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TBH Land > Blog > Islands > U.S. Islands > Exploring the Best Island Vacation Homes in the US
Exploring the Best Island Vacation Homes in the US
U.S. Islands

Exploring the Best Island Vacation Homes in the US

TBH LAND
Last updated: October 25, 2025 8:38 pm
TBH LAND Published October 25, 2025
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Exploring the Best Island Vacation Homes in the US

1. Key West, Florida

Key West is renowned for its vibrant sunsets, lush palm trees, and eclectic culture. This Southernmost point of the continental U.S. boasts charming vacation homes, ideal for a sun-soaked escape. Couples often choose enchanting cottages adorned with Victorian-style decor, allowing for a romantic ambiance amidst the backdrop of turquoise waters.

Contents
Exploring the Best Island Vacation Homes in the US1. Key West, Florida2. Maui, Hawaii3. San Juan, Puerto Rico4. Hilton Head Island, South Carolina5. Nantucket, Massachusetts6. Galveston, Texas7. The Florida Keys8. Ocracoke Island, North Carolina9. Block Island, Rhode Island10. Cannon Beach, Oregon11. St. John, U.S. Virgin Islands12. Tybee Island, Georgia13. Vinalhaven, Maine14. Sausalito, California15. South Padre Island, Texas
  • Property Example: Historic Duval Street Bungalow
    Nestled on the lively Duval Street, this bungalow features airy rooms, a private courtyard, and proximity to local eateries. Perfect for nightlife enthusiasts, it grants easy access to bars and live music venues.

  • Amenities: Private pool, outdoor dining, bicycle rental service, and proximity to the beach.

2. Maui, Hawaii

Maui is an island paradise offering diverse landscapes, from volcanic mountains to pristine beaches. Vacation homes range from luxurious beachfront villas to cozy mountain retreats, catering to all tastes and budgets.

  • Property Example: Oceanfront Luxury Villa in Kaanapali
    This villa showcases stunning ocean views, infinity pools, and direct beach access. Ideal for families, it includes a fully equipped kitchen, spacious patios, and direct access to snorkeling sites.

  • Amenities: Chef service, private pool, outdoor showers, and nearby golf courses.

3. San Juan, Puerto Rico

With its vibrant culture, rich history, and beautiful beaches, San Juan is a fantastic destination for island enthusiasts. Colonial-style architecture meets modern amenities in the vacation homes available here, making it a unique place to stay.

  • Property Example: Historic San Juan Colonial Home
    This villa merges old-world charm with modern comforts, featuring a lovely courtyard and a rooftop terrace with city views. Positioned in Old San Juan, guests can explore nearby cultural landmarks.

  • Amenities: Wi-Fi, kitchen, walking distance to restaurants, and beach access.

4. Hilton Head Island, South Carolina

Known for its stunning beaches and golf courses, Hilton Head Island is a go-to spots for family vacations. Rentals here offer convenience and comfort, ideal for vacationing groups or families.

  • Property Example: Sea Pines Resort House
    Located within a gated community, this home boasts private beach access, a large deck, and proximity to biking trails. Perfect for those who enjoy outdoor activities.

  • Amenities: BBQ grill, bicycles included, easy access to tennis courts, and on-site dining options.

5. Nantucket, Massachusetts

Nantucket, with its picturesque landscapes and charming cobblestone streets, offers elegant vacation homes perfect for retreating from the hustle and bustle.

  • Property Example: Whaling Captain’s Antique Home
    This historically significant home combines classic architecture with modern luxury. It features spacious living areas and expansive grounds, ideal for larger families or gatherings.

  • Amenities: Private garden, fire pit, full gourmet kitchen, and walking distance to main street.

6. Galveston, Texas

Galveston Island is noted for its rich history and beautiful beachfront properties. Vacation homes here often blend modern amenities with southern charm, making it an attractive destination for families.

  • Property Example: Beachfront Condo on the Seawall
    This contemporary condo offers stunning ocean views and is just steps from the beach. It’s great for water sports enthusiasts and those looking to experience the city’s vibrant nightlife.

  • Amenities: Pool access, nearby shopping, and full kitchen with outdoor dining options.

7. The Florida Keys

The Florida Keys encompass several small islands, each offering unique vacation experiences. Homes here often feature a tropical vibe, bright colors, and open layouts that integrate outdoor living.

  • Property Example: Key Largo Waterside Villa
    This waterfront home is perfect for fishing enthusiasts, with abundant docks and water access. Renovated interiors and sunlit spaces make for a carefree vacation.

  • Amenities: Kayaks available, outdoor grilling area, and proximity to marine parks.

8. Ocracoke Island, North Carolina

Part of the Outer Banks, Ocracoke Island is known for its remote feel, scenic beauty, and rich maritime history. Vacation homes range from rustic cabins to elegant beach houses.

  • Property Example: Cozy Beachfront Cottage
    This charming cottage boasts simple, rustic decor, large decks, and spectacular ocean views. Ideal for tranquil getaways, it’s close to nature trails and the famous Ocracoke Lighthouse.

  • Amenities: Outdoor shower, hammock area, and pets allowed.

9. Block Island, Rhode Island

Block Island is an unspoiled paradise, famous for its dramatic cliffs, lush greenery, and welcoming community. Homes on the island offer a blend of modern design and coastal charm.

  • Property Example: Coastal Retreat near the North Lighthouse
    This spacious retreat features large windows overlooking expansive ocean views and allows families to unwind amid serene surroundings.

  • Amenities: Fireplaces, gourmet kitchen, proximity to hiking trails, and cycling paths.

10. Cannon Beach, Oregon

Cannon Beach is celebrated for its iconic Haystack Rock and stunning coastal scenery. Beach homes reflect the character of the Pacific Northwest, providing a cozy escape from city life.

  • Property Example: Rustic Oceanfront Cabin
    This cabin blends rustic charm with modern amenities, featuring an open-plan kitchen and living area. Ideal for families looking to explore coastal Oregon.

  • Amenities: Pet-friendly, direct beach access, and large outdoor decks for entertaining.

11. St. John, U.S. Virgin Islands

St. John is a hidden gem in the Virgin Islands, famous for its lush national parks and hidden beaches. Vacation homes here often offer stunning vistas, privacy, and luxurious amenities.

  • Property Example: Cliffside Villa with Ocean Views
    This lavish villa features a private infinity pool and spacious terraces. A perfect sanctuary for relaxation and exploration of the local flora and fauna.

  • Amenities: Chef service available, private beach access, and outdoor dining.

12. Tybee Island, Georgia

Tybee Island combines southern charm with beautiful beaches and a relaxed atmosphere. The homes here often feature historic architecture and proximity to the local fishing waters.

  • Property Example: Vintage Beach House
    This cottage-style home emphasizes comfort and simplicity, ideal for families looking for a beach getaway. Enjoy vintage decor while being steps from the shore.

  • Amenities: Shared pool access, nearby bike rentals, and complimentary beach gear.

13. Vinalhaven, Maine

For a unique off-the-beaten-path experience, Vinalhaven offers stunning coastal views and rustic cabins. It’s perfect for visitors seeking tranquility and the charms of local fishing culture.

  • Property Example: Maine Island Cabin
    A cozy cabin with handcrafted elements, it offers a retreat into nature while providing stunning waterfront views.

  • Amenities: Fire pit, extreme privacy, and hiking trails nearby.

14. Sausalito, California

Sausalito is known for its stunning views of the San Francisco skyline, making it a popular romantic getaway. Vacation homes here provide both charm and convenience.

  • Property Example: Bay View Modern Home
    Showcasing sleek design and luxury, this home boasts floor-to-ceiling windows for an unobstructed view of the bay.

  • Amenities: Hot tub, close to dining hotspots, and paths for kayaking.

15. South Padre Island, Texas

Famous for its warm Gulf waters, South Padre Island is ideal for water enthusiasts. Vacation homes range from beach cottage bungalows to luxury condos.

  • Property Example: Beachfront Luxury Condo
    This sparkling condo offers access to white sandy beaches and stunning ocean views from the balcony.

  • Amenities: Rooftop pool, modern kitchen, and pet-friendly.

These island vacation homes offer unparalleled experiences for every type of traveler. Whether you seek adventure, relaxation, or cultural enrichment, these destinations hold the key to unforgettable getaways in the United States.

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