Roosevelt Roads Cheap Vacations
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Flight and Cheap hotel deals in Roosevelt Roads
Price found within the past 48 hours. Click for updated prices.
Ocean Breeze Villa
San Juan Antiguo
Price was CA $2,053, price is now CA $1,442 per person
CA $1,442
per person
Jun 6 - Jun 12
found 9 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to San Juan (SJU)
8.8/10 Excellent! (12 reviews)
The dryer didn’t work. The room was dry but we had to keep the AC on, which was directly above the bed and made it difficult to sleep. The pool is kind of gross.
Reviewed on Apr 18, 2026
Hotel Puerto Valdes
San Juan Antiguo
Price was CA $2,824, price is now CA $1,747 per person
CA $1,747
per person
Jun 3 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to San Juan (SJU)
8.8/10 Excellent! (636 reviews)
The room is spacious and nice. There were 3 of us and the sleeper couch was not comfortable at all.
The water takes a while to warm up so the shower was a little on the chilly side.
The jacuzzi was dirty and didn't use which was a disappointment.
The shuttle was out of service. The Lyft was reasonable $5 to $10 for 3 of us to get to Old San Juan and the cruise port.
The staff was very friendly and helpful. They let us keep our luggage there after check out. They were there late for check in as well.
Reviewed on Apr 23, 2026
Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)
Condado
Price was CA $3,346, price is now CA $2,367 per person
CA $2,367
per person
Jul 20 - Jul 27
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
9/10 Wonderful! (665 reviews)
The stay was totally Amazing! The stunning decor, professional and friendly Staff, access to national park and Old San Juan were exceptional!! Without knowing the trip was to celebrate our wedding anniversary, the Staff and local community helped to make this a truly memorable experience. My wife and I have Only nice things to say about this report hotel.
Reviewed on Apr 28, 2026
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Price found within the past 48 hours. Click for updated prices.
Fairmont El San Juan Villa Experience
Isla Verde
Price was CA $3,900, price is now CA $2,847 per person
CA $2,847
per person
Jul 19 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to San Juan (SJU)
7.6/10 Good! (140 reviews)
The beach was nice but the lounge chair cushions were filthy …. The casino customer service was mediocre
Reviewed on Mar 24, 2026
Four Seasons Resort and Residence Puerto Rico
Herreras
Price was CA $4,208, price is now CA $3,921 per person
CA $3,921
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
10/10 Exceptional! (11 reviews)
Service. It’s clear everyone got the memo. David greeted us at the bell stand as we arrived and was ready to be helpful whenever we needed anything. Housekeeping was awesome, Jesus made the best Negronis at the Casa Grande bar. Breakfast staff, particularly Noel, were super friendly and helpful with local tips and suggestions - always a great way to start each day
Reviewed on Mar 1, 2026
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Price found within the past 48 hours. Click for updated prices.
Hotel Puerto Valdes
San Juan Antiguo
Price was CA $1,925, price is now CA $1,398 per person
CA $1,398
per person
Jun 24 - Jun 27
found 23 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to San Juan (SJU)
8.8/10 Excellent! (636 reviews)
The room is spacious and nice. There were 3 of us and the sleeper couch was not comfortable at all.
The water takes a while to warm up so the shower was a little on the chilly side.
The jacuzzi was dirty and didn't use which was a disappointment.
The shuttle was out of service. The Lyft was reasonable $5 to $10 for 3 of us to get to Old San Juan and the cruise port.
The staff was very friendly and helpful. They let us keep our luggage there after check out. They were there late for check in as well.
Reviewed on Apr 23, 2026
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Price found within the past 48 hours. Click for updated prices.
Isla Verde Beachfront Retreat With Parking
Isla Verde
Price was CA $2,616, price is now CA $1,570 per person
CA $1,570
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
10/10 Exceptional! (1 review)
The room was clean and spacious!
Reviewed on Mar 24, 2026
OLV Fifty Five - Adults Only
Condado
Price was CA $2,228, price is now CA $1,556 per person
CA $1,556
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to San Juan (SJU)
8.6/10 Excellent! (647 reviews)
It was overall just a great experience, the staff was so friendly, and helped us whenever we needed it. I would recommend to anyone who is is staying in new San Juan.
Reviewed on Apr 28, 2026
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