50 Best Seaside Vacation rentals on Holiday Lettings - Beach rentals

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3,164 Vacation rentals

14

Vacation home in Seaside

Florida Panhandle / Seaside

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Ask about children
"What was not to enjoy!? The proximity of the cottage to the center of town was perfect, it was nice and clean, and we will be back!"  --Shore is Fun Guest Survey, 2017  32 Pensacola Street 5-night minimum stay required during spring break and summer …see more

from $702 / night

$4,914 / week

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from $702 / night

15

Seaside Vacation home rental

Florida Panhandle / Seaside

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Ask about children
30 West Ruskin Street 4-night minimum stay required during spring break and summer Moore Fun is conveniently located just a short walk to the beach and Central Square. On the first floor, you will find a living room with a fireplace, dining room, a spac …see more

from $573 / night

$4,011 / week

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from $573 / night

15

Vacation home in Seaside

Florida Panhandle / Seaside

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Ask about children
"We had an awesome experience. We stayed in this same cottage many, many years ago and very pleased to see the updates the owners had made. Nicely done!"  --Moon Shine Guest Survey, 2017 62 Pensacola Street 5-night minimum stay required during summer …see more

from $877 / night

$6,139 / week

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from $877 / night

11

Vacation home in Seaside

Florida Panhandle / Seaside

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Ask about children
"The cottage was absolutely wonderful and had everything needed! Was perfect for large group, especially the 2nd floor den. The house was great and Seaside itself just keeps getting better and better!" --Guest Survey, 2017 20 East Ruskin Street 5-night …see more

from $971 / night

$6,797 / week

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from $971 / night

15

Vacation home in Seaside

Florida Panhandle / Seaside

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Ask about children
204 Ruskin Place Please no children under that age of 18 The Conservatory is an exquisite 1,600 sq. ft. penthouse that features panoramic views of Seaside, FL from the rooftop, which also includes a hot tub. The master bedroom suite is highlighted by a …see more

from $650 / night

$4,550 / week

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from $650 / night

15

Home rental in Seaside

Florida Panhandle / Seaside

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Ask about children
204 Ruskin Place  Please no children under the age of 18 Maiden’s Chambre is located on the second floor of Renaissance House in Ruskin Place Artist Colony. It is a lovely one1bedroom unit with an antique Belgian Walnut queen bed and a private full bath …see more

from $355 / night

$2,485 / week

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from $355 / night

15

Home rental in Seaside

Florida Panhandle / Seaside

5 13 1 night min

  • 5 bedrooms
  • Sleeps 13
  • 1 night min
  • Ask about children
117 Savannah Street 5-night minimum stay required during spring break and summer Say hello to Drift Away on quaint Savannah Street in picturesque Seaside. The house was completely remodeled top to bottom in 2017, so won't you be lucky to choose this as …see more

from $933 / night

$6,531 / week

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from $933 / night

15

Vacation home in Seaside

Florida Panhandle / Seaside

5 12 1 night min

  • 5 bedrooms
  • Sleeps 12
  • 1 night min
  • Ask about children
47 Western Lake (Watercolor) 5-night minimum stay required during spring break and summer Located across from the beach, Masterpiece is an expertly decorated home with custom fabrics, original artwork, state-of-the-art appliances and beautiful dark wood …see more

from $1,455 / night

$10,185 / week

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from $1,455 / night

30

Seaside Vacation home rental

Florida Panhandle / Seaside

3 12 Min stay varies

  • 3 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Center Stage – 63 Central Square – Seaside, FL Appropriately named “Center Stage”, this sophisticated town center apartment is ideally located in the heart of Seaside. Center Stage is directly in front of the Seaside Amphitheater where you can watch weekly plays and c …see more

from $511 / night

$3,030 - $6,491 / week

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from $511 / night

15

Vacation home in Seaside

Florida Panhandle / Seaside

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Ask about children
39 West Ruskin Street 5-night minimum stay required during spring break and summer A perfect place to escape everyday stresses, Take Five is located a few minutes from the beach and to Seaside's Central Square. This stylish cottage has a nice and co …see more

from $661 / night

$4,627 / week

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from $661 / night

15

Seaside Vacation home rental

Florida Panhandle / Seaside

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Ask about children
"We loved the house and location. I've stayed in several homes in the area and this was definitely a favorite. Thanks for the beach bag and all the extras!" --Guest Survey, 2017 52 East Ruskin Street 4-night minimum stay required during spring break and …see more

from $843 / night

$5,901 / week

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from $843 / night

15

Vacation home in Seaside

Florida Panhandle / Seaside

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Ask about children
53 West Ruskin Street 5 night minimum spring break and summer "This cottage was absolutely wonderful. We loved it, clean, spacious, close to town and beach. So nice to have the bikes, we used them all. Loved the well stocked kitchen appliances and we LO …see more

from $937 / night

$6,559 / week

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from $937 / night

15

Vacation home in Seaside

Florida Panhandle / Seaside

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • Ask about children
"We loved our stay in Love Me Tender!" - Guest Survey, 2017 2326 East County Hwy. 30A Located beachside, Love Me Tender, Love Me True is just 32 steps to the iconic East Ruskin Beach Pavilion and a step-saving, sand-path convenience to Seaside's favored …see more

from $738 / night

$5,166 / week

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from $738 / night

15

Home rental in Seaside

Florida Panhandle / Seaside

5 12 1 night min

  • 5 bedrooms
  • Sleeps 12
  • 1 night min
  • Ask about children
"It was wonderful!  The house worked so well for our group of twelve. It was very clean, and we enjoyed ourselves very much."  --Guest Survey, 2017 142 East Ruskin Street Located near the pools, fitness center and tennis courts, Big Pink is also just a …see more

from $1,205 / night

$8,435 / week

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from $1,205 / night

14

Vacation home rental

Florida Panhandle / Seaside

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Ask about children
32 Pensacola Street Please no children under that age of 9 Takin It E-sea, located down a short footpath, is the guest house for the main cottage Shore is Fun. Ideally situated, you are just a short stroll from the acclaimed white-sand beach and emerald …see more

from $354 / night

$2,478 / week

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from $354 / night

33

Vacation home with shared pool in Seaside

Florida Panhandle / Seaside

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Skye – 2026 E. County Hwy 30A – Seaside, FL Beautiful Skye is situated in the quaint town of Seaside, Florida. Located on the beach side with brilliant Gulf views and convenient access to the beach, the home has just undergone an extensive renovation...new chef’s kitch …see more

from $736 / night

$4,345 - $9,323 / week

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from $736 / night

13

Vacation home rental

Florida Panhandle / Seaside

3 11 1 night min

  • 3 bedrooms
  • Sleeps 11
  • 1 night min
  • Ask about children
2110 East County Hwy 30A 5-night minimum stay required during spring break; and 7-night minimum in summer Located on the Gulf side of 30A, Beside the Sea has just undergone renovations and has returned with an additional bedroom and another full bath, u …see more

from $1,011 / night

$7,077 / week

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from $1,011 / night

15

Vacation home in Seaside

Florida Panhandle / Seaside

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Ask about children
"Lovely cottage. It was perfect for us! We didn't realize we would have maid service - they were friendly and did a good job. We had a great time." --Southern Exposure Guest Survey, 2017 2368 East County Hwy. 30A 6-night minimum stay required during sum …see more

from $1,073 / night

$7,511 / week

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from $1,073 / night

15

Seaside Vacation home rental

Florida Panhandle / Seaside

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Ask about children
123 Grayton Street 5-night minimum stay required during summer Midsummer Night's Dream is not exactly what you'd find in Shakespeare, but definitely what you'd find in Seaside, FL. Located across from the Westside Pool and only a block from the beach, a …see more

from $663 / night

$4,641 / week

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from $663 / night

15

Vacation home in Seaside

Florida Panhandle / Seaside

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Ask about children
"We LOVED the home - it was the perfect fit for our family! We can't wait to visit again and stay here!" -- Fleur de Lis Guest Survey, 2017 66 Seaside Avenue Saturday-to-Saturday stay required during spring break and summer; 3-night minimum stay require …see more

from $702 / night

$4,914 / week

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from $702 / night

15

Vacation home rental

Florida Panhandle / Seaside

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Ask about children
2132 East County Hwy. 30A 7-night minimum during spring break & summer; 4-night minimum during Thanksgiving and Christmas holidays, spring, fall and winter seasons  This lovely 4-bedroom, four-and-a-half bath cottage has an abundance of windows on all l …see more

from $1,701 / night

$11,907 / week

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from $1,701 / night

15

Vacation home in Seaside

Florida Panhandle / Seaside

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Ask about children
127 Seaside Avenue 5-night minimum stay required during spring break and summer Located near the Adult/Family pools, tennis, and croquet recreational facilities, String of Pearls is a classic, yet inviting cottage with its antebellum columns and large o …see more

from $1,321 / night

$9,247 / week

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from $1,321 / night

(1)  

8

Vacation home in Seaside

Florida Panhandle / Seaside

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Ask about children
3-night minimum stay required; except 2-night minimum in October - January Sweetie Pie is definitely the perfect place to experience beachfront in Seaside, with its prime location with pristine views of the emerald-green waters and glorious sunrises and su …see more

from $518 / night

$3,626 / week

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from $518 / night

13

Vacation home in Seaside

Florida Panhandle / Seaside

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Ask about children
"Very comfortable cottage. Love the tower room on top!" --O Happy Day Guest Survey, 2017 61 Savannah Street 5-night minimum stay required during spring break and summer O Happy Day is a charming cottage that will have you feeling happy all day lo …see more

from $663 / night

$4,641 / week

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from $663 / night

14

Vacation home in Seaside

Florida Panhandle / Seaside

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Ask about children
19 Rosewalk Aly 3-night minimum stay required during spring break and summer Mis B’Haven is tucked away in Rosewalk, a cluster of quaint cottages with a pedestrian footpath meandering through a thick grove of oaks trees. This cozy and charming cottage f …see more

from $466 / night

$3,262 / week

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from $466 / night

13

Vacation home in Seaside

Florida Panhandle / Seaside

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Ask about children
"It was just perfect!" --Spinnaker Guest Survey, 2017 54 Robert's Way 3-night minimum stay required during spring break and summer Spinnaker offers plenty of comfort and fun for your family vacation and is just 4 houses from 30A and the beach. It …see more

from $471 / night

$3,297 / week

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from $471 / night

15

Seaside Vacation home rental

Florida Panhandle / Seaside

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Ask about children
"We have stayed at Toye three times and love the house. The recent renovations are very nice!" --Guest Survey, 2017 2454 East County Hwy. 30A Please no children under the age of 5; 5-night minimum stay required during spring break and summer A lo …see more

from $1,009 / night

$7,063 / week

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from $1,009 / night

13

Vacation home in Seaside

Florida Panhandle / Seaside

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Ask about children
152 East Ruskin Street Located near Ruskin Place Artist Colony and the beach, Somewhere is a delightful cottage to experience Seaside. Walk through Somewhere’s private canopied entrance onto its screened-in porch where you’ll find a peaceful and uplifting deco …see more

from $360 / night

$2,520 / week

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from $360 / night

27

Seaside Vacation home rental

Florida Panhandle / Seaside

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Persuasion - 42 Savannah Street – Seaside, FL Stay with Sunburst and get up to $280 in Beach Gear delivered to your vacation home! Beautiful Persuasion is situated in the quaint town of Seaside, Florida. Located in the panhandle, Seaside resembles a modernistic approa …see more

from $326 / night

$2,103 - $4,400 / week

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from $326 / night

33

Vacation home with shared pool in Seaside

Florida Panhandle / Seaside

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Above the Crowd – 25 Central Square # 301 – Seaside, FL Above the Crowd is a sophisticated and stylish two story penthouse apartment that offers the best of new urbanism living. This unit was completely renovated in 2016 and has all new floors, kitchen, additional bath …see more

from $280 / night

$1,785 - $3,920 / week

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from $280 / night

15

Vacation home rental

Florida Panhandle / Seaside

4 11 1 night min

  • 4 bedrooms
  • Sleeps 11
  • 1 night min
  • Ask about children
"Great Location! Pet friendly! Right off town center! We love the accommodation! We were able to enjoy the porch that overlooks the Seaside town center. It is a great location!"  -- Cherished Guest Survey, 2017 119 Quincy Circle 4-night minimum stay req …see more

from $754 / night

$5,278 / week

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from $754 / night

15

Vacation home in Seaside

Florida Panhandle / Seaside

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Ask about children
59 West Ruskin 4-night minimum stay required during spring break and summer Spin Echo is a well-appointed cottage located near the Seaside Lyceum and within walking distance to the sugar-white sand beach, as well as to shopping and dining in Central Squ …see more

from $506 / night

$3,542 / week

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from $506 / night

14

Home rental in Seaside

Florida Panhandle / Seaside

4 12 1 night min

  • 4 bedrooms
  • Sleeps 12
  • 1 night min
  • Ask about children
109 West Ruskin Place Saturday-to-Saturday stay required during spring break and summer Conveniently located behind the Ruskin Place Artist Colony and near the shops and restaurants of Central Square, Plum Lucky is the combination of two well-appointed …see more

from $1,144 / night

$8,008 / week

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from $1,144 / night

15

Home rental in Seaside

Florida Panhandle / Seaside

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Ask about children
842 Forest St. 5 night minimum stay required during spring and summer Named after the owners' favorite Jimmy Buffet song, Banana Republic is a 3 BR, 2.5 bath stylish combination of tropical and mid-century décor that sleeps 7 and is located near the Wes …see more

from $730 / night

$5,110 / week

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from $730 / night

16

Seaside Vacation home rental

Florida Panhandle / Seaside

4 13 1 night min

  • 4 bedrooms
  • Sleeps 13
  • 1 night min
  • Ask about children
750 Forest Street 5-night minimum spring break and summer Sandy Toes is the combination of Sea Biscuit and Grace Sea, located near the Westside Pool.  This popular Seaside rental has recently been renovated with new paint and furnishings for a fresh, re …see more

from $911 / night

$6,377 / week

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from $911 / night

(1) Good 

15

Home rental in Seaside

Florida Panhandle / Seaside

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Ask about children
"We loved every second of our stay here!  A great condo with everything we needed!"  --Guest Survey 29 Quincy Circle 3-night minimum stay required during spring break and summer Returning to our program in 2018 with all new furnishings and interi …see more

from $507 / night

$3,549 / week

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from $507 / night

15

Vacation home in Seaside

Florida Panhandle / Seaside

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Ask about children
40 Venice Circle 5-night minimum stay required during spring break and summer Splendor in the Sand is a well-appointed 3-bedroom/3.5 bath home, conveniently located near the Seaside Adult and Family Pools and the Fitness Center.  On the first floor, the …see more

from $842 / night

$5,894 / week

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from $842 / night

15

Vacation home in Seaside

Florida Panhandle / Seaside

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Ask about children
751 Forest Street 5-night minimum stay required during spring and summer Comfort and conveniences- Southern Splendor offers it all. The front entry leads you into a fully-equipped kitchen with a gas stove and bar seating, as well as a living area, a din …see more

from $889 / night

$6,223 / week

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from $889 / night

(1)  

20

Vacation home in Seaside

Florida Panhandle / Seaside

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Ask about children
2376 East County Hwy. 30A Find out for yourself why this home has more repeat guests than any other in Seaside, Florida! Savannah Sands is a classically designed Gulf front beauty with stylish West Indies décor throughout.  As you enter the house, on the first …see more

from $1,011 / night

$7,077 / week

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from $1,011 / night

13

Vacation home in Seaside

Florida Panhandle / Seaside

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Ask about children
55 Central Square 4-night minimum required during summer; 3 night minimum remainder of year Alta Vista is conveniently located in the center of town and is stunning from wall to wall. This recently renovated townhouse includes an oversized master bedroo …see more

from $868 / night

$6,076 / week

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from $868 / night