50 Best Seaside Vacation rentals on Holiday Lettings - Beach rentals

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77 Vacation rentals

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." --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 near the Seaside Chapel, directly acr …see more

from $875 / night

$6125 / week

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from $875 / 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 open furnished fro …see more

from $1321 / night

$9247 / week

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from $1321 / night

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 Modicas (of Modica M …see more

from $504 / night

$3528 / week

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from $504 / night

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
Firefly - Beachfront 8 – 2094 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 as he …see more

from $371 / night

$2215 - $4698 / week

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from $371 / 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 decor, offerin …see more

from $360 / night

$2520 / week

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from $360 / 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 LOVED the nespresso …see more

from $937 / night

$6559 / week

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from $937 / night

15

Vacation home rental

Florida Panhandle / Seaside

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Ask about children
36 East Ruskin Street 3-night minimum stay required during spring break and summer Conveniently located, Sweet Potato is just a short stroll to the beach. This cozy cottage includes a nice screened-in front porch with rockers, a large open living room with dining area, …see more

from $466 / night

$3262 / week

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from $466 / night

11

Condo rental in Seaside

Florida Panhandle / Seaside

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
Ideally located in the heart of Seaside's Ruskin Place, STAIRWAY TO HEAVEN is the consummate new urban residence. Widely admired and internationally published, this three story residence is a child of the Bauhaus International Modern Movement. Cast in the 1996 movie, ' …see more

from $495 / night

$3250 - $6250 / week

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from $495 / night

15

Vacation home in Seaside

Florida Panhandle / Seaside

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Ask about children
75 Tupelo Street 5-night minimum stay required during spring break and summer Sundance is a large beach cottage with a casual feel and natural tones throughout. Entrance is through a cozy screened-in porch where you will find a living area full of windows for lots of na …see more

from $887 / night

$6209 / week

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from $887 / 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 floors. The firs …see more

from $1456 / night

$10186 / week

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from $1456 / night

15

Vacation home in Seaside

Florida Panhandle / Seaside

5 10 1 night min

  • 5 bedrooms
  • Sleeps 10
  • 1 night min
  • Ask about children
764 Forest Street 5-night minimum stay required during spring break and summer;Saturday to Saturday required during July 4th holiday week Located near the Westside Pool, the beach and Central Square, Mojo Biblio is a unique home with an open, airy and spacious floor pla …see more

from $906 / night

$6342 / week

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from $906 / 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 End of Summer Special - 20% Off! 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 moder …see more

from $271 / night

$1763 - $3652 / week

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from $271 / night

13

Vacation home in Seaside

Florida Panhandle / Seaside

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Ask about children
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 has been completely renovated in 2017, and you will delight in the updated fu …see more

from $472 / night

$3298 / week

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from $472 / 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-green waters of …see more

from $355 / night

$2479 / week

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from $355 / 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 long. Enter and find a whi …see more

from $663 / night

$4641 / week

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from $663 / 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 Shore is Fun is conve …see more

from $702 / night

$4914 / week

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from $702 / 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
29 Quincy Circle 3-night minimum stay required during spring break and summer Just steps away from the beach and located in the Medical/Arts building of Central Square, this spacious two-bedroom is a metropolitan masterpiece. Twelve-foot high ceilings and dark hardwood …see more

from $472 / night

$3298 / week

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from $472 / night

(1)  

15

Vacation home in Seaside

Florida Panhandle / Seaside

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Ask about children
45 Central Square 5-night minimum stay required during spring break and summer Far Niente is short for “doing nothing” and this is the perfect place for doing exactly that! This grand two-story penthouse is located above Central Square in Seaside, offering panoramic vie …see more

from $1048 / night

$7336 / week

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from $1048 / night

(1)  

15

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 floor is t …see more

from $1011 / night

$7077 / week

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from $1011 / night

19

Vacation home in Seaside

Florida Panhandle / Seaside

4 7 1 night min

  • 4 bedrooms
  • Sleeps 7
  • 1 night min
  • Ask about children
2120 East County Hwy. 30A Limited Saturday-to-Saturday stay during peak summer season; please no children under the age of 3 This exclusive residence has been the cover story for several publications including Architectural Digest, Coastal Living, The Coastal Cottage, 3 …see more

from $3199 / night

$22393 / week

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from $3199 / 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 End of Summer Special - 20% Off! 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 wher …see more

from $511 / night

$3030 - $6491 / week

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from $511 / 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 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 features tongue and gr …see more

from $466 / night

$3262 / week

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from $466 / 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 minimum stay requ …see more

from $971 / night

$6797 / week

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from $971 / night

15

Seaside Vacation home rental

Florida Panhandle / Seaside

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Ask about children
"Great house, town, beach, food. This house was a very nice place to say." --Starry Night Guest Survey, 2017 13 Odessa Street 5-night minimum stay required during spring break and summer This spectacular cottage is located directly across the street from the beach. The …see more

from $878 / night

$6140 / week

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from $878 / night

11

Home rental in Seaside

Florida Panhandle / Seaside

2 7 1 night min

  • 2 bedrooms
  • Sleeps 7
  • 1 night min
  • Ask about children
210 Ruskin Place 3-night minimum stay required during spring break and summer Tuscany is a spacious, stately townhome perfectly located in the heart of Ruskin Place Artist Colony. The second floor includes a fully-equipped kitchen with granite counter tops, bar seating …see more

from $506 / night

$3542 / week

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from $506 / night

15

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, relaxed beach home a …see more

from $911 / night

$6377 / week

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from $911 / night

14

Seaside Vacation home rental

Florida Panhandle / Seaside

6 13 1 night min

  • 6 bedrooms
  • Sleeps 13
  • 1 night min
  • Ask about children
147 Grayton Street The Old Natchez Compound is conveniently located across from the Westside Pool and combines three separate living areas- perfect for a large family or group. On the left side of the compound, Oak Creek Annie’s (OAKCR) speaks of rustic times and folklo …see more

from $1011 / night

$7077 / week

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from $1011 / 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 Adult and Family Pools/Fitness Center. On the first floor, there is a large den, a king bedroom …see more

from $842 / night

$5894 / week

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from $842 / night

0

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 New for 2017 season, the penthouse has been completely redecorated, painted and floors refinished! “A Sight to Sea” is a sophisticated and stylish two story penthouse apartment that offers the best of new urbanism …see more

from $280 / night

$1785 - $3920 / week

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from $280 / night

14

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 short walk to Ruski …see more

from $1205 / night

$8435 / week

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from $1205 / 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, class, 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 dining area …see more

from $889 / night

$6223 / week

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from $889 / 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
2060 East County Hwy. 30A 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 sun …see more

from $518 / night

$3626 / week

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from $518 / 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 bedroom that is elegant …see more

from $868 / night

$6076 / week

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from $868 / night

15

Seaside Vacation home rental

Florida Panhandle / Seaside

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Ask about children
561 Forest Street 5-night minimum stay required during spring break and summer Soulshine is conveniently located just minutes away from Ruskin Place Artist Colony and the Seaside Chapel. This cottage has lots of floor space and comfortably embraces large families. The f …see more

from $714 / night

$4998 / week

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from $714 / night

15

Seaside Vacation home rental

Florida Panhandle / Seaside

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Ask about children
2454 East County Hwy. 30A Please no children under the age of 5; 5-night minimum stay required during spring break and summer A lovely, colorful home with lots of windows to enjoy the Gulf and Seaside views, not to mention porches and patios on every level, Toye Cottage …see more

from $1009 / night

$7063 / week

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from $1009 / 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 duringThanksgiving 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 levels and in all dir …see more

from $1701 / night

$11907 / week

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from $1701 / night

31

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 Special pricing for open summer weeks! Four-night minimum! “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 …see more

from $336 / night

$2155 - $4560 / week

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from $336 / 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 $1051 / night

$6180 - $13415 / week

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from $1051 / 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 Special pricing for open summer weeks! Four-night minimum! Pure, simple and elegant. These series of beachfront “Honeymoon Cottages,” designed by architect Scott Merrill, who at one time was Seaside …see more

from $356 / night

$2125 - $4500 / week

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from $356 / night

15

Vacation home rental

Florida Panhandle / Seaside

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 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 features expansive windows and high ceilings, providing guests with gorgeous Gulf views. The first floor includes a m …see more

from $1011 / night

$7077 / week

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from $1011 / night