Caribbean Isle Vacations from $320

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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.
30A Inn & Suites

30A Inn & Suites

3 out of 5
Dune Allen Beach
Price was $441, price is now $320 per person
$320
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Walton Beach (VPS)
9/10 Wonderful! (649 reviews)
No staff available on premises. We were four and had only three pillows all weekend. Noone available in spite of getting texts urging one to contact them if we need anything. Room has a coffee maker but no coffee to make

Reviewed on Nov 17, 2025

The Original Romar House B&B Inn

The Original Romar House B&B Inn

4 out of 5
Save 100% on your flight
Price was $658, price is now $418 per person
$418
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pensacola (PNS)
9.8/10 Exceptional! (22 reviews)
Amazing nostalgic bed and breakfast!! Top notch breakfast Great hospitality Beachfront easy walking distance to beach

Reviewed on Oct 14, 2025

The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

5 out of 5
Crystal Beach
Price was $2,028, price is now $1,333 per person
$1,333
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Walton Beach (VPS)
9.2/10 Wonderful! (1,000 reviews)
The staff was incredibly friendly. The room was spotless. The pool areas were excellent and well stocked. The private beach was the BEST! Thank you to The Henderson team for a wonderful stay!

Reviewed on Nov 19, 2025

Sandestin Golf and Beach Resort

Sandestin Golf and Beach Resort

4 out of 5
Price was $635, price is now $452 per person
$452
per person
Feb 5 - Feb 8
found 19 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Fort Walton Beach (VPS)
7.8/10 Good! (3,841 reviews)
We love staying here been a couple times always great.

Reviewed on Nov 13, 2025

The Lodge at Gulf State Park, A Hilton Hotel

The Lodge at Gulf State Park, A Hilton Hotel

4 out of 5
Price was $519, price is now $382 per person
$382
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pensacola (PNS)
9.2/10 Wonderful! (1,004 reviews)
Good room nice staff

Reviewed on Nov 26, 2025

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Caribbean Isle Hotel Deals

Surf & Sand Hotel

Surf & Sand Hotel

2 out of 5
40 Fort Pickens Road Pensacola Beach FL
Fully refundableReserve now, pay when you stay
The price is $66 total per night from Nov 30 to Dec 1
$66 total
per night
Nov 30 - Dec 1
8.6/10 Excellent! (2,910 reviews)
Yes . Very nice and friendly!! I booked a 2nd night stay and accidentally booked the wrong night and the staff corrected it for me!!

Reviewed on Nov 25, 2025

Surf & Sand Hotel
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 $161 total per night from Dec 10 to Dec 11
$161 total
per night
Dec 10 - Dec 11
9.4/10 Exceptional! (2,644 reviews)
The hotel and area were beautiful. Rooms large and comfortable.

Reviewed on Nov 27, 2025

The Pensacola Beach Resort
Hampton Inn Pensacola Beach

Hampton Inn Pensacola Beach

2.5 out of 5
2 Via De Luna Drive Pensacola Beach FL
Fully refundableReserve now, pay when you stay
The price is $109 total per night from Dec 4 to Dec 5
$109 total
per night
Dec 4 - Dec 5
8.2/10 Very Good! (2,247 reviews)
Staff was great - breakfast was superb!

Reviewed on Nov 23, 2025

Hampton Inn Pensacola Beach
See all 6,784 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.
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Beach Vacations
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Discover the most popular places to visit in Caribbean Isle

Navarre Beach

Navarre Beach

Head over to Navarre Beach, a favorite beach in Navarre to enjoy the surf and sand, along with fishing. Wander the seaside or discover the sunsets in this relaxing area.

Navarre Beach

Navarre Beach Fishing Pier

Explore the waterfront in Navarre with a trip to Navarre Beach Fishing Pier. Wander the beautiful beaches in this relaxing area.

Navarre Beach Fishing Pier

Navarre Beach Marine Park

Explore the great outdoors at Navarre Beach Marine Park, a lovely green space in Navarre. Wander the beautiful beaches in this relaxing area.

Navarre Beach Marine Park

Things to do

Florida: Emerald Coast Sunset & Dolphin Cruise with Guide

Florida: Emerald Coast Sunset & Dolphin Cruise with Guide

$41
per adult
92% of travellers recommend
Florida: Emerald Coast Sunset & Dolphin Cruise with Guide
Destin: Buccaneer Pirate Cruise

Destin: Buccaneer Pirate Cruise

$55
per adult
100% of travellers recommend
Destin: Buccaneer Pirate Cruise
Clear Kayak Ecotour Destin Ft. Walton Beach

Clear Kayak Ecotour Destin Ft. Walton Beach

$80
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.