Directory

Sponsored

New Orleans House

Part of the world famous Bourbon Street Complex. Tropical pool bar open to 4 am. Waterfall pool and 15-man Jacuzzi. Clothing optional sun deck and secure hotel parking.

Address:

724 Duval Street

Phone: 305-293-9800

Website: view our site

Sponsored

The Perry Hotel Key West

Located one bridge away from Key West at the state-of-the-art Stock Island Marina, the award-winning Perry Hotel offers a respite from the hustle & bustle of downtown Key West, yet easy access to those looking to explore Old Town via scheduled shuttle service. This award-winning property features luxury accommodations, two waterfront pools, three dockside restaurants, onsite distillery, direct access to South Florida’s best water activities, art studios, and more.  The Perry is more than just a boutique hotel, it’s [...]

Address:

7001 Shrimp Rd

Phone: 305-296-1717

Website: view our site

Sponsored

Alexander’s Guesthouse

Luxury guesthouse catering to gay and lesbian Clientele. Complimentary daily breakfast, buffet & open bar. Multiple sun decks, 24 hour pool and hot tub. Toll Free: 800-654-9919

Address:

1118 Fleming Street 33040

Phone: 305-294-9919

Website: view our site

Sponsored

Equator Resort (Male Resort)

Located at 822 Fleming street is only 3 blocks from famous Duval St. With 2 heated pools and 2 Hot tubs, the resort caters to all the “fun” you want in a relaxed open and secure resort atmosphere. A full-service bar that offers a complimentary Happy Hour daily as well as a complimentary continental breakfast.

Address:

822 Fleming Street

Phone: 305-294-7775

Website: view our site

Sponsored

Marriott Beachside Key West

Here personalized service combines with luxury conveniences to make every moment of your stay a memory not to be forgotten.

Address:

3841 North Roosevelt Blvd 33040

Website: view our site

Sponsored

Silver Palms Inn

Enjoy affordable elegance at Key West’s newest hotel, Silver Palms Inn, located in Historic Old Town Key West!

Address:

830 Truman Avenue 33040

Phone: 305-294-8700

Website: view our site

Rent Key West Vacations

We offer romantic hideaways, distinctive private Old Town residences and elegant waterfront condos to fit any lifestyle or budget.

Address:

1075 Duval Street

Phone: 305-294-0990

Website: view our site

24 North Hotel

24 North is Key West’s answer to casual-resort luxury offering guests a genuine island experience.

Address:

3820 North Roosevelt Boulevard

Phone: 305-320-0940

Website: view our site

Vacation Key West

Key West Hotels, Florida Keys Condo Rentals, Attractions and more. Complimentary Key West Map With Every Reservation

Address:

100 Grinnell St at the Ferry Terminal

Website: view our site

Key West Vacation Properties & Realty

We are a family owned full service real estate company that specializes in property management of vacation rentals and long-term rentals. With over 30 years experience. Jaime Caballero who is born and raised in Key West is the Real estate broker and currently President of the key West Association of Realtors.

Address:

915 Eisenhower Drive

Phone: 305-296-6667

Website: view our site

Island House

Clothing-optional resort for men. Poolside cafe and bar. Luxury rooms with our heavenly beds. Heated pool, fully equipped gym, sauna, steam room, two Jacuzzi's, erotic video room. Island House was recently named The best gay men’s resort in the world.” by OUT Traveler Magazine. Toll Free 800-890-6284

Address:

1129 Fleming Street 33040

Phone: 305-294-6284

Website: view our site

Parrot Key Resort

Address:

2801 N. Roosevelt Blvd

Phone: 305-600-0097

Website: view our site

Casa Marina Resort & Beach Club

Savor a taste of tropical living at the most beloved choice of Key West hotels and resorts – Casa Marina Resort. Nestled on the island’s southern edge – spanning more than 1,100 feet of private beach. Toll Free: 877-397-6342

Address:

1500 Reynolds Street

Phone: 305-295-3535

Website: view our site

Cayo Hueso Resorts & Cottages

Offering private homes, cottages & bungalows. Tropically elegant vacation rentals just steps off Duval-true Key West living.

Address:

1205 Calais Lane

Phone: 305-797-1500

Website: view our site

The Saint Hotel

Boutique Hotel with a Burgundy Bar and Tempt Restaurant

Address:

417 Eaton Street

Phone: 305-294-3200

Kimpton Key West

A collection of five boutique hotels in Old Town Key West within walking distance to Duval Street. From honey mooners to adventure seekers, or even group getaways. We have you covered!

Pier House Resort & Spa

Experience a collection of specially designed, island-chic accommodations tucked into a lush, tropical paradise. Pier House Resort & Spa offers a private white sand beach, renowned spa, and legendary bars and dining that set this island resort apart from the rest.

Address:

1 Duval Street

Phone: 305-296-4600

Website: view our site

Amsterdam’s Curry Mansion Inn

Historic Mansion close to restaurants & nightlife. Full hot breakfast, daily cocktail party, live music & free parking.

Address:

511 Caroline Street

Phone: 305-294-5349

Website: view our site

Simonton Court

The cottages of Simonton Court retain their original 19th century charm, yet are updated with modern amenities.

Address:

320 Simonton Street

Phone: 305-294-6386

Website: view our site

Oceans Edge Key West

Address:

5950 Peninsular Ave

Phone: 305-809-8204

Website: view our site

LaTeDa

  Lateda - Beautiful Hotel, Restaurant, Piano Bar, Outdoor Bar, & Cabaret  

Phone: 305-296-6706

Website: view our site

The Gates Hotel

Mixing contemporary design and retro Floridian flair, The Gates Hotel features guestrooms with modern amenities that uniquely combine upscale sophistication and polished service with the island’s casual laid back vibe.

Address:

3824 North Roosevelt Boulevard

Phone: 305-320-0930

Website: view our site

Southernmost Hotel Collection

From our AAA four diamond boutique hotels to luxury two bedroom suites to a full service Key West beach resort atmosphere, the variety of properties provide something for everyone.

Address:

1319 Duval Street

Phone: 305-296-6577

Website: view our site

The Capitana Key West

The Capitana Key West Hotel is a luxury boutique hotel with two bedroom private cottage, furnished balconies, family suites with small kitchen and dining area, and gulf view guest rooms with modern amenities. A casual island inspired design.

Address:

2401 N Roosevelt Blvd

Phone: 305-296-6925

Website: view our site

C Todd Kemp & Brian Boyer Vacation Rentals

Address:

PO Box 527, Key West

Phone: 904-910-1072

Fairfield Inn

Address:

2400 N Roosevelt Blvd

Phone: 305-296-5700

Website: view our site

The Tropical Inn

Boutique hotel-style casual chic seamlessly blends with bed-and-breakfast warmth to create the Tropical Inn’s mellow ambience.

Address:

812 Duval Street

Phone: 888-611-6510

Website: view our site

Crowne Plaza – La Concha

Discover a rich history, an enviable Old Town location and sun-drenched island charm when you choose the Crowne Plaza Key West - La Concha Hotel. Located on Duval St., La Concha, is the ideal Key West hotel. Guests can enjoy a leisurely stroll to nearby attractions like the Mel Fisher Museum, Hemingway House and Mallory Square. Duval Street offers fine dining, chic boutiques, the hottest clubs in town and iconic bars like Sloppy Joe's. If the walls of our Key West hotel [...]

Address:

430 Duval Street

Phone: 305-296-2991

Website: view our site

The Gardens Hotel

The Gardens estate houses 17 luxurious guest suites amidst one of Florida’s oldest and most respected tropical gardens. d’Vine Wine Gallery Wed-Sun 5-10P. Sunday Jazz 5-7:30P

Address:

526 Angela Street

Phone: 305-294-2661

Website: view our site

Hyatt Key West Resort & Spa

Ours is a year-round Key West resort on the Gulf of Mexico, within walking distance of shops and attractions. Come savor the Hyatt experience at the best of resorts in Key West, Florida.

Address:

601 Front Street

Phone: 305-809-1234

Website: view our site

Suite Dreams Inn by the Beach

Get pampered in our lush garden oasis of tropical elegance, steps from sandy Higgs Beach, our City Park with tennis, pickleball, and more, water sports, outstanding restaurants, and world-famous Duval St. Known for our 7 person Hemingway Retreat, a 1,100 sqft townhouse suite with a private lagoon pool & sundeck its perfect for honeymooners or rooms can be added to sleep up to 13. We offer 4 other reasonably priced family & pet-friendly accommodations. Enjoy our sparkling cocktail pool. [...]

Address:

1001 Von Phister St

Phone: 305-849-3437

Website: view our site

The Southernmost House

A sophisticated setting at ocean’s edge, The Southernmost House stands out as Key West’s most striking oceanfront bed and breakfast, with 18 spacious, exquisitely appointed guestrooms and suites.

Address:

1400 Duval Street

Phone: 305-296-3141

Website: view our site

Fairfield Inn & Suites The Keys Collection

Our brand new hotel showcases intelligently appointed rooms & suites; each hotel room includes a flat screen TV, a mini-fridge, and plush bedding.

Phone: 305-320-0910

Website: view our site

Winslow’s Bungalows

Winslow's Bungalows spans a lush, landscaped campus in the heart of Old Town. Named for famous painter and summer resident Winslow Homer, this expansive haven boasts three private pools, an outdoor bar and vibrant gardens. It’s an idyllic scene for couples, families, groups and wedding parties.

Address:

725 Truman Avenue

Phone: 305-294-5229

Website: view our site

Historic Key West Vacation Rentals

Address:

425A Eaton Street

Phone: 305-296-1010

Website: view our site

Key West Hideaways

Nightly, Weekly, and Monthly vacation rentals. We have approximately 100 rentals in Key West!

Address:

828 White Street, #3

Phone: 305-296-9090

Website: view our site

Opal Key Resort & Marina

Address:

245 Front Street

Phone: 305-294-4000

Website: view our site

The Laureate Key West

The Laureate Key West, Key West’s all-new all-suite retreat offers guests modern, luxurious accommodations and a prime bay front location that serves as the perfect jumping off point for exploring the colorful town of Key West. Taking inspiration from all the great writers who have called Key West home and found haven here, The Laureate Key West was designed to be a traveler’s haven, where guests can rest, recoup, and reflect from a sun-filled day. From the beautiful bay [...]

Address:

3444 N Roosevelt Blvd

Phone: 305-295-7509

Website: view our site

Hilton Garden Inn

Address:

3850 N Roosevelt Blvd

Phone: 305-320-0920

Website: view our site

Old Town Manor

Ideally located just steps from famous Duval Street in the heart of Old Town Key West. This 14 room bed & breakfast has modern amenities,free wi-fi,,lush gardens and generous continental breakfast

Address:

511 Eaton Street

Phone: 305-292-2170

Website: view our site

Margaritaville Beach House Key West

Previously Barbary Beach House, Margaritaville Beach House Key West is ideally located just across the street from Key West’s largest beach. The 186-room hotel has an upscale yet laid back vibe with modern and bright rooms, a poolside sundeck with cabana loungers, restaurant and bar, garden hammocks, and a 24-hour fitness center. Hotel guests enjoy a daily shuttle service to and from the airport and Key West’s lively historic waterfront.  

Address:

2001 South Roosevelt Blvd

Phone: 305-292-9800

Website: view our site

Havana Cabana

The new Havana Cabana Resort, formerly The Inn At Key West, sits waterfront in Key West, a destination steeped with charm and character. Taking nostalgic influences from the art and culture of our neighbors in Cuba, the Cabana is a lush escape from reality. ​Mid-century cars greet resort guests as they arrive, birds of paradise punctuate the outdoor landscape, and the sweet sound of Flamenco guitar can be heard poolside. Relax and unwind with a midday mojito or explore the [...]

Address:

3420 N Roosevelt Blvd

Phone: 305-294-5541

Website: view our site

VHKW – Vacation Homes of Key West

We are locally owned and operated full service vacation rental company. We are proud to offer a wide range of unique vacation rentals (something for everyone), from intimate charming cottages, to ocean view condos, to luxury island estate – each reflecting the island style of their individual owners. Our website provides detailed information about each home, a descriptive map of the neighborhoods of Key West where they are located, vacation rental management services and vacation rentals as an investment.

Address:

507 Whitehead Street

Phone: 305-294-7358

Website: view our site

Andrews Inn & Garden Cottages

Andrews Inn is a superbly situated tropical boutique guesthouse where time slows in tune with the island’s relaxed essence. You will find us in the very heart of the famous historic Old Town Key West, down a shady lane just off Duval Street and bordering on the Hemingway House.

Address:

0 Whalton Lane

Phone: 1888-263-7393

Website: view our site

The Reach Resort

Boasting Key West’s only natural beach as our backyard, we offer the perfect blend of glistening white sand and breathtaking sunshine. Pamper yourself at this enchanting Old Town Key West hotel, complete with 150 elegant guest rooms, sweeping beach views, and attentive guest services. Toll Free: 877-397-6427

Address:

1435 Simonton Street

Phone: 305-296-5000

Website: view our site

Ocean Key Resort

Ideally situated at Zero Duval Street, between Key West Harbor and lively Mallory Square.

Address:

Zero Duval Street

Phone: 305-296-7701

Website: view our site

The Grand Guesthouse

A classic Key West inn, exudes charm by means of a bed & breakfast style in a totally un-touristy Old Town Key West neighborhood. If you prefer a good night’s sleep over the noise of Duval Street, but you want to be within easy walking distance to shops, restaurants, museums, art galleries, beaches, the Southernmost Point, and Hemingway’s House you’ll love our location. We’re just five short blocks to Duval Street and five blocks to the beach.

Address:

1116 Grinnell Street

Phone: 305-294-0590

Website: view our site

Susan’s Key West Condos

Vacation in PARADISE! Truman Annex Shipyard condos in Old Town, Key West are enhanced with bicycles, full kitchen, washer & dryer, swimming pool, parking space and high speed wifi. Quiet pristine condos a few minutes from zany Duval Street or relaxing Fort Zachary Taylor State Park and Beach. You can stay for a week in Truman Annex or a month on Terry Lane beside Hemingway House and the Lighthouse with a lazy river pool.

Website: view our site