Discover a selection of 1,000 vacation rentals in Seaside that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $87 per night, and houses and cottages are popular options for a stay in Seaside. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Seaside
Destination guide

Fun in the sun at Seaside vacation home rentals

Perched on Florida's coast, Seaside is as renowned for its pastel-hued cottages and gleaming white clapboard post office as it is for its sandy beach and tranquil waters. Seaside was in fact only founded in 1981, as one of the first American towns designed around the principles of New Urbanism, a movement focused on eclectic architecture, walkable districts, and sustainable living. With an abundance of pristine Seaside vacation rentals to choose from, you can make yourself right at home in this one-of-a-kind destination.

Things to do

Attractions near your Kissimmee summer rental

If you need a break from beach life, you'll find an eclectic array of attractions within easy reach of your Seaside vacation rental. The Fusion Art Glass Gallery showcases a diverse collection of eye-catching sculptures, pottery, glassware, vintage jewelry, and avant-garde blown glass art. If you're after a unique vacation souvenir, the best news is that everything's for sale. A drive down the coast will bring you to Gulf World, the ideal spot for a fun-packed family day out. This marine park is home to adorable sea lions, sleek sharks, stately sea turtles, and all manner of other ocean dwellers.


Things to do near Seaside vacation rentals

Seaside is a shopper's paradise, particularly if you prefer quirky independent retailers to big brands. Here, you'll find gourmet grocery stores, alluring fashion boutiques, and endlessly browsable book and music shops. If you're in town on a summer Saturday, don't miss the market, where you can pick up artisan soaps and homewares, phenomenally fresh local produce, and irresistible baked goods and sweet treats. The al fresco dining scene is similarly enthralling. You can feast on everything from fresh chilled oysters to decadent Southern BBQ, all whilst taking in breathtaking ocean views. If you feel the need to burn off some calories, rent a kayak or paddle board and explore the sensational shoreline.


Local weather for your stay in Kissimmee vacation homes

Seaside vacation rentals are in particularly high demand during the peak summer season of June to August. Humidity can be high at this time of year, but the heat is generally less intense than many other parts of Florida, with ocean breezes keeping things agreeable. Late spring and early fall are also great times to visit, with blissfully warm temperatures, slightly less rain, and slightly fewer out-of-towners jostling for a prime spot on the beach. Winters are usually pleasantly mild, but usually a little too cool for swimming and sunbathing.

Natural features

Animal encounters at Seaside

Seaside is an enthralling destination for nature and wildlife lovers. If you're visiting between April and November, you might be lucky enough to catch sight of sea turtles crawling out of the ocean to lay their eggs in the sand. You don't need to be a seasoned birder to make some new feathered friends here. Keep one eye on the sky and you may glimpse pelicans, egrets or herons, while between May and August, rare snowy plovers and least terns can be spotted nesting in the sand. A highlight for many Seaside visitors is a trip out to sea to watch acrobatic bottlenose dolphins frolicking in their natural habitat.

What are the top vacation rentals in or near Seaside?

Whatever you're looking for in a getaway, you'll find a rental in or around Seaside that suits your style. Why not try these on for size?:

  • "Totally Renovated Oceanfront Condo. . . Bikes And Beach Service Included" is a hit with guests. Around 1 mile from Seaside, it has 2 bedrooms and plenty of handy amenities, including a heated pool and cable/satellite TV services.
  • Another excellent choice is "Palma Beachfront 2 Bd; 2 Ba + Bunks", which is around 2 miles from Seaside. Featuring 2 bedrooms, a washing machine and a nearby laundromat, it has everything you need to make your stay comfortable.

For even more great options, use the search bar at the top of the page to find the perfect Seaside vacation rental for you.

What are the best tiny house vacation rentals in or near Seaside?

For a different kind of vacation experience, book a tiny house rental in Seaside. We warn you though — after you've experienced the tiny house lifestyle, the urge to move into one of thes miniature digs will be tough to resist!

  • Leave the world behind and disappear to "Santa Rosa Beach Tiny House". This property in Gulfview Heights packs plenty of comforts into its small space, such as a garden and off-street parking options.
  • Alternatively, base yourself at "Private Pool, Prime Location - Charming Tiny House". Located in Seagrove Beach, this petite abode comes with off-street parking options and air conditioning.

What are the top-rated vacation rentals for weekend getaways in or near Seaside?

There's nothing better than a short escape to dust away the cobwebs. Pack your overnight bag and get comfy in one of these weekend getaways in and near Seaside:

  • Located 1 mile to the west of the center of Seaside, "Exquisite Watercolor Carriage House" is a good match for adventure lovers and nature fans. Get out and see nearby attractions, such as Destin Harbor and Destin History and Fishing Museum. Then, take the opportunity to try windsurfing or water skiing.
  • "South Of 30a, Bmb, Steps To The Beach" is another great property where you can escape the everyday. Around 5 miles west of Seaside, use it as a base to try some water skiing or fishing. Seagrove Beach East and Hurlburt Field Visitor Center should also be on your to-do list while you're here.

Can I find studio apartments for rent in and around Seaside?

Studio apartments are a tough act to follow when it comes to location, convenience and character. Choose one of these studio apartments for rent in or near Seaside and experience a taste of the local vibe:

  • Make "Exquisite Watercolor Carriage House" your home for a couple of days or more. This top property comes with amenities including a smart TV and a hair dryer.
  • "Peaceful Easy Living, - - Just 3 Blocks To The Beach And A Short Walk To Seaside" is another great option. Get comfortable and enjoy the use of a balcony, free WiFi and more.

There are loads of highlights around Seaside you won't want to miss. Nourish the culture vulture within by visiting Seaside Repertory Theatre and Fusion Art Glass Gallery.

Can I find short term rentals in or near Seaside?

Sometimes, you've just got to get away from it all, even if it's only for a few days. Enjoy a nice combination of rest and recreation at one of these short-term rentals in or around Seaside:

  • "Peaceful Easy Living, - - Just 3 Blocks To The Beach And A Short Walk To Seaside" is close to the center of Seaside, so you'll have lots of things to do and see. Explore notable attractions like Grayton Beach State Park and Seaside Beach when you're not chilling in your cozy digs.
  • Eat, sleep and explore what's around you from "2 Master Suites, Enjoy The Beautiful Emerald Waters Of The Gulf Of Mexico", another good option. 30A Bike Trail and South Walton Visitor Center should be on your must-do list when it's time to go sightseeing.

What are the best romantic weekend getaways in or near Seaside?

Nothing says "I love you" like a romantic weekend escape. If you'd like to spend a couple of evenings away with your beloved, we've got some romantic getaways in and around Seaside that will get your heart racing:

  • Put on some mellow music and slow dance the nights away at "Totally Renovated Oceanfront Condo. . . Bikes And Beach Service Included". Around 1 mile from Seaside, this property has everything you could want for a couple's weekend away, including a restaurant dining guide and air conditioning.
  • Alternatively, spend your mini break drinking wine and canoodling at "Palma Beachfront 2 Bd; 2 Ba + Bunks", around 2 miles from Seaside. Beauty services and a music library will help set the scene for romance.

Are there mansions for rent in or near Seaside?

Nothing screams "Best. Vacation. Ever." like staying in a mansion. Indulge your nearest and dearest with a memorable getaway at one of these mansions for rent in or near Seaside:

  • Located approximately 1 mile to the southeast of Seaside, "Exquisite Gulf Front Luxury Mansion Walk To Seaside 7br" is the place to go for a luxurious escape. Amenities on offer here include a fireplace and a firepit.
  • With beauty services, a swimming pool and plenty of other top-rated amenities, "Commanders Palace | Beach View Mansion | Heated Pool | Cabana | 2 Kitchens" will get your squad's nod of approval. This opulent home is around 7 miles to the west of Seaside.

What are the best large group vacation rentals in or near Seaside?

Big groups mean gigantic fun. They also mean finding a place that'll easily fit your whole crew. Browse our large group vacation rentals in or around Seaside and spend time with your favorite people under the same roof:

  • A range of amenities including a swimming pool and a kitchen make "2 Master Suites, Enjoy The Beautiful Emerald Waters Of The Gulf Of Mexico" a favorite with groups. This expansive property has 4 bedrooms and sleeps up to 12 guests. From the center of Seaside, it's around 4 miles away to the northwest.
  • Nothing is more important than being with the people you love, and "Beautiful Owner - Managed Beach Home. Walk To Beach" makes it easy to do that. Located around 6 miles to the west of Seaside, as many as 14 people can stay in this vacation rental which has 4 bedrooms. A swimming pool and a kitchen are among the various amenities on offer here.

What are the best houses for rent with a pool in or near Seaside?

Of all the conveniences a vacation rental can have, a pool is without a doubt the most fun. Take a peek at these houses for rent with a pool in or near Seaside and spend your time splashing around. Just don't forget your flamingo floatie:

  • Pack your swimming gear and book a few days or more at "Exquisite Watercolor Carriage House". There are plenty of other appealing amenities here, including a nearby bay and books.
  • Otherwise, recharge your batteries at "The Smith House - Updated Historic Charm". Along with an invigorating pool, you can also make use of a toaster and a nearby bay.

Unsure how to pack your bags for your Seaside escape? This appealing destination has a humid subtropical climate. During the summer months, you can expect average temperatures of between 80 ºF and 90 ºF. Check out our selection of Seaside vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more inspiration on where to stay.

What are the best large family vacation rentals in or near Seaside?

Great family getaways are about spending some quality time together and sharing experiences. If you're after a home away from home that'll fit your entire crew, check out a few of our large family vacation rentals in and around Seaside:

  • Make memories at "2 Master Suites, Enjoy The Beautiful Emerald Waters Of The Gulf Of Mexico". Featuring 4 bedrooms sleeping up to 12 guests, this spacious retreat is located 4 miles northwest of Seaside. There are lots of amenities to take advantage of here, such as a balcony and childrens activities.
  • Another option is "Beautiful Home In Cassine Village". It's about 2 miles to the east of Seaside, has 3 bedrooms and accommodates up to 8 guests. A dishwasher and a kitchen are just a few of the conveniences here.