Holiday rentals with a kayak in Jacksonville

Luxury Riverfront Retreat|Dock, Sunsets & Dolphins

💎 Spacious coastal retreat near Jax stadium, airport,Amelia, shops/dining, beaches! Excellent mid/long term rental-Mayport naval base and near all PORTS. Watch dolphins,sunsets, fish/crab, kayaks,cornhole, firepit & grill. Chef’s kitchen, coffee/tea bar & breakfast starters. Comfortable beds, large gaming console,adventures nearby boat tours, horses, history. Locally managed Superhosts LOVE hospitality, well stocked & five-star guest favorite. Book Now or inquire on corporate longer.

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.

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).

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.

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!

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

Near Amelia Island. KingBed. Pool. Pickle Ball Gym

Step into a tropical escape where a stunning floor-to-ceiling botanical mural greets you and warm terracotta tones wrap you in calm. Sleep like royalty in a plush king suite or bring the whole crew — we comfortably sleep 6 across two bedrooms with five beds. Wake up to lake views, kayak at sunrise, cool off at the resort-style pool, or challenge someone to pickleball. Everything you need is here, nothing you don't. This is the stay your group will still be talking about next year.

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 TVs, and Wi-Fi. Meet our two 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.

Eagles Nest on Lake Ponte Vedra

Eagles Nest on Lake Ponte Vedra is a unique hidden gem nestled among coastal oaks across the street from the Atlantic Ocean. You’ll have access to a true nature get away rarely seen by even most residence of NE Florida. Redfish and Trout are abundant - kayaks are available for a leisurely paddle or a fishing adventure. Sleeping arrangements - king in bedroom, double in living room, 2 fold down chairs in loft. A $400 security deposit is required to be returned if nothing damaged.

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.

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.)

Heated Pool + PlayStation 5 + Lake - Sleeps 9

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!