50 Best Seaside Vacation rentals on Holiday Lettings - Beach rentals

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2,584 Vacation rentals

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

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

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

15

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

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

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

(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

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from $290 / 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

Vacation home in Seaside

Florida Panhandle / Seaside

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Ask about children
"Beautiful place. Perfect location!  We loved the amazing town, the condo and our entire trip!" --Guest Survey 2018 55 Central Square 4-night minimum required during summer; 3 night minimum remainder of year Alta Vista is conveniently located in …see more

from $868 / night

$6,076 / week

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from $868 / night

(2) Excellent 

33

Vacation home with shared pool in Seaside

Florida Panhandle / Seaside

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Sea Sabella – 2314 E. County Hwy 30A – Seaside, FL This luxurious three story home has fifty feet of Gulf frontage and features a beautiful and spacious floor plan. Sea Sabella's specially milled sunken cypress siding was reclaimed from some of North Florida's own rive …see more

from $1,101 / night

$6,465 - $13,965 / week

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from $1,101 / 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 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

13

Vacation home in Seaside

Florida Panhandle / Seaside

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Ask about children
"The cottage is so truly perfect for our needs. So beautifully decorated, well maintained, well located, comfortable. We will use this one next year as well." --Guest Survey 2018 "Very comfortable cottage. Love the tower room on top!" --Guest Survey, 2017 …see more

from $663 / night

$4,641 / week

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from $663 / 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

(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

Vacation home in Seaside

Florida Panhandle / Seaside

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Ask about children
"This is a GREAT house in Seaside. We have recommended it to all of our friends and had the best time staying here, loved everything about it!"  --Guest Survey 2018 19 Rosewalk Aly 3-night minimum stay required during spring break and summer Pret …see more

from $466 / night

$3,262 / week

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from $466 / night

16

Seaside Vacation condo rental

Florida Panhandle / Seaside

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Life in Shorts– 46 Tupelo Street – Seaside, FL Stay with Sunburst and get up to $280 in Beach Gear delivered to your vacation home! If you've ever been to Seaside, you will agree that Life in Shorts is exactly what Seaside stands for and was meant to be.... everythi …see more

from $284 / night

$1,838 - $3,758 / week

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from $284 / 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

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from $702 / 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

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

(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

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

14

Home rental in Seaside

Florida Panhandle / Seaside

4 12 1 night min

  • 4 bedrooms
  • Sleeps 12
  • 1 night min
  • Ask about children
"We had three families stay here and all of us enjoyed our vacation so much!  The tower is amazing, the home has so much charm, each section of it was great!" --Guest Survey 2018 109 West Ruskin Place Saturday-to-Saturday stay required during spring bre …see more

from $1,144 / night

$8,008 / week

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from $1,144 / night

15

Vacation home in Seaside

Florida Panhandle / Seaside

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Ask about children
"The cottage was in a great location and is a really nice place to be on vacation." --Whatcha Dune Guest Survey, 2017 608 Forest Street 5-night minimum stay required during spring break and summer Whatcha Dune is family-friendly cottage located n …see more

from $875 / night

$6,125 / week

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from $875 / 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

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 "What a beautiful vacation spot on a quiet street. Such a lovely home to spend our vacation in. Thank you for sharing yo …see more

from $702 / night

$4,914 / week

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from $702 / night

14

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 one bedroom 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

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Ask about children
"We enjoyed this home so much. It was so clean and well kept, we loved the atmosphere and everything being so close by. Thank you for sharing your home!" --Our Place Guest Survey, 2017 652 Forest Street …see more

from $387 / night

$2,709 / week

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from $387 / 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 - $3,885 / week

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from $285 / night

14

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, 2018 2454 East County Hwy. 30A Please no children under the age of 5; 5-night minimum stay required during spring break and summer One …see more

from $1,009 / night

$7,063 / week

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from $1,009 / 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 

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

17

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

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

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

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

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 - $3,885 / week

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from $285 / night

(3)  

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

(1) Excellent 

32

Vacation home rental

Florida Panhandle / Seaside

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Tresor de la Mer – 25 Central Square #304 – Seaside, FL Exciting 2018 renovation – 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-story penthouse a …see more

from $275 / night

$1,770 - $3,810 / week

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from $275 / night

12

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
West Indian – 23 Odessa Street – Seaside, FL Stay with Sunburst and get up to $280 in Beach Gear delivered to your vacation home! This 1 bedroom, 1 bath carriage home is the perfect spot for 1 or 2 guests. Located just 4 homes north of Seaside’s private beaches and m …see more

from $169 / night

$1,118 - $2,174 / week

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from $169 / night