Holiday rentals with a kayak in Santa Rosa Island

4.94 out of 5 average rating, 17 reviews

Reef Retreat 153 @ El Matador - Gulf front resort

NEW! Bring the whole family to enjoy this newly renovated and updated two bedroom/ two-bathroom beach condo. New updated kitchen and new furnishings and decor throughout! Great expansive views from master bedroom and balcony - views even from the kitchen to the Gulf! We are literally at the end of road where you won't have to fight to get a spot on the beach - plenty of room to spread out on our lovely white sand beach and enjoy the emerald waters of the Gulf! Deal directly with the owner!

LocationAccuracyAccess

4.99 out of 5 average rating, 179 reviews

A wooden dock extends into Poquito Bayou, featuring a green umbrella providing shade over a seating area. The clear blue water reflects the sky, while the shoreline is lined with lush greenery. Nearby, a flag is visible, indicating a peaceful outdoor setting.

Apartment in Shalimar

Sylvia's Suite Dreams-kayak & paddleboard free

Live like a local on beautiful Poquito Bayou in Shalimar, FL. This detached guest house will give you access to a gorgeous dock complete with private parking and located less than 20 minutes, by boat or car, from world class beaches and Destin. Our property can accommodate a 2-axle boat trailer. Wake up in the morning and watch the dolphin jump off the dock, fish, go for a swim, paddleboard, kayak or just relax with a cup of coffee. We will work with ALL DOD and DOD contractors and personnel.

Outdoor spacesLocationHospitality

4.98 out of 5 average rating, 202 reviews

An open studio layout is presented with a spacious king-size bed and a comfortable sofa. A round table sits nearby, while large glass doors lead to a balcony with ocean views. Soft, neutral tones are used throughout, enhancing the serene atmosphere.

Condo in Sandestin

Zen Retreat ON Beach~Golfcart*~Oceanview~ Hot Tub

STUNNING VIEW -8th fl. stylish open studio. Beachfront in Sandestin Resort between Destin & 30A. 🛺 Golf cart w/5+ nts. NEW Pool & Hot Tub. Pottery Barn furniture & King size bed w/oceanview. Sleek Kitchen w/dishwasher & Keurig. WiFi, 55” smart TV. Washer/dryer. Huge balcony to gaze @ the sea. Enjoy the beach, dining, shopping, trails, golf & entertainment all without leaving the resort. Tram pass & Gym. Perfect for honeymoon, baby moon, girls trip, solo travel or lil family vacay *NO animals

Outdoor spacesLocationParking

A waterfront property featuring a private pool surrounded by a spacious yard. A large dock extends into the water, offering areas for seating and easy access for fishing or boating. Lush greenery and palm trees frame the picturesque setting, enhancing the overall outdoor appeal.

4.95 out of 5 average rating, 83 reviews

Waterfront~Retreat ~Pool & Deep Dock~Boats welcome

Luxury Waterfront escape w/ Pool , Deep-Water Dock & Sunset Views🌴 Bring your boat or jet skis and enjoy direct access to the intercoastal bay—just minutes from Crab Island. Relax poolside, unwind on the water, and enjoy peaceful sunset views while still being only 10 minutes from the beach, dining, and downtown Fort Walton Beach. 🚤 Private deep-water dock (boat & jet ski ready) 💦 Heated pool for year-round use 🌅 Waterfront views + outdoor living 🏖️ Quick drive to beaches & attractions

Outdoor spacesLocationIndoor spaces

Townhouse in Santa Rosa Island

An outdoor dining area features a white circular table surrounded by six adirondack chairs. A partial view of the ocean and sandy beach is visible in the background, under a clear blue sky with few clouds.

Luxury Beachfront Home, Sleeps 12, Kayaks, SUPs

🏖 Luxury Beachfront Home for multi-family stays with everything included! Sleeps 12, 3 BR/3.5 BA + 4 Parking spots. On the beach! Unlike most beachfront rentals, this home includes full beach setup and toddler gear—no rentals needed. 🛏 Sleeps up to 12 comfortably 🛌 Beds 1 King, 3 Queens (1 pullout) & 2 sets of bunks 🛁 3 full baths + 1/2 bath 🚗 Parking for 4 cars 📶 Fast Wi-Fi + computer monitor 📺 4 Smart TVs 🚣‍♂️ 3 Kayaks, 2 SUPs, beach chairs, umbrellas, boogie boards, beach toys!

ValueLocationParking

4.99 out of 5 average rating, 79 reviews

4.98 out of 5 average rating, 120 reviews

115+ Five-Star Reviews | Renovated Gulf View Condo

Relax and unwind in our beautifully renovated Island Princess condo on Okaloosa Island. With 10 years of hosting experience and 115+ five-star reviews, we provide a clean, comfortable vacation home guests return to year after year. Enjoy beautiful Gulf and bay views from our oversized private balcony, comfortable beds, fully equipped kitchen, spacious living area, direct beach access, and complimentary beach service (2 chairs + umbrella) Mar–Oct. Located in Fort Walton Beach, near Destin.

Outdoor spacesValueNearby

A modern living area is depicted with a wooden coffee table at the center. Two blue sofas provide seating, complemented by a flat-screen TV mounted on the wall. Large sliding glass doors offer unobstructed views of the Gulf of Mexico, with outdoor seating visible on the balcony.

4.96 out of 5 average rating, 169 reviews

Beachfront 6th Floor 1BR at Pelican, Amazing Views

Completely renovated 6th floor, Pelican Beach condo is right on the beach with unobstructed views of the Gulf of Mexico. It has 1 bedroom, 2 full bathrooms, full kitchen, custom bunks and sleeps 6. Located in the heart of Destin in popular Pelican Beach Resort, you will enjoy the beach, the view, brand new appliances, furniture, and updated kitchen. Linens and towels are among the amenities included. High quality mattresses even for the pullout bed. We follow highest cleaning standards.

ValueLocationParking

Apartment in Santa Rosa Island

Newly renovated gulf-front condo on 1st floor

Enjoy your beach getaway in this spacious 2BR/2BA Gulf-front condo! This first-floor unit sleeps 8 with private patio to experience sunrise views over gulf, updated kitchen w/ quartz countertops, renovated baths w/ walk-in shower in the primary, and in-unit laundry. Relax w/ beachfront access, beach chair service (march-oct), pool, fitness center, tennis court, grill, volleyball net, picnic area, kayak, books, games, & dry bar w/ beverage cooler. Close to shopping, dining & attractions!

LocationValueView

5.0 out of 5 average rating, 21 reviews

4.82 out of 5 average rating, 146 reviews

Home in Santa Rosa Beach

Waterfront! Sleeps 14 & TWO Story Waterslide Fun!!

This family fun home has a 2 story super fast custom water slide, large pool, (extra charge to heat pool) swim up bar, outdoor tiki hut bar with sink and gas grill, charcoal grill, fire pit, sandy beach, dock, boat slip, (no boat lift) paddle boards. Private suite with kitchen & bathroom on lower level with private access leading out to bay. bring your own fishing gear if you like to fish. Home is a labor of love and has brought so much joy to our family & hopefully to yours.

Outdoor spacesValueCheck-in

Townhouse in Miramar Beach

Gulf Walk * House with Pool & Golf Cart

1 Block to the Beach! Enjoy a beach equipped garage with golf cart, backyard pool, and plenty of space for families or groups — all in one of Miramar Beach’s most desirable locations. This beautifully designed 2BR / 2.5BA townhouse is located in the popular Gulf Walk comm just a short 5-minute walk or 1-minute golf cart ride to Private Beach. With custom coastal-modern design, high-end furnishings, and thoughtful details throughout, this home is the perfect beach getaway.

Outdoor spacesValueWalkability

4.85 out of 5 average rating, 136 reviews

4.95 out of 5 average rating, 84 reviews

A sweeping view from the balcony showcases the resort's multiple swimming pools, surrounded by lounge chairs. The ocean sparkles under clear skies, with boats visible in the marina and a scenic shoreline in the distance.

Condo in Destin Harbor

Perrydise@ Emerald Grande 3BR Harbor & Gulf Views!

Enjoy a spacious 3-bedroom, 2-bath condo at Emerald Grande with stunning harbor and gulf views. Relax on your balcony, stroll to HarborWalk Village for dining, bars, and shops, or hop on the complimentary shuttle to the private beach with full service including chairs and umbrellas. 2026 exterior improvements mean discounted rates, while your interior experience, amenities, and views remain fully unaffected. Perfect for families, groups, or weekend getaways.

ValueOutdoor spacesIndoor spaces

5.0 out of 5 average rating, 31 reviews

WaterScape | Resort | Renovated | Beach steps away

Welcome to our 3 bedroom, 2.5 bathroom condo at WaterScape Resort, where beach days, pool time, and easy family living come together. • Complimentary beach service with 2 chairs, umbrella, and table • Two King suites, private bunkroom, and TVs throughout • Coffee Bar, milkshake bar, and themed selfie wall • About 1 min walk to the pools and beach access Bring the family, settle in, and enjoy the resort extras that make every day simple.

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Popular amenities for Santa Rosa Island kayak rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

4.84 out of 5 average rating, 116 reviews

Home in Destin

Beach+Pool+Hot Tub | Golf Cart(incl) + Game Room

Outdoor spacesLocationBathroom

4.95 out of 5 average rating, 128 reviews

Home in Santa Rosa Beach

4 BR 3 BA | Pool | Gym | Pets | 0.7 mi to beach

LocationOutdoor spacesLong stay

A spacious backyard features a private pool surrounded by a grassy area, with lounge chairs positioned for relaxation. A covered patio offers seating for guests, while a large tree provides shade. The home structure is positioned nearby, enhancing the outdoor retreat.

4.85 out of 5 average rating, 54 reviews

Sleeps 12* Private POOL * Backyard * Ranch Home

LocationOutdoor spacesPets

A wooden dock extends over calm waters, with two gray deck chairs positioned for relaxation. Lush green trees line the shoreline, and a few houses are visible in the distance under a bright blue sky with scattered clouds.

4.92 out of 5 average rating, 24 reviews

On the water! 7 minutes to the beach!

LocationOutdoor spacesBathroom

4.77 out of 5 average rating, 44 reviews

Home in Miramar Beach

Walk to Beach | Golf Cart | Pool | Air Hockey

ValueLocationAccess

5.0 out of 5 average rating, 10 reviews

Home in Santa Rosa Beach

Boat dock, Pool/ Cabana, Pet-Friendly, On the Bay

LocationValueFamily

A serene waterfront scene is presented at sunset, showcasing a wooden dock extending into calm waters. Six chairs are arranged on the dock, while a boat is docked nearby. The sky is filled with soft hues of purple and pink, reflected on the water.

5.0 out of 5 average rating, 24 reviews

Boater/fisherman’s paradise with on-site launch!

Outdoor spacesLocationComfort

4.64 out of 5 average rating, 11 reviews

Home in Mary Esther

Villa Rosa | Private Water Access | Pool | Kayaks

Outdoor spacesCheck-inFamily

Cottages with a kayak

4.83 out of 5 average rating, 170 reviews

A welcoming entrance features a covered porch adorned with vibrant pink flowers and a birdhouse. Two white chairs are positioned beside a small table, inviting guests to enjoy the serene setting. A decorative wind chime adds a touch of charm to the doorway.

Cottage in Mary Esther

Nature's Nest Cottage on the Sound - Pets Welcome!

Outdoor spacesLocationAmenities

Cottage in Fort Walton Beach

A spacious grassy area extends towards the water's edge, framed by trees. A wooden dock stretches into the calm bay, featuring a covered seating area. Swing benches are available on the shoreline, providing a perfect spot for relaxation while enjoying the scenic view of the water.

Waterfront Bliss Beach Cottage

Outdoor spacesLocationHospitality

5.0 out of 5 average rating, 39 reviews

4.93 out of 5 average rating, 67 reviews

Cottage in Freeport

Bayview Cottage | Dog Friendly | 15 Min to Beach

ValueLocationLaundry

A serene waterway reflects the soft colors of sunset, with trees lining the banks and tall grasses swaying gently at the water's edge. The landscape showcases a blend of greens and browns, creating a calm and tranquil atmosphere.

Cottage in Freeport

2 bedroom cottage with hot tub

LocationValueBeach

4.88 out of 5 average rating, 50 reviews

Other holiday rentals with a kayak

A lush tropical landscape is featured, with tall palm trees surrounding a winding lazy river. Colorful inflatable floats are visible in the water, while lounge chairs and umbrellas provide shaded seating areas. The beach and resort buildings are seen in the background, enhancing the relaxing atmosphere.

5.0 out of 5 average rating, 20 reviews

DW Sandpiper L03 ~ Walk Out Lanai ~ Lazy River!

LocationKitchenFamily

4.97 out of 5 average rating, 76 reviews

The living area features a light-colored sofa with decorative pillows and a patterned area rug. A large flat-screen TV is mounted on the wall above a rustic wooden console. Floor-to-ceiling glass doors open to a private balcony with ocean views and two chairs.

Condo in Miramar Beach

Majestic Sun 6th Floor View of Emerald Waters -New

LocationValueHot tub

4.91 out of 5 average rating, 53 reviews

Townhouse in Destin

Destin Beach House•Sleep12•Hot Tub•Pool•RoofDeck B

Outdoor spacesValueSleep quality

4.94 out of 5 average rating, 99 reviews

A spacious living area is highlighted by large windows offering views of the beachfront. Light blue seating arrangements complement the neutral decor. A dining table for four is positioned beside artwork featuring herons. Direct access to the outdoor patio is visible.

Condo in Miramar Beach

B105 | Beachfront with Beach Service, Pool, & WiFi

LocationCheckoutView

The large outdoor pool is surrounded by palm trees, creating a serene environment. Lounge chairs are arranged around the pool, and glowing lights reflect off the water. The beach and ocean are visible in the background, enhancing the coastal ambiance.

4.95 out of 5 average rating, 21 reviews

Beachfront Condo | Resort Pool | Sleeps 6

LocationValueDecor

4.96 out of 5 average rating, 24 reviews

NEW Listing! Beachfront 1st Floor w/Amazing Views!

LocationFamilyCleanliness

The main living area is characterized by a queen-size bed and a cozy sofa. Barstools are positioned at the kitchen counter, which features stainless steel appliances. Natural light fills the space, highlighting the soft color palette and natural textures, with an entryway visible in the background.

4.95 out of 5 average rating, 39 reviews

Sandpiper Cove 8233 FREE Beach Service Destin, FL

LocationAccuracyBathroom