50 Best Santa Rosa Beach Vacation rentals on Holiday Lettings - House rentals

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1,798 Vacation rentals

23

Vacation home in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
'BUTTERCUP': 144 Buttercup Street Large Watercolor home with carriage house located in the heart of the Park District, only steps away from the beach, the Boat House, the Bait House and Fish Out of Water restaurants, as well as Town Center shopping and everything you n …see more

from $375 / night

$2,625 - $7,140 / week

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from $375 / night

(2) Excellent 

24

Santa Rosa Beach Vacation home rental

Florida Panhandle / Santa Rosa Beach

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Feel like royalty in the newly constructed Fleur de Lee. Fleur de Lee is a magnificent 4 bedroom home situated on a corner lot in the picturesque 30A neighborhood of NatureWalk at Seagrove. This immaculate, professionally decorated 2 story home can accommodate up to 10 …see more

from $204 / night

$1,428 / week

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Responds fast!
avg. 3 hours 40 minutes

from $204 / night

31

Santa Rosa Beach Vacation cottage rental

Florida Panhandle / Santa Rosa Beach

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Now is the time for you to pack your bags and head to “Good To Go” located in the community of Old Florida Village! This community consists of 75 homes nestled among brick pathways and lush tropical vegetation. Conveniently located in Santa Rosa Beach, you can drive, h …see more

from $190 / night

$950 - $1,900 / week

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Responds fast!
avg. 1 hour 9 minutes

from $190 / night

24

Grayton Beach Vacation home rental

Santa Rosa Beach / Grayton Beach

6 16 Min stay varies

  • 6 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Large Family Home w/Private Pool in Watercolor with Stunning Upscale Furnishings, Golf Cart and Game Room! 424 E Royal Fern Way, WaterColor Crossings District Your family will be excited to call this property "home" during your WaterColor vacation. If the beautiful, u …see more

from $300 / night

$2,100 - $5,880 / week

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from $300 / night

40

Vacation home in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
'Siena by the Sea': 55 Spartina Circle, WaterColor Specifically located in the Camp District of Watercolor on Spartina Circle, the culmination of architecture, interior design, and comfort come together at our Watercolor masterpiece just a short walk or bike ride to th …see more

from $300 / night

$2,100 - $5,180 / week

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from $300 / night

23

Vacation home with shared pool in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
'Soulshine' 201 East Royal Fern Way - WaterColor Crossings District Welcome to "Soulshine"! This professionally decorated 5 bedroom/ 4.5 bathroom coastal home offers spacious accommodations for up to 11 guests. The first floor is comprised of a fully equipped gourmet k …see more

from $230 / night

$1,610 - $3,682 / week

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from $230 / night

24

Santa Rosa Beach Vacation home rental

Florida Panhandle / Santa Rosa Beach

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
164 Pond Cypress Way, Camp District As soon as you walk in this home you get a wonderful sense of beach elegance. The owner has taken great care in decorating and furnishing all rooms in a nautical theme with gorgeous wearable fabrics that evoke a sense of luxury at th …see more

from $335 / night

$2,345 - $4,550 / week

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from $335 / night

22

Vacation apartment with shared pool in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
At Seagrove Highlands 2107 you can skip the elevator and stairs with this conveniently located ground floor vacation rental in a newer South Walton condo complex. Features a swimming pool, fishing desk, grills, spacious and private grounds, short biking distance to beac …see more

from $43 / night

$900 - $3,150 / week

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from $43 / night

(2) Very Good 

12

Apartment rental in Santa Rosa Beach with shared pool

Florida Panhandle / Santa Rosa Beach

1 6 4 nights min

  • 1 bedroom
  • Sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
You deserve a stay at Gulf Place Getaway! This comfy top floor beach condo unit is perfect for families, snowbirds, and anyone else who loves the gorgeous aqua-blue gulf waters. Tastefully appointed with everything you need to unwind, relax and soak up the lovely Gulf P …see more

from $140 / night

$850 - $1,250 / week

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from $140 / night

(35) Excellent 

Certificate of Excellence

26

Home rental in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Child friendly
Don't Blink is a super cute fully renovated 1940s cottage in Seagrove Beach, south of 30A. She is nestled in pines and surrounded by beautiful natural vegetation with a very short 3 minute stroll to the beautiful beach. The home is on a dead end street with no thru traf …see more

Certificate of Excellence

from $165 / night

$1,100 - $1,900 / week

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from $165 / night

37

Vacation condo rental

Santa Rosa Beach / Grayton Beach

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Relax and unwind in a completely remodeled one bedroom condo at Gulf Place Caribbean. The Gulf Place Town Center is a unique property situated directly on scenic Hwy 30-A along the Beaches of South Walton. The property offers 3 pools, hottubs, tennis and shuffle board c …see more

from $150 / night

$1,050 - $1,250 / week

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Responds fast!
avg. 3 hours 58 minutes

from $150 / night

(1) Excellent 

24

Grayton Beach Vacation home rental

Santa Rosa Beach / Grayton Beach

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
Located between Seaside and Destin in beautiful Santa Rosa Beach, Gone To The Beach is a 4 bedroom, 3 bath cottage with a tower that is part of a small neighborhood of only 75 cottage style homes called Old Florida Village, on the north side of 30A. A community pool jus …see more

from $182 / night

$1,250 - $2,300 / week

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from $182 / night

23

Vacation home with swimming pool in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

5 13 Min stay varies

  • 5 bedrooms
  • Sleeps 13
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
'LIBBYSAND': 243 PINE NEEDLE WAY, FOREST DISTRICT - PRIVATE POOL/SPA, 5 BEDROOM/5.5 BATH, SLEEPS 11+, BOOK NOW! Fabulously elegant yet beachy and whimsical home with expansive indoor living space for the whole family/group and private outdoor entertaining oasis make th …see more

from $500 / night

$3,500 - $9,275 / week

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from $500 / night

24

Vacation apartment with shared pool in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Exhale: 45 Central Square Condo Unit B-2, Seaside, FL LARGE CONTEMPORARY CONDO IN THE HEART OF SEASIDE! SLEEPS 12, GULF AND CENTRAL SQUARE VIEWS. 2528 Sq. Ft. Private elevator access to this beautiful large, high ceiling, limestone floor condo in the heart of Seaside …see more

from $323 / night

$2,261 - $8,750 / week

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from $323 / night

23

Grayton Beach Vacation home rental

Santa Rosa Beach / Grayton Beach

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
HOME HIGHLIGHTS: ~ Located in Watercolor's most desired Camp district ~ High Speed Wireless Internet ~ 5 Adult Bicycles ~ Gas Grill ~ Unlimited Long Distance Calls ~ Plasma TV's and DVD Players ~ Game Loft with Foosball Table and Pool Table ~ Large porch balcony that …see more

from $205 / night

$1,425 - $4,475 / week

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from $205 / night

24

Vacation home in Grayton Beach

Santa Rosa Beach / Grayton Beach

4 14 Min stay varies

  • 4 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
This brightly decorated 4 bedroom, 3 bathroom, three-story beach home is nestled in the quiet community of Dune Allen. Hang out on one of the porches and enjoy the breeze coming in over the ocean while watching the sunset on the horizon. A king bed in the master with ad …see more

from $83 / night

$1,495 - $6,600 / week

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from $83 / night

24

Santa Rosa Beach Vacation home rental

Florida Panhandle / Santa Rosa Beach

5 22 Min stay varies

  • 5 bedrooms
  • Sleeps 22
  • Min stay varies
  • Child friendly
  • Air conditioning
** Special Weekly Pricing for April! (Please Inquire With Evolve) ** Find your utopian beachfront getaway when you stay at this luxurious vacation rental house on the shores of Santa Rosa Beach. With 5 bedrooms, 4 bathrooms, and a mother-in-law suite, this home comfort …see more

from $350 / night

$2,450 - $5,397 / week

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Responds fast!
avg. 21 minutes

from $350 / night

(5) Very Good 

18

Apartment rental in Santa Rosa Beach with shared pool

Florida Panhandle / Santa Rosa Beach

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
***Brand new AC, Sofa Sleeper, rug, TV/DVD and barstools. *** ***comfortably sleeps 4 adults and 2 kids*** Nice, quiet and perfectly located affordable 1BR condo in Seagrove. Cool hallway bunks for the kids and a brand new comfortable sofa sleeper. We are right i …see more

from $115 / night

$749 - $1,395 / week

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from $115 / night

12

Home accommodation in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
Surprise your special someone with an escape to this charming carriage home located in the famous Seaside community. Featuring shared pools (available for a fee), easy beach access, and all the amenities of home, your stay promises to be hassle-free so you can spend you …see more

from $145 / night

$1,015 / week

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Responds fast!
avg. 38 minutes

from $145 / night

21

Santa Rosa Beach Vacation cottage rental

Florida Panhandle / Santa Rosa Beach

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
'Key Lime Cottage' is very bright and the decor is very "beachy." Numerous windows abound. This vacation home has parking for two cars, community Pool (20 yards away) and gas grills just out the back door. A short 3.5 minute walk to the beach with showers and access ove …see more

from $216 / night

$1,250 - $1,889 / week

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from $216 / night

32

Vacation home in Grayton Beach

Santa Rosa Beach / Grayton Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets
Sugar Dunes #19 Make your escape to this extravagant 3 bedroom, 3 bathroom condo on the beach! This beautifully decorated unit is not your standard condo rental as it offers a fireplace, vaulted ceiling, and loft!. The living area is equipped with sparkling floor to ce …see more

from $143 / night

$998 - $3,743 / week

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from $143 / night

24

Santa Rosa Beach Vacation apartment rental

Florida Panhandle / Santa Rosa Beach

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Includes 2 complimentary beach chairs and umbrella with every stay March 1st through November 26! This exclusive perk is only available with select participating units. Don't miss your opportunity to book a Redfish condo with the vacation extras that make your vacation …see more

from $56 / night

$999 - $3,100 / week

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from $56 / night

31

Grayton Beach Vacation townhouse rental

Santa Rosa Beach / Grayton Beach

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
Prominence - 30A ~ Beach vacation townhome rental "The Sand Dollar" located at 58-B York Lane, Watersound Beach, Florida along 30A boasts one of the most incredible locations on 30A and the hottest new place to spend a family beach vacation. 30A's newest beach town dev …see more

from $200 / night

$1,265 - $2,640 / week

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from $200 / night

15

Santa Rosa Beach Vacation home rental

Florida Panhandle / Santa Rosa Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
As we all know 30a is known for exceptional beach vacations. However, what makes this particular vacation home and its location is as follows: - South side of 30a in a quiet neighborhood. - Steps away from the private neighborhood beach access. - This home has 2 full …see more

from $175 / night

$1,225 / week

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from $175 / night

24

Vacation home in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
37 Royal Fern Way, WaterColor Nestled in the Forest District of WaterColor on Royal Fern Way, the culmination of WaterColor unique architecture, interior design and comfort come together at our WaterColor cottage just a short walk or bike ride to the beach and the Famo …see more

from $235 / night

$1,645 - $5,355 / week

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from $235 / night

38

Grayton Beach Vacation home accommodation

Santa Rosa Beach / Grayton Beach

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
Find year-round warmth and sunshine at this three-bedroom Seagrove escape, a charming, beautifully appointed Florida home with a wrap-around porch and firepit, shared use of a swimming pool and tennis courts, and easy walking access to the spectacular beaches of 30A. T …see more

from $99 / night

$693 / week

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Responds fast!
avg. 38 minutes

from $99 / night

(1) Excellent 

19

Vacation apartment with shared pool in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

1 6 1 night min

  • 1 bedroom
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning
This second floor one bedroom, one bathroom Gulf Place condo can comfortably sleep 6 guests. It is located right in the heart of all the Gulf Place action and just across the street from the beach. The Inn at Gulf Place offers the unique experience of an intimate, excl …see more

from $40 / night

$710 - $6,000 / week

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from $40 / night

33

Home rental in Santa Rosa Beach with swimming pool

Florida Panhandle / Santa Rosa Beach

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! Sea Bluffs #12 is a Newly Remodeled 2BR/2.5 BA beach condominu …see more

from $141 / night

$862 - $2,192 / week

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Responds fast!
avg. 8 minutes

from $141 / night

(1) Excellent 

29

Grayton Beach Vacation home rental

Santa Rosa Beach / Grayton Beach

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
SandyToes - 34 Gulf Breeze Drive – Grayton Beach, FL Stay with Sunburst and get up to $280 in Beach Gear delivered to your vacation home! SandyToes is a freshly renovated 3 bedroom, 3 bathroom home sleeps 10. This affordable yet well-equipped home in desirable, family …see more

from $281 / night

$1,828 - $3,718 / week

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from $281 / night

25

Vacation apartment with shared pool in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Compass Point 1 #407 - WaterSound ULTIMATE IN LUXURY CONDO RENTAL WITH THE BEST VIEWS ON 30A! SLEEPS 8, 3 BATHROOMS. GOLF CART** FOR IN NEIGHBORHOOD USE INCLUDED. 1818 Sq. Ft. As soon as you open the front door to Compass Point 1 #407 (top floor), the views, high cei …see more

from $295 / night

$2,065 - $6,993 / week

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from $295 / night

(2) Excellent 

26

Santa Rosa Beach Vacation home rental

Florida Panhandle / Santa Rosa Beach

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Gorgeous Three bedroom, 3 bathroom sleeps 6-8. This home is located south of 30 A in the Blue Mountain Beach Community. This home is a short 5 minute walk from access to some of the most beautiful stretch of beach you will ever see. Your accommodations features an open …see more

from $206 / night

$1,442 / week

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Responds fast!
avg. 3 hours 40 minutes

from $206 / night

37

Vacation apartment rental

Florida Panhandle / Santa Rosa Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! Grand Isle ~ SunDune #204 - NEWLY REDECORATED AND REMODELED FAL …see more

from $118 / night

$722 - $1,309 / week

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Responds fast!
avg. 8 minutes

from $118 / night

(1) Good 

35

Vacation home in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

2 12 Min stay varies

  • 2 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! Sea Bluffs #11 is a beautifully appointed 2BR/2.5 BA condominiu …see more

from $141 / night

$862 - $1,933 / week

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Responds fast!
avg. 8 minutes

from $141 / night

(1) Excellent 

23

Home rental in Santa Rosa Beach with swimming pool

Florida Panhandle / Santa Rosa Beach

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
SS Minnow, 94 Betty Street, Santa Rosa Beach The S.S. Minnow's "beach" charm, colorful and comfortable furnishings and private pool will satisfy each member of the family. Carpeted bedrooms, tile softened by area rugs downstairs and generous balconies with wonderful gu …see more

from $270 / night

$1,575 - $3,010 / week

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from $270 / night

17

Vacation apartment with shared pool in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

1 6 3 nights min

  • 1 bedroom
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
The one bedroom, one bathroom plus bunk bed condominium at Beachside Condos is a great way to enjoy every bit of the 30A lifestyle. With a queen in the master bedroom a set of bunk beds inset in the hall and a queen sized pull out sofa in the living area you will be abl …see more

from $40 / night

$740 - $3,060 / week

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from $40 / night

(2) Excellent 

13

Vacation home rental

Florida Panhandle / Santa Rosa Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
Van Gogh’s View is a luxurious 2 bedroom/2 full bath upstairs unit located in the heart of beautiful Santa Rosa Beach, Florida along the natural beauty of Scenic 30-A. It also a large private outdoor space for you and your family to enjoy complete with remote controlle …see more

from $199 / night

$1,393 / week

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from $199 / night

23

Vacation home in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
63 Western Lake Drive This brand new spacious and phenomenal property includes a luxurious King Master Suite with lush seating area, private porch and spacious master bathroom appointed with limestone, marble, glass and pebble tile. This home also features three large …see more

from $720 / night

$5,040 - $18,480 / week

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from $720 / night

(1) Excellent 

23

Vacation home in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Our house welcomes you with an open-design living room and kitchen area with a custom-tiled center island and seating area. The master bedroom has a top of the line king size bed, huge walk-in closet, and sliding glass doors to the back porch and large fenced in backyar …see more

from $200 / night

$1,300 / week

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from $200 / night

(1) Excellent 

9

Santa Rosa Beach Vacation home rental

Florida Panhandle / Santa Rosa Beach

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Chelsea Loop is a charming circular drive through this Gulf front community. The activities are endless for the casual beach goer who enjoys coffee on the balcony in the morning to the fun seeker who spends hours by the community pool or in the swells of the Gulf of Mex …see more

from $122 / night

$1,075 - $3,600 / week

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from $122 / night

(3) Very Good 

47

Vacation apartment rental

Florida Panhandle / Santa Rosa Beach

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Visit Gulf Place Cabanas- 75 yards from Santa Rosa’s beautiful white sandy beaches, surrounded by three heated pools, Jacuzzi, tennis, shuffle board, biking and walking trails. We are just 10 minutes & 6 miles away from Seaside and Watercolor. Barbecue grills on prop …see more

from $70 / night

$540 - $1,599 / week

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Responds fast!
avg. 3 hours 14 minutes

from $70 / night