Holiday rentals with a kayak in Santa Rosa Island

4.94 out of 5 average rating, 17 reviews

Condo in Okaloosa Island

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!

LocationCheck-inAccess

4.92 out of 5 average rating, 166 reviews

Townhouse in Destin

Harbor-front Oasis| Steps to the Beach

LOCATION, LOCATION, LOCATION! 5-min walk to the beach. 5-7 minute short drive to exciting Harbor Walk Village or Henderson State Park, what more could you ask for? The unit is conveniently situated in a very quiet, safe neighborhood. One of Destin’s most desirable locations. Open, spacious floor plan, dual balconies, water views, activity space in the garage and extra comfortable bedrooms await you. Arrange for a water taxi to pick you up directly from your boat slip-just outside of your condo!

ValueLocationView

4.99 out of 5 average rating, 178 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.

ValueOutdoor spacesComfort

4.97 out of 5 average rating, 199 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~Pool

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

ValueOutdoor spacesAccess

A dining area features a round table surrounded by woven chairs. A cozy sofa and a decorative console table are positioned nearby. Large sliding glass doors provide unobstructed views of the beach, while soft natural light fills the space, enhancing the coastal decor.

4.9 out of 5 average rating, 301 reviews

Beachfront 8th Fl. 1 BR at Pelican, Stunning Views

Completely renovated 8th floor condo right on the beach with unobstructed views of the Gulf and the beach. Located in the heart of Destin in popular Pelican Beach Resort, you will enjoy the private beach, multiple outdoor pools, an indoor pool, hottubs and more. Our beachfront condo has been professionally renovated with brand new cabinets, AC, floors, appliances, furniture, kitchen and more. All mattresses are brand new, cool-gel memory foam for a cool night's sleep. Fully stacked kitchen.

LocationValueCheck-in

Townhouse in Okaloosa 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.

4.99 out of 5 average rating, 77 reviews

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!

LocationOutdoor spacesIndoor spaces

4.98 out of 5 average rating, 119 reviews

Condo in Okaloosa Island

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 spacesLocationWi-Fi

Apartment in Okaloosa Island

5.0 out of 5 average rating, 18 reviews

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!

LocationConditionDecor

4.82 out of 5 average rating, 144 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 spacesLocationAmenities

A tranquil lagoon pool meanders through lush tropical landscaping, with palm trees lining the perimeter. Clear blue water reflects the sky, inviting relaxation. Pathways connect various seating areas and greenery, enhancing the serene resort atmosphere.

4.92 out of 5 average rating, 142 reviews

21017 Stunning Views ~ Pools ~ Gym ~ Book Aug 30th

Gorgeous Panoramic Gulf Views from this 10th floor, 3 bedrooms end unit, all bedrooms have access to the 100 ft extra large balcony with gulf views. Seating for 8. Resort Lagoon Pool and second Heated pool, 2 King Beds, 1 Queen Bed and a Queen Sofa Sleeper All the comforts of home, easy walk to the beach, or free Shuttle. 5 Star Resort, onsite Restaurant, coffee shop and pool side Tiki bar, Tennis, pickle ball, basketball, state of the art gym & BBQ grill area

ValueLocationWalkability

5.0 out of 5 average rating, 27 reviews

Condo in Okaloosa Island

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.

Outdoor spacesLocationAccess

4.96 out of 5 average rating, 70 reviews

Home on Bay-Private Pool-Boat Access-Kayaks-Fish!

Step into this artsy mid-century bayfront home where dolphins play in Choctawhatchee Bay! One story, all tile, sleeps 10 on half an acre of lush tropical landscaping with sweeping bay views from nearly every room. Gourmet kitchen, private pool, bayfront swim & fishing platform, 3 kayaks, 2 paddleboards, 2 bikes & hammocks. Circular drive — bring your boat or jet skis! Dog friendly! Just 6 min to beach. Pool unheated. Guests 25+ to book

Outdoor spacesLocationBiking

Popular amenities for Santa Rosa Island kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

4.95 out of 5 average rating, 127 reviews

Home in Santa Rosa Beach

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

Outdoor spacesValueCondition

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

LocationOutdoor spacesDecor

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, 53 reviews

Sleeps 12* Private POOL * Backyard * Ranch Home

LocationOutdoor spacesAmenities

4.77 out of 5 average rating, 43 reviews

Home in Miramar Beach

Walk to Beach | Golf Cart | Pool | Air Hockey| BBQ

Outdoor spacesValueSleep quality

4.91 out of 5 average rating, 11 reviews

A spacious screened-in patio presents a serene view of the waterfront. Comfortable seating arrangements are complemented by a dining table, while natural light illuminates the terracotta floor. The outdoor scenery features lush greenery and a distant dock, enhancing the tranquil atmosphere.

Home in Miramar Beach

Jet Ski Adventure - Family Getaway

Outdoor spacesLocationFamily

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, 22 reviews

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

LocationOutdoor spacesBeach

4.6 out of 5 average rating, 10 reviews

Home in Mary Esther

Private Water Access | Heated Pool | Kayaks

Outdoor spacesLaundryFamily

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.

4.91 out of 5 average rating, 23 reviews

On the water! 7 minutes to the beach!

LocationOutdoor spacesQuiet

Cottages with a kayak

4.83 out of 5 average rating, 169 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!

LocationOutdoor spacesBathroom

Cottage in Fort Walton Beach

Two lounge chairs are positioned on a wooden dock, facing tranquil green waters under a bright blue sky. The expansive waterway is visible, with a distant pier extending into the horizon, inviting relaxation and enjoyment of the coastal scenery.

5.0 out of 5 average rating, 37 reviews

Waterfront Bliss Beach Cottage

LocationOutdoor spacesQuiet

4.93 out of 5 average rating, 67 reviews

Cottage in Freeport

Bayview Cottage | Dog Friendly | 15 Min to Beach

ValueOutdoor spacesPets

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

4.88 out of 5 average rating, 50 reviews

2 bedroom cottage with hot tub

ValueOutdoor spacesAccess

Other holiday rentals with a kayak

4.95 out of 5 average rating, 83 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!

Outdoor spacesValueGetting around

A balcony features two blue chairs and a small table, offering a direct view of the beach and the shimmering gulf waters. The sandy shore is visible below, lined with beach umbrellas, while the vibrant blue sky enhances the scenic coastal horizon.

4.89 out of 5 average rating, 28 reviews

Pelican Beach Top Floor Beachfront with Best Views

LocationValueParks

4.92 out of 5 average rating, 50 reviews

Townhouse in Destin

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

ValueLocationShared spaces

4.94 out of 5 average rating, 18 reviews

8th floor Beachfront at Pelican Stunning Views

LocationAmenitiesCleanliness

4.98 out of 5 average rating, 91 reviews

The living room features a light-colored sofa paired with two modern armchairs, creating an inviting seating area. Floor-to-ceiling windows provide unobstructed ocean views. A coffee table and side tables complement the space, while a large wall-mounted TV and tasteful artwork enhance the atmosphere.

Condo in Sandestin

Stunning beach views *Not your grandma’s condo*

LocationValueBeach

4.95 out of 5 average rating, 79 reviews

The living and dining area features comfortable seating arranged around a large window that offers views of the Gulf. A rustic dining table is paired with woven chairs, and light fixtures create a relaxing ambiance throughout the space.

Condo in Miramar Beach

D102 | Beachfront with Beach Service, Pool, & WiFi

ValueLocationAmenities

5.0 out of 5 average rating, 4 reviews

Gulfgate Destination 0505 2BD/2BA

LocationAmenitiesView