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Point of Paradise

Coastal Luxury | 5200 Sqft Mansion With Private Pool, Near Beach Access

Bedrooms: 8

Bathrooms: 8 Full, 1 Half

Sleeps: 18

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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

Overview ↑↓

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.

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.

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Reviews ↑↓

Total reviews: 16

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Review Date: August 1, 2026

"This house was the perfect spot for our family reunion! Everyone felt comfortable in the space and there was plenty of room for our large group. The beach was lovely and we had the best time!

Reviewed By: Kendall

Review Date: July 25, 2026

"Hermosa casa , bien equipada, todo funcionando correctamente, solicitudes con respuestas y solución inmediatas.

Reviewed By: Isandra

Review Date: July 7, 2026

"Beautiful home and very easy to get to the beach. Check in process was very easy and the host very helpful. If it needs anything it’s an ice machine and bathroom by the pool area. But regardless probably my favorite house I have stayed!

Reviewed By: Kevin

Response from The Cottages on the Key:
Hi Kevin, Thank you so much for your wonderful review! We’re thrilled to hear you loved the home and that it’s your favorite house you’ve stayed in, that truly means the world to us! We’re so glad you enjoyed the easy beach access, smooth check-in process, and helpful service from our team. We also appreciate your thoughtful suggestions regarding an ice machine and a bathroom near the pool. Feedback like yours is invaluable as we continue looking for ways to enhance the guest experience. Thank you again for choosing to stay with us. We truly appreciate your kind words and hope to have the pleasure of welcoming you back for another unforgettable vacation! Warm regards, Guest Services Team

Review Date: June 27, 2026

"This house was AMAZING! Plenty of room for all 18 of us. Loved having an en-suite for each bedroom. The pool & hot tub were great and just a short walk to the beach. Cottages on the Key were one of the BEST rental management companies we have ever dealt with! Immediate response to us any time we contacted them. Highly recommend this wonderful place & company!

Reviewed By: Pat

Response from The Cottages on the Key:
Hi Pat, Thank you so much for your incredible review! We’re thrilled to hear the home was such a perfect fit for your group of 18 and that everyone enjoyed having their own en-suite bathroom. It’s wonderful to know the pool, hot tub, and easy walk to the beach helped make your vacation even more memorable. Your kind words about The Cottages on the Key truly mean the world to us. Hearing that we’re one of the best rental management companies you’ve ever worked with is an incredible compliment. Our team takes great pride in providing prompt, attentive service, and we’re so happy we could help make your stay a great one. Thank you for your heartfelt recommendation and for choosing to stay with us. We hope to have the pleasure of welcoming your group back for another unforgettable getaway! Warm regards, Guest Services Team

Review Date: June 6, 2026

"Excellent house, amazing pool/hot tub, close to the beach. Very clean and the size was perfect for our group of 17 people.

Reviewed By: Donald

Response from The Cottages on the Key:
Hi Donald, Thank you so much for your wonderful review! We’re thrilled to hear the home was a perfect fit for your group and that you enjoyed the pool, hot tub, and convenient proximity to the beach. It’s great to know the home was clean, comfortable, and provided plenty of space for everyone to gather and make memories together. Thank you again for choosing to stay with us. We’d love to welcome your group back for another great stay in the future. Warm regards, Guest Services Team

Review Date: May 27, 2026

Reviewed By: Justin O.

Response from The Cottages on the Key:
Hi Justin, Thank you so much for your five-star rating! We truly appreciate you choosing to stay with us and are so glad you had a great experience. We hope to have the pleasure of welcoming you back again soon. Warm regards, Guest Services Team

Review Date: May 24, 2026

"The property was exactly how it was advertised. Was close to the beach, supplied sufficient towels, utensils, toiletries and even included a great welcoming tray of delicious cupcakes! Great swimming pool area and living space for old and young visitors.

Reviewed By: Michael

Response from The Cottages on the Key:
Hi Michael, Thank you so much for your wonderful review! We’re delighted to hear the home was exactly as advertised and that you enjoyed the convenient beach access, well-stocked amenities, and welcoming cupcakes upon arrival. It’s great to know the pool area and living spaces worked well for your group of all ages. We truly appreciate you staying with us and hope to welcome you back again in the future! Regards, The CottageCrew

Great location!

Review Date: March 10, 2026

"Everything was as advertised, would stay here again. Great location!

Reviewed By: Adam Yoder

We will most definitely rent here again if possible.

Review Date: February 12, 2026

"Our stay was fantastic. The home is beautiful, well maintained and impeccably clean. The property management team is the best I have worked with. They were proactive and engaged throughout the stay. The entire process to book, check-in and check-out was easy. The pool was incredible and the home was comfortable and engaging. The bedrooms and bathrooms had everything we needed. There were 2 laundry rooms. The kitchen was well stocked. I would rate this a 10 out of 10. We will most definitely rent here again if possible.

Reviewed By: Mark Cravotta

Beautiful location and the house looked better in person than in pictures.

Review Date: February 6, 2026

"Beautiful location and the house looked better in person than in pictures. All guests had a great time. I highly recommend this Airbnb if you're coming with a larger group!

Reviewed By: Madeline Kossin

Nothing but good things.

Review Date: January 19, 2026

"Nothing but good things.

Reviewed By: Annie Medlock

The house was amazing!

Review Date: November 24, 2025

"The house was amazing!

Reviewed By: Tamara Denicker

The hosts were so nice and helpful. We will definitely be going back!

Review Date: November 18, 2025

"This place was amazing!! We were with a large group of family and fit everyone perfectly. The outside area with the pool was perfect and spacious. So close to restaurants and things to do. The hosts were so nice and helpful. We will definitely be going back!

Reviewed By: Tammy Brennan

This is such a beautiful house and it looks exactly as listed.

Review Date: October 20, 2025

"This is such a beautiful house and it looks exactly as listed. The location is perfect - you can walk to the beach in minutes. Plus the little trolley stops at the end of the street to take you into the Village. It was a great stay. We had a few issues with the pool heater but the host was really responsive to every request we made. Overall it was a great stay.

Reviewed By: Brooke Fox

This property was absolutely stunning!

Review Date: September 9, 2025

"This property was absolutely stunning! The inside of the house was very clean, well accommodated & very spacious. The outside of the house was amazing as well. A beautiful pool and outdoor seating for everyone makes it very comfortable and easy to relax. My group and I all agreed this spot was totally worth it!

Reviewed By: Skyla Perry

Neat place in a great location.

Review Date: February 24, 2025

"Neat place in a great location. Parking allows for three vehicles, but there is no street parking, so plan accordingly.

Reviewed By: Brian Crenshaw

Point of Paradise

Coastal Luxury | 5200 Sqft Mansion With Private Pool, Near Beach Access

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