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

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2,750 Vacation rentals

26

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
The beach is only a short walk away when you stay at this breathtaking 4-bedroom, 4-bath Santa Rosa Beach vacation rental home. Impressive finishes coupled with modern aesthetics and accommodations for 8 adults on king beds and a pullout, along with 4 children in the bu …see more

from $205 / night

$1,435 / week

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Responds fast!
avg. 41 minutes

from $205 / 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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from $204 / 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

(1) Very Good 

25

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
Includes Sterling 30A's Vacay Your Way $200 Credit. Use for free bikes, free beach service, free SUP, or toward dozens of other great Live Well 30A rentals or services! Learn more below. Make plans to spend a relaxing vacation in this cozy cottage located in the family …see more

from $149 / night

$1,469 - $5,670 / week

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from $149 / 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 $240 / night

$1,680 / week

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from $240 / night

(5) Very Good 

21

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

(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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Responds fast!
avg. 3 hours 43 minutes

from $182 / night

53

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 - $3,521 / week

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from $143 / night

31

Grayton Beach Vacation townhouse rental

Santa Rosa Beach / Grayton Beach

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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

$1,130 - $2,640 / week

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Responds fast!
avg. 3 hours 45 minutes

from $165 / 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 $185 / night

$1,250 / week

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from $185 / night

(1) Excellent 

23

Vacation home with shared pool in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
126 East Royal Fern Way "Seas the Day" is a stunning home that features 2 living areas, 2 master suites, and 3 additional bedrooms 1 additional King,1 Queen, 1 Bunk w/ Twins and twin trundle, all complete with plush bedding, sleeps a total of 11, with pull out sofa in …see more

from $230 / night

$1,610 - $3,682 / week

Inquire View

from $230 / night

(7) Excellent 

Certificate of Excellence

24

Vacation home with shared pool in Grayton Beach

Santa Rosa Beach / Grayton Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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

Certificate of Excellence

from $156 / night

$1,092 - $3,000 / week

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Responds fast!
avg. 49 minutes

from $156 / night

(36) Excellent 

Certificate of Excellence

26

Home rental in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • 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 $180 / night

$1,100 - $1,750 / week

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Responds fast!
avg. 1 hour 46 minutes

from $180 / night

(2) Very Good 

20

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
  • Child friendly
  • 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. Includes Sterling 30A's Vacay Your Way $200 Credit. Use for free bikes, …see more

from $115 / night

$949 - $3,730 / week

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from $115 / night

39

Vacation home with shared pool in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
FREE $100 Grocery Gift Card With Summer 7 Night Bookings! Includes Sterling 30A's Vacay Your Way $200 Credit. Use for free bikes, free beach service, free SUP, or toward dozens of other great Live Well 30A rentals or services! Learn more below. Located in the New an …see more

from $160 / night

$1,120 - $6,412 / week

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from $160 / 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 $105 / night

$735 / week

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Responds fast!
avg. 1 hour 16 minutes

from $105 / night

25

Vacation home with shared pool in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
971 Sandgrass Boulevard in the 'NatureWalk at Seagrove' community. Overlooking the nature preserve and pond, this beach-themed home boasts fabulous accommodations for up to 10 guests, with four bedrooms and three and a half baths. Two master suites and two living rooms …see more

from $184 / night

$1,208 - $8,665 / week

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from $184 / 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

$1,250 / week

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from $150 / night

24

Grayton Beach Vacation condo rental

Santa Rosa Beach / Grayton Beach

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Includes Sterling 30A's Vacay Your Way $200 Credit. Use for free bikes, free beach service, free SUP, or toward dozens of other great Live Well 30A rentals or services! Learn more below. This charming 3 bedroom, 2 bathroom condo in the Beachside Villas of Seagrove is …see more

from $190 / night

$1,330 - $2,170 / week

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from $190 / night

21

Santa Rosa Beach Vacation apartment rental

Florida Panhandle / Santa Rosa Beach

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Includes Sterling 30A's Vacay Your Way $200 Credit. Use for free bikes, free beach service, free SUP, or toward dozens of other great Live Well 30A rentals or services! Learn more below. This beautiful two bedroom, two bathroom unit is just 100 short yards from Santa …see more

from $137 / night

$944 - $4,519 / week

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from $137 / night

32

Vacation home in Grayton Beach

Santa Rosa Beach / Grayton Beach

7 18 Min stay varies

  • 7 bedrooms
  • Sleeps 18
  • Min stay varies
  • Child friendly
  • Air conditioning
241 Red Cedar Way is beach elegance at its finest with custom décor and an amazing lake-side location which makes this the perfect home for your family's vacation. The luxurious main floor is home to an open concept living space with a large sofa and four large side cha …see more

from $650 / night

$4,550 - $10,955 / week

Inquire View

from $650 / night

(1) Very Good 

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 16 minutes

from $190 / night

(1) Excellent 

30

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

$1,130 - $2,640 / week

Book View

Responds fast!
avg. 3 hours 45 minutes

from $165 / night

(1) Excellent 

30

Vacation townhouse with shared pool, golf nearby in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Stay with us if you enjoy: 3 minute walks to the beach, a relaxing heated pool, sipping cocktails on a private rooftop deck, romantic evenings by the fireplace, free Netflix & WiFi. Whether you are looking for a getaway close to home or farther away, plan a last minute …see more

from $350 / night

$3,300 - $3,500 / week

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from $350 / night

(1) Excellent 

30

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 $351 / night

$2,258 - $4,670 / week

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from $351 / 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
  • 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 comfor …see more

from $350 / night

$2,450 / week

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Responds fast!
avg. 27 minutes

from $350 / 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

$1,130 - $2,640 / week

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Responds fast!
avg. 2 hours 42 minutes

from $165 / 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 $222 / night

$1,549 - $1,899 / week

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Responds fast!
avg. 43 minutes

from $222 / night

26

Vacation home in Grayton Beach

Santa Rosa Beach / Grayton Beach

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Experience the beauty of the Gulf Coast at 'Happy Ours,' a 5-bedroom, 4-bathroom vacation rental home in Seagrove. Perfect for snowbirds and beach bunnies alike, this 2,058-square-foot home for 12 sits just steps from the pristine sands and crystal clear waters of Seagr …see more

from $305 / night

$2,135 - $4,690 / week

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Responds fast!
avg. 41 minutes

from $305 / 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
  • Child friendly
  • Air conditioning
Includes Sterling 30A's Vacay Your Way $200 Credit. Use for free bikes, free beach service, free SUP, or toward dozens of other great Live Well 30A rentals or services! Learn more below. Chelsea Loop is a charming circular drive through this Gulf front community. The …see more

from $174 / night

$1,103 - $7,153 / week

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from $174 / 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 $176 / night

$1,153 - $2,233 / week

Inquire View

from $176 / 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

27

Vacation home in Santa Rosa Beach

Florida Panhandle / Santa Rosa Beach

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Enjoy a relaxing beach getaway at this charming 3-bedroom + loft, 3-bathroom vacation rental house that comfortably sleeps 10! Situated in a small Santa Rosa Beach neighborhood with great amenities, just 200 meters from the pristine shores, this home guarantees a rejuve …see more

from $150 / night

$1,050 / week

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Responds fast!
avg. 17 minutes

from $150 / night

(2) Very Good 

18

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
  • Child friendly
  • Air conditioning
Just a short bike ride away from the iconic American Beach Town, Seaside, Cassine Station 303 is sits right on the prestigious Scenic Highway 30A. Offering guest a tranquil environment with a bit of privacy. Cassine Station 303 is the perfect condo for a weekend geta …see more

from $110 / night

$702 - $1,234 / week

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from $110 / night

36

Grayton Beach Vacation townhouse rental

Santa Rosa Beach / Grayton Beach

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Prominence - 30A ~ Beach vacation townhome rental "Sandi Blessings" located at 49-A York Lane, Watersound, Florida 32461 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 deve …see more

from $195 / night

$1,210 - $2,640 / week

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Responds fast!
avg. 3 hours 45 minutes

from $195 / 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 - $1,100 / week

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from $90 / night

(3) 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

$1,400 / week

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Responds fast!
avg. 3 hours 46 minutes

from $250 / 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

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

Inquire View

from $230 / night

25

Vacation home in Grayton Beach

Santa Rosa Beach / Grayton Beach

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Fish Bait– 209 Defuniak St.– Grayton Beach, FL Stay with Sunburst and get up to $280 in Beach Gear delivered to your vacation home! Fish Bait is a fabulous, newly constructed 4 bedroom/3.5 bath home located in beautiful historic Grayton Beach. From the beautiful surf …see more

from $346 / night

$2,078 - $4,268 / week

Inquire View

from $346 / night