Holiday Isle Vacations from $642

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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 $890, price is now $642 per person
$642
per person
Dec 7 - Dec 13
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Walton Beach (VPS)
9/10 Wonderful! (153 reviews)
It was a beautiful place to stay and the staff were so friendly and helpful.

Reviewed on Jul 3, 2025

The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

5 out of 5
Crystal Beach
Save 100% on your flight
Price was $1,841, price is now $1,244 per person
$1,244
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Walton Beach (VPS)
9.2/10 Wonderful! (1,005 reviews)
The resort was perfect for our family of 3 kids for a fall break trip! Service at all of the dining options was excellent. Really enjoyed the pools and the private beach with chair service!

Reviewed on Oct 14, 2025

Sandestin Golf and Beach Resort

Sandestin Golf and Beach Resort

4 out of 5
Price was $1,406, price is now $988 per person
$988
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Walton Beach (VPS)
7.8/10 Good! (3,822 reviews)
We Definitely will be back soon..

Reviewed on Oct 15, 2025

Harborside by Avantstay Expansive Destin Retreat

Harborside by Avantstay Expansive Destin Retreat

3 out of 5
Holiday Isle
Save 100% on your flight
Price was $3,281, price is now $2,417 per person
$2,417
per person
Jan 3 - Jan 10
found 20 hours ago
Roundtrip flight included
Minneapolis (MSP) to Fort Walton Beach (VPS)
8/10 Very Good! (1 review)
Beach Street Cottages

Beach Street Cottages

3.5 out of 5
Price was $941, price is now $701 per person
$701
per person
Dec 7 - Dec 13
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Walton Beach (VPS)
9/10 Wonderful! (22 reviews)

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
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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
$248 nightly
The price is $280 total per night from Oct 21 to Oct 22
$280 total
Oct 21 - Oct 22
Total with taxes and fees
8.4/10 Very Good! (100 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
HARBOR OASIS-WATERFRONT/BOAT/PWC SLIPS/Dock/Pool/Spa/ Kayaks/Bikes/Volleyball++

HARBOR OASIS-WATERFRONT/BOAT/PWC SLIPS/Dock/Pool/Spa/ Kayaks/Bikes/Volleyball++

Destin
9.8/10 Exceptional! (30 reviews)
"Loved this home. The outside area is fabulous!!"

Reviewed on Aug 27, 2025

Get rates
HARBOR OASIS-WATERFRONT/BOAT/PWC SLIPS/Dock/Pool/Spa/ Kayaks/Bikes/Volleyball++
Stay directly on the beach! Beautiful Weather! Book today.. Fall Discount 149nt.

Stay directly on the beach! Beautiful Weather! Book today.. Fall Discount 149nt.

destin
8.2/10 Very Good! (51 reviews)
"Great spot! Right on the beach. Community is clean, friendly, and peaceful."

Reviewed on Sep 22, 2025

Get rates
Stay directly on the beach! Beautiful Weather! Book today.. Fall Discount 149nt.
See all 1,920 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

Nothing says vacation like spending a carefree day at Destin Beaches, a popular beach in Destin. Stroll along the area's waterfront, or simply savor its top-notch restaurants.

Destin Beaches
Big Kahuna's Water and Adventure Park

Big Kahuna's Water and Adventure Park

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
Ajs chili cheese dog

Destin Harbor Boardwalk

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

Things to do

Dolphin & Sunset Cruises

Dolphin & Sunset Cruises

$40
per adult
96% of travellers recommend
Dolphin & Sunset Cruises
SunVenture Cruises Eco-Dolphin Cruise Catamaran

Destin Harbor Sunset Eco Dolphin Cruise

$35
per adult
80% of travellers recommend
Destin Harbor Sunset Eco Dolphin Cruise
Beautiful waters of Destin

Jetski Waverunner Rental - Destin

$95
per traveler
90% of travellers recommend
Jetski Waverunner Rental - Destin
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.