Vacation rentals with a kayak in Jacksonville

CLUB MED•Family Paradise Retreat-Bring the Dogs

This beautiful home (2000sqft) is just a few blocks from the ocean which has easy beach access,including a play ground for children. Then a street over is the river which has boat ramp! You can also enjoy a local neighborhood restaurant just down the street with a water front view where the sunsets are mesmerizing! The home has been completely remodeled and has a gated back yard with a big pool for you and your family to enjoy. It is also a short drive to the historical down town St.Augustine.

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.

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!

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.

4BR Beach Escape • Steps to Sand • Family Friendly

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.

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.