Orchid Key Inn sits at the crossroads of Old Town, offering rooms with private Jacuzzi just steps from Duval Street. After dinner nearby, relax beneath tropical palms or soak in the spa’s peaceful setting. Lush gardens, cascading waterfalls, and a sun deck make this one of Key West’s most intimate and well-located escapes.
Budget value 
Romantic option 
Ambrosia Key West offers tropical charm and private hot tub in room tucked inside individually themed cottages. Spend your morning in the garden, visit Hemingway’s home, then return for a quiet swim or peaceful evening under the palms. With three pools and relaxed island décor, this stay keeps things slow and special.
Anniversary choice 
The Galleon Resort and Marina places you steps from Mallory Square with marina-facing Jacuzzi suites. After checking out Duval Street or local museums, return for cocktails at the poolside bar or quiet time on your balcony. The waterfront views and central location make this a top choice for couples staying close and connected.
Romantic option 
The Mermaid & The Alligator brings you into an art-filled Queen Anne home which includes a whirlpool in room and elegant, four-poster beds. Wake up to breakfast by the plunge pool, stroll through tropical gardens, or relax under the outdoor pavilion. Quiet, lush, and personal, this is a stay where beauty meets calm.
Romantic option 
Almond Tree Inn blends sustainability with romance, offering elegant suites that include a private spa tubs near the heart of Key West. Lounge by the palm-shaded pool or explore local art galleries just outside the gate. Quiet interiors, lush foliage, and attention to design make this a top pick for couples wanting space, style, and calm.
Romantic option 
Pier House Resort & Spa stretches into the sea near Mallory Square, offering elegant suites with an in-room hot tubs. Spend your day on the private beach or sipping a drink at the beachside bar. Evenings feel complete with a sunset from your balcony and the sound of waves just outside your door.
Honeymoon choice 
Key West Bed & Breakfast gives you a peaceful adults-only stay near Duval Street, with charming rooms that include a romantic Jacuzzi for evening relaxation. After exploring the Hemingway House or biking to Simonton Street Beach, relax in the garden or on your private balcony. The quiet location and welcoming setting offer just the right space for a simple, meaningful getaway.
Budget value Romantic option 
DoubleTree Resort by Hilton Grand Key – Key West delivers island comfort and includes a private hot tub in room, perfect after a day at the beach or roaming Duval Street. Cool off in the zero-entry pool or sip drinks at the tiki bar. The shuttle makes exploring simple, while the relaxed setting brings your focus back to each other.
Budget value Romantic option 
Courtyard Key West Waterfront offers modern convenience with suites that include a hot tub in room, just 2.9 miles from Mallory Square. Spend your afternoon by the heated pool, sip drinks at the tiki bar, or relax on the private beach. With a quiet location and practical layout, your evenings stay relaxed and comfortable.
Budget value Honeymoon choice 
The Conch House Heritage Inn places you steps from Duval Street with Victorian charm and its whirlpool suites. Walk to dinner, visit nearby museums, then return to a cottage with antique touches and a garden patio. From mimosas by the pool to the warmth of classic Key West design, everything invites connection.
Anniversary choice 
The Gardens Hotel invites you into a private oasis just off Duval Street, where upscale suites include a romantic in-room Jacuzzi and the setting feels timeless. Walk tropical paths, sip wine from the tasting bar, or listen to live jazz under the palms. With historic charm and acres of green space, this stay feels like a secret worth keeping.
Romantic option 
Hyatt Vacation Club at Beach House offers bayfront condos just minutes from Smathers Beach, complete with a Jacuzzi in room for peaceful evenings. Enjoy full kitchens, a private balcony, and a relaxed vibe after a day in the sun. With an oceanfront pool and bay-view grill, it’s the kind of stay where everything slows down to match the breeze.
Romantic option 
Hyatt Vacation Club at Windward Pointe overlooks the ocean and offers hot tub suites just minutes from the Southernmost Point. Spend the day biking through Key West or relaxing at the poolside snack shack. With breezy balconies and quiet garden paths, it’s a relaxed stay where evenings feel slow and personal.
Romantic option 
Curry Mansion Inn places you steps from Duval Street with historic charm and romantic suites that include an in-room Jacuzzi. Start your morning with breakfast on the veranda, explore local galleries, and return for live music at the cocktail hour. The Victorian setting, pool, and classic four-poster beds give your stay a timeless atmosphere.
Anniversary choice 
Beachside Resort Key West gives you access to the coast and includes a whirlpool in room, perfect after a day exploring Hemingway’s Key West. Enjoy dinner poolside, stroll the private marina, or relax in the tanning cove. Spacious kitchens and modern comforts make it easy to slow down and stay in.
Romantic option 
The Paradise Inn sits hidden in Old Town with its boutique-style Jacuzzi suites surrounded by tropical gardens. Walk tree-lined paths, relax on shaded porches, or spend a quiet hour by the fountain-fed pool. This is a quiet, floral escape where architecture, privacy, and soft light come together for something personal.
Budget value Romantic option 
Simonton Court Historic Inn and Cottages puts you a block from Duval Street in a historic setting with romantic suites that include a personal Jacuzzi. Enjoy the calm of the landscaped courtyard, take a dip in one of four pools, or relax on your private balcony. The secluded layout and timeless design make it an intimate, memorable place to stay.
Romantic option 
Ocean Key Resort & Spa offers harbor views and island-style comfort with romantic suites that include a personal Jacuzzi tub. Watch the sunset from your private balcony, then enjoy drinks by the waterfront pool. With a full spa, boutique shopping, and waterfront dining, the location puts everything within reach—without ever leaving your retreat.
Honeymoon choice 
Southernmost Beach Resort surrounds you with ocean breeze, colonial charm, and upgraded suites that include a romantic spa tub. Walk to the southernmost point, enjoy spa treatments, or relax on the private pier. With beach access, three pools, and sunrise views, this stay is made for couples looking to step away and stay close.
Honeymoon choice 
Opal Key Resort & Marina gives you ocean views and island luxury near Mallory Square, with elegant suites offering a private whirlpool. Spend the evening watching the sunset, then relax with drinks at the poolside bar. From spa time to open-air dining, every part of this resort reflects coastal elegance and easy connection.
Honeymoon choice 
Wicker Guesthouse places you in the heart of Old Town Key West, offering tropical cottages with a private jacuzzi in room. Walk to Duval Street, explore local galleries, or share breakfast under the palms. The quiet garden setting, vintage charm, and walkable location give couples a laid-back, romantic stay just steps from everything that makes Key West unforgettable.
Romantic option 
Couples can take a sunset sail, visit the Ernest Hemingway Home, or enjoy a private picnic at Fort Zachary Taylor Beach. A stroll through the Key West Butterfly Conservatory or browsing art galleries on Whitehead Street adds quiet connection. Evenings are best spent watching the sun dip below the horizon at Mallory Square.
Latitudes on Sunset Key offers oceanfront dining only accessible by boat, perfect for special evenings. Café Marquesa delivers fine dining in a cozy, candlelit setting. Hot Tin Roof combines Caribbean flavors with panoramic water views. Each provides an intimate atmosphere where couples can relax, toast to their getaway, and savor fresh coastal cuisine together.
Kayak through mangroves on a guided eco-tour, rent a tandem bike for a ride through Old Town, or snorkel together in the clear waters of Dry Tortugas National Park. Couples can also walk hand-in-hand along Smathers Beach or enjoy shaded paths at West Martello Tower’s gardens before returning to rest and recharge in private comfort.
Spring brings the Conch Republic Days with parades and island flair. Summer features quieter beaches and warm nights perfect for moonlit walks. Fall’s Fantasy Fest offers colorful, playful energy for adventurous couples. Winter sparkles with festive lights on Duval Street and harbor boat parades, all adding charm to a romantic coastal escape.
Orchid Key Inn and Almond Tree Inn provide serene, adults-only environments with stylish rooms, tropical courtyards, and poolside lounges. These intimate escapes are perfect for couples seeking privacy, personalized service, and a tranquil retreat just steps from lively Duval Street but tucked away from the crowds.
Pier House Resort & Spa and Ocean Key Resort & Spa offer romantic oceanfront suites, indulgent spa treatments, and private balconies for sunset views. These resorts blend upscale amenities with prime locations for waterfront dining and relaxing days by the sea, making them ideal for honeymoons or anniversaries.
Doubletree Resort by Hilton Hotel Grand Key and Courtyard Key West Waterfront provide spacious rooms, shuttle services, and family-friendly pools. With easy access to beaches and attractions, they offer a convenient and relaxed atmosphere for parents and children alike, making sightseeing around Key West simple and stress-free.
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