10 Homes to Fuel Your Island Getaway Daydreams

As temperatures dip lower and the dreariness of January stretches ahead of us, it’s hard not to think about physically fleeing to a sunnier locale. While that might not be possible right after the holidays, you can keep your tropical daydreams properly fueled until spring emerges.

Grab a mug of something warm and check out these 10 daydream-worthy island getaways. You might even find your next vacation destination!

Hilton Head, SC

3 Castlebridge Ct, Hilton Head, SC 29928
For sale: $3.099 million

Located on a corner lot, this exquisite home boasts a resort-like backyard with a pool and an outdoor entertaining area. Inside, you’ll find a cupola office, a theater room, two master suites and high-end Brazilian Cherry flooring.

See more homes for sale in Hilton Head.

Kihei, HI

4690 Makena Rd, Kihei, HI 96753
For sale: $10.8 million

Just 37 feet away from the beach, this Kihei residence offers stunning ocean views from nearly every room. Oversized sliding glass doors and a wrap-around porch on the upper level help flawlessly merge the indoor and outdoor spaces, allowing you to fully take in the panoramic island scenery.

See more Kihei homes for sale.

Friday Harbor, WA

52 Knights Ln, Friday Harbor, WA 98250
For sale: $3.95 million

Located in the San Juan islands, this breathtaking waterfront home maximizes light and space with oversized windows that soar all the way to the vaulted ceilings. While the interior of this residence has a rustic feeling, it comes with luxury amenities like a chef’s kitchen, a sauna, a pool, and a hot tub.

Check out other Friday Harbor homes.

Marco Island, FL

1002 Royal Marco Way, Marco Island, FL 34145
For sale: $9.49 million

Nestled away in the prestigious Hideaway Beach community, this beachfront beauty will stun visitors from the moment they set foot into the expansive foyer and work their way toward the floor-to-ceiling windows overlooking the Gulf of Mexico. Multiple backyard terraces and a second-story pool allow you to take in the sandy backyard views without even having to leave the home.

See more Marco Island homes.

Edgartown, MA

7 Starbuck Neck Rd, Edgartown, MA 02539
For sale: $19.5 million

This meticulously maintained and renovated 1890s home on Martha’s Vineyard is a classic beach house, complete with window bay reading nooks and a veranda. The ideally situated residence offers privacy, a sprawling backyard and unrestricted water views from three sides of the home.

See more homes for sale in Edgartown.

Hilton Head, SC

16 Grey Widgeon Rd, Hilton Head, SC 29928
For sale: $4.999 million

Located merely feet from the beach, this custom home features jaw-dropping 20-foot ceilings, an elevator and a top-level observation balcony. When you’re done enjoying the sandy South Carolina beach, rinse off in the luxurious walk-in shower in the master bath, or curl up for a nap in one of the many cozy living areas.

See more listings in Hilton Head.

Key West, FL

800 Georgia St, Key West, FL 33040
For sale: $2.2 million

This upscale Key West home combines fun pops of color, such as a coral wall in the foyer and lime green shutter doors, with more classic features like a floating mahogany staircase. The entire back wall of the home features sets of double doors that open directly into the backyard patio, almost creating the illusion that there is no wall dividing the spaces.

Check out other Key West homes for sale.

Kalaheo, HI

210 Kalaheo Ave, Kalaheo, HI 96734
For sale: $24.98 million

Nestled in Oahu, this beachfront estate offers the best of island living. The main residence is set on its own 1.5 acres of tropical gardens, and features a waterfall pool and a poolside cabana with its own kitchen. The home’s architecture blends the interior and exterior living spaces with expansive glass walls, sliding doors and terraces off nearly every room.

See more homes for sale in Kalaheo.

Galveston, TX

20727 E Sunset Bay Dr, Galveston, TX 77554
For sale: $799,000

This spacious home overlooks the Gulf Coast from its multiple front- and backyard balconies. The open floor plan and light interior accentuates the beach feel of this canal-front home, while a private backyard dock with an upper-level seating area allows you to bask in being right on the water.

See other listings in Galveston.

Shelter Island, NY

14 Margaret’s Dr, Shelter Island, NY 11964
For sale: $2.35 million

This spacious residence comes with its own 178 feet of shoreline, a deep water dock, and a spot right on a beach-like park. The backyard boasts a heated gunite pool and a screened-in porch, while the interior’s open floor plan and oversized windows allow light to flood the living spaces.

See more homes for sale on Shelter Island.

Related:


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