Holiday rentals with a kayak in Santa Rosa Island

Apartment in Fort Walton Beach

5 out of 5 average rating, 114 reviews

Waterfront cozy condo with king bed & resort pool

Welcome to The Salty Pirate, your waterfront vacation paradise! Kick back & relax in our calm, stylish condo featuring a king size bed, luxury bathroom & kitchenette. Relax in bed, enjoy the boats cruise by or watch the 65 inch TV. The waterfront balcony entices you to read & relax. Enjoy the resort style pool or reserve the 2-seater kayak (when available) provided for you to explore the waterway. Downtown restaurants & bars are walking distance & the white sugar sand beaches are 2 miles away!

4.91 out of 5 average rating, 215 reviews

The exterior of the cottage features a stone facade and a covered carport. A well-maintained path leads to the entrance, surrounded by established shrubs and greenery. A gravel driveway provides access, with a fenced yard visible in the background.

Cabin in Mary Esther

Safe Harbor Cottage on Santa Rosa Sound - Pets ok!

Well furnished private one bedroom cottage with sunroom, patio, and carport. Full kitchen with bar counter. Has washer/dryer! There's a fenced yard with small deck, perfect for dog owners. The home is situated under shady oak trees with access to waterfront on Santa Rosa Sound. You can enjoy playing with the pooch, swimming, boating, kayaking, fishing, and viewing beautiful sunsets. It's a perfect location for visits to Hurlburt AFB, or vacationers seeking easy access to Ft. Walton and Navarre.

4.99 out of 5 average rating, 159 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.

Flat 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.

4.97 out of 5 average rating, 149 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.

Apartment in Sandestin

Zen Retreat ON Beach -Golfcart* Hot Tub, SanDestin

8th fl. stylish open studio w/stunning VIEW, beachfront in Sandestin Resort between Destin & 30A. 🛺 Golf cart with 3+ nts. NEW Pool & Hot Tub. West Elm furniture & King size bed w/ocean view. 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

A two-story beach cottage is displayed with light-colored siding and multiple balconies. The porch extends across the front, supported by white columns. The outdoor area features paved stones, with nearby plants providing a natural touch. Nearby structures are visible in a coastal setting.

4.97 out of 5 average rating, 116 reviews

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

Gorgeous 4-bedroom 3-bath beach cottage along popular Scenic Hwy 30A. Located in the quaint coastal community of Blue Mountain Beach, this beautifully designed home is a short distance to the picturesque emerald-green waters and sugar-white sand beaches of the Emerald Coast! Our stunning home is a 13-minute walk or a 4-minute bike ride to the beach and walking distance to local restaurants and shops. You will enjoy a fully stocked kitchen, comfortable bedrooms, community pool access & more.

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.

4.98 out of 5 average rating, 66 reviews

Sea Turtle House-On Beach-Townhome-Kayaks/SUP

🏖 Steps from the Ocean | 3BR/3.5BA Townhome w/ Views + Kayaks & SUPs! Relax in this spacious 3-story townhome—literally steps from the beach! Enjoy breathtaking ocean views, modern comforts, and everything you need for fun in the sun. 🛏 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!

The image showcases a sprawling lagoon pool surrounded by lush palm trees and tropical landscaping. A playful water slide is visible, alongside winding pathways and sun loungers, creating an inviting outdoor space for relaxation and recreation.

4.95 out of 5 average rating, 147 reviews

3107 Amazing Heated Pool ~ Special ~ Book Nov 24th

One of only 14 Exclusive Poolside Villas! Welcome to the Villa Cabana Royale! 1450 sq ft of open concept space, with a walk in/ walk out setup, double sliding doors to bring the outdoors in. This poolside villa cabana sleeps 6 and is the perfect location, with an outdoor dining and patio experience in the tropical gardens alongside the gorgeous lagoon pool. The Villa Cabana Royale has 2 huge bedrooms, 2 King Beds, single chair bed, queen sofa sleeper. 4 beds in total. 65" Inch Smart TVs

Apartment in The Village of Baytowne Wharf

A light-filled living area features a cozy sofa and ceiling fan. A large TV hangs on the wall, with views of a private balcony visible through sliding glass doors. A dining table, adorned with decorative items, offers a space for meals and gatherings.

4.92 out of 5 average rating, 122 reviews

Grand Sandestin 4th flr 1 b.room-Steps to Baytowne

Elegant 1BR retreat with 4th-floor views from large balcony, steps from the Village of Baytowne Wharf. Just a 5–10 min TRAM ride to Sandestin pristine private beaches. Features a king bed, queen sofa sleeper, full kitchen, in-unit washer/dryer, and refined décor. Stay connected with high-speed Wi-Fi, unwind with Netflix, and enjoy use of beach chairs and an umbrella stored in our private garage-level storage. Perfect for couples or small families looking to relax and explore Sandestin.

Apartment in Miramar Beach

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.

4.96 out of 5 average rating, 71 reviews

D102 | Beachfront with Beach Service, Pool, & WiFi

Welcome to Beach House Condo D102, your beachfront escape! Wake up to Gulf views from your private patio and enjoy easy beach access plus a host of amenities - Private beachfront patio - Direct beach access; no roads to cross - Enjoy beach service on us | Mar 1 - Oct 31 - Fully-equipped kitchen & private laundry Your included amenities - Seasonally heated large pool & kiddie pool - Tennis courts, fitness room, free WiFi Minutes from shopping, dining, attractions, and conveniences

Houseboat in Fort Walton Beach

A houseboat is docked on a covered pier, surrounded by calm water. White chairs are positioned on the deck, offering a relaxing view of the bayou. Lush greenery frames the setting, while the dock's wooden surface provides easy access.

4.95 out of 5 average rating, 113 reviews

Unique water front stay Houseboat Destin/FWB

Seas the Day, center on Ft. Walton Beach,quiet bayou connected to bay and gulf on private 1 acre residence. We are 1 of only 3 HB for 50 miles in area. Paddle boards, kayaks , fishing poles and outdoor fire pit. Car needed to get to white sand beaches (4 miles). Shopping close by. A comfy futon in for a second bed. Boat has AC and heat. Unit is to stay docked.Recently renovated inside and out . Larger deck area with loungers . New lighting and ceiling this past spring! Rare find

4.88 out of 5 average rating, 101 reviews

A light-filled living area features a comfortable sofa with patterned upholstery and a large round coffee table. Floor-to-ceiling windows offer views of the ocean, while nautical-themed decor, including an oar and ship wheel, enhances the coastal ambiance.

Flat in Destin

Nautical Dunes - Ocean Front View!

Enjoy breathtaking views of the beach from your private balcony or take a short walk to the sparkling emerald waters and sugar-white sands. The spacious and elegantly decorated condo offers the perfect oasis for relaxation and fun. Soak in the sun by one of the pools, challenge your friends to a game of tennis, or simply unwind in the hot tubs. Bring your family and friends to create unforgettable memories at "Nautical Dunes" on your next beach vacation!

Apartment in Fort Walton Beach

A panoramic view of the beach showcases soft white sands meeting the tranquil turquoise waters of the Gulf. Beach umbrellas and chairs line the shore, with a clear blue sky above enhancing the serene coastal landscape.

4.98 out of 5 average rating, 110 reviews

Island Princess 618 | Gulf Views & Beach Service

Experience the ultimate beach getaway at our renovated condo on stunning Okaloosa Island. This beachfront retreat features two spacious bedrooms, two modern bathrooms, and a rare oversized balcony perfect for soaking in the breathtaking views. Relax on the sugar-white sands and take in the emerald-green waters of the Gulf with complimentary beach service, including two chairs and an umbrella, provided from March 1st to October 31st.

Popular amenities for kayak rentals in Santa Rosa Island

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

A dining area is displayed featuring a white table with natural wood legs, surrounded by four black chairs. A woven centerpiece holds greenery. The kitchen in the background includes white cabinets and modern appliances with a breakfast bar and additional seating. Natural light fills the space.

4.95 out of 5 average rating, 41 reviews

Bungalow by the Bayou

4.96 out of 5 average rating, 23 reviews

The exterior of the waterfront home features a spacious deck connected by a wooden walkway. Surrounding palm trees and lush greenery create a tropical ambiance. A sandy area can be seen by the water's edge, inviting outdoor activities and relaxation.

Home in Niceville

Waterfront Haven - Perfect for Family Vacations

5 out of 5 average rating, 17 reviews

A spacious outdoor dining area is visible, featuring a sturdy table set against a backdrop of tall pine trees and a clear view of the water. The scene is framed by a screen, allowing for an unobstructed view of the serene landscape.

Home in Mary Esther

Tropic Like It's Hot

4.9 out of 5 average rating, 10 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

4.95 out of 5 average rating, 37 reviews

A wooden boardwalk leads from the sandy beach to the beachfront house, surrounded by tall pine trees and palm plants. A shaded lounge area with comfortable seating is visible on the lawn, inviting relaxation by the water's edge.

Home in Mary Esther

Waterfront - Beachfront Home (Destin) w/Hot tub!

Waves gently lap at a sandy beach, reflecting the soft hues of a sunset. The sky is filled with clouds, creating dynamic patterns above. The coastline stretches into the distance, bordered by greenery and beachside structures.

4.99 out of 5 average rating, 76 reviews

The Seahorse 30A! Golf cart included! Sleeps 10!

Superhost

5 out of 5 average rating, 3 reviews

The Retreat in Santa Rosa Beach- Bungalow E

4.94 out of 5 average rating, 54 reviews

A dining area is presented with a wooden table and matching bench, surrounded by light blue chairs. A large octopus-themed artwork adorns the wall, while a vase with white flowers sits as a centerpiece. Natural light enters through a glass door, enhancing the space.

Home in Mary Esther

Beach house 2 min from the Boat Ramp and Dog Beach

Cottage rentals with a kayak

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

4.86 out of 5 average rating, 42 reviews

2 bedroom cottage with hot tub

5 out of 5 average rating, 13 reviews

A serene canal view is captured under a clear blue sky, showcasing calm waters reflecting the surroundings. Wooden docks line the canal, leading to several boats moored along the edges. The distant structures provide a backdrop to the tranquil setting.

Cottage in Destin

Boat,Beach &view! Boat slip/walk to the beach

4.84 out of 5 average rating, 156 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!

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 out of 5 average rating, 25 reviews

Luxury Beach Cottage With Private Beach

Other holiday rentals with a kayak

Apartment in Santa Rosa Beach

A modern kitchen is presented with white cabinetry, a central island topped with light-colored stone, and bar stools. Pendant lights with woven shades hang above the island. Appliances, including a stainless-steel refrigerator and a stove, complete the open layout that connects to a living area with ample natural light.

5 out of 5 average rating, 11 reviews

Steps to Beach w/ View, Pool + Tennis | Sea La Vie

A serene beach view features gentle waves lapping at the soft, white sand. The clear blue water transitions from a lighter shade near the shore to a deeper turquoise further out, under a bright, cloudless sky.

4.94 out of 5 average rating, 68 reviews

Beach Cottage • Private Beach • Gated •Heated Pool

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.

4.93 out of 5 average rating, 14 reviews

Pelican Beach Top Floor Beachfront with Best Views

The living area features a spacious layout with a large sectional sofa and a comfortable armchair. A 65-inch curved TV is mounted on a decorative cabinet. Floor-to-ceiling windows provide views of the Gulf, and a dining area is visible in the background.

4.81 out of 5 average rating, 77 reviews

IRC 604: Gulf Front Luxury (2 Bed / 2 Bath)

Apartment in Miramar Beach

4.99 out of 5 average rating, 88 reviews

Contact for Snowbird rates! Stunning Gulf and Bay

Apartment in Santa Rosa Beach

A spacious private balcony features comfortable seating, including colorful lounge chairs and a glass-top table. The view overlooks the tiered pool area, surrounded by the resort's elegant architecture and lush greenery under a partly cloudy sky.

5 out of 5 average rating, 56 reviews

Top Floor | Heated Pool | Steps to Beach

Superhost

4.78 out of 5 average rating, 41 reviews

Brand New Luxury Beach Home!