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TBH Land > Blog > Islands > U.S. Islands > The Ultimate Getaway: Top US Islands for Vacation Home Buyers
U.S. Islands

The Ultimate Getaway: Top US Islands for Vacation Home Buyers

TBH LAND
Last updated: January 15, 2026 1:50 pm
TBH LAND Published January 15, 2026
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The Ultimate Getaway: Top US Islands for Vacation Home Buyers

1. Nantucket, Massachusetts

Nantucket is synonymous with charm, offering stunning beaches, quaint shops, and rich history. As a sought-after destination, its real estate market reflects a blend of classic and modern homes, often featuring ocean views. Buyers can expect luxury cottages and historical whaling homes, making it ideal for both summer escapes and year-round living. The island’s culinary scene is vibrant, populated with award-winning restaurants and casual lobster shacks. With ample outdoor activities, from sailing to beachcombing, Nantucket fosters a picturesque lifestyle, perfect for family retreats or romantic getaways.

2. Maui, Hawaii

Maui boasts some of the most breathtaking scenery in the world, with lush landscapes, pristine beaches, and the famous Road to Hana. The island’s real estate is diverse, offering high-end beachfront condos and sprawling oceanfront estates. Buyers are drawn not only by the island’s natural beauty but also by its active lifestyle opportunities, including surfing, hiking, and snorkeling in the crystal-clear waters of Molokini Crater. The laid-back vibe of island life is complemented by local culture, festivals, and an array of culinary delights, making Maui a prime location for vacation homeowners.

3. The Florida Keys

Comprising over 1,700 islands, the Florida Keys cater to various buyers seeking unique properties. From lively Key West, with its vibrant nightlife and rich history, to the tranquil charm of Islamorada, each island offers distinct lifestyles. Buyers can find everything from luxurious waterfront estates to more affordable canal-side homes. The Keys are a paradise for boating enthusiasts, divers, and anglers, with world-class fishing and diving spots readily accessible. The pace of life here is relaxing, characterized by a strong sense of community, tropical climate, and an abundance of outdoor recreation activities year-round.

4. San Juan Islands, Washington

The San Juan Islands offer a tranquil escape with stunning landscapes, from rolling hills to picturesque shorelines. Buyers can choose from cozy cottages to modern waterfront homes, typically featuring expansive views of the Puget Sound and the Olympic Mountains. The islands are renowned for their outdoor activities, including whale watching, kayaking, and hiking. There’s also a burgeoning food scene that includes local seafood and artisanal products, making it a haven for food lovers. The relaxed lifestyle, coupled with the islands’ natural beauty, makes the San Juan Islands a compelling option for vacation homes.

5. Martha’s Vineyard, Massachusetts

Famous for its breathtaking vistas and quaint New England charm, Martha’s Vineyard attracts those looking for a luxurious vacation home. Properties range from opulent oceanfront estates to charming cottages that exemplify the island’s rich history. Known for its vibrant art scene and abundant outdoor activities—from sailing and fishing to exploring lush hiking trails—Martha’s Vineyard presents an ideal combination of leisure and culture. With a strong sense of community and seasonal festivals, the island offers a perfect backdrop for creating lasting memories with family and friends.

6. Hilton Head Island, South Carolina

Hilton Head Island is a premier vacation destination known for its sandy beaches and world-class golf courses. Buyers are drawn to its family-friendly atmosphere and diverse property options, from oceanfront villas to golf course homes. The island’s commitment to preserving its natural beauty ensures expansive sun-soaked beaches and lush marshlands. Outdoor enthusiasts can indulge in a plethora of activities, including biking, kayaking, and paddleboarding. Its rich cultural offerings, dining options, and activities create a vibrant community that caters to all kinds of vacationers.

7. Galveston Island, Texas

Galveston Island has witnessed a renaissance, making it an appealing spot for vacation home buyers. Sporting a rich history, the island offers Victorian-style mansions and modern condos with ocean views. Its long stretches of sandy beaches are perfect for sunbathing and water sports. Home to a lively arts community, Galveston hosts events that celebrate music, food, and cultural heritage. The island’s burgeoning food scene, featuring fresh seafood and Tex-Mex cuisine, complements its vibrant atmosphere, making it an exciting place to invest in a vacation property.

8. Key Biscayne, Florida

Key Biscayne is an upscale island community just minutes from Miami, offering a quieter alternative to its bustling neighbor. With luxury condos and oceanfront estates available, the island attracts discerning buyers seeking a mix of luxury and leisure. Residents enjoy easy access to beautiful beaches, parks, and recreational facilities, including tennis courts and golf courses. The island is also home to boutique shops and fine dining establishments that provide a taste of Miami’s vibrant culture. The relaxed lifestyle combined with proximity to Miami’s urban attractions makes Key Biscayne a fabulous choice for vacation homeowners.

9. Kodiak Island, Alaska

For those seeking a unique escape, Kodiak Island offers a blend of rugged beauty and adventure. This historically rich island showcases an array of stunning landscapes, from mountains to coastal areas, attracting buyers looking for retreats in nature. Real estate options include cozy cabins and waterfront homes with incredible views. Outdoor activities abound, including fishing, hiking, and wildlife viewing—particularly for sea otters and brown bears. Kodiak is also known for its rich Native Alaskan culture and community events. Buyers in search of a retreat far removed from the bustle of city life will find Kodiak a captivating option.

10. Block Island, Rhode Island

Block Island captivates with its serene beaches and dramatic landscapes. Its real estate market features an eclectic mix of historic homes and modern cottages, often with spectacular ocean views. The island is renowned for its eco-friendly initiatives, making it a great option for the environmentally conscious buyer. With an active outdoor lifestyle that includes biking, sailing, and beachcombing, Block Island promotes a strong sense of community through local events and festivals. The untouched beauty and charming character make it an attractive retreat for those looking to invest in a vacation property.

11. Tybee Island, Georgia

Tybee Island is a charming beach destination close to Savannah, making it a popular vacation spot with a laid-back ambiance. The real estate options range from beach bungalows to historic homes that reflect the island’s character. Importantly, Tybee is famous for its stunning beaches, inviting waters, and opportunities for dolphin watching. Dining options feature fresh seafood, and local festivals celebrate arts and culture. The friendly community and easy accessibility to Savannah create a welcoming environment for second homeowners and vacationers alike.

12. Jekyll Island, Georgia

Jekyll Island offers a unique historical background coupled with unspoiled natural beauty. The island’s real estate includes quaint cottages and luxurious oceanfront homes, perfect for nature lovers and history buffs. With miles of beaches and beautiful landscapes, Jekyll offers numerous recreational activities such as biking, kayaking, and golfing. The island is also engaged in conservation and education, providing a perfect blend of relaxation and exploration for vacation homeowners. The allure of history intertwined with natural beauty makes Jekyll Island an outstanding escape.

13. Orcas Island, Washington

Orcas Island, the largest of the San Juan Islands, is renowned for its stunning scenery, artistic community, and vibrant outdoor life. Buyers here can find beautiful waterfront homes and secluded properties tucked away in lush forests. The island promotes a myriad of recreational activities—from sailing to hiking the breathtaking Moran State Park, known for its panoramic views. Orcas Island’s thriving arts scene, along with local farmers’ markets and culinary festivals, provides a rich cultural landscape for homeowners. Ideal for those seeking a combination of adventure and serenity, Orcas is a hidden gem among US islands.

14. Fire Island, New York

Fire Island combines natural beauty with an eclectic community atmosphere that attracts vacation home buyers. The island features charming beach cottages and modern homes, often only accessible by foot or bicycle, which contributes to its relaxed ambiance. With gorgeous beaches and picturesque sunsets, Fire Island is a haven for relaxation and outdoor fun. The island also boasts an active social scene with numerous events throughout the summer. Life on Fire Island is all about embracing the outdoors and enjoying the local culture, perfect for weekend escapes or extended summer stays.

15. Shelter Island, New York

Nestled between the North and South Forks of Long Island, Shelter Island offers a peaceful and upscale retreat. Known for its lush landscapes and historic homes, the real estate market features a range of options, catering to different tastes and budgets. The island is car-free, promoting a leisurely lifestyle rich in outdoor activities like boating, biking, and fishing. The charm of the local dining scene, coupled with a strong sense of community and seasonal events, makes Shelter Island an appealing choice for vacation homeowners looking for a serene yet vibrant atmosphere.

Each of these islands boasts unique attributes and environments, catering to diverse preferences for vacation homes. From the cultural richness of Nantucket to the tropical allure of Maui, buyers are sure to find their perfect getaway in one of these stunning US islands.

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