Holiday rentals with a kayak in Jacksonville

4.91 out of 5 average rating, 307 reviews

A vibrant sunset casts a golden hue across the calm water, with silhouettes of docks and a distant boat in view. The sky is filled with layered clouds, creating a serene atmosphere that invites relaxation and reflection.

Home in Panama Park

Serenity and Amazing Views - Home on River w/ Pool

Beautiful House: Quiet with all amenities on deep water with pool. 12 minutes from Jax Airport, 5 min from Zoo and 10 min from Cruise Ports. Jax Beaches are just a short beautiful drive. Downtown, Stadium, Arena etc. 10 min Lounge on the deck or sit pool side while watching the sunrise/ sunset. Bring your kayaks and paddle across the river to the zoo, or find sharks teeth on the river islands. Fish off the dock and catch some of Florida's best: Reds, Trout, Flounder, Snapper, Blue Crabs.

Home in Green Cove Springs

An open living area features a stone fireplace as a focal point, surrounded by light-colored walls and wooden beams on the ceiling. Comfortable seating is arranged in front of the fireplace, with a television mounted nearby. The kitchen and dining area are visible in the background.

4.94 out of 5 average rating, 50 reviews

Arthurs Lake House

Leave your worries behind & escape to our spacious, serene getaway. Relax by the pool overlooking the lake starting each day with coffee & breathtaking views. Enjoy a day filled with swimming, paddling, boating, yard games & quality family time. As the sun sets, gather around the fire pit on the water for a mesmerizing experience. With cozy accommodations for 2 - 12 guests, this home offers an amazing entertainment space with fine finishes & a lake view, perfect for creating lasting memories.

4.95 out of 5 average rating, 61 reviews

A serene view of the riverfront at sunset is captured, showcasing vibrant colors across the sky. Silhouetted palm trees frame the scene, while a sparkling pool reflects the fading light. Lounge chairs are positioned nearby, inviting relaxation outdoors.

Home in Fleming Island

Sunset River Retreat

Escape to this stunning 3-bedroom, family-friendly oasis nestled along Doctors Lake riverfront. With a sparkling pool and breathtaking sunset views every evening, this is the ultimate haven for relaxation and fun. Home has a pool, firepit, outdoor pool table, and direct access to the river, ideal for fishing or kayaking. 30 min to downtown Jacksonville, 10 min from NAS Jax Naval Base. 10 minutes to boat ramp. 2 story house, bedrooms on 2nd floor Inquire for Events ($850 Event Fee, Max 50 ppl).

Camper van/Motorhome in Jacksonville

A large swimming pool is bordered by a stone patio, featuring several loungers and umbrellas. Lush palm trees surround the area, providing a tropical feel. In the background, the river can be seen beneath a partly cloudy sky.

4.97 out of 5 average rating, 258 reviews

Couples clothing optional escape hot tub deck

You'll love this unique and romantic escape. Designed to create an intimate setting to enhance your time together. The RV is quite large and fully equipped . Master bedroom features a cashmere topped California king bed. The property has so many amenities starting with a very large pool, lighted at night. A dock on the river to enjoy the views. Access to kayaks on premises. There’s a private clothing optional area/deck with a massage table , hot tub and loungers. We recently added a fire pit.

Apartment in Nassau County

A sunlit living area features a spacious leather sectional sofa arranged around a wooden coffee table. Art pieces adorn the walls, and a large television is mounted opposite the seating. Windows provide views of the exterior, with light curtains framing the space.

4.95 out of 5 average rating, 131 reviews

Oceanfront with Included Golf Cart & Kayak

This fully renovated condo is in The Sandcastles complex within Amelia Island Plantation. It has 1 bedroom, 1 bath, a flex room that can be used as an office or a sleeping space with a king trundle bed. Single kayaks & gas golf cart are included to explore Drummond Park, Walker's Landing, Nature Center, mini golf, multiple shops and restaurants all within Amelia Island Plantation. The location is great, views are incredible and is a very comfortable space for couples, and small families!

4.93 out of 5 average rating, 15 reviews

A spacious living area features a stone fireplace beneath a mounted TV. Comfortable seating is provided by a light-colored sofa and a green loveseat. Natural light streams in from two windows, enhancing the neutral-colored walls and wooden flooring. A ceiling fan offers a cooling element to the space.

Home in Jacksonville

New! Lakefront Home—Near Mayo & JAX Hotspots!

Welcome to this peaceful lake-house retreat with a first-floor main suite for ultimate convenience! Located in a quiet neighborhood, yet just minutes from Jacksonville’s beaches, Mayo Clinic, St. Johns Town Center, and major attractions like TIAA Bank Field, JAX Airport, JAXEX, the Zoo and +10 Museums! Enjoy waterfront views, a grill-ready backyard, a private workout zone, smart TVs in every room, fast Wi-Fi, seamless self check-in, and a dedicated workspace—perfect for business or leisure.

4.88 out of 5 average rating, 43 reviews

Townhouse in Beaches

4BR Beach Escape • Steps from the Sand

Welcome to your ideal beach getaway! This updated two-story home is perfect for families or groups. Just four blocks from the beach, it’s easy to enjoy sun, sand, and surf any time of day. Back at the house, the open-concept kitchen and living area offer plenty of seating for meals, or just relaxing together. Step outside and enjoy your favorite channels through outdoor Bluetooth speakers, or spend the afternoon playing on the mini golf course or at the garden after a fun day by the ocean.

The outdoor area features a private saltwater pool with a custom spa, surrounded by lush tropical landscaping. A spacious cabana is included, with comfortable seating beneath flowing white drapes. A shaded umbrella is positioned beside the pool, enhancing the relaxation space.

4.99 out of 5 average rating, 141 reviews

2023 Lux Home 4bd/3.5ba + SaltPool + HotTub + Walk2Beach

* Built in 2023- luxe coastal furnishings & linens * Featured in 2024 Good Housekeeping Mag🌟 * 2 King Suites (1 on each floor) | 2 Queen Bedrooms | 3.5 Baths * Private Saltwater Pool & Spa/Hot Tub * Poolside Cabana | Outdoor Kitchen | Front Porch * Bikes, Beach Toys, Beach Chairs * Lush Tropical Landscaping * 0.2 miles - gorgeous quiet beach * 5.5 miles- historic downtown St Augustine- The oldest city in the United States! * 0.2 miles - Cap's Restaurant for sunset dinner on the water

Guest suite in Jacksonville

A spacious bedroom features a large bed with a neutral-colored spread and an array of patterned throw pillows. Light filters in through two large windows, with a view of greenery outside. A simple nightstand stands beside the bed, enhancing the room's tranquil aesthetic.

4.9 out of 5 average rating, 59 reviews

The Waddle Inn

Peaceful modern farmhouse 2-bed, 1-bath private 2nd-floor suite on our 2-acre creekfront mini farm. Built in 2023, it offers high-quality linens, smart TV, and reliable Wi-Fi. Meet our rescue draft horses, friendly chickens and curious turkey; guests are welcome to help feed treats. Enjoy pool, firepit and on-site kayak rentals on the creek to the St. Johns River. 30–35 minutes to beaches, NAS JAX, TPC Sawgrass and historic St. Augustine. Perfect for couples, families and remote work.

5 out of 5 average rating, 27 reviews

The charming craftsman-style exterior features a welcoming porch with light fixtures and a red front door. Lush greenery and flowering plants enhance the front yard's natural beauty, while a paved pathway leads up to the entrance, contributing to the inviting atmosphere of the home.

Home in Riverside

Willowbranch Bungalow

Charming 1920s craftsman directly across from Willowbranch Park in the heart of Riverside/Avondale. Two queen bedrooms plus office w/available air mattress. Cozy living room w/brick fireplace, built-ins, and Samsung Frame TV. Large well-equipped kitchen. Dining room w/original artwork, and vintage record collection. Beautiful Southern front porch and backyard complete w/ Solo Stove, grill, string lights, and raised gardens. Steps to King Street, Five Points, and Avondale.

Home in Green Cove Springs

A spacious outdoor deck features comfortable seating arrangements with plush cushions and a dining table. Lush greenery surrounds the area, with views of Lake Asbury in the background. Strands of lights hang above, creating a relaxed atmosphere perfect for enjoying the scenery.

4.9 out of 5 average rating, 49 reviews

Lakeside, Water View, Kayak, BBQ Grill, Fire Pit

Save my home, click the <3 in the upper corner! NO cleaning fee! No surprise fees! >Lakeside Wonderland - Lake Asbury >Pet friendly with fee and restrictions >2 miles from Old Ferry Boat Ramp >Backyard + patio with stunning lake views >Minutes from St. Johns River >Sleeps 6 >Kayaks + SUP with waiver >Drip Coffee Maker + Nespresso >Wood burning fire pit >Propane BBQ >Washer + Dryer >Nearby restaurants and shopping >3 days of supplies (TP, trash bags, pods, etc.)

4.94 out of 5 average rating, 72 reviews

A sparkling heated pool is surrounded by a spacious patio featuring lounge chairs and colorful inflatable toys. Lush trees provide shade in the background, while play equipment offers options for children in the private yard. A sense of relaxation and enjoyment is established.

Home in San Jose

Heated Pool - Sleeps 9 - Lake + Kayak + Games

Make some memories at this unique and family-friendly place. Enjoy the history of San Jose Lake in this charming fully renovated home. One of the few houses inside the city limits with a pool on a lake. Enjoy lush ameneties and a tranquil backyard with something for all ages to enjoy. Pool is heated for year round use. High speed Wifi and a 75" Big Screen make staying in a relaxing time. 15 minutes to daily's place which hosts major concerts every week!

Popular amenities for kayak rentals in Jacksonville

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.86 out of 5 average rating, 22 reviews

A living room space is displayed, featuring a light-toned sofa complemented by decorative cushions. A dark blue couch is positioned opposite, with a glass coffee table in the center. A neutral rug anchors the area, while natural light fills the room from nearby openings.

Home in Oceanway

Family Retreat by the Pond

Home in Ponte Vedra Beach

A bright living area is filled with natural light from large windows offering ocean views. A light-colored sectional sofa is complemented by assorted decorative pillows. A round coffee table, adorned with greenery, is placed in the center, enhancing the inviting space.

5 out of 5 average rating, 7 reviews

Freshly Renovated Oceanfront Gem near St Augustine

A light-filled living area features a comfortable grey sofa paired with a lounge seat, both positioned near an expansive window. A unique wooden coffee table rests on a patterned area rug, enhancing the inviting space with neutral tones and soft textures.

Home in Jacksonville

4.52 out of 5 average rating, 44 reviews

Coastal Island Getaway

5 out of 5 average rating, 18 reviews

A wooden balcony offers a serene view of the water and surrounding wetlands. Two wicker chairs are positioned beside a small table, with a guitar resting against one chair. A notebook is placed on the table, inviting quiet reflection.

Home in St. Johns County

Eagles Nest on Lake Ponte Vedra

Home in Springfield

4 out of 5 average rating, 6 reviews

Lg 3 bdrm near chic downtown-TIAA stadium

A well-maintained single-level home features a welcoming yellow exterior and a charming front entryway. Lush greenery and neatly trimmed hedges surround the house, while a driveway leads to a spacious garage. Tall trees provide shade, enhancing the outdoor appeal of the property.

Home in Fernandina Beach

4937 Windward Place

5 out of 5 average rating, 33 reviews

5BR, Pool,HotTub, Putput, Walk to Beach,Game RM!

The outdoor area features a pool with a stone deck, overlooking tranquil water and trees. A hot tub is situated near the edge, offering picturesque views of the landscape at sunset, with pastel colors illuminating the sky.

4.75 out of 5 average rating, 16 reviews

Oyster Cut

Other holiday rentals with a kayak

4.92 out of 5 average rating, 24 reviews

An open living area features a light blue sofa and cozy seating arrangements. Large windows offer expansive ocean views, while decorative ceiling beams enhance the airy ambiance. A wooden coffee table and stylish accents provide functional elements, with a glimpse of the well-equipped kitchen in the background.

Flat in Fernandina Beach

Sunrise Heaven at Shipwatch Villas in Amelia

Superhost

Two wooden chairs are positioned on a deck overlooking a calm water body, surrounded by greenery. A small table holds a bottle of red wine and two glasses, accompanied by a plate of grapes. A textured blanket drapes over one chair, inviting relaxation.

Home in Green Cove Springs

4.89 out of 5 average rating, 35 reviews

Governors creek Waterfront, King Bed w/Water View

The outdoor area features a circular pool surrounded by tropical greenery. A red lounge chair is positioned nearby, while a wooden deck with seating can be seen in the background. Sunlight filters through the trees, creating a serene atmosphere.

Private room in Jacksonville

4.71 out of 5 average rating, 14 reviews

The Mandarin Hideaway Poolside

Apartment in Amelia island

A comfortable living room is furnished with a neutral-toned sofa and armchairs. A round coffee table sits in the center, complemented by a large TV mounted on the wall. Natural light enters through the glass doors leading to a balcony, adorned with greenery outside.

4.9 out of 5 average rating, 10 reviews

AIP Resort, Spacious,Ultimate Comfort,Privacy

A private backyard features a sparkling blue pool surrounded by a tiled deck. Lounge chairs are positioned on one side, while vibrant red chairs sit nearby. Sunlight filters through the trees, creating a serene atmosphere in the outdoor space.

4.93 out of 5 average rating, 76 reviews

Beach House, Pool, Golf Cart, Game Room, BBQ,

Apartment in Fernandina Beach

A spacious living area features large windows offering unobstructed ocean views. Comfortable seating includes a blue sofa with decorative pillows and two accent chairs, situated on a soft area rug. Natural light fills the space, complemented by a glass coffee table and tasteful lighting.

4.92 out of 5 average rating, 12 reviews

Sandy Shoreline with insane views of the beaches