Holiday Isle Vacations from $443

Book a Hotel + Flight or Car together to unlock savings

Photo by Brent Hill

Your Holiday Isle Vacation

Our Holiday Isle vacation packages are a fast and practical way to organize and reserve your next escape. Uncover the magic of this unique neighborhood without the stress of planning it all yourself. Some popular nearby attractions to check out during your trip to Holiday Isle include Big Kahunas Water and Adventure Park, Destin Harbor Boardwalk and HarborWalk Village. Don't just wish for it — turn it into a reality! Lock in your ideal Holiday Isle vacation with Expedia and experience travel your way.

The Latest Holiday Isle Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Bay Club of Sandestin

Bay Club of Sandestin

3.5 out of 5
Price was $615, price is now $443 per person
$443
per person
Feb 21 - Feb 25
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Walton Beach (VPS)
9/10 Wonderful! (154 reviews)
Stayed here many times. It is my happy place and will continue to go! Plenty to do and the beach is always a crowd pleaser. The resort is family friendly, safe and has so much to offer.

Reviewed on Oct 25, 2025

The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

5 out of 5
Crystal Beach
Save 100% on your flight
Price was $1,573, price is now $912 per person
$912
per person
Feb 12 - Feb 19
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
Save 100% on your flight
Price was $1,138, price is now $715 per person
$715
per person
Feb 12 - Feb 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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

WaterColor Inn & Resort

WaterColor Inn & Resort

4 out of 5
Watercolor
Save 100% on your flight
Price was $991, price is now $742 per person
$742
per person
Feb 1 - Feb 4
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Walton Beach (VPS)
9.4/10 Exceptional! (258 reviews)
Stunning property. They really take care of you here with a lot of value added perks. Easy to checkout bikes for easy ride to Seaside town.

Reviewed on Oct 17, 2025

Miramar Beach Studio w/ Pool, Tennis & Walk to Beach Luau Eastern Sky

Miramar Beach Studio w/ Pool, Tennis & Walk to Beach Luau Eastern Sky

3 out of 5
Save 100% on your flight
Price was $1,262, price is now $972 per person
$972
per person
Feb 21 - Feb 28
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Walton Beach (VPS)
9.6/10 Exceptional! (5 reviews)
This was the perfect place to stay during our vacation! From the personalized text messages to make sure we found everything we needed all the way to reminders for our exit, we couldn’t have asked for a better place to be made feel at home!

Reviewed on Jul 14, 2025

Where to stay in Holiday Isle

Find the best Holiday Isle areas and neighborhoods for the activities you enjoy most. Learn more about Holiday Isle
Default Image

Crystal Beach

4.5/5(75 area reviews)

If you're spending some time in Crystal Beach, Henderson Beach State Park and Henderson Beach are top sights worth seeing.

Find hotels in Crystal Beach

Holiday Isle Hotel Deals

Sandpiper Cove

Sandpiper Cove

2 out of 5
775 Gulf Shore Dr Destin FL
$235 nightly
The price is $265 total per night from Dec 7 to Dec 8
$265 total
Dec 7 - Dec 8
Total with taxes and fees
8.2/10 Very Good! (103 reviews)
Nice place but very poor communication. Was told the room was ready before it actually was. Vacasa’s team came in and brought needed supplies quickly but was a bit frustrating at first. The condo itself was nice, clean, and quiet. Would recommend.

Reviewed on Oct 12, 2025

Sandpiper Cove
716 Gorgeous Gulf View ~ 3 NT HOT Saving ~ Book Nov 15th ~ Hot Tub & Heated Pool

716 Gorgeous Gulf View ~ 3 NT HOT Saving ~ Book Nov 15th ~ Hot Tub & Heated Pool

Destin FL
9.8/10 Exceptional! (35 reviews)
Exquisite location, views, cleanliness! We thoroughly enjoyed our Thanksgiving week stay at this beautiful home. Will definitely return when the opportunity arises. Thank you for sharing with us

Reviewed on Nov 29, 2025

Get rates
716 Gorgeous Gulf View ~ 3 NT HOT Saving ~ Book Nov 15th ~ Hot Tub & Heated Pool
Wow!! Amazing view updated 5th fl bch front condo. Inc beach service

Wow!! Amazing view updated 5th fl bch front condo. Inc beach service

Destin FL
9.6/10 Exceptional! (195 reviews)
Yes it was beautiful

Reviewed on Oct 29, 2025

Get rates
Wow!! Amazing view updated 5th fl bch front condo. Inc beach service
See all 1,911 properties in Holiday 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
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Holiday Isle

Beach Vacation!! #florida #beach

Destin Beaches

4.5/5(568 reviews)

Why not spend a lazy afternoon at Destin Beaches during your trip to Destin? Stroll along the area's waterfront, or simply savor its seafood restaurants.

Destin Beaches
Ajs chili cheese dog

Destin Harbor Boardwalk

4.5/5(751 reviews)

Destin Harbor Boardwalk is just one of the places to see in Destin, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's beautiful beaches and enjoy its lively bars.

Destin Harbor Boardwalk
Big Kahuna's Water and Adventure Park

Big Kahuna's Water and Adventure Park

4/5(109 reviews)

Enjoy the thrill rides with your kiddos at Big Kahuna's Water and Adventure Park during your trip to Destin. Wander the beautiful beaches or discover the beautiful sunsets in this family-friendly area.

Big Kahuna's Water and Adventure Park

Things to do

Dolphin & Sunset Cruises

Dolphin & Sunset Cruises

$40
per adult
96% of travellers recommend
Dolphin & Sunset Cruises
One Hour Harbor Shared Tour with Dolphin Watching

One Hour Harbor Shared Tour with Dolphin Watching

$30
per adult
100% of travellers recommend
One Hour Harbor Shared Tour with Dolphin Watching
SOL y LUNA cruising from the Baytowne Marina for a sunset dolphin cruise.

Sandestin Sunset Eco-Dolphin Cruise Aboard Sol y Luna

$35
per adult
100% of travellers recommend
Sandestin Sunset Eco-Dolphin Cruise Aboard Sol y Luna
See all activities in Destin
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.