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.
Sundrift Inn

Sundrift Inn

3 out of 5
Okaloosa Island
Price was $800, price is now $628 per person
$628
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Pensacola (PNS)
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
Villa Sabine
Price was $992, price is now $788 per person
$788
per person
Oct 24 - Oct 28
found 22 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Pensacola (PNS)
Portofino Island Resort

Portofino Island Resort

4 out of 5
Save 100% on your flight
Price was $1,962, price is now $1,617 per person
$1,617
per person
Oct 15 - Oct 22
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
Okaloosa Island
Price was $798, price is now $658 per person
$658
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Pensacola (PNS)
Wavecrest Lodge

Wavecrest Lodge

2.5 out of 5
Okaloosa Island
Price was $763, price is now $629 per person
$629
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Pensacola (PNS)
SpringHill Suites by Marriott Navarre Oceanfront

SpringHill Suites by Marriott Navarre Oceanfront

4 out of 5
Price was $1,172, price is now $985 per person
$985
per person
Oct 15 - Oct 21
found 17 hours ago
Roundtrip flight included
Dallas (DFW) 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 $588, price is now $475 per person
$475
per person
Oct 9 - Oct 12
found 19 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Pensacola (PNS)
The Bluefin - Ultra Luxury Beach Home

The Bluefin - Ultra Luxury Beach Home

3 out of 5
Save 100% on your flight
Price was $2,600, price is now $1,970 per person
$1,970
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
Price was $701, price is now $550 per person
$550
per person
Oct 29 - Nov 1
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 $1,014, price is now $799 per person
$799
per person
Oct 10 - Oct 13
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Sundrift Inn

Sundrift Inn

3 out of 5
Price was $714, price is now $576 per person
$576
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Wavecrest Lodge

Wavecrest Lodge

2.5 out of 5
Price was $684, price is now $554 per person
$554
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Landing Furnished Apartments - Orange Beach 

Landing Furnished Apartments - Orange Beach 

3 out of 5
Price was $1,067, price is now $866 per person
$866
per person
Oct 9 - Oct 12
found 20 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Pensacola (PNS)
Landing Apartments Gulf Shores

Landing Apartments Gulf Shores

3.5 out of 5
Price was $848, price is now $700 per person
$700
per person
Oct 9 - Oct 12
found 19 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Pensacola (PNS)
The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

5 out of 5
Price was $1,003, price is now $831 per person
$831
per person
Oct 29 - Nov 1
found 1 day 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 $2,352, price is now $1,955 per person
$1,955
per person
Oct 11 - Oct 14
found 14 hours ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
Sea Oats Motel

Sea Oats Motel

2 out of 5
Price was $866, price is now $722 per person
$722
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
Club Wyndham at Majestic Sun

Club Wyndham at Majestic Sun

3.5 out of 5
Price was $853, price is now $715 per person
$715
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)

4-night Santa Rosa Island vacations

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

Hotel Margot

3 out of 5
Price was $720, price is now $600 per person
$600
per person
Oct 5 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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
Save 100% on your flight
Price was $1,927, price is now $1,452 per person
$1,452
per person
Oct 5 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Pensacola (PNS)
Landing Furnished Apartments - Orange Beach 

Landing Furnished Apartments - Orange Beach 

3 out of 5
Price was $1,312, price is now $990 per person
$990
per person
Oct 7 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Pensacola (PNS)
Sundrift Inn

Sundrift Inn

3 out of 5
Price was $800, price is now $628 per person
$628
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Pensacola (PNS)
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
Price was $992, price is now $788 per person
$788
per person
Oct 24 - Oct 28
found 22 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) 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 $1,053, price is now $856 per person
$856
per person
Oct 7 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Pensacola (PNS)
The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
Price was $798, price is now $658 per person
$658
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Pensacola (PNS)
Wavecrest Lodge

Wavecrest Lodge

2.5 out of 5
Price was $763, price is now $629 per person
$629
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Pensacola (PNS)
Landing Apartments Gulf Shores

Landing Apartments Gulf Shores

3.5 out of 5
Price was $902, price is now $746 per person
$746
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Pensacola (PNS)
Phoenix III 3031 3BR 2BA End Unit on 3rd Floor Beachfront

Phoenix III 3031 3BR 2BA End Unit on 3rd Floor Beachfront

2 out of 5
Price was $1,617, price is now $1,339 per person
$1,339
per person
Oct 7 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Pensacola (PNS)
Spanish Key 404

Spanish Key 404

3 out of 5
Save 100% on your flight
Price was $1,938, price is now $1,611 per person
$1,611
per person
Oct 5 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Pensacola (PNS)
Phoenix I 1047 Gulf-front 2 2 A Amenities

Phoenix I 1047 Gulf-front 2 2 A Amenities

2 out of 5
Price was $1,288, price is now $1,077 per person
$1,077
per person
Oct 7 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Pensacola (PNS)

5-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 $603, price is now $509 per person
$509
per person
Oct 23 - Oct 28
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
Bay Club of Sandestin

Bay Club of Sandestin

3.5 out of 5
Price was $795, price is now $608 per person
$608
per person
Oct 23 - Oct 28
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
Club Wyndham at Majestic Sun

Club Wyndham at Majestic Sun

3.5 out of 5
Price was $1,040, price is now $798 per person
$798
per person
Oct 16 - Oct 21
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
Price was $840, price is now $646 per person
$646
per person
Oct 23 - Oct 28
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
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 $697, price is now $552 per person
$552
per person
Oct 23 - Oct 28
found 18 hours ago
Roundtrip flight included
Dallas (DFW) 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 $1,133, price is now $918 per person
$918
per person
Oct 23 - Oct 28
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
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
Price was $950, price is now $791 per person
$791
per person
Oct 16 - Oct 21
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
The Grand Grove by Avantstay Beach Access + Pool + Golf + Tennis Walk to Baytowne Wharf

The Grand Grove by Avantstay Beach Access + Pool + Golf + Tennis Walk to Baytowne Wharf

4 out of 5
Price was $855, price is now $716 per person
$716
per person
Oct 16 - Oct 21
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
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 $787, price is now $663 per person
$663
per person
Oct 23 - Oct 28
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
Wavecrest Lodge

Wavecrest Lodge

2.5 out of 5
Price was $751, price is now $637 per person
$637
per person
Oct 23 - Oct 28
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
Hilton Grand Vacations Club in Sandestin Golf & Beach Resort

Hilton Grand Vacations Club in Sandestin Golf & Beach Resort

3 out of 5
Price was $792, price is now $682 per person
$682
per person
Oct 23 - Oct 28
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
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
Price was $841, price is now $729 per person
$729
per person
Oct 23 - Oct 28
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)

6-7 night Santa Rosa Island vacations

Price found within the past 48 hours. Click for updated prices.
Wavecrest Lodge

Wavecrest Lodge

2.5 out of 5
Price was $906, price is now $718 per person
$718
per person
Oct 17 - Oct 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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
Price was $1,393, price is now $1,143 per person
$1,143
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Fort Walton Beach (VPS)
Wharf & Wander by Avantstay Walk to Village + Beach Tram + Resort Pool + Golf Baytowne Wharf

Wharf & Wander by Avantstay Walk to Village + Beach Tram + Resort Pool + Golf Baytowne Wharf

4 out of 5
Price was $1,599, price is now $1,334 per person
$1,334
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Fort Walton Beach (VPS)
Pelican Beach 0216 2 Bedroom Condo by Pelican Beach Management

Pelican Beach 0216 2 Bedroom Condo by Pelican Beach Management

3 out of 5
Price was $2,213, price is now $1,875 per person
$1,875
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Fort Walton Beach (VPS)
Pelican Beach 1508 1 Bedroom Home

Pelican Beach 1508 1 Bedroom Home

3 out of 5
Price was $1,976, price is now $1,686 per person
$1,686
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Fort Walton Beach (VPS)
Pelican Beach 1910 1 Bedroom Condo by Pelican Beach Management

Pelican Beach 1910 1 Bedroom Condo by Pelican Beach Management

3 out of 5
Price was $1,976, price is now $1,686 per person
$1,686
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Fort Walton Beach (VPS)
The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
Save 100% on your flight
Price was $1,361, price is now $981 per person
$981
per person
Oct 17 - Oct 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,586, price is now $1,158 per person
$1,158
per person
Oct 15 - Oct 22
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 $1,180, price is now $895 per person
$895
per person
Oct 17 - Oct 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 $1,523, price is now $1,174 per person
$1,174
per person
Oct 17 - Oct 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Fort Walton Beach (VPS)
Sundrift Inn

Sundrift Inn

3 out of 5
Price was $963, price is now $746 per person
$746
per person
Oct 17 - Oct 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pensacola (PNS)
The Bluefin - Ultra Luxury Beach Home

The Bluefin - Ultra Luxury Beach Home

3 out of 5
Save 100% on your flight
Price was $3,685, price is now $2,935 per person
$2,935
per person
Oct 17 - Oct 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.

Mon, Sep 28 - Thu, Oct 1
ATL
Atlanta
PNS
Pensacola
$180 Roundtrip, found 3 days ago
$180
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Sep 28 from Atlanta to Pensacola, returning Thu, Oct 1, priced at $180 found 3 days ago
Sun, Oct 18 - Thu, Oct 22
MSP
Minneapolis
VPS
Fort Walton Beach
$216 Roundtrip, found 11 hours ago
$216
Roundtrip
found 11 hours ago
Select Sun Country Airlines flight, departing Sun, Oct 18 from Minneapolis to Fort Walton Beach, returning Thu, Oct 22, priced at $216 found 11 hours ago
Thu, Sep 17 - Sun, Sep 20
DFW
Dallas
PNS
Pensacola
$222 Roundtrip, found 6 days ago
$222
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Sep 17 from Dallas to Pensacola, returning Sun, Sep 20, priced at $222 found 6 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
$163 nightly
The price is $184 total per night
$184 total
Sep 29 - Sep 30
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
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
$234 nightly
The price is $262 total per night
$262 total
Sep 7 - Sep 8
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.
Pool
Spa
Surf & Sand Hotel

Surf & Sand Hotel

2 out of 5
40 Fort Pickens Road Pensacola Beach FL
25.07 mi from city center
$141 nightly
The price is $159 total per night
$159 total
Sep 9 - Sep 10
Total with taxes and fees
With a stay at Surf & Sand Hotel in Pensacola Beach, you'll be 0.3 mi (0.5 km) from Pensacola Beach Gulf Pier and 6.7 mi (10.8 km) from Fort Pickens.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in Santa Rosa Island
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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.