Holiday rentals with a kayak in Okaloosa Island

Townhouse in Miramar Beach

4.89 out of 5 average rating, 108 reviews

2 min 2 Private Beach* House with Pool & Golf Cart

New Remodeled Beach House. Located in just 5 min walk or 1-2 min Golf Cart ride to private Beach Access. Custom design, High-end furniture, high quality mattresses, linen beddings, soft towels and fully equipped kitchen Attention to the details Relaxing view overlooking the pool and LOCATION- all this make this townhouse the perfect Vacation Destination. Garage access: Family 6 seater Golf Cart, beach chairs, Umbrellas, 2 Paddle Board, coolers, beach toys, bicycle set additional $60/day.

4.82 out of 5 average rating, 199 reviews

Apartment in Sandestin

Sandestin Resort Studio, Spectacular Bay Views

Our Bayside Studio offers spectacular panoramic views of Choctawhatchee Bay. Located in Sandestin Resort on a quite enclave framed by Florida pines and the fairways of The Links Course, your own personal balcony on the third floor serves as the perfect viewpoint of the Bay. Guests and children will enjoy our relatively low nightly rates but also have access to all the amenities Sandestin has to offer (Beach, golf, tennis, water-sports, spa, nature trails, many kids activities, dining, shopping).

Apartment in Fort Walton Beach

5 out of 5 average rating, 99 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!

4.9 out of 5 average rating, 199 reviews

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, 152 reviews

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, 150 reviews

Apartment in Sandestin

Light&Airy ON Beach -Golfcart* in Sandestin Resort

Updated 1st fl. Sleek studio ON the Beach. 🛺 Golf cart w/3+ nts. Between Destin & 30A in gated Sandestin Resort. Kitchen w/coffee cart. West Elm furniture & King bed has tropical view. Relax on the patio’s round Bali bed & listen to the waves. WiFi & 55” smart TV. Washer/dryer in condo. Free gym! Tram passes. Enjoy the beach, trails, golf, dining, shopping & entertainment all without leaving the resort! Perfect honeymoon, baby moon, romantic getaway, girls trip or lil’ fam vacay! *no animals

Townhouse in Okaloosa Island

4.98 out of 5 average rating, 55 reviews

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

Literally steps from the water, this spacious 3-story, 3 bed, 3.5 bath townhome features breathtaking ocean views. 2 Kayaks, SUP, beach chairs, umbrellas, outdoor games, boogie boards & beach toys for use on patio & side yard. 3rd floor has Bedroom #1 (king) and Bedroom #2 (queen & double bunk beds). Bedroom #3 (queen) is located on the 1st floor. Each bedroom has its own full bathroom. The 1/2 bath is on the 2nd floor. Computer monitor for remote work with high speed Wifi and 4 Smart TVs.

4.87 out of 5 average rating, 101 reviews

Apartment in Destin

21201 Penthouse Gulf/Pool Views~Discount July 16th

COMPLETELY RENOVATED! Top Floor, 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!

Home in Fort Walton Beach

5 out of 5 average rating, 7 reviews

The Ancker Boat House • Waterfront on the Bayou

🌴The Ancker Boat House☀️ Escape to your own slice of paradise at this stunning waterfront haven in Fort Walton Beach! Nestled at the end of a private drive, this 4-bed, 3-bath gem offers nearly an acre of serene bayou-front living with 101 feet of shoreline. After visiting Crab Island, dock your boat & jetski's, sit back & relax under the sunset sky, and maybe toss a line in the water. Or sit around the fire pit with friends & family while you enjoy the picture-perfect memories to be made.

Flat in Fort Walton Beach

5 out of 5 average rating, 39 reviews

Pink Flamingo Okaloosa Island

Sitting DIRECTLY ON THE BEACH look out from your private balcony looking over the white sand and Emerald Green water. One bedroom, one bath. The condo is on the 3rd floor middle unit. Newly renovated and decorated beach retro with a pink flamingo twist. Your stay includes keyless entry, private patio, 55" Smart TV, Wi-Fi, and record player with vinyl collection. Note: The couch is not pullout, but two twin rollout mattresses are provided upon request. No pets. Sorry. THERE IS A 2 ADULT LIMIT.

4.95 out of 5 average rating, 117 reviews

Apartment in Sandestin

Sandestin Elation Studio - Baytowne - Golf Cart

Ground-floor studio in Sandestin Golf & Beach Resort with serene golf course and lake views. Steps from Baytowne Wharf’s dining and entertainment. Features a king bed, queen sofa bed, full bath, and kitchenette with microwave and mid-size fridge. Enjoy Wi-Fi, Netflix, resort tram access, and beach gear in garage storage. Golf cart available - please inquire about availability and fee. Perfect for a relaxing escape in the heart of Sandestin. And Yes! you may drive the golf cart to the beach.

4.82 out of 5 average rating, 123 reviews

Home in Sandestin

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.

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Popular amenities for kayak rentals in Okaloosa Island

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

5 out of 5 average rating, 17 reviews

Home in Destin

Waterfront, Boat dock, Bikes, BEACH, HOT TUB

DonnaRating, 5 starstoday

Our stay at this condo was lovely! The unit was clean, comfortable, and well-maintained. One of the highlights was having the convenience of a boat lift and being so close to Crab Island—it made our trip even more enjoyable. The management team was accessible and responsive to our needs throughout the stay. Thank you for a wonderful experience!

4.94 out of 5 average rating, 64 reviews

Home in Santa Rosa Beach

Blue Palm Beach House|Heated Pool|Hot Tub

ShelbyRating, 5 stars2 weeks ago

We booked this Airbnb for 12 people and it exceeded our expectations! The house is beautiful and we loved the pool and hot tub. The location is conveniently located right down the road from a lot of restaurants and several beach access points. The host, Josh, was very informative and very quick to respond. I highly recommend booking this house for your next group vacation!

Home in Fort Walton Beach

4.97 out of 5 average rating, 60 reviews

WATERFRONT~Home~PRIVATE~POOL & DEEP DOCK bring 🚤⛵️⚓️

RebeccaRating, 5 stars2 weeks ago

This house had everything we needed and all was in great working order. The kitchen was exceptionally stocked for our home cooked meals. The extra refrigerator came in handy for our beverages. Plenty of sitting room so we could spread out a bit. Karen was wonderful and always helpful. Everyone in my family wants to come back next year.

4.96 out of 5 average rating, 50 reviews

Home in Sandestin

GolfCart*SanDestin*Pool*Arcade*Fireworks*Disc 4NT+

NatashaRating, 5 stars2 weeks ago

Nicole's place was fantastic! Super comfortable and had all needed amenities. Definitely recommend, you won't be disappointed. Our host was very responsive and helpful in every way. We really enjoyed our vacation that much more because of the place we stayed.

4.93 out of 5 average rating, 55 reviews

Home in Destin

Perrydise @ Emerald Grande

TravisRating, 5 stars2 weeks ago

Perry was an amazing host! I don't think there would be a better place in Destin. Being right on the Harborwalk, we were able to walk to everything. The private beach is amazing as well. Perry was very responsive and accommodating. I will definitely be staying here again!

5 out of 5 average rating, 6 reviews

Home in Miramar Beach

Jet Ski Adventure - Family Getaway

EsmeraldaRating, 5 stars1 week ago

The home is beautiful and very clean! Plenty of amenities and amazing views. The kitchen is large and spacious! Master bedroom has view to the bay! Coffee on the outside patio was peaceful and amazing! Definitely recommend and definitely will comeback!

Home in Fort Walton Beach

4.86 out of 5 average rating, 22 reviews

The Pink Cottage

JanelleRating, 5 stars1 day ago

Susan was quick to respond and very accommodating with anything we needed. The home was clean and worked perfectly for the space we needed to crate our dog while we were away at the beach. The beach is a short drive away with the bay being within walking distance. We were able to fish at the bay and visit the beach daily. Definitely a top notch host and we will be back!

5 out of 5 average rating, 6 reviews

Home in Sandestin

PlayaBella-Sandestin® Escape|Golf Cart Included

JulieRating, 5 stars2 weeks ago

We had an amazing stay at this villa! The house was exactly as pictured—clean, comfortable, and with a stunning view of the lake. We spent hours enjoying the excellent fishing right from the property. The golf cart was a game-changer and made getting around the area super easy and fun. We truly loved the entire property. We made full use of the pools, the gym, and even grabbed bites and coffee from both the bayside and beachside cafés. Everything was convenient, relaxing, and beautifully maintained. Our host, Shelena, was extremely helpful and very responsive throughout our stay. This is by far our favorite vacation spot, and we will definitely be back next year!

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Cottage rentals with a kayak

4.85 out of 5 average rating, 103 reviews

Cottage in Freeport

Waterfront Cottage Unit, Keyless, mins to beach

RachelRating, 5 stars2 weeks ago

Had the best time here! Beautiful marsh area and so fun to explore with canoe and kayak. Such a peaceful and relaxing space.

Cottage in Freeport

4.86 out of 5 average rating, 36 reviews

2 bedroom cottage with hot tub

DomRating, 5 stars3 weeks ago

Loved the place! It was peaceful and quiet literally across the street from the beautiful Bay. Was very homey, able to cook, wash clothes, had smart tv, and internet and all the appliances you would have at home. Marianne is very responsive and was always available. Even saw the neighbors gorgeous peacock 🦚 Cool little spot!

4.84 out of 5 average rating, 143 reviews

Cottage in Mary Esther

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

KatharineRating, 5 stars2 weeks ago

We’re repeat visitors and our stay this time was just as lovely as the last. The Nest offers a cozy place to hang out, bed down, and base from. We love spending time kayaking the sound and watching for wildlife. Beaches, seafood, and all the Ft.Walton/Destin vacation fun is close by, but the Nest is homey and easily fit our family of four. Very grateful for laundry to wash bathing suits in between beach days!