
Roosevelt Roads Adventure Vacations
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Flight and Adventure hotel deals in Roosevelt Roads
Price found within the past 48 hours. Click for updated prices.

Hotel Puerto Valdes
San Juan Antiguo
Price was CA $2,372, price is now CA $1,540 per person
CA $1,540
per person
Aug 12 - Aug 19
found 22 hours ago
Roundtrip flight included
Edmonton (YEG) to San Juan (SJU)
8.8/10 Excellent! (662 reviews)
Staff were wonderful. So helpful and gave great suggestions on things to do and places to eat! Clean and well stocked kitchen. Nice rooftop area with hot tub. The hot tub could use an update or just cleaning. A few of the floor planks were loose and sticking up but this didn’t really cause any issues. Could use better pillows and maybe directions on how to use the coffee maker. Other than that would definitely recommend staying here.
Reviewed on May 20, 2026


SELVA by DW
Pitahaya
Price was CA $7,428, price is now CA $5,050 per person
CA $5,050
per person
Aug 14 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
10/10 Exceptional! (2 reviews)
This was our 1st experience in PR. This house was AMAZINGLY beautiful and really show cased the outdoor space!! It was VERY clean, high quality linens. Had a nice cook space. The space it self was STUNNING!! The outdoor space was PERFECTION!!!! We actually booked for the lounge net area, and it did not disappoint!!
**Downfalls [we understand that somethings are out of anyones control so more of a FYI]
-There was nothing "comfy" about the house. It is all cement: bed frame, entire bathroom so alot of sharp edges, the sitting area had maybe 3 inch foam with a canvas topper. When the floor had ANY moisture and you are bare foot YOU WILL FALL! In the master bath between the mirrors have open spaces straight to outside no glass or screen. Which allows natural to come inside the house. Lizards and frogs find there way inside daily. The doors are super heavy, difficult to open but again its a giant piece of glass of course its heavy. At no time did we feel unsafe, with that being said you are literally on top of a mountain alone. And thats scary to think about.
Lets talk about the road. I had never been to PR so i was not aware of how tight and tiny the roads are. The drive to the house is TIGHT & STEEP!! Some areas are so steep our tires would slip while going up the incline! Only rent a SUV, our 4 door Nissan HARDLY made it, returned it for a SUV our 2nd day. Roads are unmarked and HARD to see the edge. The cell service on the way comes in an out as you go, dont rely on it.
Reviewed on Sep 19, 2025

Ocean Breeze Villa
San Juan Antiguo
Price was CA $2,937, price is now CA $2,028 per person
CA $2,028
per person
Aug 12 - Aug 19
found 22 hours ago
Roundtrip flight included
Edmonton (YEG) to San Juan (SJU)
8.8/10 Excellent! (12 reviews)
Clean, communicative host, great location. All you need.
Reviewed on May 21, 2026

PAZ by DW
Santurce
Price was CA $2,825, price is now CA $1,954 per person
CA $1,954
per person
Aug 14 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
9/10 Wonderful! (26 reviews)
Beautiful room. Every part of the room was my favorite. Customer service was amazing as well.
Reviewed on Feb 12, 2026
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Price found within the past 48 hours. Click for updated prices.

Fairmont El San Juan Hotel
Isla Verde
Price was CA $2,381, price is now CA $1,828 per person
CA $1,828
per person
Aug 12 - Aug 19
found 22 hours ago
Roundtrip flight included
Edmonton (YEG) to San Juan (SJU)
8.6/10 Excellent! (2,093 reviews)
Love the breakfast buffet, worth every penny
Reviewed on May 22, 2026


Fairmont El San Juan Villa Experience
Isla Verde
Price was CA $3,465, price is now CA $2,454 per person
CA $2,454
per person
Jul 2 - Jul 7
found 23 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to San Juan (SJU)
7.6/10 Good! (143 reviews)
Room had some stains on the carpet that h
Reviewed on May 20, 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 $1,843, price is now CA $1,226 per person
CA $1,226
per person
Jul 2 - Jul 5
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
8.8/10 Excellent! (662 reviews)
Staff were wonderful. So helpful and gave great suggestions on things to do and places to eat! Clean and well stocked kitchen. Nice rooftop area with hot tub. The hot tub could use an update or just cleaning. A few of the floor planks were loose and sticking up but this didn’t really cause any issues. Could use better pillows and maybe directions on how to use the coffee maker. Other than that would definitely recommend staying here.
Reviewed on May 20, 2026

Hotel El Convento
Old San Juan
Price was CA $1,831, price is now CA $1,372 per person
CA $1,372
per person
Jul 2 - Jul 5
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
9/10 Wonderful! (1,010 reviews)
El Convento is a wonderful boutique hotel filled with old world charm. The staff is friendly and accommodating. It’s a great spot to stay if you want to explore historic San Juan.
Reviewed on May 21, 2026

OLV Fifty Five - Adults Only
Condado
Price was CA $1,826, price is now CA $1,382 per person
CA $1,382
per person
Aug 7 - Aug 10
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to San Juan (SJU)
8.6/10 Excellent! (664 reviews)
Place is excellent! Staff amazing and location 5 Stars
Reviewed on May 20, 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 $2,252, price is now CA $1,296 per person
CA $1,296
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to San Juan (SJU)
10/10 Exceptional! (1 review)
The room was clean and spacious!
Reviewed on Mar 24, 2026


Villa Tropicana
Cangrejo Arriba
Price was CA $2,742, price is now CA $1,809 per person
CA $1,809
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to San Juan (SJU)
10/10 Exceptional! (2 reviews)
This house is truly a hidden gem. When I first read the description, I thought, “Okay, just a house that sleeps 14,” but once I saw the photos, I was amazed at how spacious it actually is. The home is a two-floor apartment, with both the top and bottom floors fully equipped—each has a full bathroom, stove, and everything you could possibly need for a comfortable stay.
The hostess was incredibly attentive and responsive, always quick to reply. The house itself is BIG, beautiful, and exceptionally clean. Everything was well maintained and thoughtfully set up. I would absolutely stay here again without hesitation.
On top of that, my sister accidentally left her medication behind, and the hosts were kind enough to hold onto it for us until we returned from our cruise. That level of care really meant a lot.
Highly recommended!
Reviewed on Dec 22, 2025
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