Cheap Vacations in Santa Rosa Island

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Santa Rosa Island vacations

Price found within the past 48 hours. Click for updated prices.
Portofino Island Resort

Portofino Island Resort

4 out of 5
Save 100% on your flight
Price was $2,226, price is now $1,505 per person
$1,505
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
El Matador

El Matador

4 out of 5
Okaloosa Island
Save 100% on your flight
Price was $3,150, price is now $2,385 per person
$2,385
per person
Jun 8 - Jun 15
found 22 hours ago
Roundtrip flight included
Dallas (DAL) to Pensacola (PNS)

3-night Santa Rosa Island vacations

Price found within the past 48 hours. Click for updated prices.
Beachside Resort Hotel

Beachside Resort Hotel

2 out of 5
Price was $811, price is now $629 per person
$629
per person
Jun 4 - Jun 7
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Sandestin Golf and Beach Resort

Sandestin Golf and Beach Resort

4 out of 5
Price was $1,141, price is now $829 per person
$829
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
Homewood Suites by Hilton Destin

Homewood Suites by Hilton Destin

3 out of 5
Price was $1,251, price is now $942 per person
$942
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
Back to the Beach by Avantstay with Pool Access

Back to the Beach by Avantstay with Pool Access

3 out of 5
Save 100% on your flight
Price was $2,668, price is now $2,011 per person
$2,011
per person
May 28 - May 31
found 4 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 $1,798, price is now $1,365 per person
$1,365
per person
May 28 - May 31
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Portofino Island Resort

Portofino Island Resort

4 out of 5
Price was $1,566, price is now $1,199 per person
$1,199
per person
May 28 - May 31
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Walk to Santa Rosa Beach Private Pool, Balcony, and Coastal Views

Walk to Santa Rosa Beach Private Pool, Balcony, and Coastal Views

3 out of 5
Save 100% on your flight
Price was $1,939, price is now $1,492 per person
$1,492
per person
Jun 9 - Jun 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
Price was $1,381, price is now $1,070 per person
$1,070
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

5 out of 5
Price was $1,338, price is now $1,040 per person
$1,040
per person
Jun 15 - Jun 18
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Shine on the Shore by Avantstay Pool + Golf Cart

Shine on the Shore by Avantstay Pool + Golf Cart

3 out of 5
Save 100% on your flight
Price was $2,052, price is now $1,606 per person
$1,606
per person
May 28 - May 31
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
SummerPlace Inn Destin

SummerPlace Inn Destin

3 out of 5
Price was $1,089, price is now $853 per person
$853
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
Hibiscus Coffee & Guesthouse

Hibiscus Coffee & Guesthouse

3 out of 5
Price was $999, price is now $794 per person
$794
per person
May 28 - May 31
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)

4-night Santa Rosa Island vacations

Price found within the past 48 hours. Click for updated prices.
OYO Hotel Pensacola I-10 & Hwy 29

OYO Hotel Pensacola I-10 & Hwy 29

2 out of 5
Price was $688, price is now $530 per person
$530
per person
Jun 8 - Jun 12
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Sandestin Golf and Beach Resort

Sandestin Golf and Beach Resort

4 out of 5
Price was $1,085, price is now $740 per person
$740
per person
May 25 - May 29
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
The Lodge at Gulf State Park, A Hilton Hotel

The Lodge at Gulf State Park, A Hilton Hotel

4 out of 5
Save 100% on your flight
Price was $1,407, price is now $996 per person
$996
per person
May 21 - May 25
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Pensacola (PNS)
Hotel Indigo Orange Beach - Gulf Shores by IHG

Hotel Indigo Orange Beach - Gulf Shores by IHG

3.5 out of 5
Price was $1,285, price is now $915 per person
$915
per person
May 21 - May 25
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Pensacola (PNS)
Bay Club of Sandestin

Bay Club of Sandestin

3.5 out of 5
Price was $1,037, price is now $751 per person
$751
per person
May 25 - May 29
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
Save 100% on your flight
Price was $1,649, price is now $1,217 per person
$1,217
per person
Jun 1 - Jun 5
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Carmine by Avantstay 2022 Remodeled Destin Home

Carmine by Avantstay 2022 Remodeled Destin Home

3 out of 5
Save 100% on your flight
Price was $2,583, price is now $1,925 per person
$1,925
per person
May 26 - May 30
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
Oyster Bay Boutique Hotel

Oyster Bay Boutique Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,575, price is now $1,180 per person
$1,180
per person
Jun 8 - Jun 12
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Homewood Suites by Hilton Destin

Homewood Suites by Hilton Destin

3 out of 5
Price was $1,201, price is now $906 per person
$906
per person
May 25 - May 29
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
Price was $1,221, price is now $924 per person
$924
per person
Jun 8 - Jun 12
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Surf & Sand Hotel

Surf & Sand Hotel

2 out of 5
Price was $1,086, price is now $835 per person
$835
per person
Jun 8 - Jun 12
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Baytowne Wharf by Avantstay Sandestin Condo + Communal Pool + Resort Amenities + Near Beach, Dining & Marina

Baytowne Wharf by Avantstay Sandestin Condo + Communal Pool + Resort Amenities + Near Beach, Dining & Marina

4 out of 5
Save 100% on your flight
Price was $1,502, price is now $1,160 per person
$1,160
per person
Jun 11 - Jun 15
found 21 hours ago
Roundtrip flight included
Minneapolis (MSP) to Fort Walton Beach (VPS)

5-night Santa Rosa Island vacations

Price found within the past 48 hours. Click for updated prices.
OYO Hotel Pensacola I-10 & Hwy 29

OYO Hotel Pensacola I-10 & Hwy 29

2 out of 5
Price was $742, price is now $553 per person
$553
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Hotel Indigo Orange Beach - Gulf Shores by IHG

Hotel Indigo Orange Beach - Gulf Shores by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,250, price is now $827 per person
$827
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Portofino Island Resort

Portofino Island Resort

4 out of 5
Save 100% on your flight
Price was $2,226, price is now $1,505 per person
$1,505
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Sandestin Golf and Beach Resort

Sandestin Golf and Beach Resort

4 out of 5
Price was $1,126, price is now $763 per person
$763
per person
Jun 1 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
The Lodge at Gulf State Park, A Hilton Hotel

The Lodge at Gulf State Park, A Hilton Hotel

4 out of 5
Save 100% on your flight
Price was $1,374, price is now $960 per person
$960
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Bay Club of Sandestin

Bay Club of Sandestin

3.5 out of 5
Price was $1,303, price is now $921 per person
$921
per person
Jun 5 - Jun 10
found 4 hours ago
Roundtrip flight included
Chicago (CHI) to Fort Walton Beach (VPS)
The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

5 out of 5
Save 100% on your flight
Price was $1,872, price is now $1,329 per person
$1,329
per person
Jun 1 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Candlewood Suites Pensacola - University Area by IHG

Candlewood Suites Pensacola - University Area by IHG

2.5 out of 5
Price was $859, price is now $627 per person
$627
per person
Jun 5 - Jun 10
found 4 hours ago
Roundtrip flight included
Chicago (CHI) to Pensacola (PNS)
Embassy Suites by Hilton Destin Miramar Beach

Embassy Suites by Hilton Destin Miramar Beach

3.5 out of 5
Save 100% on your flight
Price was $1,604, price is now $1,172 per person
$1,172
per person
Jun 1 - Jun 6
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 $1,363, price is now $1,002 per person
$1,002
per person
Jun 1 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Oyster Bay Boutique Hotel

Oyster Bay Boutique Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,858, price is now $1,376 per person
$1,376
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Beachside Resort Hotel

Beachside Resort Hotel

2 out of 5
Price was $915, price is now $690 per person
$690
per person
May 24 - May 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)

6-7 night Santa Rosa 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 $1,179, price is now $895 per person
$895
per person
May 27 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Sandestin Golf and Beach Resort

Sandestin Golf and Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,470, price is now $908 per person
$908
per person
May 27 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Landing Apartments Santa Rosa Beach

Landing Apartments Santa Rosa Beach

4 out of 5
Save 100% on your flight
Price was $2,057, price is now $1,325 per person
$1,325
per person
May 24 - May 31
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Bay Club of Sandestin

Bay Club of Sandestin

3.5 out of 5
Save 100% on your flight
Price was $1,411, price is now $933 per person
$933
per person
May 27 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Sea Love by Avantstay Coastal Retreat Near Miramar Beach Pool Access, Patio + Grill

Sea Love by Avantstay Coastal Retreat Near Miramar Beach Pool Access, Patio + Grill

3 out of 5
Save 100% on your flight
Price was $5,589, price is now $3,902 per person
$3,902
per person
May 30 - Jun 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
Hibiscus Coffee & Guesthouse

Hibiscus Coffee & Guesthouse

3 out of 5
Save 100% on your flight
Price was $1,592, price is now $1,133 per person
$1,133
per person
May 24 - May 31
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Back to the Beach by Avantstay with Pool Access

Back to the Beach by Avantstay with Pool Access

3 out of 5
Save 100% on your flight
Price was $5,374, price is now $3,839 per person
$3,839
per person
May 24 - May 31
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Embassy Suites by Hilton Destin Miramar Beach

Embassy Suites by Hilton Destin Miramar Beach

3.5 out of 5
Save 100% on your flight
Price was $1,629, price is now $1,178 per person
$1,178
per person
May 27 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
Residence Inn by Marriott Sandestin at Grand Boulevard

Residence Inn by Marriott Sandestin at Grand Boulevard

3 out of 5
Save 100% on your flight
Price was $1,344, price is now $973 per person
$973
per person
May 27 - Jun 3
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 $1,317, price is now $971 per person
$971
per person
May 27 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)
El Matador

El Matador

4 out of 5
Save 100% on your flight
Price was $3,150, price is now $2,385 per person
$2,385
per person
Jun 8 - Jun 15
found 22 hours ago
Roundtrip flight included
Dallas (DAL) to Pensacola (PNS)
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 $1,840, price is now $1,411 per person
$1,411
per person
May 27 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Fort Walton Beach (VPS)

Flight deals to Santa Rosa Island

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

Thu, May 14 - Sat, May 16
BWI
Baltimore
PNS
Pensacola
$167 Roundtrip, found 5 days ago
$167
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Thu, May 14 from Baltimore to Pensacola, returning Sat, May 16, priced at $167 found 5 days ago
Wed, Jun 10 - Sun, Jun 14
ATL
Atlanta
PNS
Pensacola
$188 Roundtrip, found 3 days ago
$188
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed, Jun 10 from Atlanta to Pensacola, returning Sun, Jun 14, priced at $188 found 3 days ago
Thu, May 28 - Sun, May 31
MSP
Minneapolis
VPS
Fort Walton Beach
$196 Roundtrip, found 3 days ago
$196
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, May 28 from Minneapolis to Fort Walton Beach, returning Sun, May 31, priced at $196 found 3 days ago

Top rated hotels for your Santa Rosa 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
8.35 mi from city center
$182 nightly
The price is $205 total per night
$205 total
Apr 26 - Apr 27
Total with taxes and fees
Located in Fort Walton Beach (Okaloosa Island), The Island Resort at Fort Walton Beach is within a 15-minute walk of Fort Walton Beaches and Okaloosa Island Beach.
Pool
Hot Tub
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
165 Fort Pickens Road Pensacola Beach FL
Free Cancellation
Reserve now, pay when you stay
25.36 mi from city center
$285 nightly
The price is $320 total per night
$320 total
Apr 20 - Apr 21
Total with taxes and fees
With a stay at The Pensacola Beach Resort in Pensacola Beach (Villa Sabine), you'll be a 1-minute drive from Pensacola Beach Beaches and 6 minutes from Opal Beach.
Pool
Parking 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
6.82 mi from city center
$169 nightly
The price is $191 total per night
$191 total
Apr 26 - Apr 27
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.
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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.