Family-friendly holiday rentals in Santa Rosa Island

An aerial view of a beachfront pool area is presented, showing a rectangular pool surrounded by white lounge chairs and shaded areas. The sandy beach is visible just beyond the pool, with a wooden boardwalk leading to the shore.

4.96 out of 5 average rating, 105 reviews

Beach Penthouse on Okaloosa Island in FWB, FL

Unit 301 has the best views being it is an end unit on the top floor. It also feels very spacious with its vaulted ceilings and unique loft area. Sleeps up to 6 people. Queen bed in Master. Another Queen bed and bath in loft. One full size sleeper sofa in living room. Owners have used the unit for past 9 years and have just decided to offer it as a rental. Freshly painted, and updated with new carpets, floors, furniture and appliances. Unit has everything you need for a wonderful vacation.

A bright and airy room features large glass sliding doors that open to a private balcony with an ocean view. The space includes a spacious bed adorned with a patterned blue coverlet and a cozy loveseat, with a TV mounted on the wall.

4.95 out of 5 average rating, 208 reviews

GULF FRONT TopFloor Amazing VIEW Directly On Beach

Cozy oasis with a view that takes your breath away! You'll enjoy relaxing on the private balcony overlooking the ocean. King bed and twin pullout loveseat. Beautifully renovated kitchen and bath. Fully stocked kitchenette with granite countertops. The full sized refrigerator is a special perk in this Luxury Honeymoon suite. Charming coastal accents throughout. Special attention has been given to this unit to ensure everything is top notch with professional upgrades. Waves roll in, cares roll out

4.98 out of 5 average rating, 120 reviews

Beachfront Bliss! Gulf Waves at The Palms #201

Nestled on shimmering Gulf shores, The Palms #201 invites you to unwind with jaw-dropping oceanfront views. This 2-bed, 2-bath sanctuary is your ticket to an unforgettable coastal retreat. Steps from the water, this guest favorite blends relaxation and rejuvenation for a home-away-from-home feel. From March through October, we provide complimentary beach service with two chairs and umbrella—a $40 daily value included free! Pure paradise is at your doorstep. Book this dream coastal escape today!!

The image captures an expansive view of the tranquil Gulf of Mexico. Gentle waves roll onto a sandy beach, while a clear blue sky stretches above, dotted with soft clouds. The horizon blends seamlessly with the serene water, creating a calming seaside atmosphere.

4.94 out of 5 average rating, 199 reviews

Sunshine and beach time /Okaloosa Island

Plan your SUMMER at the BEACH! SNOWBIRDS message us for a monthly rate (Oct-Feb). Steps to the sand, Ocean view , top floor unit, sleeps 5,(queen bed, single day bed, and queen sofa sleeper). (USB port outlets, no carpet, stainless appliances, and keyless entry). A one minute walk to the white sand, wifi in the unit, 2 beach chairs, cooler, beach towels, and beach umbrella. Laundry onsite, Tom Thumb next door for items you might need. Everything for a great beach vacation! 683 Nautilus court

A spacious living area features a large sofa and a mounted television, along with soft blue lighting that creates a calming atmosphere. The decor includes a decorative wall unit and stylish accents, contributing to a welcoming environment for relaxation.

4.96 out of 5 average rating, 105 reviews

Luxury 1-bdrm Studio. 2 Pools/Sauna/Hot Tub/Beach

Newly renovated! - Welcome to The Oasis, a luxury beach studio at El Matador Condos on Okaloosa Island, Fort Walton Beach, FL. Be our guest at this beautifully decorated, clean, comfortable studio, ideal for small families, small groups, couples, singles, & business travelers. You'll have direct access to the private beach & all the amenities including a seasonally heated outdoor pool, Gulf view pool, hot tub, sauna, gym, tennis/pickleball & basketball court, BBQ areas, & a laundry room.

A view showcasing a lazy river surrounded by lush palm trees and a spacious pool area. The ocean is visible in the background, with several lounge chairs scattered throughout the landscape. Modern resort buildings are positioned in a welcoming arrangement, enhancing the tropical atmosphere.

4.84 out of 5 average rating, 105 reviews

DestinWest Pelican Bayside, Lazy River, Hot Tub.

Master bedroom with bathroom, bunk room with bathroom (the bunk room has one bunk bed and no door), sofa sleeper. Balcony with lazy river and bay view. You will find everything here from Lazy River, seven pools (one heated, one with waterfall), hot tubs, zero entry pool, gym, bbq area. Next door is an arcade with virtual reality, bar and food. You have access to swim and play in both the ocean and the bay. It is a short walk to the Okaloosa boardwalk for shopping, restaurants and fun

The living area features a spacious gray sectional sofa arranged around a low coffee table. A large television is mounted on the wall across from the seating. Natural light enters through windows covered by light curtains, contributing to a relaxed ambiance.

4.94 out of 5 average rating, 340 reviews

2BR Condo With in a 3 minutes walk to a beach

Due to the coronavirus, we’re taking extra care to disinfect frequently touched surfaces between reservations. Beddings, towels washed with hot water Welcome to our beautiful furnish 2 bedrooms 1.5 bath condo. This 3rd floor condo is located at Okaloosa Island across the street from beautiful Gulf of Mexico beaches in just 3 minutes walk. A wonderful place to stay! Perfect location, close to everything Fort Walton Down town, Destin Harbor, Crab Island. Walking distance to restaurants

The living area features soft blue walls and large windows providing natural light. A comfortable sofa is complemented by decorative pillows, while a wooden coffee table creates a focal point. A flat-screen TV and light blue curtains enhance the serene atmosphere.

4.95 out of 5 average rating, 177 reviews

Waterscape A207/Free BCH SVC/2 Kings/75' TV

Waterscape Resort A207 (just steps to the beach & pools) ~ Ocean view from kitchen/Master BRs/living room/patio ~ FREE beach service (2 CHRs+umbrella) during 3/1-10/31 ~ 2 King BRs with their own en suite + 1 half bath in the living area ~ One bunk room with a DOOR for privacy (two twin beds) ~ Q pullout sleeper ~ Pack 'n Play ~ Highchair ~ 4 smart TVs (1x75’’, 2x50’’, and 1x32’’) ~ Upgraded appliances & quartzite countertops ~ Tiles throughout ~ Washer/dryer in unit

A spacious pool area is visible, surrounded by palm trees and lounge chairs. The sparkling water reflects sunlight under a clear blue sky, leading to the ocean in the background. The resort buildings are seen on either side of the pool, enhancing the inviting atmosphere.

4.9 out of 5 average rating, 125 reviews

Ocean view condo, Lazy River & Beach, Destin West

From your unit on the Gulf side of the resort, enjoy the spectacular ocean view, award winning lazy river, and many pools in this family friendly Destin West Beach and Bay Resort with private beach. Your unit is a couple blocks from Gulfarium Marine Adventure park, where you can swimming with dolphins. Enjoy the Broadwalk Okaloosa Island with seaside shops, eats, and entertainment within a block. Okaloosa Island fishing pier is within 2 blocks for fishing enthusiasts.

A spacious living area is highlighted by a light-colored sectional sofa and a modern coffee table on a patterned rug. A flat-screen TV is mounted on the textured blue wall, and natural light filters through sheer curtains, enhancing the inviting ambiance.

4.96 out of 5 average rating, 130 reviews

2 min walk to Beach/Free Beach Service/Pool

Elevate your vacation experience with a stay at the Beach Hive! Conveniently located less than 2 minutes from the shores of the Gulf. Complimentary beach service (2 beach chairs and 1 umbrella) is available from 3/1-10/31. Escape the crowd & enjoy time at the Beach, lay by the pool or visit all that Okaloosa Island & the Emerald Coast have to offer. Then, return to this modern beach cottage to wind down and relax in style and comfort after a long day.

A wide expanse of pristine white sand stretches along the tranquil shoreline of Okaloosa Island. The sun reflects off the calm waters, creating a gentle shimmer. Soft clouds drift across the sky, adding a serene backdrop to the beachside scene.

4.91 out of 5 average rating, 230 reviews

Sunny Happy Place by the Beach, Pool, Ocean View

A few feet from the beautiful beaches of Okaloosa Island! 1 Bedroom condo, sleeps 6, Ocean View from the front balcony. Heated pool. Private access to the beach. 2 chairs and 1 umbrella reserved at the beach, plus 4 chairs in the condo. Beach service offers kayak, paddleboard and chair rentals (March 1 to Oct 31). Close to Conference center, Ft Walton Bch and Destin. Special rates offered to military on TDY (must show orders), and snowbirds.

An expansive view of the Gulf of Mexico is seen from the balcony, showcasing the sandy beach and turquoise water. The beach is lined with sun loungers, and the resort pool is visible nearby. Lush palm trees and pavilions add to the coastal landscape.

4.84 out of 5 average rating, 205 reviews

Islander Resort Okaloosa IsIand Beach Condo

Escape to Okaloosa Island and stay at this cozy studio condominium at the Islander Resort. This 6th-floor unit is perfect for couples or small families looking for a beach getaway. Wake up to stunning views of the Gulf of Mexico from the private balcony, relax on the pristine white sand beach, or take a dip in the Gulf-front pool. Take advantage of the resort's amenities, including a fitness center, shuffleboard, and barbecue grills.

Popular amenities for Santa Rosa Island family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A scenic view of the beach at sunset, with the sun dipping below the horizon. Gentle waves lap against the shore, while silhouettes of people can be seen strolling along the sandy beach. The sky is tinted with soft orange and yellow hues, enhancing the tranquil atmosphere.

4.82 out of 5 average rating, 144 reviews

Keeler Island Princess #508 Okaloosa Island Bchfrt

4.79 out of 5 average rating, 156 reviews

Amazing Top-Floor Condo, Free Beach Service!

4.96 out of 5 average rating, 131 reviews

The beach cottage features a welcoming exterior framed by palm trees and tropical foliage. A white picket fence surrounds the property, leading to a spacious porch with multiple steps. The home’s two levels and large windows create an open and airy appearance.

Home in Destin

Sugar Sand Cottage at Destin Pointe

The exterior of Waterscape Resort is showcased, featuring a welcoming entrance with a prominent sign. Surrounding palm trees and landscaped gardens create a pleasant atmosphere. The U-shaped building with multiple balconies stands against a clear blue sky, contributing to the resort's tropical feel.

4.63 out of 5 average rating, 8 reviews

Waterscape A622 - Gulf View, Lazy River and Water

The living room features soft leather sofas and a glass-top table, with large sliding doors that open to a balcony offering expansive ocean views. Natural light fills the space, accentuated by light-colored walls and a ceiling fan. A potted plant adds a touch of greenery.

4.9 out of 5 average rating, 106 reviews

Amazing View Beach Front Condo

A bright kitchen features modern stainless steel appliances and quartz countertops, with soft-close cabinets providing ample storage. The cozy living area includes a comfortable sofa and colorful decor, while the serene beachfront is visible through the window, where gentle ocean waves meet a colorful sky.

4.93 out of 5 average rating, 188 reviews

Beautiful Emerald Beach Condo

A scenic view captures the landscaped courtyard of the resort, featuring palm trees and a swimming pool. The background displays condominium buildings against a colorful sunset sky, providing a serene atmosphere. Soft lighting begins to illuminate the courtyard, enhancing the visual appeal.

4.86 out of 5 average rating, 100 reviews

Waterscape 3rd Floor 1 Bedroom - on the beach -

A serene view of the Gulf waters features soft blue hues blending into the horizon. A long wooden pier extends into the distance, providing a focal point against the clear skies and white sandy beach in the foreground.

4.88 out of 5 average rating, 128 reviews

Direct Beach FRONT-Amazing Views-Lazy River-Beach

Family- and pet-friendly home rentals

A bright living area is highlighted by a large television and comfortable leather furniture, arranged around a vibrant leaf-patterned rug. Sheer curtains allow natural light to filter in, complemented by potted plants that add a touch of greenery to the space.

4.87 out of 5 average rating, 151 reviews

Modern Island Condo: Walk to Beach, Private Yard!

4.84 out of 5 average rating, 118 reviews

The living area features a comfortable sofa facing a large television mounted against a light-colored wall. An open kitchen with modern appliances is visible, complemented by a wooden island with seating for four. Warm wooden tones and elegant flooring enhance the space.

Home in Ferry Park

House 5 min to Beach, Fire Pit, Deck, Pickleball

Townhouse in Santa Rosa Island

An open living space features a large flat-screen television mounted on a white wall. A comfortable sectional sofa is positioned around a coffee table, complemented by decorative elements such as a plant and books. A sleek kitchen bar with stools enhances the layout, creating a welcoming atmosphere.

4.95 out of 5 average rating, 205 reviews

Beauty & The Beach near Gulf Beaches & Bay

4.88 out of 5 average rating, 162 reviews

Waterfront Paradise•2.5 Miles from Beach•Boat Slip

Guest house in Garniers Beach

A spacious outdoor area features a blue umbrella over a dining table, adjacent to a clear swimming pool. Lush greenery surrounds the pool deck, with views of the tranquil water in the background. The scene is complemented by palm trees and a well-maintained lawn.

4.84 out of 5 average rating, 190 reviews

Private Guest House on the Water | Boat Docks!

Home in Fort Walton Beach

4.96 out of 5 average rating, 185 reviews

Clancy's Celtic Clouds-home near Destin, FL

A pair of flip-flops rests atop soft, white sand, framed by delicate sea oats and bright sunflowers. A large sea shell is positioned nearby, with the gentle waves of the Gulf visible in the background under a clear blue sky.

4.87 out of 5 average rating, 121 reviews

“Sandy Thongs” Beachfront Oasis Amazing Gulf View

Home in Fort Walton Beach

The outdoor area features a non-heated swimming pool surrounded by a concrete patio. A small table with chairs is positioned nearby, offering a space for relaxation. Lush greenery provides shade, and a seating area with chairs is visible on the lawn.

4.9 out of 5 average rating, 320 reviews

#1 4BR HUGE PET Friendly Home Away from Snow!

Family-friendly home rentals with a pool

Flat in Santa Rosa Island

An open concept living area features a comfortable gray sofa, a light wooden coffee table, and a vibrant floral chair. Natural light fills the space, highlighting the dining area with seating for six. Access to the kitchen is visible in the background.

5 out of 5 average rating, 29 reviews

Venus by the Sea – Unit #103

5 out of 5 average rating, 16 reviews

3BR ~ Beachfront ~ Huge Balcony ~ 2 Pools ~ Luxury

A view from the balcony captures the surrounding landscape, featuring buildings in the distance and palm trees along the street. The clear blue sky and sunlight enhance the open atmosphere, while the nearby sandy beach is visible, inviting outdoor relaxation.

4.98 out of 5 average rating, 41 reviews

Sandy Cheeks/Okaloosa Island

Flat in Santa Rosa Island

A welcoming living area is captured with a light grey sofa and a coordinating loveseat, providing comfortable seating. A round coffee table sits in front, and natural light enters through the open door, highlighting the modern decor and tasteful wall accents.

4.95 out of 5 average rating, 20 reviews

Seaside getaway !

4.97 out of 5 average rating, 90 reviews

Stars & Sea•Overlooking Pool & Sound•Sleeps 4

A serene beach scene captures gentle waves lapping against soft, white sand. Tall grasses and wooden fencing frame the foreground, while a pastel sky transitions from pink to blue at sunset, creating a tranquil atmosphere on the shoreline.

4.95 out of 5 average rating, 55 reviews

Updated, Gulf front family-friendly condo!

A private balcony offers stunning views of the Gulf, featuring two turquoise chairs and a table with two cocktails. The tranquil beach and rolling waves can be seen beyond the white railing, with umbrellas lined up along the shoreline.

4.96 out of 5 average rating, 135 reviews

Star Of The Sea

An aerial view of a resort-style condominium showcases a large swimming pool surrounded by palm trees and lounge chairs. The multi-story building, featuring multiple balconies, is situated near the water, with the coastline visible in the distance under a clear blue sky.