Vacation rentals with a kayak in Santa Rosa 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!

Location · Hot tub · Nearby

Majestic Sun 6th Floor View of Emerald Waters -New

Enjoy breathtaking Gulf views from the spacious balcony of this beautifully updated 6th floor 1BR/2BA condo in Majestic Sun’s sought-after A building—just steps from covered parking with 3rd-floor overpass access. This serene coastal retreat sleeps six and features a king bedroom with en-suite bath, hallway bunk beds, and an open-concept living area with queen sleeper sofa, dining space, and a full kitchen with modern appliances. Designed in soothing coastal tones for a relaxed, upscale getaway.

Location · Value · Condition

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 spaces · Location · Long stay

Light & Airy ON Beach ~Golfcart*~Oceanview~Hot Tub

ON BEACH-Sleek airy 1st floor studio. Sandestin Resort between Destin & 30A. Beach/Pool/HotTub 1 min from patio. 🛺Golf Cart w/3+ nts. Pottery Barn King bed with beachfront view. Step off private patio to the beach or relax on the patio Bali bed. WiFi, 55” smart TV, Kitchen, Washer/dryer. Enjoy free gym, tram, beach, trails, golf, dining, shopping & entertainment all without leaving resort! Perfect honeymoon, baby moon, romantic getaway, girls trip, solo travel or lil’ fam vacay! NO animals

Value · Outdoor spaces · Access

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 spaces · Location · Parking

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.

Value · Location · Air conditioning

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.

Value · Outdoor spaces · Cleanliness

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!

Value · Location · Pool

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.

Value · Location · Beach

21201 Gulf & Pool Views ~ Dining ~ Book Sept 20th

Penthouse views! 2 King Suites, 11,000 square foot Lagoon Pool with five waterfalls. Children's Pool, Playground, Tennis Courts and Basketball court. This corner Penthouse Suite has the absolute BEST view of the resort including the pool & gorgeous Gulf of Mexico! The Palms of Destin Florida is a beautiful resort with excellent 5 Star amenities including the Palms Bistro, Poolside tiki bar and coffee house! Something for everyone! This resort has it all!

Value · Location · Comfort

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.

Location · Outdoor spaces · Parking

3 Br Waterfront Florida Classic on the Bayou

Enjoy the comfort and beauty of classic old Florida at this beautiful waterfront home. Moments away from white sand beaches and downtown, you are in an oasis of relaxation here at the Florida Classic on the Bayou. This home was thoughtfully designed and cherished by a prominent local family and features rich Florida history and details. It is our pleasure to share this oasis with you.

Location · Value · Quiet