Hotels We Love: Top Gay Guesthouses

5. Cawthra Square and Gloucester Square Bed and Breakfast Inns, Toronto

Cawthra Square and Gloucester Square Bed and Breakfast Inns are composed of three separate, nearby buildings offering a total of 32 upscale guest rooms and suites, most with private baths. The Jarvis Street location has two neighboring, nicely restored Victorian mansions with a comfortable old-fashioned boarding house feel and excellent on-site spa services. The Edwardian Cawthra Square location is on a much quieter street and all rooms have private terraces, but there is no reception on-site. All three offer the unusual mix of hotel office-away-from-home conveniences (voicemail, wireless internet, PC, copier) with four-star B&B individuality and charm.
512-514 Jarvis St, and 10 Cawthra Square; 800-259-5474; www.cawthrasquare.com; C$129+

4. Pineapple Point, Fort Lauderdale

Originally built in the 1930s as a guesthouse in the old-world-Florida tradition, the Pineapple Point Guest House offers Fort Lauderdale's most lavish d?cor and lush landscaping. Lovely fabrics, beautiful wood floors, antique furniture, and tropical colors are combined to create a world of casual elegance. The grounds, jungle-like and spectacular, surround an adorable Jacuzzi and pool. The cottage, with its own veranda, fireplace and two king rooms is perfect for sharing. Newspapers, a continental breakfast, and snacks are all complimentary. An on-site massage therapist and workout facility round out the top-notch amenities. Pineapple Point, located in the Victoria Park neighborhood, is 10 minutes by car from the beach.
>315 NE 16th Terrace; 888-844-7295 or 954-527-0094; www.pineapplepoint.com; $199+

3. The Parker House, San Francisco

The Parker House is the Castro's luxury gay inn, comprising a pair of stunningly restored Edwardian buildings with charming, sunny grounds and a great location close to Castro nightlife and the Mission?s great restaurants. All but two of the 21 rooms feature private baths, cable TV, and voice mail/data port phones. Rates include breakfast and a wine social. Access to the onsite steam room has proven popular with guests.
>520 Church St; 415-621-3222 or 888-520-7275; www.parkerguesthouse.com; $139+

2. Pearl?s Rainbow, Key West

In quaint and quirky Key West, two-pool, two-hot tub, women-only Pearl?s Rainbow, Key West is situated in a re-born 1950s-era ?Surf Motel,? an 1889 cigar factory and three former cigar maker?s cottages. The sole exclusively women's guesthouse on the island, Pearl?s is clothing optional, although not that many women seem to take full advantage of that. Pearl?s wins the top women?s slot for its excellent array of accommodations, offering options for all sorts of budgets and inclinations. Whether you want a room with the most titillating pool view or prefer to create your own excitement in more secluded surrounds, Pearl?s has rooms to fit. Frequented by women in their 30s, 40s, and 50s, manager Lorraine estimates that 75 to 80 percent of guests are couples, but it?s a friendly place to mingle whether you?ve brought a date or are looking to find one. Pearl's Patio (Pearl's Rainbow), provides a laidback nightlife option for women.
>525 United St., 800-749.6696; www.pearlsrainbow.com, $89+

1. Brass Key, Provincetown

From the elegant yet comfortable furnishings to the thoughtful amenities to the professional, hardworking, and friendly staff, Brass Key is a class act and our top choice in town. The Brass Key is a destination in and of itself, with its extensive grounds that include a huge hot tub, infinity-edge pool, landscaped brick pool deck, and all-around fabulous resort atmosphere. Rooms have Bose CD clock radios and luxury bath amenities; some even have grand balconies and fireplaces. There are iPods and laptops on request. The location is just steps from Commercial Street. The 42-room property offers excellence at every turn.
>67 Bradford St; 800-842-9858 or 508-487-9005; www.brasskey.com; $130+