Montage, Las Ventanas, Chileno Bay, or Four Seasons? Here’s How to Decide
After our recent visit to Four Seasons Cabo Del Sol, and with buzz building around the upcoming Amanvari and the newly opened Park Hyatt Los Cabos, it’s clear that Cabo is stepping further into the spotlight as a premier luxury destination. The challenge? With so many top-tier options, choosing the right resort can feel overwhelming. They all offer five-star service, stunning design, and a strong sense of place. So what really makes one stand out from another?
That’s where we come in. As advisors who have been in the industry since 2006, we’ve experienced these resorts firsthand and guided numerous clients through the decision-making process. This blog isn’t about naming a single “best” resort—it’s about the nuances. The small touches. The details that don’t always show up on a website but can elevate your stay from great to unforgettable.
Whether you’re planning your honeymoon, a milestone celebration, a wellness retreat, or a winter escape, we’re diving into what makes each of these standout properties—Four Seasons Cabo Del Sol, Montage, Chileno Bay, and Las Ventanas al Paraíso—shine in its own way.
Let’s help you find your version of paradise.
Why Choose Cabo for Luxury Travel?
Before we explore the resorts, let’s set the stage for what makes Cabo San Lucas such a coveted destination year after year. Located at the southern tip of Mexico’s Baja California Peninsula, Cabo blends untamed natural beauty with polished luxury. The dramatic meeting point of the Pacific Ocean and the Sea of Cortez is punctuated by the iconic El Arco, while the waters, hailed by Jacques Cousteau as “the aquarium of the world”, host an extraordinary array of marine life.
With over 350 days of sunshine annually, it’s a year-round destination, though the ideal time to visit is from November through May, when the weather is warm but dry and the ocean is calm, perfect for whale watching, golfing, or lounging seaside. For travelers seeking convenient access, nonstop flights to Los Cabos International Airport (SJD) are widely available from major U.S. gateways, including Los Angeles, Dallas, New York, Chicago, Phoenix, and San Francisco, making it an easy escape whether you’re coming from the West Coast or further afield.
What truly sets Cabo apart is its universal appeal. Adventure seekers can explore the desert on ATVs or dive alongside whale sharks, while food lovers can indulge in Baja-Med cuisine and sip mezcal under the stars. Golfers have access to world-renowned courses designed by the likes of Jack Nicklaus and Greg Norman. For families, honeymooners, wellness devotees, and multi-generational travelers alike, Cabo offers an abundance of thoughtfully designed resorts and experiences tailored to every style of travel. The key is finding the right home base—one that aligns with your pace, priorities, and vision of luxury.
Curious about which Cabo resort tops the charts for romance, family-friendliness, dining, and more? Keep reading for our final rankings of Montage Los Cabos, Las Ventanas al Paraíso, Chileno Bay Resort, and Four Seasons Cabo Del Sol!
Four Seasons Resort Los Cabos at Cabo Del Sol
Four Seasons Resort Cabo San Lucas at Cabo Del Sol offers a luxurious blend of hacienda-style charm and modern sophistication, set against the stunning backdrop of Baja California Sur.
You might wonder if Four Seasons already has a Cabo property—yes, in Costa Palmas, an hour north of San Jose del Cabo Airport. The new Four Seasons Cabo del Sol mirrors the vibrant Four Seasons Maui at Wailea, blending luxury with visibility, while Costa Palmas resembles the serene Hualalai.
Guests can relax at three pools—adults-only, family-friendly, and a lap pool—or enjoy beachside lounging and water sports like snorkeling and paddleboarding, though the rocky beach isn’t ideal for casual swimming, but great for experienced swimmers and whale watching. Golfers access the Cabo Del Sol Desert Course (Cove Club is members-only), while the Tierra Mar Spa offers holistic treatments and fitness facilities. Dining shines with eight venues, from Palmerio’s Mediterranean fare to Cayao’s Nikkei fusion, plus casual spots like Mercado and Sora’s ocean-view cocktails. Families benefit from the Kids for All Seasons program, teen adventures, and infant amenities, blending indulgence, adventure, and vibrant cuisine for a dynamic Cabo getaway. Read our full recap here.
This resort is ideal for couples, families with younger children, wellness seekers, and discerning travelers who appreciate elevated cuisine, personalized service, and a relaxed yet stylish beachfront atmosphere.
Montage Los Cabos
Montage Los Cabos offers a refined yet laid-back luxury experience, perfectly set on the shores of Santa Maria Bay—one of Cabo’s best and swimmable beaches. This Virtuoso gem features 122 spacious rooms and suites, plus 52 private residences, all designed in a modern hacienda style that certainly maximizes indoor-outdoor living. Think open-air showers, private terraces, and sweeping ocean views that make it easy to settle in and soak up the surroundings. With three pools, a beautiful Spa Montage, a top-notch fitness and movement studio, a fun kids’ club for ages 5–12, and a scenic 18-hole golf course, there’s truly something for everyone.
Dining here feels intentional and inspired. Marea and Mezcal serve up fresh, locally rooted cuisine with views that rival the menu. One of our favorite spots, though, is Paletas—a playful little market where you’ll find house-made popsicles, great coffee, and a curated selection of local crafts and gifts. We’ve stayed at Montage ourselves, and it’s an easy recommendation for couples on a romantic getaway, families who want beach access without the crowds, and travelers who appreciate relaxed, thoughtful luxury with warm, attentive service.
Chileno Bay Resort & Residences
Part of the Auberge Resorts Collection, Chileno Bay Resort & Residences opened in 2017 and sits right on one of Cabo’s best swimmable beaches in the Tourist Corridor. It has a modern, upbeat vibe that feels stylish yet relaxed, perfect for travelers who love luxury without the formality. It’s also just 15 minutes from Cabo San Lucas, making nightlife and marina access super easy.
Rooms, suites, and villas here are sleek and spacious, with clean lines, bright pops of color, and amazing ocean views. Entry-level rooms start at 600 square feet, and villas can go up to 6,000 square feet with private pools and outdoor kitchens. Most units feature floor-to-ceiling sliding doors that open onto terraces—ideal for seamless indoor-outdoor living.
Dining includes Comal’s elevated Mexican cuisine with ocean views, TnT’s poolside tacos and cocktails, The Market’s grab-and-go snacks, and surprise pop-up dinners. Enjoy three pools (one adults-only infinity), a spa with holistic ocean therapies, a calm swimmable beach for snorkeling and paddleboarding, plus sailing, fishing, and a kids’ club for activities.
Chileno Bay is great for families, friend groups, and couples who want a livelier luxury experience. It’s perfect if you’re looking for five-star service with a fun, social atmosphere.
Rosewood Las Ventanas al Paraíso
Since opening in 1997, Las Ventanas al Paraíso, a Rosewood Resort, has become a legendary escape in Cabo’s Tourist Corridor, just 15 minutes from downtown. Fresh off a renovation, the property combines timeless style with thoughtful updates, making it a favorite for romantic getaways. Its name—“Windows to Paradise”—really does say it all.
With just 83 rooms, suites, and villas, the vibe is intimate and luxurious. Entry-level suites start at a spacious 960 square feet and include rooftop terraces (complete with telescopes), cozy fireplaces, and many have private hot tubs. The Junior Suites and Residences at Las Ventanas feel dated, so we highly suggest booking the Signature Villas with full-size infinity pools and a dedicated host for a luxurious stay and ultimate privacy. Interiors mix local Mexican design with clean, modern touches.
Dining at Las Ventanas is unforgettable, with four venues: Arbol’s Asian-Indian coastal cuisine, Alebrije’s Italian-Mexican fusion, The Sea Grill’s beachside ceviche, and El Restaurante’s traditional Mexican dishes, plus La Botica’s speakeasy jazz bar.
You’ll find four pools (including a jaw-dropping infinity one), a 13,000-square-foot spa with dreamy treatments like moonlight massages, and curated off-property experiences like whale watching and private yacht outings. While the beach here isn’t swimmable, the resort more than makes up for it with service and creativity. Their “Romance Department” helps guests plan everything from surprise proposals to vow renewals, and kids are well looked after with the Rosewood Explorers program.
Las Ventanas is ideal for couples chasing a romantic escape, travelers who value world-class service, and anyone who loves a boutique feel over beach access.
Comparing Montage, Las Ventanas, Chileno, or Four Seasons: Which Resort Wins?
Location
- Four Seasons: gated community of Cabo Del Sol along the Baja Peninsula’s Golden Corridor, 15 minutes from Cabo San Lucas
- Montage: Santa Maria Bay, 20 minutes from both towns.
- Chileno Bay: Tourist Corridor, 15 minutes from Cabo San Lucas.
- Las Ventanas: Tourist Corridor, 15 minutes from Cabo San Lucas.
Winner: Four Seasons Cabo Del Sol wins the location category with its ideal mix of exclusivity and accessibility, set in the private Cabo Del Sol community just 10–15 minutes from Cabo San Lucas for easy outings (e.g., boat trips to El Arco, dining) and 20 minutes from San José del Cabo for cultural experiences. The resort’s overall location advantages—proximity to attractions, gated community vibe, and family-friendly amenities—make it a standout.
Beach Access
- Four Seasons: Swimmable for strong swimmers, navigating around rocky conditions.
- Montage: Swimmable, protected cove.
- Chileno Bay: Swimmable, lively beach.
- Las Ventanas: Non-swimmable, strong currents.
Winner: Montage Los Cabos wins the swimmable beach category with its consistently safe, swimmable beach at Santa Maria Cove, a protected cove with calm waters and one of Cabo’s rare spots for ocean swimming. Its soft sand, clear waters, and spaciousness make it ideal for families, offering easy snorkeling and water sports without the rocky challenges of Four Seasons or the narrower, sometimes crowded feel of Chileno Bay. Chileno Bay is a close second with its swimmable beach and snorkeling, but Montage’s larger, less crowded beach gives it the edge. Four Seasons Cabo Del Sol falls short due to inconsistent swimmability, and Las Ventanas is out of contention with its non-swimmable beach.
Dining
- Four Seasons: Diverse, upscale, Mexican-inspired.
- Montage: Creative, Mediterranean flair.
- Chileno Bay: Vibrant, modern Mexican.
- Las Ventanas: Innovative, romantic, diverse.
Winner: Las Ventanas al Paraíso wins the dining category for its exceptional variety, innovative cuisine, and diverse ambiance. With four venues—Arbol’s Asian-Indian coastal fusion, Alebrije’s Italian-Mexican experience, The Sea Grill’s beachside grilled fare, and El Restaurante’s traditional Mexican dishes—it offers a culinary range unmatched by the others. The addition of La Botica’s speakeasy bar with live jazz elevates the experience further. While less family-focused, the quality and creativity make it a standout.
Family-Friendliness
- Four Seasons: Kids’ club, teen lounge, watersport activities
- Montage: Swimmable beach, kids’ club, diverse activities.
- Chileno Bay: Swimmable beach, Kids’ club, great for teens, social/active vibe.
- Las Ventanas: Explorers program, less focus on families.
Winner: Four Seasons Cabo Del Sol wins the family-friendliness category for its comprehensive family-oriented offerings. The Kids For All Seasons and Baja 360° teen adventures provide tailored activities, while La Plaza Mágica’s Friday events (mariachi, local treats) create immersive family experiences. The resort’s modern hacienda vibe, swimmable beach (despite challenges), golf, and spacious suites make it welcoming for all ages. Chileno Bay is a close second with its teen club and swimmable beach, but Four Seasons’ broader range of activities gives it the edge. Montage offers a swimmable beach but lacks teen programs, and Las Ventanas prioritizes couples over families.
Romance
- Four Seasons: Intimate oceanfront villas.
- Montage: Serene beachfront romance and vibrant people-watching.
- Chileno Bay: Intimate dining options.
- Las Ventanas: Two words – Romance Department.
Winner: Las Ventanas al Paraíso wins the romance category for its unparalleled focus on couples. Its secluded ambiance, dedicated Department of Romance curating bespoke experiences (e.g., private beach dinners, fireworks display, stargazing), and magical dining options (Arbol, La Botica) create an intimate escape. Suites with private plunge pools, rooftop terraces, and telescopes further enhance the romantic experience. Montage and Chileno Bay offer romantic elements but are overshadowed by family-friendly vibes, while Four Seasons prioritizes families over couples. Las Ventanas is the clear choice for a romantic getaway in Cabo.
Final Thoughts: Your Cabo Escape Starts Here
Choosing between Cabo’s top resorts is more than just a matter of amenities—it’s about curating an experience that aligns with your travel style. That’s where we come in. At Ourisman Travel, we don’t just know these resorts—we’ve stayed at them, built personal relationships with the teams, and experienced every detail firsthand. As a Four Seasons Preferred Partner, Rosewood Elite, and Virtuoso member, we’re able to elevate your stay with complimentary daily breakfast, upgrade priority, resort credits, personalized welcome amenities, and VIP status, at no additional cost to you. Whether it’s the best room for a sunset soak or where to find the perfect mezcal cocktail, we’re here to guide you with insider insight.
Cabo is a destination filled with magic, and these four resorts each offer a distinct version of it. Four Seasons blends contemporary luxury with beachside ease, Montage delivers relaxed elegance on a swimmable bay, Chileno Bay buzzes with youthful energy and modern style, and Las Ventanas is a dream for romantics and privacy seekers. No two travelers are alike, and we specialize in matching you with the resort that fits your vision best. Craving a private villa? We have a blog for that, too. Let us take care of the details so you can focus on what matters most—unwinding in paradise. Fill out a Travel Request Form to get started.
