These sister hotels in the upscale Condado neighbourhood of San Juan offer two unique styles, featuring stunning art and design with gorgeous rooms and divine public spaces. Just a block apart, and owned by an award-winning husband and wife design team, these intimate, bespoke hotels are romantic, fashionable and chic options for a Caribbean island stay.

O:LV FIFTY FIVE

SEXY | SOPHISTICATED | ULTRA-CHIC | LAVISH | FASHIONABLE

The Infinity Suite at O:LV Fifty Five.

Ultra-modern, with a sexy, sublime, totally stunning look, the 26 spacious guest suites are magnificent. High ceilings, marble floors, gorgeous, velvety plush fabrics and an art deco sensibility are just some of the elements. With leather and brass walls behind each large, comfortable bed, the accommodations have custom furnishings, burnished dark wood doors and an exquisite design. Some have large balconies with great views over the Condado lagoon and all the amenities one would expect, with huge bathrooms and remarkable art at every turn. Ideal for romantics and design lovers, the objets d’art scattered throughout include exquisite pieces and funky chandeliers, glamorous spaces, and an impressive attention to detail, all combining to offer a luxurious feel. The rooftop bar has a chic vibe and is the place to see and be seen. With RAYA, its small restaurant, lovely terrace, a two-level infinity pool and casual furnishings, it’s a very fashionable spot to see and be seen at this adults-only hotel. A 1977 Rolls Royce doubles as a DJ booth too – you get the drift. Celebrated local chef Mario Pagan also operates RAYA, a Caribbean/fusion restaurant on the main level. It’s incredibly gorgeous with high-design at every turn, a super glam bar and a sophisticated yet welcoming feel. Some suites do not have windows/ views – but that doesn’t seem to matter. And there are several different types of accommodation, so check before booking. The whole hotel is a superb work of art, will wow you at every turn and the staff are both helpful and friendly.

O:LIVE BOUTIQUE HOTEL

EARTHY | RUSTIC | STYLISH | LAID BACK | COUNTRY CASUAL

A guest room at O:live Boutique Hotel.

Just around the corner on a neighbouring street from sister hotel O:LV, this small boutique hotel has a completely different feel. Think rustic chic with a more casual, yet stylish Mediterranean feel. The story is that while the owners were on honeymoon in Europe, they were inspired to bring back their many finds including furniture, small pieces, antiques and more, thus creating a hotel from their travel experience. The art of simple living is practiced here and has been cultivated to showcase a laid-back relaxed lifestyle and an intimate feel. Frankly it’s hard to choose between the two hotels but they certainly have a very different vibe. The rooms are varied in every way and each is quirky. All are delightful and funky – some quite small while others feature interesting balconies or terraces. Art and marvellous creative pieces are everywhere. A dish here, a candlestick, a beautiful chair, a photo over there – it’s an oasis of clever and thoughtful design with the most amazing lighting everywhere. Honeymoon photos of the gorgeous couple are in the corridors and there are no room numbers, just differently coloured tasselled keys, to identify each room. O:live exudes the kind of atmosphere that makes you feel as if you’re living in a small, secluded spot on an island in Greece or off the Italian coast. There’s a real feeling of being in the countryside, especially on the fabulous rooftop terrace, which is full of wood, soft furnishings, a bar, small pool, and many fascinating design elements. It’s beautiful and peaceful and feels just like an outdoor living room that you never want to leave. The ultra-chic Sage Restaurant, also by chef Mario Pagan, is a steakhouse with reinvented fare and is situated just off the lobby which, in itself, is very welcoming, as is the staff. Stay at one – use both rooftops and if one restaurant is closed, food can be ordered from the other. Both properties are beyond fabulous – colour me impressed.

Rooftop terrace at O:live Boutique Hotel.