Key West Romantic Resorts & Inns in the Florida Keys

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By: Greg Mattson, ERV Editor - Updated: Mar 9, 2019   

For a little taste of Caribbean weather and laid-back attitude in America, the destination is Key West, Florida. Just 3 hrs south of Miami on US 1 Overseas Hwy, Key West makes you feel like you are really on a romantic tropical holiday.

The geographic make-up this southern tip of the Florida Keys means that many of the Key West's most romantic resorts are not sprawling mega all-inclusives, but instead are rather smaller boutique-like inns and hotels with plenty of color and character.

We recently spent a very relaxing weekend here, and would love to show you some great spots for your Key West romantic getaway or vacation... 

Featured Resort: Southernmost Hotel

Room at Southernmost Hotel, Key West FL
  • Southernmost Beach Resort - we spent 2 nights at one of Key West's most romantic resorts, located at the quiet end of famous Duval Street in Old Town Key West, and just loved it. The 118 guest rooms have recently undergone a complete renovation, and the adult-only tranquility pool has also been upgraded. There’s a second pool as well with a great pool bar, and if that’s not enough, guests also have use of the ocean-side pool, tanning beach and private pier at the sister-property across the lane called Southernmost on the Beach. Great restaurants, galleries and all that makes Key West famous are a short walk away, including Key Lime pie! 2019 ERV Rating* for Key West Romantic Resorts: 90% - Excellent. (1319 Duval St, Key West FL  888-449-0633)
Pool at Southernmost Hotel, Key West FL

More Key West Romantic Resorts:

Orchid Key Inn

Orchid Key Inn, Key West FL
  • Orchid Key Inn - an award-winning romantic place to stay close to the heart of Key West. With only 24 rooms and suites, this cozy inn assures your privacy, yet keeps you just steps away from all the things that make Key West famous. The complimentary breakfast and happy hour are nice perks, as are the free WiFi and in-room fridge and microwave, coffee maker and turn down service. Soak up the sun at the pool or rent bikes and ride around town. Spend the day at the beach and return for sunset drinks and snacks by the softly-lit pool. Romantic Room Tip: Request a poolside room and away from the street. 2019 ERV Rating* for Key West Romantic Resorts: 98% - Excellent. (1004 Duval St, Key West FL  800-845-8384)

Santa Maria Suites Resort

Santa Maria Suites Hotel, Key West FL
  • Santa Maria Suites Resort - this charming inn is one block from the ocean and famous Duval Street. It’s a beautifully-restored hotel, where historical significance meets stylish elegance. All suites have a private balcony or patio and are designed around a private garden with two heated pools and a relaxing tropical landscape. Grab a smoothie or some fresh fruit poolside. However, free parking is provided, as is a daily Happy Hour with complimentary glass of wine. Little extras like complimentary muffins, chocolates and ice cream, and an on-site Japanese restaurant all make the Santa Maria Suites ideal for your romantic Key West vacation. Tip: For a special romantic surprise, ask about the Romance Escape Package. This includes a rose petal turndown service, bottle of champagne and a couple’s in-room massage. 2019 ERV Rating* for Key West Romantic Resorts: 96% - Excellent. (1401 Simonton St, Key West FL  305-296-5678)

Casa Marina

Casa Marina Resort, Key West FL
  • Casa Marina -  a real landmark in old Key West, and the largest resort in the Florida Keys. There are a variety of rooms and suites to choose from, most with terraces or lanais, and many with ocean views. Enjoy the sunset from your balcony or swing in a hammock to wind down after a day of fun. A Romance package can be arranged in advance which includes sparkling wine on arrival and breakfast buffet daily. Tip: Ask about the sunset sailboat cruise around Key West. Or get a couple’s Ocean Breeze Massage. 2019 ERV Rating* for Key West Romantic Resorts: 70% - Good. (1500 Reynolds St, Key West FL  305-296-3535)

Almond Tree Inn

  • Almond Tree Inn - one of the highest rated of all Key West romantic resorts, this charming 22-suite inn is just a short walk from all the things you want to see in Key West. A continental breakfast, nightly turn-down service with chocolates, wine or beverage and snacks at happy hour, plus WiFi in each room are among the complimentary extras. There’s a well-maintained heated pool and spa, waterfall, koi pond, and “Hemingway inspired” décor. 2019 ERV Rating* for Key West Romantic Resorts: 97% - Excellent. (512 Truman Ave, Key West FL  800-311-4292)

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Ocean Key Resort & Spa

  • Ocean Key Resort and Spa - check into this romantic Key West hotel and you'll discover an expansive paradise with plenty of things to do. We suggest the very romantic Deluxe Oceanfront guest rooms, which have in-room Whirlpool tubs, private ocean-view balconies, mini-bar and cozy robes. Try some of the activities available at the resort: sunset sailing, fishing, a guided kayak tour, dolphin watching, water sports of all kinds….Dine at the Hot Tin Roof restaurant, overlooking Key West Harbor. Or eat outside at any time of day at the Sunset Pier.  In-room dining is available for those intimate evenings in, or when you can’t be bothered to take off that fluffy robe. 2019 ERV Rating* for Key West Romantic Resorts: 90% - Excellent. (0 Duval St, Key West FL  305-296-7701)

A Note About Key West Resort Fees:

A resort fee is a daily surcharge that many hotels and resorts, particularly in the states of Florida, Hawaii and Nevada tack on to the listed nightly price of the resort. Theoretically, this fee is used to cover “extras” like pool use, towels, fitness center, newspapers and wifi. However, you pay this fee whether you use these extras or not. The resort is able to advertise a nightly rate without mentioning the additional charge, so certain resorts may seem like a better deal than they actually are. It’s very easy to be misled, so ALWAYS ask about the existence of a resort fee and exactly how much it is before making your final decision. It can’t hurt to ask management to waive the fee, but doing so is becoming quite rare. Also keep in mind the county sales tax and Florida State sales tax. 

*ERV Rating: our unique, non-scientific ratings for romantic accommodation include:

  • Amenities: including Whirlpool bath or JACUZZI® Tub, scenic view, fireplace, lounge, etc
  • Location: proximity of hotel to restaurants, pubs, downtown, etc
  • Clientele: demographic the hotel attracts (couples, families, business travelers, etc)
  • Popularity: based social media & crowd-sourced reviews 
  • Value: product offered compared to room rate 
  • Please Note: percentage ratings are not absolute but for comparative use only  

√ COVID Safety Plan: identifies hotels and inns that clearly indicate they are taking measures to prevent the spread of COVID-19.

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