I stayed at the Wyndham El Conquistador in Fajardo, Puerto Rico (about 30 miles from San Juan). It's a bit of a controversial hotel in the eyes of many. It's a huge resort -- 900 or so rooms. My general take is most complaints stem from room choice or being surprised at the price of food. A little careful planning, combined with realizing the food at resorts are expensive (think eating out in Manhattan for every meal), and this place can be truly outstanding.
It's phenomenally beautiful. The grounds are great. But some of the rooms and furniture show their wear.
This property also has a five-diamond resort within the larger complex called Las Casitas Village. It gets lots of good press, and is known for hosting J. Lo and Ricky Martin.
My stay was complimentary, direct-billed to Wyndham, the result of winning a door prize at the Freddie Awards.
I didn't get a Casita, but I did have a junior suite on the Marina with a direct ocean view and a huge balcony. That struck me as being just as good as having a Casita, just without the butler service. My advice would be to book the deluxe ocean view and request the Marina level. Join Wyndham's ByRequest program and then either request and hope for a room upgrade, or ask the ByRequest Manager about buying an upgrade to a room like I had (1208, right at the very far end of the Marina).
Aside from the Casitas, the resort is broken up into four areas: the Vista and Brisas wings of the main hotel, Las Olas Village half-way between the main hotel and the ocean level, and the Marina right on the water.
When you land in San Juan, you'll likely see an El Conquistador staff member and a Westin Rio Mar staff member waiting at baggage claim. The El Conquistador staffer will walk you over to their airport transfer desk. Transportation is $60 roundtrip per person. A cab runs about $75, so if there are more than two people in your party and your rate doesn't include transfers, get your own cab. Otherwise go with the hotel's shuttle. It is a van with a VCR (on the return we were shown old Hooneymooners episodes taped off television in the 1980s) and a bar (complimentary drinks).
When I arrived the van wasn't at the airport, so they had us wait for about 20 minutes while they gathered up some other folks coming in on another flight and then stuck us in a shared cab.
I noticed that the other folks on my shuttle were ahead of me in line to checkin and I saw they got placed in the main hotel. One had a confirmation printed with a hotels.com logo. That person seemed to get a pretty standard room, assigned to them at checkin. I got to the front of the line and the clerk saw that I had been preblocked in a room that I was ultimately very pleased with. My stay was arranged directly by Wyndham's Vice President for the ByRequest program, and the ByRequest manager picked an appropriate room (and checked on me more than once during my stay).
On the way to the room I walked through the main hotel and to the funicular, the "elevator" on a track that takes you down from the main property (Las Vistas and Las Brisas) to the middle level (Las Olas) and down to the Marina. There are two funiculars -- one that's an express straight to the marina and one that stops at the Las Olas level.
Once down at the marina we walked to the far end where we were shown a secluded room. Despite the size of the property, it was very quiet at the far end of the Marina and almost secluded. The room was large. The bathroom was huge. There was a pool that was seldom used right next to the room. The bed was very comfortable.
But the real benefit was the balcony. It was huge and had a direct ocean view, with the pool off to the right (and a mountain behind it). Absolutely stunning. My favorite part of my long weekend was just sitting out on the balcony and relaxing.
In the morning I went to breakfast at the buffet restaurant. For a resort with so many food options (more than a dozen) they're lacking a bit at breakfast. The Casitas have their own complimentary continental breakfast, but for the rest of us there's the Cafe Caribe in the main hotel, the Las Brisas restaurant which has only a buffet (but stunning view) and more or less just room service as the other option. On future days I just popped up to the little bakery in the hotel first thing in the morning for a mocha (I hate in-room coffee) and then ordered room service which I enjoyed out on the balcony.
Next I went out to Palomino Island, the resort's leased private island which is the site of the beach. Plenty of chairs and shade and good bar/cafe service as well as watersports and horseback riding. The boat leaves every half hour from 9-3 and takes about 20 minutes to get there.
Came back to the room and made dinner reservations at the seafood restaurant at the Marina. The menu wasn't all that exciting, and didn't live up to its billing for Carribean-influenced cuisine. Everything was offered either with rice or truffled mashed potatos. So I made a meal of soup, two appetizers, and dessert which was really excellent.
The next night I had dinner at the teppan yaki restaurant, which is a bit of a factory and the whole affair was over in 45 minutes or so. That restaurant also offers sushi and chinese -- the chinese I ordered the following night as room service and enjoyed it on the balcony.
The rooms outside of the Casitas aren't quite as finely appointed. The archetypical example would be that the toilet paper was Scott tissue. The Spa phone line rings off the hook... if I were in a Casita I would have had the butler make my appointment for me. As it is, I should have had the ByRequest desk do it. Instead I waited 20 minutes to schedule a massage. But the Spa itself was quite nice.
In the end, the resort had everything I wanted. The weather was perfect and I was perfectly located on the property. My balcony absolutely made the trip. The grounds are huge, and with such a large resort comes an enormous number of options. The place is really a self-contained city (there's even a Sunglass Hut franchise on the property, along with several other shops). It's far away from anywhere one would want to go, but there's an Avis rent a car on property and several hotel sponsored excursions.