
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.

310Guest-House LaVida
Old San Juan
Price was CA $2,032, price is now CA $1,434 per person
CA $1,434
per person
Jul 6 - Jul 13
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to San Juan (SJU)
8.8/10 Excellent! (40 reviews)
Yes there were many shops in this area. No we fid not ho to the National Parks, but we did go to the Fort.
Reviewed on Apr 27, 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 $3,207, price is now CA $2,180 per person
CA $2,180
per person
Jul 19 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to San Juan (SJU)
9/10 Wonderful! (665 reviews)
From the moment we booked this trip, the staff at the hotel were very communicative and very easy to work with. We stayed with them for our 20th wedding anniversary and they were so kind and helpful. They gave us suggestions of places to go and things to do. You could tell they were very proud of the island and what it had to offer. One note: the pool on the 4th floor was what I consider odd. Not really a pool to swim in. Although we did not take advantage of it, the sister property around the corner had a pool available for our use. We did visit the bar and had some of the best drinks, with and without alcohol. It was a very chic vibe. We felt very welcomed and taken care of. I would recommend staying here.
Reviewed on Apr 7, 2026

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 3 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
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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 $5,813, price is now CA $5,199 per person
CA $5,199
per person
Jul 19 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) 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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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 17 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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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 24 hours 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)
Upon arrival you are greeted with valet service for luggage and opening doors. The hotel check in process was smooth. Very clean polite service desk. Provided me with New towel throughout the stay. Clean up service came to clean up on Day 2 of my stay. Plus a brunch bar on the rooftop and a restaurant on the main floor open at 5pm-11pm. I will book again work the money
Reviewed on Apr 28, 2026
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