Holiday rentals with a kayak in Destin

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!

LocationValueHospitality

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 spacesLaundry

Condo in Lower Grand Lagoon

5.0 out of 5 average rating, 121 reviews

Mermaids Calling 2302Beach Front~Free Beach Chairs

Mermaids Calling Penthouse 2302 GulfCrest is gated and has full time security. Open wide spacious floor plan that’s very roomy with floor to ceiling windows and a 40 ft tiled balcony with lots of seating to observe sea life and the most beautiful sunsets. Two gulf front pools, two hot tubs and a kiddie pool. On the pool deck we have a tiki hut where you can get drinks and food(seasonal), lounges, deck chairs and a gazebo with picnic tables. A set of free Beach Chairs & umbrella (seasonal).

Outdoor spacesValuePool

4.98 out of 5 average rating, 146 reviews

The exterior of the bungalow showcases a heated pool surrounded by lounge chairs and a dining area under an umbrella. A gas grill is visible near the shaded seating areas, set against a backdrop of lush greenery and a clear blue sky.

Home in Inlet Beach

New Heated (opt) Pool/Interior/Walk-Private beach

Brand New Heated (optional) Pool & all new interior renovation is stunning! Rare Private Beach-easy walk (1 block).. Kid’s Bunk-n-play room -65” Smart and Ping Pong Table. Newly renovated “Lux Bungalow” is designed for big family entertaining inside and out or cozy adult time poolside or by 2 fireplaces! 3 brms/2.5 baths-sleeps 10! NOTE: For pool, an additional heated fee daily rate of $45/Day-ONLY for stays Oct- March! Other months no heat is required (80° )NO CONSTRUCTION NEXT DOOR!

Outdoor spacesValueNearby

Condo in Panama City Beach

4.98 out of 5 average rating, 217 reviews

Beachfront Penthouse! Scenic Views! 10ft Ceilings!

BeachView Paradise is a beautiful 1 bedroom/1 bathroom BEACHFRONT corner penthouse condo located at Tidewater Beach Resort on the 27th floor with jaw dropping views. Recently renovated down to the studs, it was curated with thoughtful design and high end finishes. A quick elevator ride down and you are right at the pools or the beach. All of this in a beachfront resort full of amenities and a quick walk to Pier Park loaded with restaurants, shopping and family fun. Take a look!

ValueLocationDecor

4.82 out of 5 average rating, 144 reviews

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.

LocationOutdoor spacesBackyard

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

LocationValueCondition

4.84 out of 5 average rating, 114 reviews

Home in Destin

Beach+Pool+Hot Tub | Golf Cart(incl) + Game Room

Welcome to Destin Beach House — a spacious, FULLY RENOVATED (March 2026) Crystal Beach retreat just steps from Destin’s famous white-sand beaches. You'll love the open Kitchen, private pool (optional heating), hot tub, Outdoor TV, game room, and FREE 6-passenger golf cart, making it easy to cruise around. Perfect for family vacations and group getaways, with open living spaces and a private backyard oasis designed for relaxing after a day on the Emerald Coast.

LocationOutdoor spacesComfort

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.

4.9 out of 5 average rating, 192 reviews

Beachfront, 7th Flr at Pelican, Breathtaking Views

Spacious one bedroom two bathroom unit with unobstructed spectacular views of the Gulf of Mexico. Recently renovated and decorated professionally, guests will enjoy a new kitchen with granite counter-tops, stylish cabinets, and stainless steel appliances. Kitchen is fully equipped for a family or group of 6. Our guests just step out to the white sand beach from the resort, no streets to cross.

ValueLocationParking

Home in Fort Walton Beach

A classic waterfront home is shown from the outside, featuring a large front porch with white railings. Colorful kayaks and paddleboards are displayed on a wooden rack beside a grassy yard, surrounded by lush greenery. Ceiling fans hang above, providing comfort.

4.95 out of 5 average rating, 110 reviews

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.

Outdoor spacesLocationView

A light-filled bedroom showcases lake views through large windows. A spacious bed is adorned with soft linens and pillows. A wall-mounted TV is positioned across from the bed, while outdoor seating with an umbrella can be seen on the deck, enhancing the serene ambiance.

4.99 out of 5 average rating, 120 reviews

Romantic Seagrove Palmetto Bungalow 30A Lakefront

Welcome to the Palmetto Bungalow! Recently chosen by Brides magazine as one of the top 20 most romantic airbnbs in the country! Truly a special place to unwind, refresh, reconnect, honeymoon or just fall in Love again! This romantic lakefront gem takes you back to yesterday, the simpler times…the way it used to be. Love is in the air.

LocationOutdoor spacesCondition

4.86 out of 5 average rating, 145 reviews

Illuminated palm trees frame a serene lakeside setting at night. A covered cabana sits nearby, featuring seating arrangements. Soft lighting gently highlights the landscape, reflecting on the water, while a grassy area offers space for relaxation.

Cabin in Panama City

Cabin on Private Beach with Tiki Bar & Cabana

3 Queen beds, 2 bedrooms, queen futon sofa. Lake front, tiki bar with swings, covered cabana. Gated property for privacy. 20 minutes from Panama City Beach. Ten minutes from Ecofina Springs. Stone tiki kitchen with fireplace, open fire Argentine grill and smoker. Beach side cabana with 10 inch mattress, 43 inch smart TV, wood stove.

Outdoor spacesLocationBarbecue

Popular amenities for Destin 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

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

Outdoor spacesLocationPool

Home in Fort Walton Beach

4.96 out of 5 average rating, 70 reviews

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

LocationValueIndoor spaces

4.77 out of 5 average rating, 43 reviews

Home in Miramar Beach

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

LocationValuePool

5.0 out of 5 average rating, 60 reviews

Home in Panama City

The Sage House

ValueLocationSleep quality

4.97 out of 5 average rating, 35 reviews

A scenic waterfront view captures a modern home with large windows reflecting the colorful sunset. A boat is docked at a covered structure, surrounded by calm water. Palm trees and homes are visible in the background, completing the serene landscape.

Home in Lynn Haven

Waterfront Home - Dock & Pool

LocationOutdoor spacesPets

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 spacesLocationKitchen

4.91 out of 5 average rating, 74 reviews

Home in Laguna Beach

Casa De Riviera | Pool, Dock + Lakefront Views

ValueLocationDecor

A serene outdoor space features four wooden Adirondack chairs arranged around a fire pit, set on lush green grass. A wooden dock extends into the water, leading to a calm bay with a floating inflatable. Clear blue skies stretch overhead.

4.96 out of 5 average rating, 45 reviews

Bayside Beauty - Private Dock - Kayak - Fishing

ValueOutdoor spacesCondition

Cottages with a kayak

4.95 out of 5 average rating, 154 reviews

A scenic view of a wooden dock extending into the calm water, bordered by lush greenery. A lounge chair sits on the grass nearby, complemented by a potted plant. The tranquil blue sky reflects off the water, enhancing the serene outdoor setting.

Cottage in Panama City

Water front amazing views and private beach

LocationOutdoor spacesCondition

4.97 out of 5 average rating, 174 reviews

A wooden boardwalk leads to a scenic beach view. Gentle waves meet a soft white sand shore, with patrons enjoying the beach under a clear blue sky. Vibrant umbrellas dot the shoreline, and native grass is visible in the foreground.

Cottage in Laguna Beach

Private home 1 blk beach screen porch close to 30a

LocationValueFamily

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!

Outdoor spacesLocationComfort

4.9 out of 5 average rating, 127 reviews

An aerial view of Turtle Cove Water-Front Cottage is presented, highlighting its proximity to the waterfront canal. Lush green landscapes and trees surround the property, with the cottage positioned near the yard. The serene canal leads to the bay, showcasing a peaceful natural environment.

Cottage in St. Andrews

Private Water Front Cottage - Panama City, FL

Outdoor spacesValueParks

Cottage in Fort Walton Beach

A spacious grassy area extends towards the water's edge, framed by trees. A wooden dock stretches into the calm bay, featuring a covered seating area. Swing benches are available on the shoreline, providing a perfect spot for relaxation while enjoying the scenic view of the water.

5.0 out of 5 average rating, 37 reviews

Waterfront Bliss Beach Cottage

LocationOutdoor spacesView

4.94 out of 5 average rating, 48 reviews

The cottage features a large wrap-around porch supported by light blue columns. Rocking chairs and a swing are positioned for seating. Lush greenery surrounds the home, and multiple windows provide natural light, contributing to a spacious and inviting exterior.

Cottage in St. Andrews

Cozy 2 bdrm cottage with sunny wrap around porch

ValueOutdoor spacesAmenities

4.93 out of 5 average rating, 61 reviews

A serene lakeside scene features a person playing with two dogs on a private white sand beach. The sun sets in the background, casting warm hues over the calm water, while a pavilion stands nearby, enhancing the tranquil setting.

Cottage in Chipley

Lakefront Home+Private Beach+Firepit+Kayaks+Pets

ValueOutdoor spacesHospitality

4.93 out of 5 average rating, 67 reviews

Cottage in Freeport

Bayview Cottage | Dog Friendly | 15 Min to Beach

ValueOutdoor spacesLong stay

Other holiday rentals with a kayak

A bright living space features a cozy sofa, armchair, and a dining table. Large windows provide expansive views of the beach and ocean. Light-colored walls and neutral decor create a relaxed ambiance, while a flat-screen TV and artwork add character to the room.

4.96 out of 5 average rating, 112 reviews

Renovated Beachfront at Pelican, Stunning Views

ValueLocationSleep quality

5.0 out of 5 average rating, 4 reviews

Gulfgate Destination 0505 2BD/2BA

LocationHospitalityFamily

5.0 out of 5 average rating, 27 reviews

Condo in Okaloosa Island

WaterScape | Resort | Renovated | Beach steps away

LocationOutdoor spacesRiver

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!

ValueOutdoor spacesBeach

The large outdoor pool is surrounded by palm trees, creating a serene environment. Lounge chairs are arranged around the pool, and glowing lights reflect off the water. The beach and ocean are visible in the background, enhancing the coastal ambiance.

4.95 out of 5 average rating, 21 reviews

Beachfront Condo | Resort Pool | Sleeps 6

LocationValueWi-Fi

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.

4.93 out of 5 average rating, 70 reviews

Pelican Beach 19th Floor 1 Br - on the Beach

ValueLocationHot tub

5.0 out of 5 average rating, 16 reviews

A spacious game room features a billiards table with a vibrant blue felt surface and a shuffleboard table nearby. Natural light fills the room through multiple windows, illuminating the white shiplap walls and dark wood accents overhead. Green pendant lights add a modern touch.

Home in Destin

Across Str+GOLF CART+Chair Srvc+priv pool+6 KINGS

LocationLaundryHospitality