Holiday houses in Dark Island

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Top-rated holiday rentals in Dark Island

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Guest favourite
A wooden dining table is surrounded by six rustic chairs, positioned in a warmly lit space. Natural light filters through the blinds of a large window, illuminating the wooden walls. A wooden cabinet is present in the corner, enhancing the cabin feel.
Cabin in Live Oak
4.92 out of 5 average rating, 217 reviews

Florida Country Cabin Getaway

Nestled in the heart of rural North Florida, this picturesque log cabin on 3 acres offers a tranquil retreat enveloped by majestic oaks and towering pines. Stepping inside, they find themselves embraced by the warmth of a cozy interior, where comfortable furnishings invite relaxation. However, the true allure lies where a sprawling outdoor deck beckons guests to unwind amidst the serenity of nature while enjoying their morning deink from the extensive selection of coffee, tea and hot chocolate.

Top Guest favourite
A newly built cottage is illuminated at night, showcasing a wraparound porch with multiple steps leading to the entrance. An American flag hangs proudly from the front of the building. The surrounding area is quiet, enhancing the serene atmosphere.
Cottage in Perry
4.95 out of 5 average rating, 44 reviews

Secluded cottage in Keaton Beach

Relax & unwind in this newly built secluded cottage! It is located just 1/4 mile away from an airboat/kayak ramp (Adams Beach) and 3 miles away from Keaton Beach & the public boat ramp. Enjoy the sunset from the upper deck back porch or a short 1/4 mile walk to Adams beach. Bring your boat and enjoy making memories on the water! This beautiful area is famous for some of the best redfish, trout, or red snapper fishing the gulf coast of Florida has to offer! Check out my guide book for more info!

Top Guest favourite
The lodge features a two-level design with a spacious upstairs screened porch illuminated by warm lights. A staircase connects to the lower level, where additional seating is visible, surrounded by lush greenery, creating a comfortable outdoor space.
Home in Branford
4.99 out of 5 average rating, 173 reviews

The Suwannee River Rest & Adventures

Nestled in Branford, FL, along the scenic Suwannee River in Hatch Bend, this pet friendly, three-bedroom, three-bath lodge is perfect for weekends or extended stays. Upstairs features two king bedrooms with ensuite baths, a cozy living area with a gas fireplace, and a fully equipped modern kitchen. Downstairs offers a king bedroom, full bath, kitchenette, and living space. An enclosed elevator makes transporting gear easy. Experience comfort, charm, and Suwannee River beauty at our retreat!

Guest favourite
A rustic cabin exterior is framed by surrounding trees, featuring a wooden facade and a green metal roof. A welcoming front porch with steps leads to the entrance, while a hose and water source are visible on the side of the cabin.
Cabin in Live Oak
4.8 out of 5 average rating, 296 reviews

Suwannee River Paradise

Remote cozy cabin-Two riverfront acres, 2 solo kayaks + 1 tandem for use with $300 loss and injury liability waiver Private walk 500 ft through woods path to the riverfront. The well water is sulfur and tanic, so please bring drinking water! Sleeping loft for two more guests upstairs. Springs galore in this section of the Suwannee. Diver's paradise, "Peacock Springs" network is a short drive. Springs map provided. Conditions vary with river. It is advised to check with your host a week prior.

Top Guest favourite
A well-lit wooden boardwalk extends toward the lake, flanked by trees. The scene is set during twilight, with a soft glow illuminating the path. The reflection of the evening sky and trees on the calm water enhances the tranquil ambiance of the location.
Home in Branford
4.96 out of 5 average rating, 385 reviews

Papa Joe’s Lake House

Quiet little piece of heaven on earth. Enjoy the lake, sit by a fire, enjoy the nature God has provided in our sanctuary on Pickett Lake. Boat ramp is 100 yards down the road. 4 kayaks, canoe, and paddleboard are provided, all of which can be launched from the house. Fish from the dock or explore the lake. Use the grill or take a short drive to Branford or Mayo and enjoy some of the restaurants. Come boat, fish, or swim in the lake or just enjoy the lake view. Outdoor fire pit includes wood.

Guest favourite
A modern cabin is situated directly on the Steinhatchee River, featuring large windows that provide views of the lush surroundings. A spacious balcony extends from the cabin, overlooking a floating dock, which is accessible by a ramp. Tropical vegetation enhances the natural setting.
Cabin in Steinhatchee
4.87 out of 5 average rating, 15 reviews

Snappin Turtle Cabin. Riverfront with dock.

Our cabin is located directly on the Steinhatchee River with a balcony that looks over it for you to enjoy your morning coffee and relax. You can fish off the floating dock or just sit back and watch for wildlife. The land on the other side of the river is a wildlife management area and has plenty of wildlife for you to enjoy and watch. There are 4 kayaks for adult guest use at the house to help you take full advantage of the river. PFD's are supplied and recommended.

Guest favourite
A wooden staircase leads down from a balcony to a sandy shoreline. The ocean is visible in the background, reflecting the colors of a sunset, while a wooden railing offers safety. The peaceful scene invites relaxation near the water's edge.
Home in Taylor County
5 out of 5 average rating, 9 reviews

Sunset Cottage at Keaton, gulf front

Sunset Cottage at Keaton is sure to be your favorite place to stay! The unobstructed views are always incredible, you’ll have a hard time leaving the porch or sitting under the house. In the evening after you had a fun day on the water, start up the grill, cook your catch from the day and have enjoy friends and family. Rather you are just relaxing all day to a full day on the gulf, you are going to make some of your favorite memories staying at the Cottage.

Top Guest favourite
A serene view of the upper Steinhatchee River is captured, reflecting the surrounding greenery and trees along the banks. Nature thrives with an array of plants, while a small dock is visible on one side, offering a peaceful connection to the water.
Home in Steinhatchee
5 out of 5 average rating, 68 reviews

"High On The River"

Take it easy at this unique and tranquil getaway located along the upper Steinhatchee River. Located down a dead end road in the woods. Across the river is Conservation Land so you will hear lots of birds, crickets, owls, and frogs. If you’re lucky you may even spot deer, wild boar, bobcats, otter, gators or manatee. This is a natural "Old Florida " environment complete with critters and bugs. Bug spray is recommended when outdoors in the warmer months.

Guest favourite
Apartment in Perry
4.93 out of 5 average rating, 86 reviews

Hermit Crab 4.8 miles to Keaton Beach

No children under 10 One bedroom sleeps 2 one queen bed / two guest's per night . Living room can be set up for one to two extra people charge of $15 Per night per person Two twin beds in LR This property is rural. The property is fenced in. Boat and vehicle parking. There is a charcoal grill, fish cleaning table, (Private patio with table and chairs for four. Minutes to Keaton Beach and boat ramp. We have power and Internet co

Top Guest favourite
Tiny home in Live Oak
4.96 out of 5 average rating, 388 reviews

Goat House at Cypress Oaks Farm

In addition to a TV, high speed internet and a coffee bar, we’ve recently improved our outdoor area with a paved patio! Enjoy the cool shaded area and BBQ after a day in the sun. The Goat House is tucked away on the edge of woods on the outskirts of Live Oak. Close enough to run to the store and far enough for a quiet starlit night relaxing in a hammock or enjoying a small bonfire on cool nights.

Top Guest favourite
A multi-level house elevated on stilts showcases a mix of light green siding and a gray metal roof. Large balconies extend from the front, offering expansive views. Surrounding palm trees complement the coastal setting, while steps lead gracefully from the shore.
Home in Perry
4.9 out of 5 average rating, 240 reviews

Book scalloping now 15% off! Jun 15 - Sep 7, 2026

Our 2 bedroom 1 bath house sits on high stilts directly overlooking the Gulf of Mexico. Located in undiscovered Dekle Beach, Florida. It is a retreat from everything. We are about three miles up the coast from Keaton Beach. Known for scalloping! Three open bays for your vehicles. Boat launch one block away. Beautiful sunsets, stargazing, birding, reading, fishing and scalloping during the season.

Superhost
A spacious outdoor deck is shown, featuring several seating options including a picnic table and two rocking chairs. Sunlight filters through the posts, illuminating the wood flooring. Tall trees are visible in the background, complementing the tranquil setting overlooking the serene water.
Home in Perry
4.84 out of 5 average rating, 19 reviews

Waterfront Scallop & Fish Spot! Dock + Ice + Pets

Skip the long idle times and the morning ice run. Located just 200 yards from the open Gulf, Heron House is a waterfront paradise designed for those who live for the water. Whether you’re here for the legendary scalloping or world-class fishing, our private dock and 160lb/day commercial ice machine ensure your catch stays fresh and your cooler stays full.

Popular amenities for Dark Island holiday rentals

  1. Airbnb
  2. United States
  3. Florida
  4. Taylor County
  5. Dark Island