Best Months to Visit. The best time to visit Key West is between March and May. The winter crowds will taper off, the hotel rates become reasonable and the weather is remarkably similar to winter ... 3850 North Roosevelt Boulevard, Key West, FL 33040, United States of America – Good location – show map. This Key West Hilton Garden Inn from the The Keys Collection is 2 minutes' drive from the Key West International Airport and 10 minutes' drive from Duval Street. Features include a restaurant, tiki bar, and rooms with free WiFi. Hyatt Vacation Club at Beach House, Key West Book Now 5051 Overseas Highway, Key West, Florida, United States, 33040 Tel: +1 305 294 0059 | Fax: +1 305 295 0519Ambrosia Key West. 1,753 reviews. #13 of 28 B&Bs in Key West. 622 Fleming St, Key West, FL 33040-6826. Write a review. Check availability. Full view. Coconut Mallory Resort And Marina. 618 reviews. #7 of 10 small hotels in Key West. 1445 S Roosevelt Blvd, Key West, FL 33040-4538. Write a review. Check availability. Hilton Garden Inn Key West / The Keys Collection. Based on 1965 guest reviews. Read 5 reviews. 1 of 12. 1 / 12. Call Us. +1 305-320-0920. Address. 3850 North Roosevelt Boulevard Key West, Florida 33040 USA, Opens new tab.These downtown hotels in Key West have been described as romantic by other travelers: Almond Tree Inn - Traveler ... Breakfast Key West Vacation Rentals Flights to Key West Key West Restaurants Things to Do in Key West Key West Travel Forum Key West Photos Key West Map. ... Hotels near Florida Keys Community College Hotels near …Book now with Choice Hotels in Key West, FL. With great amenities and rooms for every budget, compare and book your Key West hotel today.Start your day satisfied with favorites from our free buffet breakfast served daily, and enjoy the convenience of local restaurants near our hotel like Bagatelle, Sloppy Joe's, and Alonzo's. We also have a poolside tiki bar. Stay active with cardio equipment and free weights at our 24-hour fitness center, and unwind in our resort-style outdoor ...Located in Key West, Florida, this adult-only hotel offers two outdoor pools. Duval Street is a 1-minute walk away, and Key West Butterfly and Nature Conservatory is 3 minutes’ drive from the hotel. The Key West Shipwreck Museum, Key West Aquarium, and Conch Tour Train are all located less than 2 km away. Simonton Court Historic Inn & Cottages is a tropical oasis located in the heart of Old Town Key West. Whether you’re relaxing by one of our four pools, enjoying the lush secluded beauty of our gardens and restored Victorian and Conch architecture, or exploring the world-famous historic attractions of Key West just steps from our property, how you enjoy Key West is entirely up to you. KIMPTON KEY WEST COLLECTION. 725 Truman Avenue Key West FL 33040. 8005494430 3052945229 E-mail Website. Facebook Twitter Instagram. Five newly renovated boutique hotels in the heart of Old Town, Key West, with unique flairs for every traveler. Play and explore by day or night, and retreat to our bohemian s.239. Choose. 1 of 3. Priceline™ Save up to 60% Fast and Easy 【 Key West Hotels 】 Get deals at Key West’s best hotels online! Search our directory of hotels in Key West, FL and find the lowest rates. Our booking guide lists everything from the top 10 luxury hotels to budget/cheap hotels in Key West, FL .Sandspur Beach (Bahia Honda State Park) Big Pine Key, Florida. 34 mi from Key West, FL. Anne’s Beach. Islamorada, Florida. 68 mi from Key West, FL. +1. Dry Tortugas National Park Beach (Seaplane Beach) Key West, Florida.However, it’s actually against the law to feed them and it’s punishable by a $250-$500 fine. So keep the bread crumbs in your bag and enjoy the chickens from a distance. 16. Key West is a big cruise ship port. The last good thing to know before visiting Key West, Florida is that Key West is a big cruise ship port.However, it’s actually against the law to feed them and it’s punishable by a $250-$500 fine. So keep the bread crumbs in your bag and enjoy the chickens from a distance. 16. Key West is a big cruise ship port. The last good thing to know before visiting Key West, Florida is that Key West is a big cruise ship port. WARMEST. 124 mm. WETTEST. Sep - Nov. $510. 26º C. 122 mm. Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed hotels in Key West. Select dates and complete search for nightly totals inclusive of taxes and fees. Jul 28, 2020 · The Capitana Key West offers the intimacy of a B&B and the well-curated luxury of a boutique hotel, in a sublime coastal setting. You’ll find waterfront views, a beautifully landscaped pool (complete with tiki bar), delicious dining options, and well-appointed accommodations here. Our hotel is also pet-friendly, and conveniently located near ... The Palms Hotel. Hotel in Downtown Key West, Key West. Located just 1 mile from historic Duval Street, this Key West hotel features a heated swimming pool and a daily continental breakfast. Free WiFi is available throughout the property. Show more. Coconut Mallory Resort And Marina. 618 reviews. #7 of 10 small hotels in Key West. 1445 S Roosevelt Blvd, Key West, FL 33040-4538. Write a review. Check availability.Condo in Key West. 4.93 (132) Beach Club Ocean Front 2BR Condo. Come fall in love with Key West in our luxurious ocean front condo. The Key West Beach Club is located directly on the Atlantic in a quiet residential secured building. It is a 2BR, 2 1/2 Bath located in Mid-Town. Oct. 2 – 9. $1,242 CAD night.Key West Night Life; Local Map; Explore. 305-296-5678 Call. Book Now Rooms Gallery Offers Book Now. Best Rate ... Experience the luxurious dining scene at Key West. Start right here, at our hotel, with an opulent Latin dining experience at The Milagro Restaurant. ... 1401 Simonton Street Key West, Florida, US 33040. Connect with us. Call: 305 ...The Saint Hotel Key West, Autograph Collection. $$. A departure from the area's pastel B&Bs and kid-packed resorts, The Saint is a swanky, sexy boutique hotel with just 36 rooms tucked away from ...Hotel Map. restaurant Map. bus maps. 3-D Map of Key West – Shows a birds eye view of the island, with a few important points marked. Map of South Florida and the Keys. …Southernmost Beach Resort. Pier House Resort & Spa. Hyatt Centric Key West Resort and Spa. The Galleon Resort And Marina. Sunset Key Cottages. The Reach Key West, Curio Collection by Hilton. Hyatt Vacation Club at Beach House. Casa Marina Key West, Curio Collection by Hilton.Hampton Inn Key West. 389 reviews. NEW AI Review Summary. #11 of 14 resorts in Key West. 3755 S. Roosevelt Boulevard, Key West, FL 33040. Visit hotel website. 1 (855) 605-0317. Write a review. Check availability. The Local Side of Key West (podcast) 172: Take Your Friend to Work Day; Making Your Own Way with G. Love; Backyards of Key West Podcast with Mark Baratto 241: Episode 241 – A Taste of Key West, Savoring The Flavors of Community and Charity; The Local Side of Key West (podcast) 171: Keith interview on The Backyard of Key West Podcast ….II Popular hotels close to Key West Intl Airport include Hyatt Vacation Club at Windward Pointe, Hampton Inn Key West, and DoubleTree Resort by Hilton Hotel Grand Key - Key West. See the full list: Hotels near Key West Intl Airport. Here are our customers' top places to stay in Old Town Key West: Almond Tree Inn Hotel - Adults Only. Adults-only hotel with outdoor pool, pool bar. Free breakfast • Free WiFi • Spa tub • Bar • Walkable location. LA TE DA Hotel - Adults Only. Adults-only hotel with outdoor pool, restaurant. Ambrosia Key West Pet Policy Ambrosia Key West accepts two pets of any size in designated rooms for an additional fee of $25 per pet, per night. Guests with pets must call (877) 411-3436 prior to booking to verify availability of a pet-friendly room or risk not being able to check in with a pet and/or incurring any associated cancellation penalties.Apr 6, 2024 · 4. Bar Hopping on Duval Street. For many in the over-21 crowd, bar hopping along Duval Street may be one of the best things to do in Key West. In fact, many people travel to Key West to simply partake in endless days of bar hopping and partying. Sloppy Joe’s is Key West’s most famous bar. Hyatt Centric Key West Resort and Spa. Key West, FL. [See Map] #7 in Best Resorts in Key West, FL. Tripadvisor (3809) $50.63 Nightly Resort Fee. 4.0-star Hotel Class. 4.0-star Hotel Class. $50.63 ...1 room, 2 adults, 0 children. 400 Wall St, Key West, FL 33040-6633. Read Reviews of Mallory Square.Charming historic hotel located in Key West’s Old Town neighborhood. Imagine yourself in a place where the trials and tribulations of everyday life just disappear, where tropical breezes gently lift your cares away. Lush, inviting, eclectic- just like the town in which it resides- the Casablanca Hotel beckons you to the heart of Old Town Key ...The Saint Hotel Key West, Autograph Collection. $$. A departure from the area's pastel B&Bs and kid-packed resorts, The Saint is a swanky, sexy boutique hotel with just 36 rooms tucked away from ...Located in Key West, Florida, this adult-only hotel offers two outdoor pools. Duval Street is a 1-minute walk away, and Key West Butterfly and Nature Conservatory is 3 minutes’ drive from the hotel. The Key West Shipwreck Museum, Key West Aquarium, and Conch Tour Train are all located less than 2 km away. Hyatt Centric Key West Resort & Spa. 601 Front Street, Key West, FL 33040, United States of America. +1 305 809 1234. 4.5 (1332 Reviews) Book. 4.8. Service. 4.6. Value. 4.4. Travelers' Choice. Oceans Edge Resort & Marina Key West is the newest Florida Keys hotel, and the largest in Key West. Featuring 100% ocean views, six amazing pools and the best restaurant in Key West, you have everything here to enjoy an exhilarating Key West escape. Brands. Key West. Autograph Collection (Marriott Bonvoy) Curio Collection by Hilton. Hyatt Vacation Club. Show more. SAVE! See Tripadvisor's Key West, Florida Keys hotel deals and special prices all in one spot. Find the perfect hotel within your budget with reviews from real travelers. Hotels near Key West Express - Key West, Key West on Tripadvisor: Find 166,254 traveler reviews, 106,441 candid photos, and prices for 165 hotels near Key West Express - Key West in Key West, FL.Southernmost Beach Resort. Ibis Bay Beach Resort. Margaritaville Beach House Key West. Hilton Garden Inn Key West / The Keys Collection. DoubleTree Resort by Hilton Hotel Grand Key - Key West. Oceans Edge Resort & Marina Key West. Best Hyatt Hotels in Key West: find 5,774 traveler reviews, candid photos, and prices for 3 … Map of Key West Hotels. Map of Key West area hotels: Locate Key West hotels on a map based on popularity, price, or availability, and see Tripadvisor reviews, photos, and deals. Map of Key West area hotels: Locate Key West hotels on a map based on popularity, price, or availability, and see Tripadvisor reviews, photos, and deals.Douglas House. 975 reviews. #6 of 11 guest houses in Key West. 419 Amelia St, Key West, FL 33040-3120. Write a review. Check availability.1. Walk along Duval Street. Duval Street in Key West. Highlights: Vibrant entertainment and shopping street with attractions and restaurants. Duval Street is Key West's main tourist strip, with restaurants and shops designed to entertain tourists and cruise ship passengers. Both Old Town and Hemingway House are within 12 minutes' drive away. A free shuttle is provided to Old Town Key West. Guests can also enjoy a 24-hour front desk, a lobby with ample seating and on-site parking available throughout their stay at a charge of $15.00 per night. Stock Island Marina is 1.6 mi away. Hotel. Condo. Apartment. House. Cottage. Stay close to Duval Street. Find 2,584 hotels near Duval Street in Key West from $182. Compare room rates, hotel reviews and availability. Most hotels are fully refundable. Hyatt Beach House Resort is located in Key West 6.4 km from Duval Street. An outdoor pool and hot tub are featured. You can engage in various activities, such as snorkelling, windsurfing and fishing. The resort also offers bike hire and a small bar on site called Jimmy's Ocean Blue, which serves lite fare.Explore Hotels in Key West, FL. Search by destination, check the latest prices, or use the interactive map to find the location for your next stay. Book direct for the best price and …The Reach Key West, Curio Collection by Hilton. Hotel Details >. 1.06 miles. From* $484. Honors Discount. Select Dates. There are no more Curio hotels in this search area. Search again by zooming out or adjusting any filters. Explore our other hotels in this area.Apr 6, 2024 · 4. Bar Hopping on Duval Street. For many in the over-21 crowd, bar hopping along Duval Street may be one of the best things to do in Key West. In fact, many people travel to Key West to simply partake in endless days of bar hopping and partying. Sloppy Joe’s is Key West’s most famous bar. Key West Hotels on Tripadvisor: Find 1,66,405 traveller reviews, 106,576 candid photos, and prices for hotels in Key West.Hotel Map. restaurant Map. bus maps. 3-D Map of Key West – Shows a birds eye view of the island, with a few important points marked. Map of South Florida and the Keys. …These downtown hotels in Key West have been described as romantic by other travelers: Almond Tree Inn - Traveler ... Breakfast Key West Vacation Rentals Flights to Key West Key West Restaurants Things to Do in Key West Key West Travel Forum Key West Photos Key West Map. ... Hotels near Florida Keys Community College Hotels near …Explore Hotels in Key West, FL. Search by destination, check the latest prices, or use the interactive map to find the location for your next stay. Book direct for the best price and …The Conch House Heritage Inn Key West 10 rooms from £209. Seaside - Ideal for a seaside holiday. A tropical and elegant inn situated in Old Town Florida Keys. Rooms are classical and coastal with ceiling fans, traditional antique furnishings, artworks and large bathrooms with walk-in showers.Lake Buena Vista 59 hotels. Tallahassee 58 hotels. The Inn at Key West 3420 N Roosevelt Blvd, Key West Score from 5,868 reviews: Very Good 8.1 Average price per night: from USD 202. Southernmost Inn 525 United Street, Key West Score from 1,759 reviews: Very Good 8.3 Average price per night: from USD 195. Heron House 512 …Hyatt Centric Key West Resort and Spa. Key West, FL. [See Map] #7 in Best Resorts in Key West, FL. Tripadvisor (3809) $50.63 Nightly Resort Fee. 4.0-star Hotel Class. 4.0-star Hotel Class. $50.63 ...Sunset Key Cottages. 1,043 reviews. NEW AI Review Summary. #3 of 14 resorts in Key West. 245 Front St, Key West, FL 33040. Visit hotel website. 1 (786) 839-4140. Write a review. Check availability.Enjoy a wide range of things to do in Key West, on or off the water. We can help you find family-friendly activities, couples adventures and everything in between. Located in the heart of the Conch Republic, feel at home in one of the best hotels in Key West with white sand beaches, a chic island design, and a private spa.Enjoy FREE high-speed Internet access at the Courtyard Key West Waterfront. This Key West hotel is located on the Gulf of Mexico in the "New Town" section of Key West. The Courtyard Key West is located within a 10 minute drive of any attraction on the island and features spacious guest rooms and suites.Location and transportation. DoubleTree Resort by Hilton Hotel Grand Key - Key West. 3990 S. Roosevelt Blvd, Key West, Florida, 33040, USA. Directions Opens new tab. Key West's only DoubleTree Resort, only minutes from …Show on map. Travel Proud. The Gardens Hotel. 526 Angela Street, Downtown Key West, Key West, FL 33040, United States of America – Excellent location – show map. 9.6. Exceptional. 142 reviews. Amazing and beautiful oasis in the middle of Key West. Lovely grounds that are so peaceful but still only steps away from the action on Duval street.Hyatt Beach House Resort is located in Key West 6.4 km from Duval Street. An outdoor pool and hot tub are featured. You can engage in various activities, such as snorkelling, windsurfing and fishing. The resort also offers bike hire and a small bar on site called Jimmy's Ocean Blue, which serves lite fare.Airport shuttle. Beachside Resort & Residences. Beachside Resort & Residences. 3841 North Roosevelt Boulevard, Key West, FL 33040, United States of America–Good location – show map. After booking, all of the property’s details, including telephone and address, are provided in your booking confirmation and your account. 7.7. Scored 7.7. Good.Home. Hotels. United States of America. Florida (FL) Key West – 137 hotels and places to stay. See the latest prices and deals by choosing your dates. Silver Palms Inn. Hotel …Here are our recommendations based on travel style and budget. If you want to stay in a boutique hotel or bed and breakfast, we recommend H20 Suites, the Southernmost Point Guesthouse, the Artist House, and the Almond Tree Inn. For couples, we recommend H2O Suites, Key West Harbor Inn, and the Almond Tree Inn.The Reach Key West, Curio Collection by Hilton. 1435 Simonton Street, Key West, FL. $509. $633 total. includes taxes & fees. May 14 - May 15. Stay at this 4-star beach hotel in Key West. Enjoy a private beach, a full-service spa, and breakfast. Our guests praise the pool and the helpful staff in our ...Map of Key West area hotels: Locate Key West hotels on a map based on popularity, price, or availability, and see Tripadvisor reviews, photos, and deals.Key West Hotels on Tripadvisor: Find 1,66,405 traveller reviews, 106,576 candid photos, and prices for hotels in Key West.The Florida Department of Transportation maintains green and white mile markers in the Florida Keys along both sides of the road. The signs start at MM 0 Key West and increase every mile as US 1 winds its way east and eventually goes all the way to Maine. The map of the Florida Keys with mile markers below show the major Keys and corresponding ...Ocean Marina. Central to the Beachside experience, the on-resort Marina is a hub for fun and adventure that connects guests to all there is to see and do in Key West. Beachside serves as the gateway to the backcountry of the Florida Keys and the National Marine Sanctuary - where you will find endless sandbars, abundant wildlife and brilliant ...6 Best All-Inclusive Resorts In Key West, Florida. Top 12 Vacation Rentals With A Boat In Florida Keys - Updated 2024. 1. Crowne Plaza Key West-La Concha (from USD 349) Show all photos. Competitive pricing for a prime location on Duval Street. Historic charm, rooftop views, and a pool bar.The Conch House Heritage Inn Key West 10 rooms from £209. Seaside - Ideal for a seaside holiday. A tropical and elegant inn situated in Old Town Florida Keys. Rooms are classical and coastal with ceiling fans, traditional antique furnishings, artworks and large bathrooms with walk-in showers.The only thing better than a Florida vacation is an all-inclusive Florida vacation. Gwen Pratesi|Amanda Norcross January 5, 2024 24 Top All-Inclusive Resorts in the U.S. for 2024View map. Popular hotels in Key West right now. 2023. Travellers' Choice. Kid-friendly. 5-star stay. Traveller rating: Very good. Pool on site. Good for luxury stays. 1. 2. 3. 4. 5. 6. Key West Hotels Information. Key West Hotel Rooms & Suites . Step inside any of the beautiful rooms or suites at Margaritaville Beach House Key West and slip into the island state of mind. The laid-back, island-inspired decor will help you kick back in style, while the full range of high-end amenities keep you comfortable. Hotel. Condo. Apartment. House. Cottage. Stay close to Duval Street. Find 2,584 hotels near Duval Street in Key West from $182. Compare room rates, hotel reviews and availability. Most hotels are fully refundable.Get the free printable map of Key West Printable Tourist Map or create your own tourist map. See the best attraction in Key West Printable Tourist Map.Jan 24, 2024 · The Reach Key West, Curio Collection by Hilton. Hampton Inn Key West. Havana Cabana at Key West. Southernmost Beach Resort. Ibis Bay Beach Resort. Margaritaville Beach House Key West. Oceans Edge Resort & Marina Key West. Best Hilton Hotels in Key West: find 17,929 traveler reviews, candid photos, and prices for 5 Hilton Hotels in Key West, FL. 6 Best All-Inclusive Resorts In Key West, Florida. Top 12 Vacation Rentals With A Boat In Florida Keys - Updated 2024. 1. Crowne Plaza Key West-La Concha (from USD 349) Show all photos. Competitive pricing for a prime location on Duval Street. Historic charm, rooftop views, and a pool bar.Coconut Mallory Resort And Marina. 618 reviews. #7 of 10 small hotels in Key West. 1445 S Roosevelt Blvd, Key West, FL 33040-4538. Write a review. Check availability.Hotels between Miami and Key West are located along US 1 in Florida. Key West is 165 miles southest of Miami. Also called the Overseas Highway, this 113-mile section of US 1 connects the Florida Keys to mainland Florida and offers beautiful ocean vistas. From Northeast to Southwest US 1 travels along the east coast of Florida.See our guide to hotels near Key West. A clickable map of Key West hotels and motels - Key West, Florida FL. Enjoy FREE high-speed Internet access at the Courtyard Key West Waterfront. This Key West hotel is located on the Gulf of Mexico in the "New Town" section of Key West. The Courtyard Key West is located within a 10 minute drive of any attraction on the island and features spacious guest rooms and suites.
Hampton Inn Key West. 389 reviews. NEW AI Review Summary. #11 of 14 resorts in Key West. 3755 S. Roosevelt Boulevard, Key West, FL 33040. Visit hotel website. 1 (855) 605-0317. Write a review. Check availability.. Midnight sun pdf
Plan your vacation with our interactive Key West Map. User-friendly design with detailed info about all the tourist attractions and Old Town Trolley route. ... Roosevelt Station at Gates Hotel. 3824 N Roosevelt Blvd, Key West, FL 33040, USA. Stop #7 is temporarily in front of the Gates Hotel. Hampton Inn. 3835-3911 S Roosevelt Blvd, Key West ...Havana Cabana at Key West. 3,195 reviews. NEW AI Review Summary. #12 of 55 hotels in Key West. 3420 N Roosevelt Blvd, Key West, FL 33040-4224. Write a review. Find hotels in Key West, FL from $180. Most hotels are fully refundable. Because flexibility matters. Save 10% or more on over 100,000 hotels worldwide as a One Key member. Search over 2.9 million properties and 550 airlines worldwide. Home. Hotels. United States of America. Florida (FL) Key West – 131 hotels and places to stay. See the latest prices and deals by choosing your dates. Silver Palms Inn. Key …Home. Hotels. United States of America. Florida (FL) Key West – 137 hotels and places to stay. See the latest prices and deals by choosing your dates. Silver Palms Inn. Hotel …Enjoy FREE high-speed Internet access at the Courtyard Key West Waterfront. This Key West hotel is located on the Gulf of Mexico in the "New Town" section of Key West. The Courtyard Key West is located within a 10 minute drive of any attraction on the island and features spacious guest rooms and suites.El Meson de Pepé. First State Bank of the Florida Keys. Fury Water Adventures. Gay Key West Visitors Center. Ghosts & Gravestones. Grand Café. Great Locations Florida Keys & Key West Area Guidebook. Hard Rock Cafe Key West. Harry S. …The Saint Hotel Key West, Autograph Collection. 859 reviews. NEW AI Review Summary. #25 of 55 hotels in Key West. 417 Eaton Street, Key West, FL 33040. Visit hotel website. 1 (844) 631-0595. Write a review.La Concha Key West. hotel • Free WiFi • Restaurant • 2 bars • Walkable location. Heron House - Adult Only. B&B • Free breakfast • Free WiFi • Rooftop terrace • Walkable location. The Marker Key West Harbor Resort. hotel • Free WiFi • Restaurant • 3 outdoor pools • Walkable location.4. Bar Hopping on Duval Street. For many in the over-21 crowd, bar hopping along Duval Street may be one of the best things to do in Key West. In fact, many people travel to Key West to simply partake in endless days of bar hopping and partying. Sloppy Joe’s is Key West’s most famous bar.Home. Hotels. United States. Florida (FL) Key West – 137 hotels and places to stay. See the latest prices and deals by choosing your dates. Silver Palms Inn. Hotel in Downtown …Southernmost Point. You can find out about the history of Key West with a stop at Southernmost Point. Discover the area's lively bars and its lively festivals. Flexible booking options on most hotels. Compare 7,906 hotels in Florida Keys using 20,680 real guest reviews. Get our Price Guarantee - booking has never been easier on Hotels.com!A contemporary boutique hotel in the heart of Old Town Key West. Escape to the beauty and serenity of Key West, Florida, where the water is turquoise blue and the sunsets are radiant. With its island inspired charm and chic contemporary spaces, the Silver Palms Inn is a green boutique hotel where you can relax as well as discover new adventures.The island of Pigeon Key is a historic 5-acre island located in the heart of the Florida Keys! It was once the home of over 400 workers who built the Overseas Railway from Miami to Key West. Today, the island is operated by the Pigeon Key Foundation, a 501 (c)-3 not for profit organization. Our Visitor's Center, which is the address listed, is ...Home. Hotels. United States of America. Florida (FL) Key West – 137 hotels and places to stay. See the latest prices and deals by choosing your dates. Silver Palms Inn. Hotel …Best Months to Visit. The best time to visit Key West is between March and May. The winter crowds will taper off, the hotel rates become reasonable and the weather is remarkably similar to winter ...Clothing Optional Gay Hotels and Resorts in Key West. Island House Key West – Luxury Playground in Paradise. A gay guest house since 1974, the current owners purchased the property in 1999 and completely renovated the complex. Now it’s an award-winning clothing-optional resort for gay men and one of the most popular in Key West..