Family-friendly holiday rentals in Okaloosa County

Sugar Sand Cottage at Destin Pointe

This beautiful four bedroom beach cottage is located in the exclusive gated community of Destin Pointe. The home offers a tranquil setting and unsurpassed amenities that include a private lakefront pool for relaxation and entertainment-perfect for sipping your evening cocktails while overlooking the lake, direct lake views for the multiple levels of decks, private beach access to the sugar sands of Destin, and three community pools (one with a hot tub and splash pad) for guests use.

The secret spot!

Simple, very clean, and 2 minute walk to all destin night life and all best restaurants.right across to harbor walk village.4 minute drive to the beach! this place is for couple ONLY and small family of 3!absolutely NO SMOKING, VAPING INSIDE .you are next to the Main Street so you will ear some light traffic at night! All the water activity are in front of you to choose! 1 parking for 1 car only! Read my review or text me for any questions!small dog (1) are welcome whit pet free!

Luxurious BeachHouse Pickeball+HeatedPool

🏖️ Our beautiful one-story open-floor house is the best choice for your beach vacation with your beloved family and friends. Perfectly located in a quiet community just a few minutes walk (~10 mins). White Sand Beach is close to the community pool and minutes away from shops, restaurants, and everything you need. With 3 bedrooms, 2 bathrooms, and a lovely private backyard, there is more than enough room for 11 guests and your pup, so you won't have to leave anyone behind!

100 ft to sand, Corner unit, Hot Tub, Garden view

Step out and hit the beach—just 100 ft to the sugar sand beach from this charming condo. Featuring a King master suite w/private bath, 2nd King room, plus a bunk-bed cubby for kids with a hall shared bath. Ground level, corner unit. The fully stocked kitchen includes Keurig w/pods. 3 TVs. Private patio. Just steps from pool & hot tub. Wi-Fi, washer/dryer w/starter pods. Stroll to dining and local attractions. 2 FREE parking spots. Rent 25+ unless active duty military.

Crestview Retreat

Welcome to Crestview Retreat! Your peaceful Florida getaway awaits! Relax in a quiet neighborhood with a private screened-in pool, soothing jacuzzi, and cozy fire pit. Inside, enjoy a fully equipped kitchen, smart TV & fast Wi-Fi, and two comfy bedrooms. Sip coffee by the pool or stargaze by the fire—comfort and calm surround you here. Perfect for - Family getaways & romantic escapes - Visiting Eglin or Hurlburt Air Force Base - Remote work or long weekends away

18th Floor Pelican Beachfront with Ocean View

Welcome to your family vacation home at Pelican Beach Resort, Destin; with all the conveniences of a direct beach vacation rental. Your beachfront condo is on 18th floor, optimizes your endless gulf view with the ease of beach access. With our upgrades, we want our guests to feel like they are staying on their beach home. Your home is in the heart of Destin and just a short distance from The Harbor Walk, directly across the street from The Big Kahuna Water Park.

On the Gulf 2 Bed, 2 Bath Third Floor Condo

Third floor condo has panoramic views of the East Pass and Gulf. Spacious 2 bed and 2 bath with nice kitchen and laundry in unit. Right on the dunes with the beautiful white sand. The beach and snorkeling are a short walk. Sit on the patio and hear and see the ocean. Take an evening walk along the beach or the beautifully landscaped streets of Holiday Isle with the harbor right across the water. Watch the fishing boats in the morning out the living room window.

Steps to Private Beach • Gulf Views • Kids Pool

Wake up to turquoise Gulf views and your own stretch of sugar-white sand. Beach days are easy with chairs, umbrellas, and toys ready for you—just grab and go. From your private balcony, enjoy your morning coffee or evening drink while the kids play below in the courtyard. In the summer, s’mores nights, outdoor movies, and live music are all included and just steps away. Big Kahuna’s Water Park and The Track are right nearby—walkable and easy, no car needed.

Florida Vacation Home, destin beaches

Location, location, location, you'll be close to everything when you stay at this centrally-located place. Close to Crestview for all your shopping needs and a straight shoot on the hwy to Fort Walton/Destin beaches! Spacious updated home with luxury touches to enjoy your vacation. We think of everything so you can show up and relax. 3 bedrooms/2 baths, office space, laundry room, screened in porch, and large fenced in back yard.

Newly remodeled cottage with Shoal River access

Take it easy at this unique and tranquil getaway. Recently rebuilt cottage with modern touches amidst open spaces on wooded acreage. Tranquil deck and fire pit. Access to kayaking and walking trail on owner's nearby property on the Shoal River. Conveniently located 10 minutes from shops and restaurants, but peaceful and serene. Master suite has a king bed (with massage feature), second bedroom has a full sized bed.

Sunsail Cottage-Golf Cart Deals-Pool Heat Deals

Sunsail Cottage is a gorgeous, coastal modern styled 3 bedroom home, nestled in a quaint neighborhood in the heart of Crystal Beach! Accommodating up to 8, it's perfect for two small families, a couples trip, or a friends getaway! Our spacious layout, modern design, and private pool will have you entering "relax" mode from your first steps inside. Come sail away with us at Sunsail Cottage!!

3 Br Waterfront Florida Classic on the Bayou

Enjoy the comfort and beauty of classic old Florida at this beautiful waterfront home. Moments away from white sand beaches and downtown, you are in an oasis of relaxation here at the Florida Classic on the Bayou. This home was thoughtfully designed and cherished by a prominent local family and features rich Florida history and details. It is our pleasure to share this oasis with you.