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

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542 Vacation rentals

35

Vacation townhouse with shared pool in Grayton Beach

Santa Rosa Beach / Grayton Beach

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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

(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 - $4635 / week

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from $346 / 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 $99 / night

$693 - $1750 / week

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from $99 / 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 - $2206 / week

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Responds fast!
avg. 1 hour 49 minutes

from $156 / night

35

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
Aspen Beach House – 299 Defuniak St – Grayton Beach, FL Stay with Sunburst and get up to $280 in Beach Gear delivered to your vacation home! Aspen Beach House is a beautiful 3000 square foot 4 bedroom/4 bath home located in beautiful historic Grayton Beach. Located ju …see more

from $276 / night

$1793 - $3683 / week

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from $276 / night

20

Vacation townhouse rental

Santa Rosa Beach / Grayton Beach

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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

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 $119 / night

$722 - $1309 / week

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Responds fast!
avg. 51 minutes

from $119 / night

16

Grayton Beach Vacation townhouse rental

Santa Rosa Beach / Grayton Beach

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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

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

(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 - $5113 / week

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from $376 / 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 Special pricing for open June weeks! Four-night minimum! 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 …see more

from $171 / night

$1118 - $2198 / week

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from $171 / 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 - $3683 / week

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from $276 / night

6

Vacation home in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Ask about children
  • Pet friendly
Features: Beach Chairs & Umbrella (Seasonal-Fee) / Bike Rentals (Seasonal-Free) / Pet-Friendly / Free Wi-Fi."Even Keel" is the perfect beach getaway for your next trip to South Walton along 30A! Located in the quaint community of Old Florida Village, you'll experience …see more

from $167 / night

$1092 - $2254 / week

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from $167 / night

25

Vacation home in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

5 14 7 nights min

  • 5 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Top 10 Reasons to Stay at “Blue Mountain Beach House” #10. Private Heated Pool Because jumping into an ice cold swimming pool can make a grown man sing soprano. #9. Private Hot Tub/Spa Because hot tubs aren’t just for reality TV bachelors. Hot tubs rock!  #8 Walk to …see more

from $225 / night

$1500 - $4543 / week

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from $225 / night

(1) 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

$1050 - $1250 / week

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from $185 / night

(4) 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 - $1249 / week

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Responds fast!
avg. 1 hour 57 minutes

from $115 / 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 stun …see more

from $240 / night

$1750 - $3745 / week

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Responds fast!
avg. 1 hour 2 minutes

from $240 / night

(4) Excellent 

27

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
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The house is the perfect little beach getaway. It's been freshly painted inside and out with new appliances, new furniture, flat screen TVs in each room, travertine floors, and granite countertops. Good Day Sunshine is a gorgeous 3 story beach house directly acr …see more

from $183 / night

$1275 - $1625 / week

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Responds fast!
avg. 3 hours 14 minutes

from $183 / night

32

Vacation home rental

Florida Panhandle / Santa Rosa Beach

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Suitable for children age 5+
The funky and fabulous decor sets the tone for a fun and memorable vacation for any group. This home features hardwood floors, stainless steel appliances, a private outdoor shower and a balcony off of the master bedroom with a gorgeous view of the Gulf. Each room is a …see more

from $205 / night

$1435 - $4655 / week

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Responds fast!
avg. 1 hour 2 minutes

from $205 / night

21

Vacation home in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 fa …see more

from $100 / night

$700 - $1505 / week

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Responds fast!
avg. 1 hour 2 minutes

from $100 / night

(28) 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 $170 / night

$1150 - $1900 / week

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Responds fast!
avg. 52 minutes

from $170 / 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 - $4500 / week

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from $350 / 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 $145 / night

$1000 - $1900 / week

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Responds fast!
avg. 3 hours 21 minutes

from $145 / night

31

Vacation townhouse rental

Santa Rosa Beach / Grayton Beach

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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

16

Vacation home with shared pool in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
If you are looking for a custom built, private home for your family's vacation look no further! Crosswinds Beach House is a beautiful home set in the gated community of Lakeside at Blue Mountain Beach. Adjacent to Redfish Village off scenic highway 30A, this property i …see more

from $325 / night

$1350 - $2195 / week

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Responds fast!
avg. 1 hour 29 minutes

from $325 / night

(1) Excellent 

25

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
Crow’s Nest - 22 N. Grande Beach Drive - Blue Mountain Beach, FL Stay with Sunburst and get up to $280 in Beach Gear delivered to your vacation home! Soak up the sun in this perfect rental market home with fabulous views of the Gulf of Mexico and the community pool. T …see more

from $211 / night

$1368 - $2748 / week

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from $211 / 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

$693 / week

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from $99 / night

(2) Good 

34

Grayton Beach Vacation home rental

Santa Rosa Beach / Grayton Beach

8 17 Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Spoiled Rotten – 375 Defuniak Street – Grayton Beach, FL Special pricing for open June weeks! Four-night minimum! Stay with Sunburst and get up to $280 in Beach Gear delivered to your vacation home! Located in the heart of Old Grayton Beach, pet-friendly Spoiled Rott …see more

from $366 / night

$2348 - $4868 / week

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from $366 / 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

(3) Very Good 

18

Vacation apartment in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Ask about pets
Features: Beach Chairs & Umbrella (Seasonal-Free) / Bike Rentals (Seasonal-Fee) / Free Wi-Fi. This modern, tropical 3-story townhome is located within the quaint resort of Gulf Place in Santa Rosa Beach. Gulf Place is a family friendly resort with an artist’s village, …see more

from $130 / night

$847 - $2114 / week

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from $130 / night

(1) Excellent 

18

Santa Rosa Beach Vacation apartment rental

Florida Panhandle / Santa Rosa Beach

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Relax and unwind in our newly remodeled and upgraded one bedroom condo at Gulf Place Caribbean. If it is true that Location is everything, then this is the place to stay! This whimsical Beach condo features a well-stocked kitchen with stainless steel appliances and g …see more

from $250 / night

$1250 - $1400 / week

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from $250 / night

26

Townhouse rental in Grayton Beach with shared pool

Santa Rosa Beach / Grayton Beach

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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

32

Townhouse rental in Grayton Beach with shared pool

Santa Rosa Beach / Grayton Beach

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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

(2) Very Good 

33

Grayton Beach Vacation home accommodation

Santa Rosa Beach / Grayton Beach

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • 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

$1541 - $4620 / week

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from $240 / 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 $99 / night

$693 / week

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from $99 / night

(4) Very Good 

22

Vacation home with swimming pool in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly
Features: Beach Chairs & Umbrella (Seasonal-Fee) / Bike Rentals (Seasonal-Free) / Pet-Friendly / Free Wi-Fi.Old Seagrove Beach at its finest! This cozy property is a few steps from the beach and one block east of Seaside. Kick back and enjoy the Seaside lifestyle becaus …see more

from $207 / night

$1351 - $2926 / week

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from $207 / night

33

Vacation townhouse with shared pool in Grayton Beach

Santa Rosa Beach / Grayton Beach

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Prominence - 30A ~ Beach vacation townhome rental "Sea Bliss" 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. Prominenc …see more

from $165 / night

$1155 - $2640 / week

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from $165 / night

15

Vacation apartment in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Ask about pets
Features: Beach Chairs & Umbrella (Seasonal-Free) / Bike Rentals (Seasonal-Fee) / Free Wi-Fi.This gorgeous condo offers wonderful views of the rare coastal dune lake and emerald Gulf waters. If you are looking for a quiet and relaxing retreat, you have found the perfect …see more

from $250 / night

$1624 - $4998 / week

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from $250 / night

(1) Very Good 

24

Vacation home 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
Book Your Summer 7 Night Stay Now (may/june/july/aug) And Choose From Either A Free Beach Bonfire or $200 Of Free Groceries Delivered To Your Door! Call And Use Promo Code: 30AFREE Or Book Now Online And Type Promo Code 30AFREE In Reservation Notes!Includes 4 free bikes …see more

from $150 / night

$1050 - $2635 / week

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from $150 / night

22

Vacation home in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

4 13 Min stay varies

  • 4 bedrooms
  • Sleeps 13
  • Min stay varies
  • Ask about children
  • Pet friendly
Features: Beach Chairs & Umbrella (Seasonal-Fee) / Bike Rentals (Seasonal-Fee) / Pet-Friendly / Free Wi-Fi.Located in gorgeous South Walton in Northwest Florida, the Santa Rosa area offers an attractive alternative to the sprawl of typical beach destinations. With just …see more

from $157 / night

$1022 - $2254 / week

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from $157 / night

1