Quintinha Sao Joao is a four-pearl boutique property designed to recreate the experience of staying in a traditional Portuguese manor house. Perched on a hill in a quiet residential neighborhood, guests are a 15-minute walk from downtown Funchal. All 42 air-conditioned rooms are large with firm mattresses, garden-view balconies, minibars, and flat-screen TVs with DVD players. While the spa and heated indoor and outdoor pool areas have a contemporary look, the rest of the hotel's antique decor has a dated though welcoming and homey feel to it. Expect lots of freebies, from a breakfast buffet and Wi-Fi to all-day snacks and downtown shuttle. The main bar offers happy hour and live piano music, while the restaurant serves Goan-focused dishes. Travelers looking for more modern digs should consider the nearby and slightly cheaper Four View Baia.

The Madeira Regency Cliff is a three-and-a-half-pearl, 59-room hotel set into the cliff face in Funchal's Lido area. The setting provides stunning ocean panoramas from all guest rooms, which are clean, modern, and have balconies. Sea views are also available at the two pools, as well as the bar and restaurant terraces, where free breakfast is served. A few restaurants are in walking distance, but the hotel is far from Funchal's historic center. A no-children policy makes it a particularly peaceful spot to enjoy the views, and most guests love having direct access to the pleasant coastal promenade. Swimmers, however, may be disappointed with the tiny pools and should consider the lti Pestana Grand Hotel just along the coast -- it has one of Madeira's largest outdoor saltwater pools.

Fresh, style-conscious hotels like The Vine have helped create a younger vibe in Madeira in recent years. This 79-room, four-pearl hotel is done in urban-chic decor, with bold design that oozes glamour. It’s set above one of Funchal’s shopping complexes in the city center, allowing for easy sightseeing combined with relaxation on the swish rooftop terrace with heated infinity pool. The richly hued, wine-inspired rooms have amenities like air-conditioning and sometimes tricky touch-panel lighting, but views onto the hotel's atrium from some rooms are disappointing. A decadent spa solidifies the romantic, couples-centric vibe. For a cool, low-key city stay, it’s reasonably priced, but travelers looking for a more classic high-end hotel experience might prefer the Quintinha De Sao Joao, even though it’s 10 minutes farther from the center on foot.

The three-and-a-half-pearl Hotel do Carmo is a stylish boutique property with a central Funchal location. Mid-century modern furniture and vintage details -- much of it authentic -- can be found here, although its 80 minimalist guest rooms don't have the same ambiance. They're small, and are missing considerable amenities, like AC, mini-fridges, coffeemakers, and toiletries, but they do have flat-screen TVs, bathrooms with deep tubs, and more than half have balconies. The hotel's standout feature is a rooftop pool with panoramic ocean views, an attractive restaurant that offers free breakfast, and a lobby bar with a handsome billiards table. However, the hotel lacks a gym. For a more modern alternative in the heart of town, check out Hotel Madeira.

The four-pearl Quinta Mirabela is located relatively far inland, a 30-minute walk away from Funchal's center, but this means views overlooking the city and sea are breathtaking. At just 24 rooms, the hotel's small size ensures a quiet retreat for guests, who are primarily couples. The modern rooms have a sleek black-and-yellow color scheme and marble bathrooms, plus some have furnished balconies. All rooms, however, have lovely views, which can also be found at the pool and the panoramic rooftop terrace. A comprehensive spa and on-site restaurant serving local cuisine round out the features. As there's little to occupy children, families should consider the four-pearl Vidamar Resort Madeira, which has a kid's club and sports facilities.  

Mixing African and Asian decor, the upscale, 62-bungalow Choupana Hills Resort & Spa is one of the most polished properties in the Funchal area. It's perched on the hillside above town, with spectacular views and free shuttles into Funchal throughout the day. Contemporary bungalows include four-poster beds, vaulted wooden ceilings, and balconies, some with sea views. Suites have whirlpool tubs on the balconies. The infinity pool, outdoor terraces, and the bar and restaurant with floor-to-ceiling windows, all overlook the Atlantic. While the clifftop location offers sunset vistas, there are stairs throughout the property and fees for extra in-room coffee and tea take things down a peg. Travelers might want to also check out the Vine, which is in a more walkable area and closer to Funchal, although rates are higher.