Vacation rentals with a kayak in Florida

Red Bird Cottage and Farm: Equestrian lake cottage

Step back into “Old Florida” charm at this updated 1968 lake cottage, on a 7-acre equestrian farm. Secluded from main roads yet just minutes from downtown Mount Dora and Eustis, this peaceful retreat offers the perfect blend of rustic serenity and comfort. Located on a lake that offers direct water access. Campfires are welcomed, and the tranquil setting is made even more magical by the sight of horses. Inside, you'll find cozy touches and comfortable furnishings, including pillow-top mattresses

Value · Location · Decor

LUX Villa w/ Private Salt Water Pool, Lanai, Canal

Are you looking to swim, relax outdoors, fish and take in beautiful sunsets on a wide gulf access canal? If so you will fall in love with this stunning newly constructed custom built home! The 2750 square foot home is bright & airy with two main bedroom on-suites & a separate family wing! The gourmet kitchen, dining room & great room open via large sliders to the lanai & pool w/ views of the canal in much desired SW Cape! Beach inspired villa! Large captains walk & Tiki! Check out our reviews!

Value · Location · Condition

New Waterfront Bungalow Estate + Tropical Vibes

"The River Oak Bungalow" is a brand new 4BR/2.5BA exotic, lush, private estate nestled amongst winding oaks & palms directly on the Indian River Lagoon. Located in the Downtown Eau Gallie Arts District, only a short drive to the Beaches, FIT, USSSA, & MLB Airport. Bring your boat & enjoy a private 100' dock & riverfront sandbar recreation area, huge outdoor deck, spacious backyard, fire pit, tree climbs, paddle boards, and kayaks. Perfect for Family Gatherings, Celebrations, or a staycation!

Value · Outdoor spaces · Parking

Serenity Escape lake house private beach

Serenity Escape at Hawthorne Lake Escape the hustle and unwind at Serenity Escape, a peaceful lakeside retreat nestled in the heart of Hawthorne, Florida. Whether you’re planning a family vacation, fishing trip, romantic getaway, or relaxing weekend with friends, this beautifully appointed home offers the perfect blend of comfort, privacy, and natural beauty .Wake up to breathtaking lake views, sip your morning coffee from the screened porch, and spend your days enjoying on our private beach🏖️

Outdoor spaces · Value · Beach

Getaway on the Waterway- Dock+Kayaks+SUP board

Welcome to your peaceful Getaway on the Water. Whether you or your group are visiting the Villages, or just need a peaceful getaway to recharge, this is the place!There's something for everyone! Paddleboard or Kayak (provided) the beautiful canal to either lake. Enjoy your morning coffee or evening cocktail in nature on the dock. Bring your boat/ jet ski or rent one from Eaton's Beach Aquatic sports, they also offer sunset cruises and water taxi to Eaton's Beach restaurant right from our dock!

Outdoor spaces · Value · Decor

Tropic Like It's Hot! Heated Pool/Arcade/USSSA

100% of our profits provide homes for homeless vets! Congrats! You just found the ULTIMATE vacation home! Heated pool? Check. Arcade room? Yup. Fire pit for dramatic storytelling? Absolutely. Bring the fam, the friends, even your judgy aunt—there’s room! Fast WiFi for "remote work" (aka pretending to work while watching our movie channels!), Smart TVs, Beach toys, and a fenced yard for your dog (or kids, no judgment). Oh, and a Tesla charger! Book now...so your kids don't think you're lame!

Value · Location · Air conditioning

Surfside House

This special vacation home is close to everything, making it easy to plan your visit. Ideal location across from the beach, just minutes to drive or bike into historic downtown St. Augustine. The 1950's coastal bungalow is set on Vilano Beach's historical Street. The home has been completely remodeled, plenty of parking and is pet friendly. Surfside's pet friendly beach access/parking and North Shore Community Park is 1 block away with tennis/ pickle ball courts, playground and dog park.

Value · Location · Grill

Modern Cottage on Private Spring Fed Lake

Nestled on a gorgeous spring-fed private lake in the woods, our charming cottage is your ideal retreat. Whether you're dreaming of peace and quiet, a romantic getaway, or fun with your kids, this is the place to be! Kayak around the serene lake as you witness breathtaking sunsets, take a dip in the cool water or simply unwind amidst the beautiful surroundings. As night falls, gather around a fire and gaze up at the many stars lighting the sky. Come and create many cherished memories ☀️

Value · Location · Amenities

2 Kings, Pool, Gulf Canal, Game Room and Kayaks

Unwind Cape Coral welcomes you to sunny southwest Florida, close to magnificent beaches, fishing, shelling, Minnesota Twins Spring Training & much more. Come enjoy this new construction home with heated pool, Kayaks, heated and cooled game room (PlayStation 5), gulf access - salt water canal, 4k oled tv's & many more refreshing amenities. You will love this clean & bright home with lovely décor. Located in the highly sought after Pelican neighborhood of Southwest Cape Coral! EV Charging!

Outdoor spaces · Location · Hospitality

Lake Denton Diver's Paradise Swim-Dive-Boating

Experience Lake Denton, a crystal clear 50’ deep spring fed diver’s lake where the water is so clear you can watch fish swim beneath you. There is a reason people like Tiger Woods, Whistlin Diesel, Mel Tillis and others have swam here. This family friendly getaway offers a private waterfront setting with unforgettable sunsets from the boathouse. Enjoy swimming, fishing, grilling, water toys and in water volleyball. Kayaks provided, Public boat ramp access. Voted Nicest Lake in Florida

Location · Value · Bathroom

Waterfront home heated pool+jacuzzi+game room+golf

Bring your boat or rent nearby! Minutes to prime SCALLOPING waters. Enjoy a HEATED pool, jacuzzi, putting green, ping pong table, massage chair, arcade basketball, paddle boards, kayaks, bicycles, four jetski docks & boat dock. FISH CLEANING STATION/deep canal. Open floor plan with 4 BR, 3 BA and comfortably sleeps 16. Near boat ramp w/ access to Weeki Wachee springs. Great home for fishing, scallops, dolphin &manatee watching, minutes to bike and hiking trails! Pet friendly!

Location · Outdoor spaces · Check-in

Fisherman’s Oceanfront Dream Home w/Dock & Kayaks

35% discount for monthly stays, 15% for weekly. Million$$ views of Oyster Bay & Gulf from every room. Only 40 minutes to the Florida Capital, FSU, & the Tallahassee International Airport. Private floating dock & trailer parking. Screened porch & 2 walkout decks. Views from any room are breathtaking! Enjoy the hammock under the house. Kayaks, fish cleaning station With the well appointed kitchen, gas grill & laundry you will have everything you need. (boat lift not available)

Value · Outdoor spaces · Pets