Experience the Ultimate in Coastal Luxury at A Point of Paradise

Photo gallery for Experience the Ultimate in Coastal Luxury at A Point of Paradise

A modern living room with a sectional sofa, a coffee table, and a dining area with a kitchen in the background.
A modern multi-level residential building with a central swimming pool, outdoor seating, and a balcony with furniture.
A spacious living area with a modern kitchen, large windows with a view, and a ceiling fan.
A modern two-story house with a covered outdoor area, a swimming pool, and a well-maintained lawn.
A modern living room with a white ceiling, large windows, and a central coffee table.

Reviews

9.4 out of 10
Exceptional

Highlights

  • Dive into relaxation
    Unwind in the top-rated pool, your perfect spot for relaxation.
  • Arcade/game room
    A rare find - fun for all ages with on-site arcade and game room.
  • Discover nearby landmarks
    Close to Safe Harbor Siesta Key
8 bedrooms8+ bathroomsSleeps 18

Popular amenities

  • Private pool
  • Hot tub on site
  • Garage parking available
  • Kitchen
  • Washing machine
  • Air-conditioning

Explore the area

View in a map
Sarasota, FL
  • Place, Crescent Beach
    ‪8 min walk‬
  • Place, Safe Harbor Siesta Key
    ‪17 min walk‬
  • Place, Siesta Key Beach
    ‪2 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪30 min drive‬

Rooms & beds

8 bedrooms (sleeps 18)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

Bedroom 4

1 King Bed

Bedroom 5

1 King Bed

Bedroom 6

1 King Bed

Bedroom 7

1 King Bed

Bedroom 8

4 Single Bunk Beds

8 bathrooms, 1 half bathroom

Bathroom 1

Toilet · Shower only

Bathroom 2

Bathtub · Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Bathtub · Toilet

Bathroom 5

Toilet · Shower only

Bathroom 6

Toilet · Shower only

Bathroom 7

Toilet · Shower only

Bathroom 8

Toilet · Shower only

Half Bathroom 9

Toilet · Shower only

Spaces

Kitchen
Balcony
Separate dining area
Dining area

About this property

Experience the Ultimate in Coastal Luxury at A Point of Paradise

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.

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House Rules

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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 20097942
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

About the area

Siesta Key

Located in Siesta Key, this holiday home is in the city centre and near the beach. St. Armands Circle and Mall at University Town Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Siesta Key Beach and Crescent Beach. Travelling with kids? Consider Mote Marine Laboratory & Aquarium and St. Boniface Episcopal Church Labyrinth. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and horse riding nearby.
Map
Sarasota, FL

What's nearby

  • Crescent Beach - 8 min walk - 0.7 km
  • Safe Harbor Siesta Key - 17 min walk - 1.4 km
  • Siesta Key Beach - 2 min drive - 1.8 km
  • Turtle Beach - 4 min drive - 3.8 km
  • Lido Beach - 26 min drive - 17.8 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 37 min drive

Restaurants

  • ‪McDonald's - ‬3 min drive
  • ‪Panera Bread - ‬4 min drive
  • ‪Captain Curt's Crab & Oyster Bar - ‬12 min walk
  • ‪Culver's - ‬5 min drive
  • ‪Hooters - ‬4 min drive

Frequently asked questions

Does Experience the Ultimate in Coastal Luxury at A Point of Paradise have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is Experience the Ultimate in Coastal Luxury at A Point of Paradise pet-friendly?

No, pets are not allowed at this property.

How much is parking at Experience the Ultimate in Coastal Luxury at A Point of Paradise?

On-site parking is available at the property.

Where is Experience the Ultimate in Coastal Luxury at A Point of Paradise located?

This family-friendly Siesta Key holiday home is located by the sea, within a 5-minute walk of Point of Rocks and Crescent Beach. Siesta Key Beach is 1.2 mi (2 km) away.

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 6 out of 8 reviews
Rating 8 - Good. 1 out of 8 reviews
Rating 6 - Okay. 1 out of 8 reviews
Rating 4 - Poor. 0 out of 8 reviews
Rating 2 - Terrible. 0 out of 8 reviews

8.6/10

Cleanliness

9.6/10

Check-in

9.6/10

Communication

9.6/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Donald J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent house, amazing pool/hot tub, close to the beach. Very clean and the size was perfect for our group of 17 people.
Stayed 7 nights in May 2026
Response from VrboOwner on 23 Jun, 2026
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
Verified review

8/10 Good

Kevin B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 8 nights in Jun 2026
Response from VrboOwner on 12 Jul, 2026
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
Verified review

10/10 Excellent

Michael M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in May 2026
Response from VrboOwner on 26 May, 2026
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
Verified review

10/10 Excellent

Pat G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 7 nights in Jun 2026
Response from VrboOwner on 12 Jul, 2026
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
Verified review

10/10 Excellent

Tamara D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was amazing!
Stayed 7 nights in Nov 2025
Response from VrboOwner on 24 Nov, 2025
Hi Tamara, Thank you so much! We’re delighted you enjoyed the house and would love to welcome you back anytime! Regards, The CottageCrew
Verified review

6/10 Okay

Jeff H.

Liked: Location, listing accuracy
Disliked: Cleanliness
The images and videos of the home were captivating and made it look ideal for our family gathering. With over 5,000 sq. ft., eight bedrooms, a modern design, and a high rental price tag reflecting an 8 million property, we expected a truly luxury experience.Unfortunately, what we encountered was a property that felt worn, lacked basic amenities, and showed a clear absence of attention to detail. We had to clean several toilets ourselves upon arrival, found rusted cutlery in the kitchen, and had to cover the upholstered furniture with towels because it was so visibly dirty.These maintenance and cleanliness issues are easily preventable, but they significantly detracted from our stay and impacted what should have been a five-star experience.
Stayed 5 nights in Jul 2026
Response from VrboOwner on 27 Jul, 2026
Hi Jeff, Thank you for taking the time to share your feedback. We're glad the home's layout and design made it a great fit for your family gathering, but we're truly sorry to hear that your experience did not meet your expectations. We sincerely apologize for your concerns regarding the cleanliness and condition of the home upon arrival. This is not the standard we strive to provide, and we understand how disappointing that must have been. Your comments have been shared with our housekeeping and operations teams so they can review the items you mentioned and ensure they are addressed. During your stay, we were happy to assist with your requests for additional starter supplies. We wish we had known about your concerns with cleanliness while you were here, as we would have welcomed the opportunity to send our housekeeping team back to the home immediately to make things right. We truly appreciate your feedback, as it helps us improve both our home and the experience we provide for future guests. Thank you again for staying with us, and we wish you and your family all the best. Warm regards, Guest Services Team
Verified review

10/10 Excellent

Dave J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The pool and hot tub were not heated for 4 1/2 days of our stay, but we were reimbursed for that inconvenience.
Stayed 7 nights in Jan 2026
Verified review

10/10 Excellent

Justin O.

Stayed 7 nights in Apr 2026
Response from VrboOwner on 8 Jun, 2026
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

About the host

Hosted by The Cottages on the Key, Inc.

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Languages:

English, French, German, Dutch

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