Entire home

Casamigos | West of the Trail - Private Home with Tiki Bar, Heated Pool, and Spa, Near Siesta Key!

Photo gallery for Casamigos | West of the Trail - Private Home with Tiki Bar, Heated Pool, and Spa, Near Siesta Key!

A heated pool
Bar (on property)
Fridge, microwave, oven, stovetop
4 bedrooms, iron/ironing board, WiFi, bed sheets
Interior

Reviews

9.4 out of 10
Exceptional

Entire home

4 bedrooms3 bathroomsSleeps 10211 sq m

Popular amenities

  • Parking available
  • Hot tub
  • Pool
  • Washer
  • Barbecue grill
  • Air conditioning

Explore the area

Map
Sarasota, Florida
  • Sarasota Memorial Hospital
    ‪2 min drive‬
  • St. Armands Circle
    ‪10 min drive‬
  • Lido Beach
    ‪16 min drive‬
  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪15 min drive‬

Room options

About the area

Sarasota

With a stay at this vacation home in Sarasota (South Poinsettia), you'll be a 2-minute drive from Sarasota Memorial Hospital and 7 minutes from Siesta Key Beach. .This vacation home is 5.1 mi (8.2 km) from St. Armands Circle and 6.8 mi (11 km) from Lido Beach.

What's nearby

  • Sarasota Memorial Hospital - 2 min drive - 1.7 km
  • Marie Selby Botanical Gardens - 4 min drive - 2.8 km
  • Marina Jack - 5 min drive - 4.1 km
  • St. Armands Circle - 10 min drive - 8.2 km
  • Lido Beach - 16 min drive - 11.0 km

Getting around

  • Sarasota-Bradenton Intl. Airport (SRQ) - 15 min drive

Restaurants

  • ‪Walt's Fish Market Wholesale - ‬17 min walk
  • ‪McDonald's - ‬10 min walk
  • ‪Red Barn Bar - ‬13 min walk
  • ‪CinéBistro - ‬9 min walk
  • ‪Sonny's BBQ - ‬11 min walk

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Casamigos | West of the Trail - Private Home with Tiki Bar, Heated Pool, and Spa, Near Siesta Key!

Welcome to Casamigos — the epitome of luxury living and relaxation in Siesta Key. This newly furnished, upscale 4-bedroom home (featuring all King Beds) and 3 full bathrooms offers an unparalleled vacation experience. Perfect for families or friends seeking both comfort and style, Casamigos redefines what it means to stay in paradise.

As you approach the home, the tropical landscaping immediately sets the tone for your vacation retreat. Lush Malaysian and Areca palms, vibrant bougainvillea, and soft lighting invite you to unwind as you drive up the spacious paver driveway. Step inside to be greeted by soaring 12-foot ceilings and an open, airy design that exudes elegance and coastal charm. West Indies-inspired décor, with its stunning columns and arches, ushers you into a tranquil island escape.

Every bedroom is a luxurious retreat, offering King-size beds, 55” flat-screen TVs, walk-in closets, and seating areas. The design throughout emphasizes comfort with high ceilings, ceiling fans, and impeccable attention to detail. Each room is a peaceful sanctuary for rest, ensuring your stay is both restful and rejuvenating.
The expansive living room is perfect for family gatherings, featuring ample seating, a massive wall-mounted flat-screen TV, and triple sliding doors that seamlessly open to the private screened pool and spa area. And of course, the pool is heated, perfect for a refreshing dip no matter the season.
The gourmet kitchen is a chef's dream, complete with a Wine Cooler, Keurig coffee maker, KitchenAid refrigerator/freezer with ice maker, convection oven, air fryer, and panini maker. Enjoy casual meals at the bar counter or sit down at the Tommy Bahama dining set for more formal dining. Whether you're preparing a quick snack or a gourmet dinner, this kitchen has everything you need and more.

Step outside and enjoy the covered lanai area, where you'll find a bar table perfect for poolside snacks and cocktails. The “Tres Amigos Bar” is a showstopper, offering a 10-seat authentic tiki bar in the private, walled west courtyard. This lush space features potted flowers, vibrant bougainvillea, and Areca palms, creating the perfect setting for relaxation. Enjoy a cold drink, catch a game on the 60"" TV, or simply bask in the tropical beauty. The courtyard is also equipped with polywood loungers, plenty of rockers, and the ultimate privacy — perfect for sunbathing, lounging, or entertaining.

And it doesn't stop there — Casamigos' location is simply unbeatable. Siesta Key Beach, with its powdery soft sands and clear turquoise waters, is just a short drive away. Siesta Key is an 8-mile long island with villages on both ends and the main beach in the middle. A short drive down Siesta Drive & Midnight Pass Road brings you to the beautiful main beach on Siesta Key. Plenty of parking allows you to bring your beach equipment and enjoy the white, soft sand that Siesta Key Beach is famous for. Additionally, you're within walking distance of twenty or more great restaurants, two blocks from the Publix grocery store, and easy access to downtown Sarasota, Lido Key and so many of the attractions our area has to offer. You'll love the convenience of this location for access to all that Siesta Key and Sarasota offers. Plus, downtown Sarasota, Lido Key, and all the best local attractions are within easy reach.

At Casamigos, paradise awaits. Whether you're soaking up the sun by the private pool, enjoying a drink at the tiki bar, or exploring all that Siesta Key and Sarasota have to offer, this luxurious vacation home is your ultimate getaway.
Book your stay at Casamigos today, and experience the vacation of a lifetime.

Exclusive Amenities Include:
• Private Heated Salt Pool with Spa and Lanai
• 8-seat Authentic Tiki Bar With Beer Fridge and Smart HDTV
• Just a short drive to Siesta Key Village, Siesta Key Beach, and Downtown Sarasota
• 4 Bedrooms, 3 Full Baths
• 4 King Beds & 2 Twin Rollaway Beds (Sleeps 10) with linens provided
• Private 2 Car Garage
• Free WiFi & 6 HDTV's
• Wine Bar with Wine Cooler
• Keurig Coffee Maker, Dishwasher, Washer & Dryer, 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
• Outdoor Covered Screened Patio With Dining Area
• Gas Grill
• Enhanced cleaning protocols provided by our CottageClean Team

Casamigos can accommodate up to 10 guests with a bedding configuration as follows:

• Bedroom # 1: King Bed (1) - Sleeps: 2 + Twin Roll Away Bed - Sleeps 1 - Total: Sleeps 3
• Bedroom # 2: King Bed (1) - Sleeps: 2
• Bedroom # 3: King Bed (1) - Sleeps: 2
• Bedroom # 4: King Bed (1) - Sleeps: 2 + Twin Roll Away Bed - Sleeps 1 - Total: Sleeps 3

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: ​​​​​​Cannot rent fewer than 7 nights. This pool is heated from November 15th to April 15th.
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a Smart TV. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Conveniences include a microwave and a coffee/tea maker.
Enjoy recreational amenities such as a water park and a hot tub.
Guests will find features like wireless internet access and onsite parking.

Property manager

The Cottages on the Key, Inc.

Languages

Dutch, English, French, German

Property amenities

Beach

  • Near the beach

Pool/Spa

  • Private pool
  • Heated pool
  • A hot tub

Internet

  • Wi-Fi available, with a speed of 100+ Mbps (good for 1–2 people or up to 6 devices)

Parking and transport

  • On-site parking options include a garage
  • On-site parking

Kitchen

  • Fridge
  • Stovetop
  • Microwave
  • Oven
  • Dishwasher
  • Coffee/tea maker
  • Freezer
  • Cookware/dishes/utensils
  • Toaster

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bed sheets provided

Bathrooms

  • 3 bathrooms
  • Bath or shower
  • Hairdryer
  • Towels provided

Living spaces

  • Living room
  • Dining room

Entertainment

  • Smart TV with cable/satellite service

Outdoor areas

  • Lanai
  • Barbecue

Laundry

  • Washing machine and dryer
  • Near a laundromat

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near the sea
  • Near a health or beauty spa
  • Near a hospital
  • Near outlet shopping
  • Near a zoo
  • Near the bay
  • In a village

Things to do

  • Water park
  • Cycling nearby
  • Sailing nearby
  • Swimming nearby
  • Fishing nearby
  • Wildlife and game walks nearby
  • Golf nearby
  • Snorkelling nearby
  • Scuba diving nearby
  • Jet skiing nearby

Safety features

  • Carbon monoxide detector installed (host has indicated that there is a carbon monoxide detector on the property)
  • Smoke detector installed (host has indicated that there is a smoke detector on the property)
  • Fire extinguisher
  • First aid kit
  • Deadbolt lock

General

  • Unit size: 2269 sq ft (211 sq m)

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 26

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets not allowed

Children and extra beds

Children are welcome

Important information

You need to know

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

Property is also known as

503486

Casamigos | West of the Trail - Private Home with Tiki Bar, Heated Pool, and Spa, Near Siesta Key! Reviews

Reviews

9.4

Exceptional

Rating 10 - Excellent. 24 out of 29 reviews
Rating 8 - Good. 2 out of 29 reviews
Rating 6 - Okay. 2 out of 29 reviews
Rating 4 - Poor. 0 out of 29 reviews
Rating 2 - Terrible. 1 out of 29 reviews

9.6/10

Cleanliness

Reviews

8/10 Good

Joan A.

Stayed 4 nights in Jan 2025

10/10 Excellent

Lydia D.

Liked: Cleanliness
Nice!
Location, Location, location, love the area. close to anything you might want or need. The home is well cared for by the managing company "the cottages on the Keys" Thank you! Lydia
Stayed 7 nights in Sep 2024

10/10 Excellent

Mitch M.

Liked: Cleanliness
Great Home for Family Vacation
The property and the home is beautiful. Pool and patio area are amazing! Definitely will stay again!
Stayed 7 nights in Aug 2024

2/10 Terrible

Susan H., Charlestown

Disliked: Cleanliness
Uninhabited
Stayed 7 nights in Mar 2024

10/10 Excellent

Reaper

Liked: Cleanliness
Perfect for large family
The house is fully stocked! We bought some paper products, and of course food/drinks, but everything else was here. They have all of the towels, bedding, dishes, cooking utensils, beach gear, all ready for you. We really enjoyed outdoor area and tiki bar. The house was big enough that we were able to spend time all together or separately and not being top of each other. My favorite time was in the morning by the pool with my coffee while everyone else was still sleeping. It was an absolutely perfect vacation. Thanks so much!
Stayed 7 nights in Jun 2024

10/10 Excellent

Sonya G.

Liked: Cleanliness
Wonderful stay!
My family and I loved the house. It was clean comfortable and enough space for everyone. Response to all my annoying questions 😆were quicky responded to and I appreciated that. It rained quite a bit so we didn’t get enough beach time but with the close proximity of things to do we didn’t get bored. Don't listen to any of the negative reviews because the pool is plenty big to get cooled off in on a hot day. The noise from the traffic is not noticeable because of all the laughing with Family and friends you will have. Thank You for all your thoughtfulness especially the awesome cupcakes when we arrived!
Stayed 7 nights in Jun 2024

10/10 Excellent

Nancy R.

Liked: Cleanliness
Excellent In Every Way!
The home is beautiful, well appointed and immaculate. The location is just right and made it very easy to drive everywhere that we wanted to go. It was as easy to get to the Siesta Key beach as to very fine restaurants in the area. The management company responds quickly if you have any questions, which is very helpful.
Stayed 7 nights in May 2024

10/10 Excellent

Jim C.

Liked: Cleanliness
Great place for our family to gather.
We were in Sarasota for a family wedding and gathering. The house was 10 minutes from family and it was perfect for what we needed. The days were stayed at the house we used the pool and Tiki Hut and they were both great! I really enjoyed being able to text and get quick responses to any questions we had. We recommend the house and would stay there again in the future.
Stayed 7 nights in May 2024

10/10 Excellent

Denise S., MT HOLLY SPRINGS, PA

Liked: Cleanliness
Better than expected.
There was plenty of room for everyone. The customer service was excellent. They got back to you quickly when you had a question or issue. The place sleeps 10, however there were not enough beach chairs and we had 7 people. Also, maybe 1 or 2 higher beach chairs for older people could be considered. The bathrooms were nice, but they could use more towel hooks. Overall, the place and our stay was great. Thanks!
Stayed 7 nights in Apr 2024

6/10 Okay

Cara F.

Liked: Cleanliness
Great Mgmt Company, Okay House
For the price of this home, we would not stay here again. The home is on the corner of a busy street so we heard a lot of road noise, the pool is smaller than the pictures look and in a cage, and the home decor is quite dated. On the plus side, it was definitely a comfortable home, a good overall location (minus the road noise) and the management company is extremely responsive and lovely to work with. If the house had been priced differently, we would have given it a very different review.
Stayed 6 nights in Feb 2024

10/10 Excellent

Lois D.

Liked: Cleanliness
Perfect for our stay and probably in the future.
This was a very last-minute booking for us. The management company was very attentive. Absolutely loved the layout, including the very comfortable yet functional furniture. The location is close to a variety of different vacation activities, from Siesta Key, golf, and Sarasota. The outdoor tiki bar, patio, was a lovely secluded oasis even though it was next to an invisible busy road. We enjoyed watching winter ski movies while sitting at the outside bar. Will keep this property on our list for future stays. Thank you.
Stayed 5 nights in Jan 2024

6/10 Okay

Terri E.

Liked: Cleanliness
Family Vacation
If you don't mind the owners of this property showing up unannounced everyday and yelling because the hot tub is too hot, Then this is the house for you. The house was nice, But we would never rent this property again. There was no privacy.
Stayed 5 nights in Dec 2023

10/10 Excellent

judith s.

Liked: Cleanliness
Thanksgiving visit
Fabulous!
Stayed 7 nights in Nov 2023

10/10 Excellent

Verified traveller

Liked: Cleanliness
Unforgettable vacation
Beautiful house made the perfect vacation for my parents, sisters and in-laws who came from abroad. House has everything just like described, hosts are attentive to everything you might need. Location is superb. We really really enjoyed our stay. Missing it already! Thank You!
Stayed 6 nights in Oct 2023

10/10 Excellent

Tony T., Jackson, NJ

Liked: Cleanliness
Great 80th Birthday Blast!
The whole experience was incredible. The house was Upscale but cozy. All the necessary amenities were there for us. All in all, I would very much love to use The Cottages on the Key again! The only unfortunate thing was this: On Sunday were planning to have others in my family from Sarasota join us for the Sunday football experience at our Tiki Bar. The Tiki Bar TV was not operational so we contacted help and they within 30 minutes sent a repairman. Unfortunately the TV required a special remote and he attempted to obtain another one that afternoon. He later texted me that he could not get one but would have one the next day.(our departure) It did put a huge damper on what was supposed to a great time.
Stayed 4 nights in Sep 2023

10/10 Excellent

Abir T.

Liked: Cleanliness
Beautiful house
The house was very clean, well equipped and comfortable. It has an amazing decor as well. Management was quick to response to any inquiries. We loved Sarasota! The beach was amazing. We will probably come back.
Stayed 4 nights in Aug 2023

10/10 Excellent

flora p.

Liked: Cleanliness
2023 holiday
Was as described very well equipped, very thoughtful starter packs beach supplies would definitely come again
Stayed 7 nights in Jul 2023

10/10 Excellent

Carrie H.

Liked: Cleanliness
Perfect family home
Beautiful property inside and out. Great location to enjoy all Sarasota has to offer. Lovely pool and separate lounging were where we spent our downtime.
Stayed 7 nights in Jun 2023

10/10 Excellent

William H.

Liked: Cleanliness
Awesome House!
It was perfect. Not too far from the beach. Very responsive to any needs or issues. Pool is small but we only used it for late evening relaxation after coming from the beach.
Stayed 7 nights in Jun 2023

10/10 Excellent

Mimi S.

Liked: Cleanliness
Beautiful home
We loved this property because it was so very spacious and everything was updated. We would stay here again in the future!
Stayed 7 nights in Mar 2022

10/10 Excellent

mike l.

Liked: Cleanliness
Awesome vacation
Home was amazing and we loved the Sarasota area Will try to rent again next year
Stayed 7 nights in Mar 2022

10/10 Excellent

beatrice i.

Liked: Cleanliness
Not a hot tub
It was as expected except the hot tub was part of the pool.. 88 degrees is not a hot tub.
Stayed 7 nights in Mar 2022

10/10 Excellent

Sharon G.

Liked: Cleanliness
Incredible stay!!
Casamigos is a pearl in an oyster!! We spent 5 weeks in this amazing home with every amenity you could think of. It is close to the south village, downtown and the beaches! Roger and his family were fabulous and made sure we had everything we could dream of. Thank you for the incredible memories!
Stayed 35 nights in Feb 2022

10/10 Excellent

Marc G.

Liked: Cleanliness
Great property and location
Highly recommend great location and beautiful house. Heated pool great for kids! Owners were fantastic and very responsive
Stayed 7 nights in Nov 2021

10/10 Excellent

Jennifer W.

Liked: Cleanliness
Great rental property close to beach
I stayed at this property with family for a week and we had a wonderful time. The house is beautiful, very clean and well kept. The kitchen was well stocked with all the equipment we needed, including a great coffee machine! We really enjoyed the pool and the house was a short drive to Siesta Key (and even closer to Publix). The owner and management company were also very responsive and went out of their way to make our stay perfect. I highly recommend this property and would happily return!
Stayed 7 nights in Jul 2021