
Vacation rentals with a pool in Seaside
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Seaside
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

30A Beach Villa-Steps to PrivateBeach! Dogs,Bikes
Newly renovated! Just completed a full remodel and very excited to share the GORGEOUS results with you! For more photos &insights, follow us on IG @The30ABeachHouse Our exclusive gated community is on the south side of Scenic Highway 30A in South Walton County, situated directly between Rosemary Beach and Alys Beach. Stroll down a palm tree lined walkway, with cobblestone streets, <1 min walk to the heated pool that sits high on the dunes, above the sugar white sand beach on the Gulf of Mexico.

Winter Warm Up | Walk2Beach | Pool | Shop | Eats!
8 minute walk to Ed Walline the most beautiful public beach on the Emerald Coast! Warm up on the sands of 30A enjoying beach life! Safe & peaceful community w/ pool 3 doors down! Walk to nearby restaurants! Run, walk, or ride bikes on the 19 mile 30A path Vaulted ceilings / open floor plan / beautiful rooms Features: Amazing natural light, 4 smart TV's, fast WiFi, Stocked kitchen / new appliances, Washer/Dryer, Weber Grill (BYOC), 4 beach bikes, 4 beach chairs, umbrella, beach towels & more!

30-A Getaway near Seaside 102
Contact us for long term winter rates & winter specials! Escape to paradise and indulge in the ultimate coastal retreat. Just steps away from the sugar-white sands of South Walton, this serene & stylish haven invites you to unwind in total comfort. Take a leisurely stroll to the heart of Seaside, where charming food trucks, boutique shops, & world-class dining await. Whether you're savoring gourmet cuisine or catching a golden sunset on the beach, every moment here feels like a dream come true.

"Sips & Sand" nestled b/w Rosemary & Alys Beach
Located along the infamous 30a! This light and airy 1/1 condo is perfectly nestled between Alys and Rosemary Beach. It's a short 5 minute walk or free tram ride to the deeded beach access where you will be greeted by the beautiful emerald waters of the Florida Panhandle. The condo sits beside the complex's two pools, hot tub and grilling area. Conveniently located on the property are a variety of shops, restaurants, bike rentals and seasonal activities including live music and fire pits.

FlipFlopsOn II • 80 steps to the Beach • FL 30A
Recommended by ‘TRAVEL + LEISURE’ —FlipFlopsOn II is 80 steps to Inlet Beach, where sugar-white sand meets the turquoise Gulf Coast! This sun-washed full studio for 4 (4 beds), sits beachside of the 30A National SCENIC BYWAY adjacent to Lake Powell; stroll or bike to Inlet, Alys & Rosemary Beach dining & entertainments. Featuring a clean Cali-Florida vibe with a pool, grill, pavilion, beach gear, fast Wi-Fi, 65” smart TV, & sunsets from your private patio! Park your car, walk everywhere!

One Block to Crystal Beach + Pool + King Bed + Convenient Location
- One block from the Crystal Beach area of Destin - 0.6 miles to Destin Commons w/ Whole Foods and shopping - 1.0 mile to Publix - This is the UPSTAIRS UNIT (downstairs rents separately through same host.) Each unit is fully separate. The Destin Doublemint, a bright and airy one-bedroom cottage, is the perfect spot for your beach vacation. It's less than a 2-minute walk to the sand, making it easy to pop back for a dip in the pool or a movie in the AC before walking back over for sunset.

1/1.5 Gulf View Condo Ariel Dunes 2 Beachfront
Enjoy the art, nature, and adventure of Miramar Beach in our lovely condo with beach access, on-site heated swimming pools, a fitness center with sauna, golf, tennis, pickle ball, basketball, dining and nightlife without leaving the complex! When you venture out, shopping at Silver Sands Outlet Center is a mile away, and Grand Boulevard and Sandestin Beach Resort are 3 miles away. End your relaxing day taking in the spectacular sunset with a glass of wine and loved ones on the balcony.

Small Waves-30A beachhouse w golf cart/neighb pool
Small in stature but grand in design, this 30A beach house will wow you. Access to neighborhood pool, gym, & the beautiful white sand beaches a few blocks away. Small Waves is set in the Blue Mountain Beach area, which is well-known for its charm, its restaurants, & its famous ice cream shop. We have an EV car charger for electric cars (no extra fee) plus access to an electric golf cart (extra fee). Bedroom has a king size bed & twin bed & there are also 2 twin beds upstairs.

Oceanfront in Seagrove w/private beach!
Welcome to our little piece of paradise in Seagrove! Our 2nd floor beachfront condo boasts breathtaking ocean views, private beach access, free parking, beach chairs, toys and umbrella and a fully updated interior for a comfortable and relaxing stay. Unwind in the open-concept living space, cook up a storm in the fully-equipped kitchen, and soak in the sun on your private balcony. With direct access to a private beach, you can enjoy endless days of sand, sea, and sunshine!

Luxury 30A Cottage w/ Private Pool and Golf Cart
A NEWLY BUILT LUXURY COTTAGE DESIGN BEACH HOUSE WITH PRIVATE/HEATED POOL* AND GOLF CART in the heart of Santa Rosa Beach off 30A. This beach house is nestled among the trees yet only minutes away from the white sandy beaches. Bask in the sun by day and wind down and relax in the outdoor areas surrounded by a peaceful wooded area by night. It is like stepping out of one world directly into another. Come and Relax and enjoy the peace and tranquility of this cozy retreat.

Majestic Sun Ocean view 1 Bedroom Condo
This Majestic Sun 1 bedroom condo is located across the street from the beach with unobstructed Gulf views. It is conveniently located within the Seascape Resort. Perfect for those looking to vacation within the heart of Miramar Beach while enjoying a stunning ocean view. The complex amenities include an indoor/outdoor heated pool, hot tub, and well equipped fitness center. Snowbirds if please inquire for monthly rates. **MUST BE 25 YEARS OF AGE TO BOOK PER HOA RULES**

Starr of Seagrove - 3 Min Walk to Beach!
Beautiful, renovated condo in Seagrove Beach! Steps from the beach & Cafe Thirty-A, & many other local favorites! Just a short (1-2 mile) bike ride from Seaside, Publix, shops & restaurants. On-site pools & tennis courts. Perfect for a couple's or small family beach vacation. We are open to renting directly to guests 18+ (i.e. college or high school students; children traveling with families are also welcome, of course!) See policies & rules for details.
Popular amenities for Seaside rentals with a pool
House rentals with a pool

Watercolor Resort|Close To Pool | 6 Pass Golf Cart

South of 30A. Golf Cart. Pool. Gym.

Sea La Vie

Steps to 30As Longest Public Beach,Private Pool,&

2026 Dates Open~Seaside~30A~Golf Cart Included

Heated Pool included- Golf Cart- Bikes!

Heated Pool- Steps from Seaside- View of the Gulf

Somethings Gotta Give Movie Set Replica
Condo rentals with a pool

Home at Last

30A Studio "Driftwood Dream" Hidden Beach Villas

Modern Seagrove studio steps from the beach

Beachfront 30A Private Beach Blue Mountain Paradis

Updated KING 1 Bdrm Condo Balcony, Baby Gear, Pool

Sunrise Destin-ation -Heated Pool-Beach View

Drift Away - 30A Seagrove Beach, Seaside Area

Relaxing 30A Couple's Retreat
Other vacation rentals with a pool

'Blue Mountain Beauty' Private Beach l Beachfront

Golf Cart! Walk to Beach! Pool! Bikes! Beach Gear!

Gulf-Front Corner Unit in Seagrove Facing Sunset!

Vitamin Sea -Heart of Rosemary Beach.

Private Guest Cottage in Seaside, FL - 2 Free Bike

Déjà Blue | Golf Cart • Sauna • Cold Plunge • Pets

Petite Frog/Golf Cart/Heated Pools

Thanksgiving Available -GOLF CART & Bikes included
When is the best time to visit Seaside?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $688 CAD | $643 CAD | $943 CAD | $865 CAD | $895 CAD | $1,028 CAD | $1,009 CAD | $868 CAD | $761 CAD | $1,029 CAD | $806 CAD | $981 CAD |
| Avg. temp | 12 °C | 14 °C | 17 °C | 20 °C | 24 °C | 28 °C | 29 °C | 28 °C | 27 °C | 22 °C | 16 °C | 13 °C |
Quick stats about vacation rentals with a pool in Seaside

Total vacation rentals
Explore 310 vacation rentals in Seaside

Nightly prices starting at
Seaside vacation rentals start at $183 CAD per night before taxes and fees

Verified guest reviews
Over 1,520 verified reviews to help you choose

Family-friendly vacation rentals
250 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
140 properties have a dedicated workspace

Wifi availability
310 of Seaside vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Seaside rentals

4.8 Average rating
Seaside stays are highly rated by guests—averaging 4.8 out of 5!
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- Crab Island
- Destin Harbor Boardwalk
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- St. Andrews State Park
- James Lee Beach
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- Blue Mountain Beach
- Grayton Beach State Park
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- St. Andrew State Park Pier
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- Gulfarium Marine Adventure Park
- Raven Golf Club
- Fort Walton Beach Golf Course
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