8 bedrooms
•
14 beds
•
6 bathrooms
•
24 guests
•
New
•
4018 sq. ft.
Operated by a Wander partner
Trusted operators, vetted by Wander
🌺 The Big Kahuna | Two Luxe Villas + Double the Fun Steps from Siesta Key Beach
đź’– Why You'll Love This Home
More space. More privacy. More memories. The Big Kahuna brings two luxury homes together under one roof for the ultimate Siesta Key experience. Just a 2-minute stroll to the white sands of Siesta Key Beach, this rare dual-unit retreat offers 8 bedrooms, 2 heated pools, and an unbeatable location in the vibrant heart of Siesta Key Village.
👨‍👩‍👧 Perfect For
Multi-family vacations, wedding parties, or large groups wanting separate spaces with shared outdoor fun—all just steps from the beach and dining.
🎞️ Imagine This
Picture your entire crew—24 guests strong—spread across two bright, beach-inspired homes. Each morning, gather on the balconies with coffee while the kids splash in two private pools below. Walk barefoot to the beach for a day of sun and surf, then head back for poolside cocktails in your private cabanas. When evening falls, some of you cook up seafood feasts in one full kitchen while others mix drinks in the other. Dine alfresco, laugh late into the night, and repeat it all tomorrow—because The Big Kahuna is built for togetherness without compromising personal space.
🛌 Where You'll Sleep
Casa Ohana (2nd Floor):
• Bedroom 1: King Bed + Twin Chair Sleeper, Ensuite Bath, TV
• Bedroom 2: King Bed, Shared Bath, TV
• Bedroom 3: King Bed, Shared Bath, TV
• Bedroom 4: Queen Bed + Twin Rollaway, Shared Bath, TV
• Extra: Queen Sleeper Sofa in Living Room
Casa Mahalo (3rd Floor):
• Bedroom 1: King Bed + Twin Chair Sleeper, Ensuite Bath, TV
• Bedroom 2: King Bed, Shared Bath, TV
• Bedroom 3: King Bed, Shared Bath, TV
• Bedroom 4: Queen Bed + Twin Rollaway, Shared Bath, TV
• Extra: Queen Sleeper Sofa in Living Room
Total: 8 Bedrooms | 6 Bathrooms | Sleeps up to 24
đź“Ť Explore the Area
• 0.1 miles (2-minute walk) to Siesta Key Beach
• Steps to Siesta Key Village—restaurants, bars, ice cream shops, and boutiques
• 4.5 miles to Downtown Sarasota's cultural and dining scene
• 6.5 miles to St. Armands Circle for upscale shopping and coastal charm
No cars needed—everything is a short walk or bike ride away.
⌛ Don't Wait
Homes this size and location are rare! The Big Kahuna includes our CottageClean™ promise, featuring a 6-hour deep clean and 35-point inspection for a like-new experience.
Need to Know: The Big Kahuna combines two separate units (Casa Ohana + Casa Mahalo) under one roof. Each unit has its own entrance and private interior space. Four garage spaces total (two per unit) on the 1st floor. Two private heated pools for exclusive guest use (heated Nov 15 – Apr 15). This property requires stair access. Contact us for alternatives if mobility is a concern.
Living Room
1 queen sofa
Bedroom 1
1 king bed
Bedroom 2
1 king bed
Bedroom 3
1 king bed
Bedroom 4
1 queen bed
Living Room 2
1 queen sofa
Bedroom 5
1 king bed
Bedroom 6
1 king bed
Bedroom 7
1 king bed
Bedroom 8
1 queen bed
Living Room
1 queen sofa
Bedroom 1
1 king bed
Bedroom 2
1 king bed
Bedroom 3
1 king bed
Bedroom 4
1 queen bed
Living Room 2
1 queen sofa
Bedroom 5
1 king bed
Bedroom 6
1 king bed
Bedroom 7
1 king bed
Bedroom 8
1 queen bed
Be the first to review this place.
Siesta Key, FL 34242, US
Siesta Key, FL, USSt. Armands Circle is a vibrant dining hub in Sarasota featuring an eclectic mix of restaurants ranging from upscale French and Spanish cuisine to fresh seafood and casual island-inspired fare, all set within a charming shopping district that blends cultural sophistication with laid-back tropical atmosphere.
Walt's Fish Market is a legendary Sarasota seafood destination where the fish you eat was literally caught in the Gulf the day you buy it, offering fresh catches prepared daily by Chef Rigo in a charming, laid-back tiki bar atmosphere that's been a local favorite for over a century.
Marina Jack is Sarasota's premier waterfront dining destination, offering three distinct venues from casual beachside patio dining to an upscale second-floor dining room with award-winning wines and fresh seafood, all featuring stunning bay views and live entertainment.
Dry Dock Waterfront Grill offers fresh, expertly prepared seafood and classic American dishes in a relaxed yet polished waterfront setting, featuring panoramic views of Sarasota Bay and a welcoming dockside patio. It's a local favorite for its vibrant flavors and scenic ambiance.
Columbia Restaurant, Florida’s oldest and the world’s largest Spanish restaurant, offers authentic Spanish-Cuban cuisine in a historic setting with vibrant flamenco shows and an extensive wine collection, creating a lively and elegant dining experience in Tampa’s Ybor City.
Owen's Fish Camp is a beloved Sarasota seafood destination nestled under a historic banyan tree, serving fresh Gulf catches and Southern classics in a casual, laid-back atmosphere that captures the essence of old Florida living. With its lively bar scene, live music, and warm hospitality, it's the perfect spot for an unforgettable meal among family and friends.
Siesta Key Oyster Bar (SKOB) is a laid-back beachfront hotspot in Siesta Key Village serving fresh oysters, award-winning wings, and creative seafood with a fun, tropical atmosphere complete with dollar bills adorning the ceiling and live music nightly.
Connors Steak & Seafood serves premium aged steaks and fresh seafood grilled over wood fires for a unique flavor. Enjoy upscale dining with excellent service, a lively bar, and a menu that satisfies every craving.
Captain Curt's Crab & Oyster Bar is a beloved Old Florida seafood restaurant on Siesta Key famous for its award-winning clam chowder and fresh catch, offering a relaxed island atmosphere with indoor and outdoor dining, live music, and a welcoming family-friendly vibe that keeps locals and visitors coming back.
Detwiler's Farm Market offers a vibrant farm-to-table experience with fresh produce, an old-fashioned butcher shop, Amish-style deli meats, a bakery, and an ice cream shop, all wrapped in a warm, hometown atmosphere. It’s a one-stop destination for quality, fresh food at great prices.
Marina Jack is Sarasota's premier waterfront dining destination offering three distinct venues—from the casual, breezy Blue Sunshine Patio to the sophisticated Dining Room—all serving exceptional seafood, steaks, and pasta with stunning bay views and live entertainment.
St. Armands Circle offers a vibrant dining scene with a variety of options, from fresh Gulf seafood and bold, creative dishes to Mediterranean and island-inspired flavors, all set in inviting atmospheres ranging from casual tropical vibes to elegant, panoramic beach views. Whether you crave Spanish tapas, Italian classics, or innovative coastal fare, this cultural hub delivers memorable meals with friendly service.
Walt's Fish Market Restaurant in Sarasota offers the freshest seafood caught daily, served in a relaxed, tropical setting featuring a lively tiki bar and live music, blending a century-old family tradition with modern, flavorful dishes.
Dry Dock Waterfront Grill is a polished-casual waterfront dining destination on Longboat Key renowned for its award-winning fresh grouper sandwich and Gulf seafood specialties, offering panoramic views of Sarasota Bay from both its upstairs dining room and dockside patio.
Columbia Restaurant is Florida's oldest and the world's largest Spanish restaurant, serving authentic Cuban and Spanish cuisine since 1905 in historic Ybor City with nightly Flamenco performances, elegant dining rooms, and an internationally acclaimed wine collection.
Owen's Fish Camp in downtown Sarasota serves fresh, Southern-style seafood in a relaxed, historic setting with a lively bar scene and scenic outdoor seating.
Siesta Key Oyster Bar offers a lively, beachy vibe with fresh seafood, award-winning wings, and cold drinks, all served in a fun, tropical setting with live music and friendly service. It’s the perfect spot to enjoy island spirit and great food in Siesta Key Village.
Connors Steak & Seafood is an upscale steakhouse specializing in premium aged steaks and fresh seafood, expertly prepared over wood-fired grills to deliver exceptional flavor in a refined dining atmosphere. With multiple locations across the Southeast and consistent recognition as a top-rated restaurant, it offers an impressive wine selection and memorable service for both casual lunch and special occasions.
Captain Curt's Crab & Oyster Bar serves up fresh seafood and award-winning clam chowder in a relaxed, nautical setting with both indoor and outdoor dining. Enjoy live music, a lively bar, and a true taste of Old Florida on Siesta Key.
St. Armands Circle offers a unique blend of upscale shopping, diverse dining, and charming outdoor spaces on a scenic island, perfect for visitors who enjoy a lively yet relaxed coastal atmosphere with a touch of history and culture. It’s ideal for shoppers, food lovers, and those seeking a picturesque day out.
Marie Selby Botanical Gardens Downtown Sarasota offers a unique bayfront oasis featuring the world’s only botanical garden dedicated to epiphytic orchids, bromeliads, and tropical plants, perfect for nature lovers, families, and anyone seeking a vibrant, educational outdoor experience.
Lido Beach is a sunny paradise perfect for families, where you can build sandcastles, paddle through mangrove tunnels, and spot playful dolphins. With calm waters, fun activities, and plenty of space to relax, it’s a favorite spot for kids and adults alike.
Bayfront Park in Miami offers a vibrant waterfront escape with scenic bay views, live music venues, unique monuments, and fun activities like flying trapeze and free yoga, making it perfect for families, fitness lovers, and culture seekers.
Experience world-class opera performances in an elegantly restored 1,100-seat historic theater in downtown Sarasota, where you can enjoy timeless classics like La bohème and The Merry Widow alongside fine dining and shopping. Perfect for culture enthusiasts seeking an unforgettable evening of music, drama, and theatrical splendor.
Soar 1,000 feet above crystal-clear Gulf waters while spotting dolphins and manatees, or throttle across the Intracoastal Waterway on a jet ski—Siesta Key Watersports delivers thrilling aerial views and high-speed adventures perfect for thrill-seekers and families alike.
Experience world-class contemporary art, lively music, and creative workshops in a vibrant campus that blends history and innovation. Perfect for art lovers, families, and anyone seeking inspiration and connection in a welcoming, dynamic setting.
Step into the heart of Pinecraft, where Amish and Mennonite traditions blend with Florida sunshine for a truly unique cultural experience. Visitors love the friendly vibe, handmade crafts, and delicious Amish food in this charming, bike-friendly neighborhood.
Stand before a towering 26-foot bronze sculpture immortalizing one of history's most iconic moments—a sailor and nurse embracing at the end of World War II. Perfect for history enthusiasts, photographers, and anyone seeking a meaningful waterfront experience that captures the joy and relief of peace.
St. Armands Circle is a charming, walkable island district with upscale shops, lively restaurants, and a scenic park, perfect for those who love shopping, dining, and soaking up Sarasota’s vibrant coastal atmosphere.
Lido Beach is a pristine Gulf Coast destination perfect for families and nature lovers seeking a blend of relaxation and adventure, offering everything from building sandcastles and paddling through enchanting mangrove tunnels to spotting dolphins and enjoying fresh seafood at beachside cafes.
Pinecraft is a unique Amish and Mennonite snowbird community in Sarasota where visitors can experience a simpler way of life through shuffleboard games, handcrafted goods, and authentic home-cooked meals, making it perfect for anyone curious about traditional culture or seeking a relaxed, distinctive Florida getaway.
Marie Selby Botanical Gardens is a world-renowned bayfront oasis featuring over 20,000 exotic plants, including the world's largest collection of orchids and air plants, making it perfect for nature lovers, families, and photographers seeking a tropical escape in the heart of Sarasota.
Payne Park is a lively, family-friendly destination featuring a unique circus-themed playground, a popular skate park, disc golf, tennis courts, and scenic trails, perfect for outdoor enthusiasts and kids of all ages looking for fun and adventure in Sarasota.
Bayfront Park is a vibrant waterfront oasis in downtown Miami, perfect for families, fitness enthusiasts, and culture lovers with its scenic baywalk, playgrounds, live performances, flying trapeze classes, and dazzling musical fountain shows. It offers something special for everyone seeking outdoor fun and city views.
Experience the magic of world-class opera in the historic Sarasota Opera House, where timeless stories and stunning performances captivate both seasoned opera lovers and newcomers alike. Perfect for anyone who enjoys powerful music, dramatic tales, and elegant ambiance.
Siesta Key Watersports offers thrilling parasailing, jet ski rentals, and scenic dolphin tours perfect for adventure seekers and nature lovers looking to explore crystal-clear waters and stunning coastal views. It’s ideal for families, beginners, and experienced water sports enthusiasts alike.
Stand before a towering 26-foot bronze sculpture recreating the iconic V-J Day kiss that symbolized the end of World War II—a powerful monument to history and a must-see photo opportunity for anyone visiting Sarasota's picturesque bayfront.
Experience art, music, and dance under the stars at Sarasota Art Museum’s After Hours, a monthly celebration perfect for adults and art lovers looking for a vibrant night out with live performances and creative energy.
50% refund up to 30 days before check-in. No refund after that.
Pets allowed with fee
No smoking - fees will apply
Events not allowed
Check-in after 4:00 pm
Check-out before 10:00 am
24 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Sep 2, 2026 | $2050 | Not Available |
| Sep 3, 2026 | $2163 | Available |
| Sep 4, 2026 | $2454 | Available |
| Sep 5, 2026 | $2580 | Not Available |
| Sep 6, 2026 | $2506 | Not Available |
| Sep 7, 2026 | $2481 | Not Available |
| Sep 8, 2026 | $2405 | Not Available |
| Sep 9, 2026 | $2355 | Not Available |
| Sep 10, 2026 | $2455 | Not Available |
| Sep 11, 2026 | $2322 | Not Available |
| Sep 12, 2026 | $2113 | Available |
| Sep 13, 2026 | $2133 | Available |
| Sep 14, 2026 | $2133 | Not Available |
| Sep 15, 2026 | $2133 | Not Available |
| Sep 16, 2026 | $2197 | Not Available |
| Sep 17, 2026 | $2260 | Not Available |
| Sep 18, 2026 | $2238 | Not Available |
| Sep 19, 2026 | $2197 | Not Available |
| Sep 20, 2026 | $2175 | Not Available |
| Sep 21, 2026 | $2153 | Not Available |
| Sep 22, 2026 | $2153 | Not Available |
| Sep 23, 2026 | $2153 | Not Available |
| Sep 24, 2026 | $2175 | Not Available |
| Sep 25, 2026 | $2197 | Not Available |
| Sep 26, 2026 | $2197 | Not Available |
| Sep 27, 2026 | $2197 | Not Available |
| Sep 28, 2026 | $2197 | Not Available |
| Sep 29, 2026 | $2155 | Not Available |
| Sep 30, 2026 | $2113 | Not Available |
| Oct 1, 2026 | $2133 | Available |
| Oct 2, 2026 | $2807 | Available |
| Oct 3, 2026 | $3521 | Not Available |
| Oct 4, 2026 | $3490 | Not Available |
| Oct 5, 2026 | $3338 | Not Available |
| Oct 6, 2026 | $3278 | Not Available |
| Oct 7, 2026 | $3338 | Not Available |
| Oct 8, 2026 | $3429 | Not Available |
| Oct 9, 2026 | $3490 | Not Available |
| Oct 10, 2026 | $3490 | Not Available |
| Oct 11, 2026 | $3369 | Not Available |
| Oct 12, 2026 | $3369 | Not Available |
| Oct 13, 2026 | $3460 | Not Available |
| Oct 14, 2026 | $3460 | Not Available |
| Oct 15, 2026 | $3490 | Not Available |
| Oct 16, 2026 | $3369 | Not Available |
| Oct 17, 2026 | $3188 | Not Available |
| Oct 18, 2026 | $3096 | Not Available |
| Oct 19, 2026 | $3096 | Not Available |
| Oct 20, 2026 | $3096 | Not Available |
| Oct 21, 2026 | $3188 | Not Available |
| Oct 22, 2026 | $3455 | Not Available |
| Oct 23, 2026 | $3602 | Not Available |
| Oct 24, 2026 | $3512 | Not Available |
| Oct 25, 2026 | $3331 | Available |
| Oct 26, 2026 | $3271 | Available |
| Oct 27, 2026 | $3271 | Available |
| Oct 28, 2026 | $3360 | Available |
| Oct 29, 2026 | $3510 | Available |
| Oct 30, 2026 | $3510 | Not Available |
| Oct 31, 2026 | $3631 | Not Available |
| Nov 1, 2026 | $3812 | Not Available |
| Nov 2, 2026 | $3812 | Not Available |
| Nov 3, 2026 | $3812 | Not Available |
| Nov 4, 2026 | $3873 | Not Available |
| Nov 5, 2026 | $3964 | Not Available |
| Nov 6, 2026 | $3935 | Not Available |
| Nov 7, 2026 | $3693 | Not Available |
| Nov 8, 2026 | $3481 | Available |
| Nov 9, 2026 | $3450 | Not Available |
| Nov 10, 2026 | $3481 | Not Available |
| Nov 11, 2026 | $3572 | Not Available |
| Nov 12, 2026 | $3633 | Not Available |
| Nov 13, 2026 | $3572 | Not Available |
| Nov 14, 2026 | $3481 | Available |
| Nov 15, 2026 | N/A | Not Available |
| Nov 16, 2026 | N/A | Not Available |
| Nov 17, 2026 | N/A | Not Available |
| Nov 18, 2026 | N/A | Not Available |
| Nov 19, 2026 | N/A | Not Available |
| Nov 20, 2026 | N/A | Not Available |
| Nov 21, 2026 | $5722 | Available |
| Nov 22, 2026 | $5813 | Available |
| Nov 23, 2026 | N/A | Not Available |
| Nov 24, 2026 | N/A | Not Available |
| Nov 25, 2026 | N/A | Not Available |
| Nov 26, 2026 | N/A | Not Available |
| Nov 27, 2026 | N/A | Not Available |
| Nov 28, 2026 | $6903 | Available |
| Nov 29, 2026 | $4947 | Available |
| Nov 30, 2026 | $3050 | Available |
| Dec 1, 2026 | $3050 | Available |