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.
Surf & Sand Hotel

Surf & Sand Hotel

2 out of 5
Price was $718, price is now $640 per person
$640
per person
Sep 2 - Sep 5
found 9 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Pensacola (PNS)
Emerald Isle

Emerald Isle

3 out of 5
Villa Primera
Price was $1,359, price is now $1,119 per person
$1,119
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Pensacola (PNS)
Portofino Island Resort

Portofino Island Resort

4 out of 5
Price was $1,612, price is now $1,350 per person
$1,350
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Pensacola (PNS)
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
Villa Sabine
Price was $1,001, price is now $850 per person
$850
per person
Sep 2 - Sep 5
found 9 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Pensacola (PNS)
The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
Okaloosa Island
Price was $811, price is now $704 per person
$704
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Pensacola (PNS)
Beach Club Resort Residence and Spa

Beach Club Resort Residence and Spa

4.5 out of 5
Villa Primera
Price was $1,212, price is now $1,061 per person
$1,061
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Pensacola (PNS)

3-night Santa Rosa Island vacations

Price found within the past 48 hours. Click for updated prices.
Studio 6 Pensacola, FL - West I-10

Studio 6 Pensacola, FL - West I-10

2.5 out of 5
Price was $523, price is now $439 per person
$439
per person
Sep 2 - Sep 5
found 9 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Pensacola (PNS)
Oyster Bay Boutique Hotel

Oyster Bay Boutique Hotel

3.5 out of 5
Price was $1,173, price is now $910 per person
$910
per person
Sep 2 - Sep 5
found 9 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Pensacola (PNS)
Landing Modern 1BD in Warrington

Landing Modern 1BD in Warrington

3 out of 5
Price was $1,134, price is now $931 per person
$931
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Pensacola (PNS)
Emerald Isle

Emerald Isle

3 out of 5
Price was $1,359, price is now $1,119 per person
$1,119
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Pensacola (PNS)
Portofino Island Resort

Portofino Island Resort

4 out of 5
Price was $1,612, price is now $1,350 per person
$1,350
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Pensacola (PNS)
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
Price was $1,001, price is now $850 per person
$850
per person
Sep 2 - Sep 5
found 9 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Pensacola (PNS)
The Lodge at Gulf State Park, A Hilton Hotel

The Lodge at Gulf State Park, A Hilton Hotel

4 out of 5
Price was $1,084, price is now $924 per person
$924
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Pensacola (PNS)
The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
Price was $811, price is now $704 per person
$704
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Pensacola (PNS)
Spanish Key 505 3 Bedrooms 3 Baths Next to the Flora-bama

Spanish Key 505 3 Bedrooms 3 Baths Next to the Flora-bama

2 out of 5
Price was $1,523, price is now $1,325 per person
$1,325
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Pensacola (PNS)
Landing Apartments - North Central Pensacola

Landing Apartments - North Central Pensacola

4 out of 5
Price was $647, price is now $566 per person
$566
per person
Aug 27 - Aug 30
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Beach Club Resort Residence and Spa

Beach Club Resort Residence and Spa

4.5 out of 5
Price was $1,212, price is now $1,061 per person
$1,061
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Pensacola (PNS)
Landing Apartments - Northwest Pensacola

Landing Apartments - Northwest Pensacola

4 out of 5
Price was $658, price is now $578 per person
$578
per person
Sep 2 - Sep 5
found 9 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Pensacola (PNS)

4-night Santa Rosa Island vacations

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Orange Beach Beachfront

Hilton Garden Inn Orange Beach Beachfront

3 out of 5
Price was $823, price is now $728 per person
$728
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
Price was $1,358, price is now $1,131 per person
$1,131
per person
Sep 2 - Sep 6
found 9 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Pensacola (PNS)
Sundrift Inn

Sundrift Inn

3 out of 5
Price was $1,075, price is now $896 per person
$896
per person
Sep 3 - Sep 7
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Pensacola (PNS)
Landing Furnished Apartments - Orange Beach 

Landing Furnished Apartments - Orange Beach 

3 out of 5
Price was $932, price is now $780 per person
$780
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
Price was $880, price is now $748 per person
$748
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Pensacola (PNS)
The Lodge at Gulf State Park, A Hilton Hotel

The Lodge at Gulf State Park, A Hilton Hotel

4 out of 5
Price was $1,023, price is now $885 per person
$885
per person
Sep 10 - Sep 14
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
Price was $894, price is now $780 per person
$780
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Surf & Sand Hotel

Surf & Sand Hotel

2 out of 5
Price was $910, price is now $797 per person
$797
per person
Sep 2 - Sep 6
found 9 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Pensacola (PNS)
The Original Romar House B&B Inn

The Original Romar House B&B Inn

4 out of 5
Price was $1,008, price is now $886 per person
$886
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
La Quinta Inn & Suites by Wyndham Fort Walton Beach

La Quinta Inn & Suites by Wyndham Fort Walton Beach

3 out of 5
Price was $1,073, price is now $961 per person
$961
per person
Sep 3 - Sep 7
found 8 hours ago
Roundtrip non-stop flight included
Cedar Rapids (CID) to Pensacola (PNS)
Super Clean Pool Beach Dining Fun

Super Clean Pool Beach Dining Fun

2 out of 5
Price was $1,293, price is now $1,166 per person
$1,166
per person
Sep 3 - Sep 7
found 14 hours ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
El Matador

El Matador

4 out of 5
Price was $1,161, price is now $1,050 per person
$1,050
per person
Sep 2 - Sep 6
found 4 hours ago
Roundtrip flight included
Baltimore (BWI) to Pensacola (PNS)

5-night Santa Rosa Island vacations

Price found within the past 48 hours. Click for updated prices.
Studio 6 Pensacola, FL - West I-10

Studio 6 Pensacola, FL - West I-10

2.5 out of 5
Price was $593, price is now $486 per person
$486
per person
Aug 27 - Sep 1
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Sundrift Inn

Sundrift Inn

3 out of 5
Price was $1,097, price is now $750 per person
$750
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Pensacola (PNS)
The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
Price was $1,095, price is now $793 per person
$793
per person
Aug 28 - Sep 2
found 16 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Pensacola (PNS)
Wavecrest Lodge

Wavecrest Lodge

2.5 out of 5
Price was $1,112, price is now $893 per person
$893
per person
Sep 3 - Sep 8
found 7 hours ago
Roundtrip non-stop flight included
Cedar Rapids (CID) to Pensacola (PNS)
Oyster Bay Boutique Hotel

Oyster Bay Boutique Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,561, price is now $1,257 per person
$1,257
per person
Aug 27 - Sep 1
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Holiday Inn Express & Suites Fort Walton Beach Eglin Area by IHG

Holiday Inn Express & Suites Fort Walton Beach Eglin Area by IHG

2.5 out of 5
Price was $763, price is now $617 per person
$617
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Pensacola (PNS)
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
Price was $1,219, price is now $990 per person
$990
per person
Aug 27 - Sep 1
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Landing Apartments - North Central Pensacola

Landing Apartments - North Central Pensacola

4 out of 5
Price was $796, price is now $658 per person
$658
per person
Aug 27 - Sep 1
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Landing Apartments - Northwest Pensacola

Landing Apartments - Northwest Pensacola

4 out of 5
Price was $774, price is now $640 per person
$640
per person
Aug 27 - Sep 1
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Landing Apartments Pensacola - Belleview Heights

Landing Apartments Pensacola - Belleview Heights

4 out of 5
Price was $727, price is now $611 per person
$611
per person
Aug 27 - Sep 1
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Sleep Inn & Suites Fort Walton Beach - Destin West

Sleep Inn & Suites Fort Walton Beach - Destin West

3 out of 5
Price was $728, price is now $619 per person
$619
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Pensacola (PNS)
Surf & Sand Hotel

Surf & Sand Hotel

2 out of 5
Price was $895, price is now $761 per person
$761
per person
Aug 27 - Sep 1
found 7 hours 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.
Landing Apartments Pensacola - Belleview Heights

Landing Apartments Pensacola - Belleview Heights

4 out of 5
Price was $893, price is now $700 per person
$700
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)
The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
Price was $1,403, price is now $1,051 per person
$1,051
per person
Sep 3 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Pensacola (PNS)
Landing Apartments - North Central Pensacola

Landing Apartments - North Central Pensacola

4 out of 5
Price was $992, price is now $758 per person
$758
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)
Sundrift Inn

Sundrift Inn

3 out of 5
Price was $1,362, price is now $1,067 per person
$1,067
per person
Aug 24 - Aug 31
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Oyster Bay Boutique Hotel

Oyster Bay Boutique Hotel

3.5 out of 5
Save 100% on your flight
Price was $2,091, price is now $1,648 per person
$1,648
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,570, price is now $1,245 per person
$1,245
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)
Wavecrest Lodge

Wavecrest Lodge

2.5 out of 5
Price was $1,260, price is now $1,001 per person
$1,001
per person
Aug 24 - Aug 31
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Landing Apartments - Northwest Pensacola

Landing Apartments - Northwest Pensacola

4 out of 5
Price was $954, price is now $764 per person
$764
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)
Holiday Inn Pensacola - University Area by IHG

Holiday Inn Pensacola - University Area by IHG

3 out of 5
Price was $957, price is now $773 per person
$773
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)
Holiday Inn Express & Suites Pensacola Airport North – I-10 by IHG

Holiday Inn Express & Suites Pensacola Airport North – I-10 by IHG

2.5 out of 5
Price was $889, price is now $723 per person
$723
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)
El Matador

El Matador

4 out of 5
Price was $1,489, price is now $1,220 per person
$1,220
per person
Aug 24 - Aug 31
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Emerald Isle

Emerald Isle

3 out of 5
Price was $2,374, price is now $1,945 per person
$1,945
per person
Sep 4 - Sep 11
found 8 hours ago
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)

Flight deals to Santa Rosa Island

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

Wed, Sep 2 - Sun, Sep 6
ATL
Atlanta
PNS
Pensacola
$224 Roundtrip, found 2 days ago
$224
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Sep 2 from Atlanta to Pensacola, returning Sun, Sep 6, priced at $224 found 2 days ago
Sat, Oct 3 - Thu, Oct 8
MSP
Minneapolis
VPS
Fort Walton Beach
$226 Roundtrip, found 5 days ago
$226
Roundtrip
found 5 days ago
Select Sun Country Airlines flight, departing Sat, Oct 3 from Minneapolis to Fort Walton Beach, returning Thu, Oct 8, priced at $226 found 5 days ago
Thu, Aug 6 - Thu, Aug 13
DFW
Dallas
PNS
Pensacola
$255 Roundtrip, found 2 days ago
$255
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Aug 6 from Dallas to Pensacola, returning Thu, Aug 13, priced at $255 found 2 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
$187 nightly
The price is $210 total per night
$210 total
Aug 19 - Aug 20
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 6 minutes by foot from Boardwalk on Okaloosa Island.
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
$315 nightly
The price is $354 total per night
$354 total
Aug 16 - Aug 17
Total with taxes and fees
With a stay at The Pensacola Beach Resort in Pensacola Beach (Villa Sabine), you'll be a 3-minute walk from Pensacola Beach Beaches and 11 minutes by foot from Pensacola Beach Gulf Pier.
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
$147 nightly
The price is $166 total per night
$166 total
Aug 17 - Aug 18
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.