pensacola Beach. Enjoy free breakfast, free WiFi, and free bicycles on site. Our guests praise the breakfast and the pool ...
Hampton Inn Pensacola Beach

Hampton Inn Pensacola Beach

2.5 out of 5
2 Via De Luna Drive Pensacola Beach FL
23.03 km from Caribbean Isle
Book a stay at this beach hotel in Pensacola Beach. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our ...
Hilton Garden Inn Ft. Walton Beach

Hilton Garden Inn Ft. Walton Beach

3 out of 5
1297 Miracle Strip PKWY SE Fort Walton Beach FL
29.48 km from Caribbean Isle
Book a stay at this beach hotel in Fort Walton Beach. Enjoy free WiFi, a beach locale, and room service. Our guests praise the pool and the helpful staff in ...
Holiday Inn Resort Pensacola Beach by IHG

Holiday Inn Resort Pensacola Beach by IHG

3 out of 5
14 Via De Luna Drive Pensacola Beach FL
22.76 km from Caribbean Isle
Book a stay at this beach hotel in Pensacola Beach. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the pool and the helpful staff ...
SpringHill Suites by Marriott Navarre Beach

SpringHill Suites by Marriott Navarre Beach

4 out of 5
8375 Gulf Blvd Navarre FL
2.98 km from Caribbean Isle
Book a stay at this beach hotel in Navarre. Enjoy free breakfast, free WiFi, and a beach locale. Our guests praise the breakfast and the restaurant in our reviews. ...
Hilton Pensacola Beach

Hilton Pensacola Beach

4 out of 5
12 Via De Luna Dr Pensacola Beach FL
22.88 km from Caribbean Isle
Book a stay at this beach resort in Pensacola Beach. Enjoy 2 outdoor pools, 2 restaurants, and a beach locale. Our guests praise the pool and the helpful staff ...
Waterscape Condominiums

Waterscape Condominiums

3.5 out of 5
1110 Santa Rosa Blvd Fort Walton Beach FL
29.36 km from Caribbean Isle
Book a stay at this beach condo in Fort Walton Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Okaloosa Island Beach and HarborWalk ...
Fairfield Inn & Suites by Marriott Pensacola Beach

Fairfield Inn & Suites by Marriott Pensacola Beach

3.5 out of 5
16 Via de Luna Dr Pensacola Beach FL
22.66 km from Caribbean Isle
Book a stay at this beach hotel in Pensacola Beach. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our ...
Quality Inn & Suites Pensacola Bayview

Quality Inn & Suites Pensacola Bayview

2.5 out of 5
7601 Scenic Highway Pensacola FL
28.55 km from Caribbean Isle
Book a stay at this business-friendly hotel in Pensacola. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Holiday Inn Resort Fort Walton Beach by IHG

Holiday Inn Resort Fort Walton Beach by IHG

3 out of 5
1299 Miracle Strip Parkway SE Fort Walton Beach FL
29.54 km from Caribbean Isle
Book a stay at this beach resort in Fort Walton Beach. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the pool and the helpful ...
Gulf Coast Inn

Gulf Coast Inn

2.5 out of 5
843 Gulf Breeze Parkway Gulf Breeze FL
25 km from Caribbean Isle
Stay at this motel in Gulf Breeze. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Four Points by Sheraton Destin-Fort Walton Beach

Four Points by Sheraton Destin-Fort Walton Beach

3 out of 5
1325 Miracle Strip Pkwy SE Fort Walton Beach FL
29.67 km from Caribbean Isle
Book a stay at this beach hotel in Fort Walton Beach. Enjoy free WiFi, 2 outdoor pools, and 3 restaurants. Our guests praise the helpful staff and the clean ...
Days Inn by Wyndham Fort Walton Beach

Days Inn by Wyndham Fort Walton Beach

2 out of 5
135 Miracle Strip Pkwy Sw Fort Walton Beach FL
27.08 km from Caribbean Isle
Book a stay at this business-friendly hotel in Fort Walton Beach. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Okaloosa Island ...
Don't see what you're looking for?
See all available properties in Caribbean Isle
View all properties
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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Wed, Jan 28 - Sat, Feb 14
DFW
Dallas-Fort Worth Intl.
PNS
Pensacola Intl.
$155 Roundtrip, found 1 day ago
$155
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Jan 28 from Dallas-Fort Worth Intl. to Pensacola Intl., returning Sat, Feb 14, priced at $155 found 1 day ago
Spirit Airlines
Mon, Jan 12 - Thu, Jan 29
DFW
Dallas-Fort Worth Intl.
PNS
Pensacola Intl.
$160 Roundtrip, found 1 day ago
$160
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Mon, Jan 12 from Dallas-Fort Worth Intl. to Pensacola Intl., returning Thu, Jan 29, priced at $160 found 1 day ago
Delta
Fri, Jan 9 - Sat, Jan 24
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$229 Roundtrip, found 1 day ago
$229
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jan 9 from O'Hare Intl. to Pensacola Intl., returning Sat, Jan 24, priced at $229 found 1 day ago
American Airlines
Tue, Feb 17 - Thu, Feb 26
MSP
Minneapolis - St. Paul Intl.
VPS
Northwest Florida Regional
$277 Roundtrip, found 2 days ago
$277
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Feb 17 from Minneapolis - St. Paul Intl. to Northwest Florida Regional, returning Thu, Feb 26, priced at $277 found 2 days ago
Southwest Airlines
Thu, Jan 1 - Thu, Jan 8
DAL
Love Field
VPS
Northwest Florida Regional
$281 Roundtrip, found 2 days ago
$281
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Jan 1 from Love Field to Northwest Florida Regional, returning Thu, Jan 8, priced at $281 found 2 days ago