Holiday rentals with a kayak in Okaloosa County

A balcony table with four wooden chairs is positioned overlooking the Gulf. The horizon merges the tranquil blue sea and sky, reflecting sunlight. The unobstructed view enhances the outdoor space, inviting relaxation while watching the waves below.

5 out of 5 average rating, 41 reviews

Pelican Beach 19th Floor 1 Br - on the Beach

Our family vacation condo is right at the beach with unobstructed Gulf views from the living room, balcony, kitchen and dinner area. It is newly painted and has stainless steel appliances in an updated kitchen and has new furniture. Everything is upgraded. Bunk beds have flat screen TV's. The views, especially sunsets from 19th floor patio is amazing. Most guests see the dolphins in the morning. We offer beach chairs/umbrella and free high speed Wifi. Pelican Beach Resort is the prime family des

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.

4.91 out of 5 average rating, 143 reviews

A balcony table is set for breakfast, featuring two white cups, a plate with blueberries, and a muffin. A pink orchid adds a pop of color. The background showcases a pastel sunset over water and buildings.

Townhouse in Destin

Snowbird favorite! | Heart of Destin | Waterfront

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!

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.

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!

A spacious living area features large glass doors offering unobstructed views of the Gulf. Light-colored furniture surrounds a central coffee table, while a ceiling fan hangs above. Soft natural light illuminates the room, complemented by neutral tones and beach-themed decor.

4.82 out of 5 average rating, 39 reviews

Pelican Updated 14th floor 1 bedroom Condo on the

Modern and stylish 14th-floor beachfront condo at Pelican Beach Resort with sweeping, unobstructed Gulf views from the living room, kitchen and private balcony. Newly painted and upgraded with tasteful coastal décor, this serene retreat features a king bedroom with en-suite bath, a second full bathroom, and hallway bunk beds each with their own TV. Guests often spot dolphins from the balcony. Includes high-speed Wi-Fi, Netflix on every TV, and beach chairs with umbrella stored in the unit.

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

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

4.95 out of 5 average rating, 20 reviews

Home in Destin

Paradise by the Beach|Heated Pool|Golf Cart

Trade Snow Boots for Sandals – Inquire About Monthly Beach Specials 🏖️ Welcome to this luxurious five-bedroom vacation home that offers the perfect combination of spaciousness, convenience, and indulgence. Take a leisurely bike ride around the charming neighborhood, cruise to the beach on the. 6-seater golf cart or enjoy a swim in the heated pool while basking in the sunshine. With lots of nearby attractions and activities, there's something for everyone to enjoy 🌴🌊🏖️

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.

A bright living area features a comfortable sofa and a coffee table, with a dining table set for four. Large sliding glass doors open to the balcony, offering unobstructed views of the Gulf of Mexico. Soft natural light filters through sheer curtains.