50 Best Seaside Vacation rentals on Holiday Lettings - Beach rentals

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1,977 Vacation rentals

15

Seaside Vacation home rental

Florida Panhandle / Seaside

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Ask about children
15 Tupelo Street 3-night minimum stay required during spring break and summer; please no children under the age of 12 This cottage conveniently opens onto both 30A and Tupelo Street and is just steps to the beach. Once the permanent residence of The Mod …see more

from $504 / night

$3,528 / week

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from $504 / 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

27

Vacation home with shared pool in Seaside

Florida Panhandle / Seaside

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Tuscany – 210 W. Ruskin Place – Seaside, FL Stay with Sunburst and get up to $280 in Beach Gear delivered to your vacation home! Tuscany is a spacious, stately townhome perfectly located in the heart of Ruskin Place Artist Colony. It has 2 bedrooms and 2.5 baths and s …see more

from $269 / night

$1,738 - $3,538 / week

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from $269 / night

15

Vacation home rental

Florida Panhandle / Seaside

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Ask about children
"We had the vacation of a lifetime and Stay and Little Longer was the perfect place for it. Thank you for the attention to every detail in this home. We've already booked our stay for next year!"  --Guest Survey 2017 2132 East County Hwy. 30A 5-night mi …see more

from $1,701 / night

$11,907 / week

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from $1,701 / night

(2) Excellent 

14

Home rental in Seaside

Florida Panhandle / Seaside

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Ask about children
"What a beautiful well stocked cottage!! Right from the pages of Coastal Living magazine! It made for a relaxing beautiful weekend I will remember for a long time!  I'm very lucky to have found your little piece of paradise, thank you so much for opening your home to …see more

from $680 / night

$4,760 / week

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from $680 / 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

(2) Excellent 

43

Vacation home rental

Florida Panhandle / Seaside

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
The Bothy - 304 W. Ruskin Place, Seaside, FL Rent as Bothy 1 or 2 or 3! Recently remodeled, this impressive 3 story plus roof deck town home situated in Ruskin Square has 3 Master en-suite bedrooms with King beds, a bunk room, Queen Murphy bed and Queen sleeper sofa f …see more

from $551 / night

$3,550 - $7,552 / week

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from $551 / 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

$4,355 - $9,323 / week

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from $736 / 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

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

(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 fresh new exterior paint and stylish West Indies décor throughout.  As you …see more

from $1,011 / night

$7,077 / week

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from $1,011 / night

16

Home rental in Seaside

Florida Panhandle / Seaside

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Ask about children
640 Forest Street 3-night minimum stay required during spring break and summer, please no children under the age of 5 Named by its owners from Mississippi, the Magnolia State, Suite Magnolia I is a stylish and comfortable duplex-style cottage with …see more

from $471 / night

$3,297 / week

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from $471 / night

14

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

34

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 $285 / night

$1,820 - $3,920 / week

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from $285 / night

(1) Excellent 

30

Vacation home rental

Florida Panhandle / Seaside

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Tresor de la Mer – 25 Central Square #304 – Seaside, FL Exciting renovation over winter of 2018 – all new kitchen and interior finishes plus addition of a bedroom with a Twin Bunk Bed and an additional bathroom! Tresor de la Mer is a sophisticated and spacious two sto …see more

from $215 / night

$1,385 - $2,969 / week

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from $215 / night

19

Vacation home in Seaside

Florida Panhandle / Seaside

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Ask about children
"Staying in this house was the most unbelievable vacation our family has ever had. We will never forget our stay at Narnia!" -- Guest Survey 2017 2120 East County Hwy. 30A Saturday-to-Saturday stay required spring break and summer; 5 night minimum sprin …see more

from $3,199 / night

$22,393 / week

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from $3,199 / 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 $331 / night

$2,138 - $4,400 / week

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from $331 / night

15

Vacation home in Seaside

Florida Panhandle / Seaside

5 12 1 night min

  • 5 bedrooms
  • Sleeps 12
  • 1 night min
  • Ask about children
"Beautiful home. Love renting from CRA, units are always nice & clean! Our group also loves the gift bag - we play games & use it and the contents as prizes :) The "coveted CRA bag"!!! "  --Elegance Guest Survey, 2017 161 Smolian Circle 5-night minimum …see more

from $900 / night

$6,300 / week

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from $900 / 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 $516 / night

$3,065 - $6,491 / week

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from $516 / night

32

Seaside Vacation home rental

Florida Panhandle / Seaside

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Forsythe House – 208 W. Ruskin Place – Seaside, FL Stay with Sunburst and get up to $280 in Beach Gear delivered to your vacation home! Located right on Ruskin Park, The Forsythe House is a 3BR/2.5BA townhome that combines both modern and traditional the while mainta …see more

from $276 / night

$1,798 - $3,652 / week

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from $276 / night

30

Seaside Vacation home accommodation

Florida Panhandle / Seaside

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
As Luck Would Have It – 123 Quincy Circle – Seaside, FL “As Luck Would Have It” is a sophisticated 4-story townhome situated in Ruskin Place Park in the heart of Seaside, Florida. With two bedrooms and two and one half baths, this elegant art-filled home sleeps six. Mu …see more

from $311 / night

$2,015 - $4,175 / week

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from $311 / night

19

Vacation home in Seaside

Florida Panhandle / Seaside

4 9 1 night min

  • 4 bedrooms
  • Sleeps 9
  • 1 night min
  • Ask about children
15 Natchez Street 5-night minimum is required during spring break and 7-night minimum in summer Four the Girls is just 100 steps from both the beach and the Westside Pool. This home has been lovingly decorated and maintained and will be your new favorit …see more

from $1,203 / night

$8,421 / week

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from $1,203 / 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 

29

Vacation home with shared pool in Seaside

Florida Panhandle / Seaside

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Beachfront 10-Honeymoon Cottage – 2070 E. County Hwy 30A – Seaside, FL Pure, simple and elegant. These series of beachfront “Honeymoon Cottages,” designed by architect Scott Merrill, who at one time was Seaside’s town architect, and inspired by President Thomas Jeffers …see more

from $376 / night

$2,240 - $4,670 / week

Inquire View

from $376 / night

(2) Very Good 

27

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
Bewildered - 25 Central Square #306 - Seaside, FL Bewildered is a spacious two story penthouse apartment that offers the best of new urbanism living. Located on the third and fourth floor of the 25 Central Square Building in the heart of Seaside, this unit offers panor …see more

from $260 / night

$1,685 - $3,623 / week

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from $260 / night

(3) Very Good 

29

Seaside Vacation home rental

Florida Panhandle / Seaside

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Unforgettable - 25 Central Square #307 - Seaside, FL Unforgettable is a sophisticated and spacious two story penthouse apartment that offers the best of new urbanism living. Located on the third and fourth floor of the 25 Central Square Building in the heart of Seaside …see more

from $290 / night

$1,855 - $3,997 / week

Inquire View

from $290 / night

15

Vacation home in Seaside

Florida Panhandle / Seaside

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Ask about children
"We felt so special during our vacation in this beautiful home. It was relaxing and we thoroughly enjoyed it all! Everything was just wonderful from the location to the porches to the town itself." --Guest Survey 2017 127 Seaside Avenue 5-night minimum …see more

from $1,321 / night

$9,247 / week

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from $1,321 / 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

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

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

Inquire View

from $702 / night

30

Vacation home with shared pool in Seaside

Florida Panhandle / Seaside

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
A Sight to Sea - 25 Central Square #305 - Seaside, FL “A Sight to Sea” is a sophisticated and stylish two story penthouse apartment that offers the best of new urbanism living. Located on the third and fourth floor of the 25 Central Square Building in the heart of Seas …see more

from $285 / night

$1,820 - $3,920 / week

Inquire View

from $285 / night

(2)  

15

Seaside Vacation home rental

Florida Panhandle / Seaside

3 9 1 night min

  • 3 bedrooms
  • Sleeps 9
  • 1 night min
  • Ask about children
2444 East County Hwy. 30A 7-night minimum spring break, summer, and fall/winter holidays Wilder by the Sea is a one of a kind, Gulf-front home offering gracious living on the beach with three nicely appointed bedrooms and an open, airy living space. Enj …see more

from $1,650 / night

$11,550 / week

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from $1,650 / 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

Inquire View

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

Inquire View

from $360 / night

24

Vacation home accommodation

Florida Panhandle / Seaside

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Beachfront 4-Honeymoon Cottage – 2334 E. County Hwy 30A – Seaside, FL Pure, simple and elegant. These series of beachfront “Honeymoon Cottages,” designed by architect Scott Merrill, who at one time was Seaside’s town architect, and inspired by President Thomas Jefferso …see more

from $361 / night

$2,160 - $4,500 / week

Inquire View

from $361 / 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

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 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

Inquire View

from $937 / night

(2) Very Good 

25

Vacation home with shared pool in Seaside

Florida Panhandle / Seaside

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Gift by the Sea-Beachfront 9 – 2088 E. County Hwy 30A – Seaside, FL Pure, simple and elegant. These series of beachfront “Honeymoon Cottages,” designed by architect Scott Merrill, who at one time was Seaside’s town architect, and inspired by President Thomas Jefferson …see more

from $376 / night

$2,240 - $4,670 / week

Inquire View

from $376 / 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