8 bedrooms
•
11 beds
•
8.5 bathrooms
•
18 guests
•
New
•
5210 sq. ft.
Luxury
Elevated properties with standout design
Operated by a Wander partner
Trusted operators, vetted by Wander
Experience the ultimate in coastal luxury at Point of Paradise, a stunning new retreat nestled on the peaceful southern end of Siesta Key. Designed to host up to 18 guests in style, this 8-bedroom haven combines sophisticated design with all the comforts of home. With each bedroom featuring a private ensuite, multiple living spaces, and breathtaking views, this property is the perfect setting for unforgettable gatherings with family and friends.
🌴 An Outdoor Sanctuary
Step outside and be captivated by the resort-style pool, a true centerpiece of this tropical oasis. Stretching along the western edge of the property, it features a plunge section with submerged seating, a Baja shelf crowned with a gentle fountain, and a whirlpool spa for ultimate relaxation. The pool is framed by a row of inviting chaise lounges, perfect for basking in the Florida sunshine. Around the back, enjoy the convenience of a triple charcoal grill for al fresco feasts and an outdoor shower to rinse off after a day of adventure.
Indoors, the game room awaits with a pool table and a ping pong/air hockey combo table, offering hours of entertainment for guests of all ages.
🍳 Second-Floor Elegance
Ascend to the second floor, where the home's 12-foot ceilings and expansive layout create a light and airy atmosphere. At the heart of this level is the open-concept living area, featuring a chef's dream kitchen equipped with state-of-the-art Bosch appliances, sleek finishes, and ample counter space. The spacious dining table invites lively meals, while the plush wrap-around sofa and large flat-screen TV make movie nights a delight.
Step out onto the multi-level deck to enjoy the fresh coastal breeze and tranquil views of the pool below. Surrounding this central space are four opulent King bedrooms, each offering a serene retreat, plus a convenient half-bath and a well-appointed laundry room for added comfort.
🌟 Third-Floor Indulgence
The third floor continues the luxurious experience with a cozy lounge area complete with a wet bar—the perfect spot for a quiet drink or casual conversation. This level includes three more King bedrooms, as well as a double twin bunk room, ideal for younger guests or group flexibility.
The crown jewel of this home is the rooftop patio, accessible via a dramatic spiral staircase. From this elevated perch, marvel at the sweeping panoramic views, including the shimmering Gulf waters and Siesta Key's legendary sunsets. This rooftop escape is a magical setting for evening cocktails, morning yoga, or simply gazing at the stars.
🌊 Steps to Island Bliss
A Point of Paradise is just a short stroll from the island's pristine beaches, where soft, powdery sands meet the warm Gulf waves. Explore Siesta Key's charming villages, filled with unique shops, local eateries, and endless opportunities for adventure. From paddleboarding and kayaking to sunset cruises, there's something for everyone to enjoy.
✨ Why Visit Point of Paradise?
This remarkable home offers the best of both worlds: expansive gathering spaces to bring everyone together and private retreats for moments of quiet relaxation. Whether you're savoring meals by the pool, toasting the sunset on the rooftop patio, or unwinding in your luxurious ensuite, every detail has been designed to create an unforgettable stay.
Book your stay today and capture your very own Point of Paradise—where memories are made, and dreams come to life.
Exclusive Amenities Include:
• Private Heated Plunge Pool, Baja Shelf and Whirlpool
• Pool Views on 2nd & 3rd Story Balconies
• Roof top patio with Gulf Views
• Less Than 1 mile to Crescent Village
• Less Than a 2 Minute Walk to Crescent Beach & Point of Rocks
• Just a Short Drive to Siesta Key Village & Siesta Key Beach
• Ping Pong Table / Air Hockey Table
• Outdoor Lounge Areas
• 8 Bedrooms, 8.5 Full Baths with Luxury Towels & Bed Linens provided,
• Spacious Balconies With Seating Area
• Full Gourmet Kitchen
• 2 Private Garages and Off Street Driveway Parking for 3 Cars
• Washer/Dryer Laundry Rooms on 2nd and 3rd floors
• Free WiFi & HDTV's
• Regular & Keurig Coffee Makers, Dishwasher, 2 Washers & Dryers, and Kitchen Essentials Provided
• Starter Pack of Toiletry Essentials Included - Shampoo, Conditioner, Hand / Face Soap, Body Lotion, & Makeup Wipes
• Starter Pack of Home Essentials Included - Dish Soap, Dish Sponge, Dishwasher Tablets, Laundry Tablets, & Cleaning Wipes
• Beach Towels, Chairs, Cooler, & Caddy Provided
• Triple Charcoal Grill
• Enhanced Cleaning Protocols Provided by our CottageClean Team
• Island Shuttle Transportation Available
A Point of Paradise can accommodate up to 18 guests with a bedding configuration as follows:
Bedroom 1 – King (1) - Sleeps: 2
Bedroom 2 – King (1) - Sleeps: 2
Bedroom 3 – King (1) - Sleeps: 2
Bedroom 4 – King (1) - Sleeps: 2
Bedroom 5 – King (1) - Sleeps: 2
Bedroom 6 – King (1) - Sleeps: 2
Bedroom 7 - King (1) - Sleeps: 2
Bedroom 8 – Two Twin Bunk Beds (4 twin beds) - Sleeps: 4
We go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol within our CottageClean Program. After our six hour in-depth cleaning of your home, we complete a 35 point property inspection to ensure that you feel tremendously safe and happy with this amazing home. This allows you to vacation worry free regarding the cleanliness of your home and truly relax as soon as you arrive. Our goal is to have you feel like you are walking into a brand new vacation home that no one has ever stayed at before!
PLEASE NOTE:
The pool is heated from November 15th to April 15th.
This home has stairs. If any member of your party has difficulty with stairs, please contact us to discuss alternative accommodations.
Bedroom 1
1 king bed
Bedroom 2
1 king bed
Bedroom 3
2 king beds
Bedroom 4
1 king bed
Bedroom 5
1 king bed
Bedroom 6
1 king bed
Bedroom 7
1 king bed
Bedroom 8
5 twin bunk beds
Bedroom 1
1 king bed
Bedroom 2
1 king bed
Bedroom 3
2 king beds
Bedroom 4
1 king bed
Bedroom 5
1 king bed
Bedroom 6
1 king bed
Bedroom 7
1 king bed
Bedroom 8
5 twin bunk beds
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Siesta Key, FL 34242, US
Siesta Key, FL, USCaptain Curt's Crab & Oyster Bar serves up fresh seafood and award-winning clam chowder in a lively, family-friendly setting with indoor and outdoor seating, live music, and a true taste of Old Florida.
Connors Steak & Seafood serves premium aged steaks and fresh seafood grilled over mesquite wood, offering a classic American steakhouse experience with upscale ambiance and exceptional service.
Siesta Key Oyster Bar is a lively, beachy spot known for its fresh seafood, award-winning wings, and cold beer, all served in a fun, dollar-bill-covered setting with live music and a welcoming island vibe.
Walt's Fish Market is a legendary Sarasota seafood destination that has been serving the freshest locally-caught fish since 1918, featuring daily specials from their on-site market paired with a laid-back tropical atmosphere and authentic Chickee Bar with live music.
CMX CinéBistro Siesta Key blends modern New-American cuisine with a luxurious movie-going experience, offering chef-driven dishes, handcrafted cocktails, and plush recliner seating for a truly elevated night out.
St. Armands Circle is an upscale outdoor shopping and dining destination on a barrier island featuring over 130 boutiques, galleries, and restaurants arranged in a charming circular layout inspired by circus wagon wheels, perfect for those seeking sophisticated retail therapy combined with European-style ambiance and proximity to beautiful Gulf Coast beaches.
Marie Selby Botanical Gardens Downtown Sarasota offers a stunning bayfront escape with vibrant tropical plants, a unique orchid conservatory, and an interactive Children’s Rainforest Garden, perfect for nature lovers, families, and anyone seeking a peaceful, educational outdoor experience.
Lido Beach is a pristine, relatively uncrowded Gulf Coast destination perfect for families and beach lovers seeking a relaxing day of swimming, sandcastle building, and water activities like kayaking through enchanting mangrove tunnels where you might spot dolphins and manatees.
Twin Lakes Park is a scenic spot perfect for families and outdoor lovers, offering playgrounds, picnic pavilions, sports fields, and a swimming pool, all set around a peaceful lake with trails and plenty of shade.
Bayfront Park is a vibrant waterfront oasis in downtown Miami offering scenic bay views, free yoga, flying trapeze classes, lively concerts, and a fantastic playground, perfect for families, fitness enthusiasts, and anyone seeking outdoor fun and cultural events.
Payne Park in Sarasota is a lively spot featuring a unique circus-themed playground perfect for families, a popular skate park for all skill levels, scenic trails, disc golf, and plenty of open spaces for picnics and outdoor fun. It’s ideal for kids, skaters, and nature lovers alike.
Historic Spanish Point offers a unique blend of archaeology, history, and nature across 30 scenic acres, perfect for history buffs, nature lovers, and families seeking a peaceful outdoor adventure with guided tours, beautiful bay views, and seasonal boat rides.
Siesta Key Watersports offers thrilling jet ski rides, parasailing adventures, and scenic boat tours perfect for adrenaline seekers and nature lovers wanting to explore the crystal-clear waters and spot dolphins around Siesta Key. Ideal for families, couples, and solo adventurers alike.
Pinecraft offers a rare glimpse into Amish and Mennonite life with its vibrant community, lively shuffleboard games, handmade crafts, and delicious traditional food, perfect for culture enthusiasts and curious travelers seeking a unique, laid-back experience.
Experience vibrant live music, themed dance nights, and extended gallery hours at Sarasota Art Museum’s After Hours. Perfect for music lovers, dancers, and art enthusiasts looking for a fun, social evening out.
50% refund up to 60 days before check-in. No refund after that.
Pets not allowed
No smoking - fees will apply
Events not allowed
Check-in after 4:00 pm
Check-out before 10:00 am
18 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Jul 15, 2026 | $2034 | Not Available |
| Jul 16, 2026 | $2016 | Not Available |
| Jul 17, 2026 | $3287 | Not Available |
| Jul 18, 2026 | $3912 | Not Available |
| Jul 19, 2026 | $2872 | Not Available |
| Jul 20, 2026 | $2497 | Not Available |
| Jul 21, 2026 | $2497 | Not Available |
| Jul 22, 2026 | $2520 | Not Available |
| Jul 23, 2026 | $2544 | Not Available |
| Jul 24, 2026 | $3479 | Not Available |
| Jul 25, 2026 | $4496 | Not Available |
| Jul 26, 2026 | $4577 | Not Available |
| Jul 27, 2026 | $4577 | Not Available |
| Jul 28, 2026 | $4577 | Not Available |
| Jul 29, 2026 | $4659 | Not Available |
| Jul 30, 2026 | $4740 | Not Available |
| Jul 31, 2026 | $4785 | Not Available |
| Aug 1, 2026 | $4745 | Not Available |
| Aug 2, 2026 | $4661 | Not Available |
| Aug 3, 2026 | $4745 | Not Available |
| Aug 4, 2026 | $4830 | Not Available |
| Aug 5, 2026 | $4789 | Not Available |
| Aug 6, 2026 | $4747 | Not Available |
| Aug 7, 2026 | $4325 | Not Available |
| Aug 8, 2026 | $4071 | Available |
| Aug 9, 2026 | $4240 | Not Available |
| Aug 10, 2026 | $4197 | Not Available |
| Aug 11, 2026 | $4154 | Not Available |
| Aug 12, 2026 | $4118 | Not Available |
| Aug 13, 2026 | $4081 | Not Available |
| Aug 14, 2026 | $3899 | Not Available |
| Aug 15, 2026 | $3679 | Available |
| Aug 16, 2026 | $3643 | Available |
| Aug 17, 2026 | $3643 | Available |
| Aug 18, 2026 | $3643 | Available |
| Aug 19, 2026 | $3607 | Available |
| Aug 20, 2026 | $3571 | Available |
| Aug 21, 2026 | $3426 | Not Available |
| Aug 22, 2026 | $3317 | Not Available |
| Aug 23, 2026 | $3245 | Not Available |
| Aug 24, 2026 | $3136 | Not Available |
| Aug 25, 2026 | $3136 | Not Available |
| Aug 26, 2026 | $3172 | Not Available |
| Aug 27, 2026 | $3172 | Not Available |
| Aug 28, 2026 | $3136 | Not Available |
| Aug 29, 2026 | $3136 | Not Available |
| Aug 30, 2026 | $3172 | Not Available |
| Aug 31, 2026 | $3209 | Not Available |
| Sep 1, 2026 | $3281 | Not Available |
| Sep 2, 2026 | $3498 | Not Available |
| Sep 3, 2026 | $3643 | Not Available |
| Sep 4, 2026 | $3990 | Not Available |
| Sep 5, 2026 | $4294 | Not Available |
| Sep 6, 2026 | $4124 | Not Available |
| Sep 7, 2026 | $3914 | Not Available |
| Sep 8, 2026 | $3830 | Available |
| Sep 9, 2026 | $3871 | Available |
| Sep 10, 2026 | $3912 | Available |
| Sep 11, 2026 | $3593 | Available |
| Sep 12, 2026 | $3274 | Not Available |
| Sep 13, 2026 | $3274 | Not Available |
| Sep 14, 2026 | $3274 | Not Available |
| Sep 15, 2026 | $3274 | Not Available |
| Sep 16, 2026 | $3307 | Not Available |
| Sep 17, 2026 | $3407 | Not Available |
| Sep 18, 2026 | $3474 | Not Available |
| Sep 19, 2026 | $3474 | Not Available |
| Sep 20, 2026 | $3407 | Not Available |
| Sep 21, 2026 | $3407 | Not Available |
| Sep 22, 2026 | $3474 | Not Available |
| Sep 23, 2026 | $3540 | Not Available |
| Sep 24, 2026 | $3505 | Not Available |
| Sep 25, 2026 | $3405 | Not Available |
| Sep 26, 2026 | $3307 | Not Available |
| Sep 27, 2026 | $3174 | Not Available |
| Sep 28, 2026 | $3140 | Not Available |
| Sep 29, 2026 | $3140 | Not Available |
| Sep 30, 2026 | $3207 | Not Available |
| Oct 1, 2026 | $3274 | Not Available |
| Oct 2, 2026 | $3640 | Not Available |
| Oct 3, 2026 | $3969 | Not Available |
| Oct 4, 2026 | $3933 | Not Available |
| Oct 5, 2026 | $3969 | Not Available |
| Oct 6, 2026 | $4005 | Not Available |
| Oct 7, 2026 | $4042 | Not Available |
| Oct 8, 2026 | $4078 | Not Available |
| Oct 9, 2026 | $3623 | Not Available |
| Oct 10, 2026 | $3167 | Available |
| Oct 11, 2026 | $3167 | Available |
| Oct 12, 2026 | $3114 | Available |
| Oct 13, 2026 | $3033 | Available |