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

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624 Vacation rentals

(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 $165 / night

$1125 - $2300 / week

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from $165 / night

(1) Good 

20

Home rental in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

3 10 4 nights min

  • 3 bedrooms
  • Sleeps 10
  • 4 nights min
  • Child friendly
Newly built and newly furnished 3 story 3/4 bedroom home with fenced in backyard. First floor has a separate living area with full bathroom that leads deck out back with grilling area and outdoor seating sectional. Second floor has living room, dining room, kitchen (inc …see more

from $300 / night

$2100 / week

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from $300 / night

37

Vacation condo rental

Santa Rosa Beach / Grayton Beach

1 6 3 nights min

  • 1 bedroom
  • Sleeps 6
  • 3 nights min
  • 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

$1050 / week

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from $150 / night

32

Townhouse rental in Grayton Beach with shared pool

Santa Rosa Beach / Grayton Beach

3 10 3 nights min

  • 3 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Prominence on 30A ~ Townhome rental located along 30A boasts the most incredible location on 30A and the hottest place to spend a family beach vacation. Be the first to experience a stay at South Walton's newest upscale development! Prominence on 30A beach home rental …see more

from $165 / night

$1155 - $2640 / week

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from $165 / night

(5) Very Good 

18

Apartment rental in Santa Rosa Beach with shared pool

Florida Panhandle / Santa Rosa Beach

1 6 3 nights min

  • 1 bedroom
  • Sleeps 6
  • 3 nights min
  • 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 - $899 / week

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Responds fast!
avg. 1 hour 52 minutes

from $115 / night

20

Vacation townhouse rental

Santa Rosa Beach / Grayton Beach

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Prominence - 30A ~ Beach vacation townhome rental "Beachy Keen" located 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 development is already the rage along 30A. Prominen …see more

from $165 / night

$1155 - $2640 / week

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from $165 / 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 $123 / night

$861 / week

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from $123 / night

16

Grayton Beach Vacation townhouse rental

Santa Rosa Beach / Grayton Beach

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Prominence - 30A ~ Beach vacation townhome rental "Coastal Bliss" located at 25-B Pine Lands Loop, 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 …see more

from $165 / night

$1155 - $2640 / week

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from $165 / night

31

Vacation townhouse rental

Santa Rosa Beach / Grayton Beach

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
Prominence - 30A ~ Beach vacation townhome rental "Sea You Soon" located at 24-A 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 develo …see more

from $165 / night

$1155 - $2640 / week

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from $165 / night

26

Townhouse rental in Grayton Beach with shared pool

Santa Rosa Beach / Grayton Beach

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Prominence - 30A ~ Beach townhome rental "Deer Rose-Sea" located along 30A by Panhandle Getaways 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 development is already the rage along …see more

from $165 / night

$1155 - $2640 / week

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from $165 / night

(1) Very Good 

24

Vacation home 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
  • Child friendly
  • Air conditioning
Make plans to spend a relaxing vacation in this cozy cottage located in the family-oriented community. You will be delighted with the adorable decor and colorful decorative touches found in this special cottage. Four porches provide wonderful spots to enjoy the gulf bre …see more

from $139 / night

$973 / week

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from $139 / night

(2) Very Good 

33

Grayton Beach Vacation home accommodation

Santa Rosa Beach / Grayton Beach

4 12 3 nights min

  • 4 bedrooms
  • Sleeps 12
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Prominence on 30A ~ Beach home rental located along the Panhandle of Florida boasts the most incredible location on 30A and the hottest place to spend a family beach vacation. Be the first to experience a stay at South Walton's newest upscale development! Prominence on …see more

from $240 / night

$1540 - $4620 / week

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from $240 / night

(1) Excellent 

23

Vacation home in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Suitable for children age 5+
  • Air conditioning
Discover a new way to vacation at this Old Florida style, single family home tucked away in the heart of Seagrove Beach.  Park your car and enjoy this bike friendly community.  The 17-mile dedicated bicycle path runs along Scenic Highway 30A and offers you and your fami …see more

from $100 / night

$700 - $1506 / week

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Responds fast!
avg. 1 hour 49 minutes

from $100 / night

31

Grayton Beach Vacation townhouse rental

Santa Rosa Beach / Grayton Beach

3 9 3 nights min

  • 3 bedrooms
  • Sleeps 9
  • 3 nights min
  • 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 $165 / night

$1155 - $2640 / week

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from $165 / 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
  • Child friendly
  • 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 $276 / night

$1793 - $3718 / week

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from $276 / night

35

Vacation townhouse with shared pool in Grayton Beach

Santa Rosa Beach / Grayton Beach

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Prominence - 30A ~ Beach vacation townhome rental "Xanadune" located 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 development is already the rage along 30A. Prominence …see more

from $165 / night

$1155 - $2640 / week

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from $165 / night

(3)  

34

Vacation home in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
*Please note that there is another 3BR house next to the property. Both houses can accommodate up to can accommodate up to 16 total people.* Get a taste of the simple life when you stay at this quaint Santa Rosa Beach home, settled on the banks of the Choctawhatchee B …see more

from $135 / night

$810 - $1110 / week

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Responds fast!
avg. 48 minutes

from $135 / night

37

Apartment rental in Santa Rosa Beach with shared pool

Florida Panhandle / Santa Rosa Beach

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets
This great, ground floor Gulf Place Caribbean condo is perfect for a day, weekend, or week. You'll love the convenience of the private furnished patio that has easy access to the pool, common grilling area, and beach access. This cottage style condo offers two bedroom …see more

from $130 / night

$847 - $2023 / week

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from $130 / 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
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
Weekly Discounts for Bookings in June & July! 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 comfortably sleeps 22 and is p …see more

from $350 / night

$2450 - $5400 / week

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Responds fast!
avg. 48 minutes

from $350 / night

(30) 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 $150 / night

$1100 - $1900 / week

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Responds fast!
avg. 38 minutes

from $150 / night

24

Vacation home with swimming 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
A relatively newer development in Blue Mountain Beach, the first thing you’ll notice in this 4-bedroom, 4-bathroom retreat is the astute attention to detail. Thirty Blu reflects the owner’s stylish personality, and is a wonderful combination of modernistic design and ar …see more

from $179 / night

$1253 - $3045 / week

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from $179 / 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
  • Child friendly
  • 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 $99 / night

$833 - $1399 / week

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from $99 / night

(4) Excellent 

8

Santa Rosa Beach Vacation apartment rental

Florida Panhandle / Santa Rosa Beach

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets
Features: Beach Chairs & Umbrella (Seasonal-Free) / Bike Rentals (Seasonal-Fee) / Free Wi-Fi. This cheery and colorfully styled vacation rental getaway is located at the Gulf Place Cabanas; across the street from the beach in Santa Rosa Beach, Fl; 650sq ft spacious uni …see more

from $97 / night

$630 - $1470 / week

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from $97 / night

(1) Excellent 

27

Vacation home rental

Santa Rosa Beach / Grayton Beach

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Lucky Dog – 142 Savelle Drive – Grayton Beach, FL Stay with Sunburst and get up to $280 in Beach Gear delivered to your vacation home! Lucky Dog is a gorgeous multi-story, 4 bedroom, 4 bath home in the secluded Gulf Trace neighborhood of Grayton Beach. With a spacious …see more

from $346 / night

$2223 - $4670 / week

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from $346 / night

(1) Excellent 

24

Vacation home with shared pool in Grayton Beach

Santa Rosa Beach / Grayton Beach

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The house is 1/8 of a mile from Hwy 30A & all of the fun things to do like shopping, dining, dancing & fishing. It is a private, very clean, comfortable setting in a small, unique, & quiet friendly neighborhood. There are 4 small stairs to climb, no neighbors on top or …see more

from $156 / night

$1043 - $1200 / week

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Responds fast!
avg. 1 hour 3 minutes

from $156 / night

24

Vacation apartment with shared pool in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

2 9 Min stay varies

  • 2 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
**JANUARY AND FEBRUARY SNOWBIRD SPECIAL $1850 MONTHLY RATE** Grab your swimsuit, sunglasses, and sunscreen and head down to Seagrove Beach for the ultimate getaway! Situated 150 yards from the soft white sand, this newly renovated vacation rental condo offers 2 bedroom …see more

from $80 / night

$560 - $1540 / week

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Responds fast!
avg. 29 minutes

from $80 / night

(1) 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 $115 / night

$805 / week

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from $115 / night

(5) Very Good 

13

Vacation apartment with shared pool in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets
Features: Beach Chairs & Umbrella (Seasonal-Free) / Bike Rentals (Seasonal-Fee) / Free Wi-Fi. Beautiful and affordable stay at one of Beaches of South Walton’s amazing property. This 650 sq ft unit on the 4th floor is bright and beachy. The hominess of this unit will m …see more

from $97 / night

$630 - $1470 / week

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from $97 / night

26

Vacation home in Grayton Beach

Santa Rosa Beach / Grayton Beach

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
Artless Sprite – 156 Garfield Street – Grayton Beach Stay with Sunburst and get up to $280 in Beach Gear delivered to your vacation home! Artless Sprite is the first permanent vacation home of the Covell Family who has lived in Northwest Florida since the 1920's and h …see more

from $171 / night

$1118 - $2233 / week

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from $171 / night

(2) Very Good 

12

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
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 $185 / night

$1250 / week

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from $185 / night

8

Santa Rosa Beach Vacation apartment rental

Florida Panhandle / Santa Rosa Beach

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets
Feature: Beach Chairs & Umbrella (Seasonal-Free).This charming 1 bedroom unit is located on the 3rd floor and has beautiful upgrades throughout, including a Jacuzzi garden tub in the bathroom. This unit will comfortably sleep 5 people. A king size master bedroom, Quee …see more

from $102 / night

$658 - $1547 / week

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from $102 / night

(4) Excellent 

36

Vacation home with swimming pool in Grayton Beach

Santa Rosa Beach / Grayton Beach

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
SeaBatical - 55 Gulf Shore Drive - Grayton Beach, FL Stay with Sunburst and get up to $280 in Beach Gear delivered to your vacation home! Located in the sought after Gulf Trace community, SeaBatical is situated with panoramic views of Alligator Lake, Grayton Beach Sta …see more

from $376 / night

$2443 - $5148 / week

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from $376 / night

24

Vacation home in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

4 12 3 nights min

  • 4 bedrooms
  • Sleeps 12
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
Unique property one house off the beach & sits on Oyster Lake, beach access is six houses down, a 2 minute walk. Gorgeous beach house located on the picturesque Scenic 30-A with lovely views of the Gulf of Mexico. New pool & Jacuzzi (both can be heated) with travertine …see more

from $480 / night

$3360 / week

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from $480 / night

33

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 FALL …see more

from $118 / night

$722 - $1309 / week

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Responds fast!
avg. 2 hours 27 minutes

from $118 / night

12

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
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Whits End is located in Cassine Gardens Townhomes in the midst of old Seagrove Beach. We are located on the first street in the complex, thus we are closest to the beach. About a five minute walk and you are standing on the beach. This unit has been kept current with …see more

from $90 / night

$625 - $1100 / week

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from $90 / night

51

Santa Rosa Beach Vacation home rental

Florida Panhandle / Santa Rosa Beach

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets
Features: Beach Chairs & Umbrella (Seasonal-Free) / Bike Rentals (Seasonal-Free) / Free Wi-Fi.Soak in the best views of the Emerald Coast waters from all three levels of this immaculate gulf front vacation home! This is a fabulous property, located on sand dunes, and i …see more

from $561 / night

$3654 - $8813 / week

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from $561 / night

16

Vacation apartment rental

Florida Panhandle / Santa Rosa Beach

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets
Features: Beach Chairs & Umbrella (Seasonal-Free) / Bike Rentals (Seasonal-Fee) / Free Wi-Fi.Sanctuary by the Sea boasts luxurious amenities beyond compare and is destined to be the premier resort in the exclusive 30A area. Three artfully sculpted pools including waterf …see more

from $209 / night

$1365 - $4291 / week

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from $209 / night

(2) Excellent 

10

Santa Rosa Beach Vacation apartment rental

Florida Panhandle / Santa Rosa Beach

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets
Features: Beach Chairs & Umbrella (Seasonal-Free) / Bike Rentals (Seasonal-Fee) / Free Wi-Fi.This stunning one bedroom and one bathroom condo offers a beautiful partial view of the Gulf of Mexico from your own private balcony that is located off of the living room. This …see more

from $102 / night

$658 - $1603 / week

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from $102 / night

(4) Good 

8

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
  • Swimming pool
  • Ask about children
  • Ask about pets
Features: Beach Chairs & Umbrella (Seasonal-Free) / Bike Rentals (Seasonal-Fee) / Free Wi-Fi. This exquisite one bedroom vacation rental unit includes floor to ceiling patio doors from the living room with a large patio that gives you a view of the pool. This wonderfu …see more

from $97 / night

$630 - $1470 / week

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from $97 / night

19

Vacation home in Grayton Beach

Santa Rosa Beach / Grayton Beach

3 12 Min stay varies

  • 3 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Air conditioning
Blue Bell Cottage is a beautiful beach house located in the gated community of the Preserves in Grayton Beach surrounded by unspoiled nature preserves, tall pines, oaks, palmettos and natural scrub. The beach access is a private nature trail that will lead you to stunni …see more

from $240 / night

$1750 - $3745 / week

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Responds fast!
avg. 1 hour 4 minutes

from $240 / night