Upside Boca Resort

Pros

• The rooms are nice and the facilities are really nice.
• The service is amazing and the staff are really friendly.
• The pool area is exquisite.
• The property itself is stunning.
• The food exceeded expectations and the setting is wonderful.
• The water taxi provides a convenient and pleasant way to access the beach property.
• The pools and beaches are idyllic spots to unwind.
• The spa experience was top notch, one of the best.
• The resort is absolutely amazing, clean, and comfortable.
• The staff are phenomenal and very helpful.

Cons

• The hallway doors are extremely loud when closed, causing a banging noise that disturbs guests.
• There is a 20% gratuity added to every bill, including purchases like cigars.
• The pool is not accessible to visitors; access is restricted to hotel guests and members.
• The bed is extremely firm and the pillows are flat, with foam pillows not reliably provided.
• Food and drinks are overpriced, with resort-style pricing for basic items.
• Parking costs around $60 per day with mandatory valet, and there is also a $60 per day resort fee.
• Pools can be closed for maintenance without timely communication or suitable alternatives.
• Front desk staff and management occasionally show a lack of knowledge or responsiveness, with miscommunication between staff.
• The air conditioning can break, leading to late-night repairs and little proactive follow-up from staff.

Review

The Cloister at Boca Raton draws a vivid portrait of a grand, old-world resort that pairs flawless grounds and architecture with a wide spectrum of guest experiences. Reviewers consistently praise the setting: manicured landscapes, lush gardens, elegant interiors, and a design that feels both historic and luxe. The property makes a striking impression from the moment you arrive, with features like a water taxi to the beach club and a sense of Downton Abbey-like grandeur in the common spaces. Many guests highlight the overall ambiance as a major draw, describing the resort as beautiful, tranquil, and visually impressive. The grounds and facilities are repeatedly deemed top-tier, and even those who quarrel with other aspects still concede the property's beauty and scale.

A running thread across many accounts is the service, which most guests regard as a high point. Hospitality staff are described as friendly, welcoming, and helpful, with numerous mentions of staff going above and beyond. Several guests single out particular team members for memorable, caring service - one guest specifically praises Allan R. for a warm check-in experience. Generally, the sentiment is that the staff strive to create a welcoming atmosphere and handle requests with grace. That said, there are a few exceptions: a handful of reviews point to inconsistent experiences, such as an overnight front desk interaction that left a negative impression or one-off lapses during busy or transitional periods. Some reviewers also note that the resort's large size and seasonal fluctuations can lead to uneven service levels at times, underscoring that while the staff is often excellent, reliability can vary.

The guest rooms and their presentation are another frequent topic. For many, the Cloister rooms are a standout, described as beautifully decorated with thoughtful touches - dog-friendly accommodations, high-end bathrooms with dual vanities and multi-head showers, spacious layouts, and soothing views of gardens or oasis spaces. The appearance of the rooms and the overall comfort level are praised, contributing to a strong sense of staying in a refined, elegant retreat. Yet not all feedback aligns on the bed and bedding: several guests report an extremely firm bed and flat pillows, with some noting that foam pillows - while offered - were not readily delivered despite requests. A few reviews mention room size feeling compact for the price point, and a separate note about occasional HVAC or maintenance hiccups reminds readers that, in places, older infrastructure can show its age.

Dining experiences present a mosaic of high-quality moments and sobering reminders about value. Guests recount positive meals at on-site options such as Sadelle's and Marisol, with praise aimed at food quality and overall dining atmosphere, even if service can lag at times. In contrast, some guests describe food and drinks as overpriced for a resort of this caliber, calling out specific items like tacos and drinks with price points that leave a sour taste. Harborside and other outlets receive similar mixed commentary: the dishes and flavors are often well-received, while the pace of service or perceived value varies. One recurring theme centers on the price point and the notable resort-level pricing across the board, including fees that stack on top of the base rate.

Fees and pricing emerge as a significant thread of guest sentiment, coloring overall satisfaction for many. The resort's financials - valet parking around 60 per day, a separate 60 per day resort fee, and mandatory gratuities - are frequently cited as a surprise or disappointment. Several guests report discovering resort and parking fees after booking through third parties, or after being told that programs included in third-party rates may not apply. The contrast between the resort's polished presentation and the reality of added costs is a common point of friction, with some responders advising that the total cost can feel distinctly upscale and expensive, while others maintain they perceived good value given the setting and amenities.

The pool, beach, and spa facilities sit at the heart of the resort's allure - but with caveats that reflect the scale and operation of a large luxury property. The pool area is often described as exquisite and worth the attention, with the water taxi to the beach club adding a unique, enjoyable element. However, there are notable complaints about accessibility and consistency: reports of pools being closed for maintenance, confusion around moving guests to alternate beach club access, and frustrations when management's response to issues feels slow or non-existent. The spa regularly earns high marks as a standout experience, often described as top-notch and one of the best in the area, reinforcing the resort's reputation for quality treatment and relaxation.

Overall impressions run the gamut from ecstatic praise to measured restraint. Some guests declare the Cloister to be among the best hotel experiences they've had, with reviews that rate it well above many competitors and even invite comparisons to other luxury landmarks. A number of visitors are thrilled by the architecture, the ambience, and the attentive staff, promising to return. Others acknowledge the resort's undeniable beauty and superb facilities while flagging price sensitivity, maintenance quirks, and service inconsistencies that temper their enthusiasm. A few even describe the property as a must-visit for its visual splendor and refined atmosphere, while admitting that management responsiveness and value calculus require a more balanced approach to fees and ongoing maintenance.

In sum, the Boca Raton Cloister stands as a large, aspirational luxury resort that delivers on visual grandeur, gardens, spa experiences, and many staff interactions, while reminding guests that premium hotels come with premium costs and occasional operational hiccups. The property's beauty, the distinctive on-site dining and spa experiences, and the dependable warmth of many team members combine to create memories worth savoring, with the caveat that travelers should be prepared for higher-than-average resort fees, parking charges, and a few mechanical or service-related rough edges that can pop up during peak times or while renovations are underway. For many visitors, the ensemble - rooms that feel grand and well-appointed, a setting that beguiles, and staff who genuinely aim to please - outweighs the potential drawbacks, making this a destination they could happily return to, again and again.

Located in the bustling city of Boca Raton, this area offers a variety of amenities for seniors looking to settle down in a vibrant community. With multiple restaurants nearby such as Denny's and Farmer's Table, as well as healthcare options including Baptist Health Marcus Neuroscience Institute and Aker Kasten Eye Center, residents can easily access essential services. Additionally, the presence of cafes like Starbucks provides convenient spots for socializing with friends or enjoying a quiet moment alone. Nearby pharmacies like Walgreens and CVS Pharmacy ensure easy access to medications. Furthermore, places of worship such as B'nai Torah Congregation cater to spiritual needs while parks like Mizner Bark Dog Park offer opportunities for leisurely walks in nature. Overall, this area provides a balanced mix of dining options, healthcare facilities, recreational spaces, and cultural amenities for seniors seeking an active and engaging lifestyle in Boca Raton.

Restaurants

• Denny's (0.3 miles)
• Shake Shack (1.3 miles)
• Farmer's Table (1.5 miles)
• Laspada's Original Hoagies (1.6 miles)
• The Cheesecake Factory (1.8 miles)
• Saiko-i Sushi Lounge & Hibachi (1.8 miles)
• Ichiyami (1.8 miles)

Physicians

• Baptist Health Marcus Neuroscience Institute | Boca Raton (1.1 miles)
• Boca General & Family Medicine (1.2 miles)
• Retina Group of Florida (1.3 miles)
• Aker Kasten Eye Center (1.8 miles)
• Steiger Facial Plastic Surgery: Dr. Jacob D. Steiger (2 miles)
• RevaMed Primary Care Associates (2.6 miles)
• Dermatology of Boca (3.8 miles)

Hospitals

• Christine E. Lynn Womens Health Center (1.2 miles)
• West Boca Medical Center (5.4 miles)

Cafes

• Starbucks (1.3 miles)
• Starbucks (1.6 miles)
• Starbucks (1.8 miles)
• Starbucks (3 miles)
• Starbucks (3.3 miles)
• The Seed (3.3 miles)
• Starbucks (6.4 miles)

Pharmacies

• Walgreens (1.4 miles)
• CVS Pharmacy (1.4 miles)
• Walgreens (1.7 miles)
• CVS Pharmacy (1.8 miles)
• CVS Pharmacy (2.5 miles)
• CVS Pharmacy (2.6 miles)
• Winn-Dixie (2.6 miles)

Places of Worship

• B'nai Torah Congregation (2 miles)
• Congregation B'nai Israel (3.4 miles)

Theaters

• Cinemark Premier (2.1 miles)
• Regal Shadowood (5.7 miles)

Parks

• Mizner Bark Dog Park (2.3 miles)
• Boca Tierra Park (3.4 miles)
• Spanish River Park (4.7 miles)
• Powderhorn Park (7.2 miles)
• Terramar Park (7.6 miles)