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Six-figure holiday: The most extravagant Valentine’s escapes in America

2 ultra-luxury, all-out Valentine's day escapes

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The-Preserve-Sporting-Club-Resort.
The Preserve Sporting Club & Resort

Valentine’s Day comes and goes every year, but what if you one year was the one you’d always remember? In 2026, the some couples are skipping candy hearts, chocolates, and flowers and opting for six-figure love stories that go above and beyond. This year, Ocean Key Resort & Spa in Key West, Florida and The Preserve Sporting Club & Resort are offering ultra-luxury escapes for those looking to celebrate romance on a grand scale.

With private jet arrivals and penthouse escapes, these extravagant Valentine’s Day escapes make a bold statement to impress your loved one. From the “Lovebirds of a Feather” escape to “Valentine’s Pinnacle Experience” these getaways make it easy to book a once-in-a-lifetime Valentine’s Day vacation for the special someone in your life.

Ocean Key Resort & Spa – Lovebirds of a Feather

Ocean Key Resort
Ocean Key Resort

Ocean Key Resort & Spa is setting a new standard for romance for this Valentine’s Day with a super, ultra-luxe “Lovebirds of Feather” Valentine’s Day escape. This three-night, four-day package starts at $179,000, designed for couples who want an unforgettable, once-in-a-lifetime getaway in the heart of Key West. This year’s package takes place between February 12–16 and the indulgent escape unfolds at the resort’s newly renovated oceanfront hideaway, where whimsical bird motifs, lush tropical design, and a signature blush-pink façade set the tone for an immersive celebration of love.

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Couples will stay in the Flamingo Royale Penthouse Suite as part of this luxury Valentine’s Day escape, with sweeping ocean views and enjoy a meticulously curated itinerary that includes welcome cocktails at the new Sweet Bird lobby bar, a three-hour couples’ spa immersion with tropical exfoliation and aromatherapy, and a five-course aphrodisiac dinner with literary-inspired cocktails at Hot Tin Roof. Highlights of this event include:

  • Private yacht outing featuring Dom Pérignon, Krug, and rosé caviar pairings.
  • A private seaplane journey to Dry Tortugas for snorkeling and a secluded oceanside meal, and thoughtful luxury touches such as monogrammed silk robes.
  • Fine jewelry keepsakes and daily sunrise breakfasts delivered to the balcony—creating an extraordinary Valentine’s escape that is as extravagant as it is deeply romantic. 

The Preserve Sporting Club & Resort – Preserve Valentine’s Pinnacle Experience

The Preserve Sporting Club & Resort
The Preserve Sporting Club & Resort

The Preserve Valentine’s Pinnacle Experience is an unrivaled celebration of love, crafted for couples who expect nothing less than extraordinary. Located in Richmond, Rhode Island, this year’s experience starts at $108,880 and begins with a private jet arrival to a chauffeured Bentley service. From here, the three-night escape unfolds into a luxurious getaway with landscapes of New England’s most exclusive sporting resort.

Guests retreat to a Hilltop Suite or private Townhome, where personalized touches, daily in-room breakfasts, and bespoke indulgences create a sanctuary of privacy and romance. Highlights of this Valentine’s Day event include:

  • Candlelit, chef-curated dinner inside the enchanting Hobbit House, accompanied by a private harpist or violinist.
  • Intimate moments designed exclusively for two—from a sunset carriage ride and a treetop couples massage to private wine tastings and curated adventures across the Preserve.
  • Bespoke shopping, gun fittings, and an elevated in-room gift that may include engraved crystal, fine jewelry, or a luxury timepiece. 
Emily Caldwell
Emily Caldwell
Contributor
Emily is a Features Writer at The Manual, where she specializes in food, beverage, and travel content. She focuses on weaving… Read Full Bio
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