Cheap Vacations in Okaloosa Island

Choose two or more items and save on your trip:

Okaloosa Island vacations

Price found within the past 48 hours. Click for updated prices.
The Lodge 30A

The Lodge 30A

2 out of 5
Seagrove Beach
Price was $1,255, price is now $1,019 per person
$1,019
per person
Oct 22 - Oct 26
found 13 hours ago
Roundtrip flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Coconut Cove by Avantstay Hot Tub Deck + 2 Pools Golf Cart Rentals via 30A Gulf Carts

Coconut Cove by Avantstay Hot Tub Deck + 2 Pools Golf Cart Rentals via 30A Gulf Carts

3 out of 5
Save 100% on your flight
Price was $2,151, price is now $1,722 per person
$1,722
per person
Oct 17 - Oct 24
found 12 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Barefoot Paradise by Avantstay Walk to Beach, Pool, Bikes

Barefoot Paradise by Avantstay Walk to Beach, Pool, Bikes

3 out of 5
Save 100% on your flight
Price was $1,954, price is now $1,572 per person
$1,572
per person
Oct 17 - Oct 24
found 12 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Emerald Gem by Avantstay Pool Access, 3mins to Beach!

Emerald Gem by Avantstay Pool Access, 3mins to Beach!

3 out of 5
Price was $1,667, price is now $1,341 per person
$1,341
per person
Oct 17 - Oct 24
found 12 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
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 $3,346, price is now $2,705 per person
$2,705
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
Golden Hour Retreat by Avantstay Golf Cart + Pool + Hot Tub + BBQ Gated + Steps to Sand

Golden Hour Retreat by Avantstay Golf Cart + Pool + Hot Tub + BBQ Gated + Steps to Sand

3 out of 5
Price was $1,607, price is now $1,308 per person
$1,308
per person
Oct 20 - Oct 25
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Fort Walton Beach (VPS)
Steps to the Beach, Pool + Hot Tub Renovated Retreat Sea Haven by Avantstay

Steps to the Beach, Pool + Hot Tub Renovated Retreat Sea Haven by Avantstay

3 out of 5
Seagrove Beach
Price was $1,324, price is now $1,079 per person
$1,079
per person
Oct 17 - Oct 24
found 12 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Landing Furnished Apartments near THSP

Landing Furnished Apartments near THSP

3 out of 5
Price was $1,338, price is now $1,104 per person
$1,104
per person
Oct 14 - Oct 18
found 16 hours ago
Roundtrip flight included
Minneapolis (MSP) to Fort Walton Beach (VPS)
Coral By Avantstay Gorgeous Three Story Home w/ Two Balconies

Coral By Avantstay Gorgeous Three Story Home w/ Two Balconies

3.5 out of 5
Crystal Beach
Price was $1,718, price is now $1,427 per person
$1,427
per person
Oct 23 - Oct 30
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Fort Walton Beach (VPS)

3-night Okaloosa Island vacations

Price found within the past 48 hours. Click for updated prices.
SummerPlace Inn Destin

SummerPlace Inn Destin

3 out of 5
Price was $429, price is now $379 per person
$379
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Club Wyndham at Majestic Sun

Club Wyndham at Majestic Sun

3.5 out of 5
Price was $876, price is now $737 per person
$737
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
The Bluefin - Ultra Luxury Beach Home

The Bluefin - Ultra Luxury Beach Home

3 out of 5
Price was $1,808, price is now $1,545 per person
$1,545
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
WaterSound Inn

WaterSound Inn

4 out of 5
Price was $1,461, price is now $1,257 per person
$1,257
per person
Nov 5 - Nov 8
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Walton Beach (VPS)
Harborside by Avantstay Expansive Destin Retreat

Harborside by Avantstay Expansive Destin Retreat

3 out of 5
Price was $2,305, price is now $1,985 per person
$1,985
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Walton Beach (VPS)
Bay Club of Sandestin

Bay Club of Sandestin

3.5 out of 5
Price was $732, price is now $630 per person
$630
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Pelican Beach 0815 2 Bedroom Condo by Pelican Beach Management

Pelican Beach 0815 2 Bedroom Condo by Pelican Beach Management

3 out of 5
Price was $1,249, price is now $1,078 per person
$1,078
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Fort Walton Beach (VPS)
The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

5 out of 5
Price was $991, price is now $861 per person
$861
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Homewood Suites by Hilton Destin

Homewood Suites by Hilton Destin

3 out of 5
Price was $539, price is now $469 per person
$469
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Fort Walton Beach (VPS)
WaterColor Inn & Resort

WaterColor Inn & Resort

4 out of 5
Price was $1,411, price is now $1,241 per person
$1,241
per person
Oct 19 - Oct 22
found 15 hours ago
Roundtrip flight included
Minneapolis (MSP) to Fort Walton Beach (VPS)
Hibiscus Coffee & Guesthouse

Hibiscus Coffee & Guesthouse

3 out of 5
Price was $527, price is now $465 per person
$465
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Fort Walton Beach (VPS)
Emerald Villa by Avantstay Lakefront + Communal Pool + Balcony Views + Near the Beach

Emerald Villa by Avantstay Lakefront + Communal Pool + Balcony Views + Near the Beach

3 out of 5
Price was $1,020, price is now $904 per person
$904
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)

4-night Okaloosa Island vacations

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 $837, price is now $710 per person
$710
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
The Lodge 30A

The Lodge 30A

2 out of 5
Price was $1,255, price is now $1,019 per person
$1,019
per person
Oct 22 - Oct 26
found 13 hours ago
Roundtrip flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Club Wyndham at Majestic Sun

Club Wyndham at Majestic Sun

3.5 out of 5
Price was $1,068, price is now $879 per person
$879
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Landing Furnished Apartments near THSP

Landing Furnished Apartments near THSP

3 out of 5
Price was $1,338, price is now $1,104 per person
$1,104
per person
Oct 14 - Oct 18
found 16 hours ago
Roundtrip flight included
Minneapolis (MSP) to Fort Walton Beach (VPS)
The Bluefin - Ultra Luxury Beach Home

The Bluefin - Ultra Luxury Beach Home

3 out of 5
Price was $2,283, price is now $1,913 per person
$1,913
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Harborside by Avantstay Expansive Destin Retreat

Harborside by Avantstay Expansive Destin Retreat

3 out of 5
Price was $2,647, price is now $2,237 per person
$2,237
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Fort Walton Beach (VPS)
Landing Apartments Santa Rosa Beach

Landing Apartments Santa Rosa Beach

4 out of 5
Price was $1,151, price is now $975 per person
$975
per person
Oct 22 - Oct 26
found 13 hours ago
Roundtrip flight included
Chicago (CHI) to Fort Walton Beach (VPS)
WaterSound Inn

WaterSound Inn

4 out of 5
Price was $1,824, price is now $1,549 per person
$1,549
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

5 out of 5
Price was $1,220, price is now $1,045 per person
$1,045
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
30A Inn & Suites

30A Inn & Suites

3 out of 5
Price was $897, price is now $769 per person
$769
per person
Oct 22 - Oct 26
found 13 hours ago
Roundtrip flight included
Chicago (CHI) to Fort Walton Beach (VPS)
The Beach Grove by Avantstay Gulf-view Balcony + King Suite + Sleeps 6 On the Sand + Pool Access

The Beach Grove by Avantstay Gulf-view Balcony + King Suite + Sleeps 6 On the Sand + Pool Access

4 out of 5
Price was $1,073, price is now $935 per person
$935
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)

5-night Okaloosa Island vacations

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Destin E - Commons Mall area by IHG

Holiday Inn Express Destin E - Commons Mall area by IHG

3.5 out of 5
Price was $918, price is now $754 per person
$754
per person
Oct 21 - Oct 26
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
Landing Furnished Apartments near THSP

Landing Furnished Apartments near THSP

3 out of 5
Price was $1,379, price is now $1,064 per person
$1,064
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Fort Walton Beach (VPS)
The Bluefin - Ultra Luxury Beach Home

The Bluefin - Ultra Luxury Beach Home

3 out of 5
Save 100% on your flight
Price was $2,660, price is now $2,069 per person
$2,069
per person
Oct 21 - Oct 26
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
Harborside by Avantstay Expansive Destin Retreat

Harborside by Avantstay Expansive Destin Retreat

3 out of 5
Save 100% on your flight
Price was $3,346, price is now $2,705 per person
$2,705
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
Sandestin Golf and Beach Resort

Sandestin Golf and Beach Resort

4 out of 5
Price was $1,064, price is now $861 per person
$861
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
Golden Hour Retreat by Avantstay Golf Cart + Pool + Hot Tub + BBQ Gated + Steps to Sand

Golden Hour Retreat by Avantstay Golf Cart + Pool + Hot Tub + BBQ Gated + Steps to Sand

3 out of 5
Price was $1,607, price is now $1,308 per person
$1,308
per person
Oct 20 - Oct 25
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Fort Walton Beach (VPS)
Emerald Villa by Avantstay Lakefront + Communal Pool + Balcony Views + Near the Beach

Emerald Villa by Avantstay Lakefront + Communal Pool + Balcony Views + Near the Beach

3 out of 5
Price was $1,439, price is now $1,190 per person
$1,190
per person
Oct 20 - Oct 25
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Fort Walton Beach (VPS)
30A Inn & Suites

30A Inn & Suites

3 out of 5
Price was $952, price is now $793 per person
$793
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Fort Walton Beach (VPS)
The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

5 out of 5
Price was $1,550, price is now $1,290 per person
$1,290
per person
Oct 21 - Oct 26
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
Terrace At Pelican Beach 0507 3 Bedroom Condo

Terrace At Pelican Beach 0507 3 Bedroom Condo

3.5 out of 5
Price was $1,899, price is now $1,596 per person
$1,596
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
Arcade, Bar, Prominence Resort Pool and Gym Access, Close to Beach Sea Happy

Arcade, Bar, Prominence Resort Pool and Gym Access, Close to Beach Sea Happy

3 out of 5
Price was $1,882, price is now $1,598 per person
$1,598
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Fort Walton Beach (VPS)
Hilton Grand Vacations Club in Sandestin Golf & Beach Resort

Hilton Grand Vacations Club in Sandestin Golf & Beach Resort

3 out of 5
Price was $1,324, price is now $1,131 per person
$1,131
per person
Oct 21 - Oct 26
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)

6-7 night Okaloosa Island vacations

Price found within the past 48 hours. Click for updated prices.
Gulf Terrace Getaway by Avantstay Shared Pool + Tennis Near Henderson Beach + Destin Commons

Gulf Terrace Getaway by Avantstay Shared Pool + Tennis Near Henderson Beach + Destin Commons

3 out of 5
Price was $1,147, price is now $962 per person
$962
per person
Oct 23 - Oct 30
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Fort Walton Beach (VPS)
The Bluefin - Ultra Luxury Beach Home

The Bluefin - Ultra Luxury Beach Home

3 out of 5
Save 100% on your flight
Price was $3,131, price is now $2,237 per person
$2,237
per person
Oct 23 - Oct 30
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Fort Walton Beach (VPS)
Sandestin Golf and Beach Resort

Sandestin Golf and Beach Resort

4 out of 5
Price was $1,294, price is now $1,008 per person
$1,008
per person
Oct 23 - Oct 30
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Fort Walton Beach (VPS)
Coconut Cove by Avantstay Hot Tub Deck + 2 Pools Golf Cart Rentals via 30A Gulf Carts

Coconut Cove by Avantstay Hot Tub Deck + 2 Pools Golf Cart Rentals via 30A Gulf Carts

3 out of 5
Save 100% on your flight
Price was $2,151, price is now $1,722 per person
$1,722
per person
Oct 17 - Oct 24
found 12 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Barefoot Paradise by Avantstay Walk to Beach, Pool, Bikes

Barefoot Paradise by Avantstay Walk to Beach, Pool, Bikes

3 out of 5
Save 100% on your flight
Price was $1,954, price is now $1,572 per person
$1,572
per person
Oct 17 - Oct 24
found 12 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Emerald Gem by Avantstay Pool Access, 3mins to Beach!

Emerald Gem by Avantstay Pool Access, 3mins to Beach!

3 out of 5
Price was $1,667, price is now $1,341 per person
$1,341
per person
Oct 17 - Oct 24
found 12 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
WaterSound Inn

WaterSound Inn

4 out of 5
Save 100% on your flight
Price was $2,712, price is now $2,210 per person
$2,210
per person
Oct 17 - Oct 24
found 12 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Steps to the Beach, Pool + Hot Tub Renovated Retreat Sea Haven by Avantstay

Steps to the Beach, Pool + Hot Tub Renovated Retreat Sea Haven by Avantstay

3 out of 5
Price was $1,324, price is now $1,079 per person
$1,079
per person
Oct 17 - Oct 24
found 12 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

5 out of 5
Price was $1,870, price is now $1,525 per person
$1,525
per person
Oct 23 - Oct 30
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Fort Walton Beach (VPS)
The Lodge 30A

The Lodge 30A

2 out of 5
Price was $1,321, price is now $1,087 per person
$1,087
per person
Oct 17 - Oct 24
found 12 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Coral By Avantstay Gorgeous Three Story Home w/ Two Balconies

Coral By Avantstay Gorgeous Three Story Home w/ Two Balconies

3.5 out of 5
Price was $1,718, price is now $1,427 per person
$1,427
per person
Oct 23 - Oct 30
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Fort Walton Beach (VPS)
Emerald Villa by Avantstay Lakefront + Communal Pool + Balcony Views + Near the Beach

Emerald Villa by Avantstay Lakefront + Communal Pool + Balcony Views + Near the Beach

3 out of 5
Price was $1,569, price is now $1,305 per person
$1,305
per person
Oct 23 - Oct 30
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Fort Walton Beach (VPS)

Flight deals to Okaloosa Island

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Thu, Dec 24 - Thu, Dec 31
IND
Indianapolis
VPS
Fort Walton Beach
$171 Roundtrip, found 1 day ago
$171
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Thu, Dec 24 from Indianapolis to Fort Walton Beach, returning Thu, Dec 31, priced at $171 found 1 day ago
Sun, Nov 1 - Thu, Nov 5
MSP
Minneapolis
VPS
Fort Walton Beach
$189 Roundtrip, found 1 day ago
$189
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Sun, Nov 1 from Minneapolis to Fort Walton Beach, returning Thu, Nov 5, priced at $189 found 1 day ago
Wed, Nov 4 - Sat, Nov 7
STL
St. Louis
VPS
Fort Walton Beach
$255 Roundtrip, found 12 hours ago
$255
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Wed, Nov 4 from St. Louis to Fort Walton Beach, returning Sat, Nov 7, priced at $255 found 12 hours ago

Top rated hotels for your Okaloosa Island vacation

The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
Miracle Strip Parkway Southeast, 1500 Fort Walton Beach FL
Free Cancellation
Reserve now, pay when you stay
0.58 mi from Okaloosa Island
$145 nightly
The price is $163 total per night
$163 total
Sep 30 - Oct 1
Total with taxes and fees
With a stay at The Island Resort at Fort Walton Beach in Fort Walton Beach (Okaloosa Island), you'll be steps from Okaloosa Island Beach and 9 minutes by foot from Fort Walton Beaches.
Pool
Hot Tub
Wavecrest Lodge

Wavecrest Lodge

2.5 out of 5
540 Santa Rosa Blvd Fort Walton Beach FL
Free Cancellation
Reserve now, pay when you stay
1.08 mi from Okaloosa Island
$148 nightly
The price is $167 total per night
$167 total
Sep 18 - Sep 19
Total with taxes and fees
With a stay at Wavecrest Lodge in Fort Walton Beach (Okaloosa Island), you'll be steps from Okaloosa Island Beach and Fort Walton Beaches.
Pool
Breakfast included
Wyndham Garden Fort Walton Beach Destin

Wyndham Garden Fort Walton Beach Destin

3 out of 5
573 Santa Rosa Blvd Fort Walton Beach FL
Free Cancellation
Reserve now, pay when you stay
1.01 mi from Okaloosa Island
$131 nightly
The price is $148 total per night
$148 total
Sep 20 - Sep 21
Total with taxes and fees
With a stay at Wyndham Garden Fort Walton Beach Destin in Fort Walton Beach (Okaloosa Island), you'll be within a 5-minute walk of Okaloosa Island Beach and Fort Walton Beaches.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Okaloosa Island
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 Picks

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.