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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!

Welcome to Casamigos, a striking Spanish-style exterior that sets the tone from the start.
A sweeping aerial of the front drive, framed by palms and manicured landscaping.
The handcrafted tiki bar invites you to enjoy the tropical breezes with a drink.
Mix and mingle effortlessly in this fully equipped tiki bar.
Pull up a stool and enjoy the island-inspired setup.

Reviews

9.4 out of 10
Exceptional
5 bedrooms3 bathroomsSleeps 102269 sq ft

Popular amenities

  • Private pool
  • Hot tub on site
  • Garage parking available
  • Kitchen
  • Washer and dryer
  • Air conditioning

Explore the area

View in a map
Sarasota, FL
  • Place, Coconuts Family Entertainment Center
    ‪15 min walk‬
  • Place, Sarasota Memorial Hospital
    ‪3 min drive‬
  • Place, The Landings
    ‪3 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪22 min drive‬

Rooms & beds

5 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

Bedroom 4

1 King Bed

Bedroom 5

2 Twin Beds

3 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Bathtub or shower · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Dining area

About this property

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

🌴 Casamigos | Heated Saltwater Pool, Tiki Bar, 0.8 Miles to Siesta Key Beach

💖 Why You'll Love This Home
Experience island elegance at Casamigos, a tropical oasis designed for memorable gatherings. From a private heated saltwater pool to an authentic 8-seat tiki bar, every detail invites you to unwind in style. This upscale retreat blends vibrant West Indies charm with modern luxury—ideal for creating lasting vacation memories.

👨‍👩‍👧 Perfect For
Multi-generational families, friend groups, and anyone seeking a stylish, spacious getaway near Siesta Key's best beaches and dining.

🎞️ Imagine This
Imagine waking to the soft Florida sun filtering through towering palms as you step into an airy living room with 12-foot ceilings and cool coastal breezes. Hear the gentle splash of the heated pool just beyond sliding glass doors, where the scent of bougainvillea mingles with fresh breakfast from the gourmet kitchen. In the afternoon, enjoy a fresh panini from the provided press and unwind with a glass of wine from the wine fridge. In the evening, gather with friends at the tiki bar under twinkling lights, sharing cocktails and laughter surrounded by lush tropical blooms and complete privacy.

🛌 Where You'll Sleep
• Bedroom 1: King Bed, Ensuite Bath, TV
• Bedroom 2: King Bed, Shared Bath, TV
• Bedroom 3: King Bed, Shared Bath, TV
• Bedroom 4: King Bed, Ensuite Bath, TV
• Bedroom 5: 2 Twin Beds, Shared Bath

📍 Explore the Area
• 0.7 Miles to Siesta Key Village, Full of Shops, Cafes, and Nightlife
• 1.2 Miles to Siesta Key Beach, Famous for its Powdery White Sand
• 0.3 Miles to Publix Grocery Store for all your Essentials
• Easy Access to Downtown Sarasota, just a 10-minute Drive
• Close to Lido Key's Beaches and Restaurants, about 6 minutes by Car
• Walk to Over 20 Local Restaurants within a Half-mile Radius

⌛ Don't wait—this home books fast. Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection.

📝 Need to Know: Starter packs of kitchen and toiletry essentials are provided for a seamless first couple of nights. Free high-speed WiFi included. Pool heating is available November 15 – April 15. Please inquire if any guests require stair-free access. This property is registered as a vacation rental with the City of Sarasota with a Registration Number of VR25-00068 Due to City of Sarasota vacation rental code, this property must be rented once during a seven (7) day period and have a maximum occupancy of 10 guests.
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Pool
Hot Tub
Kitchen
Washer
Dryer
Free WiFi

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House Rules

Check in after 4:00 PM
Minimum age to rent: 26
Check out before 10:00 AM
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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

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 has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

About the neighborhood

Sarasota

Located in South Poinsettia, a neighborhood in Sarasota, this vacation home is near a water park 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. Mote Marine Laboratory & Aquarium and Marie Selby Botanical Gardens are also worth visiting. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with horse riding and ecotours nearby.
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Map
Sarasota, FL

What's nearby

  • Coconuts Family Entertainment Center - 15 min walk - 1.3 km
  • Sarasota Memorial Hospital - 3 min drive - 2.1 km
  • The Landings - 3 min drive - 2.8 km
  • St. Armands Circle - 14 min drive - 9.2 km
  • Lido Beach - 15 min drive - 9.5 km

Getting around

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

Restaurants

  • ‪McDonald's - ‬10 min walk
  • ‪Walt's Fish Market - ‬17 min walk
  • ‪CinéBistro - ‬8 min walk
  • ‪Red Barn Bar - ‬13 min walk
  • ‪Connors - ‬7 min walk

Frequently asked questions

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

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

How much does it cost to stay at Casamigos | West of the Trail - Private Home with Tiki Bar, Heated Pool, and Spa, Near Siesta Key!?

As of Apr 21, 2026, prices found for a 1-night stay for 2 adults at Casamigos | West of the Trail - Private Home with Tiki Bar, Heated Pool, and Spa, Near Siesta Key! on Jul 29, 2026 start from $534, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Casamigos | West of the Trail - Private Home with Tiki Bar, Heated Pool, and Spa, Near Siesta Key!?

Check-in begins at 4:00 PM.

What time is check-out at Casamigos | West of the Trail - Private Home with Tiki Bar, Heated Pool, and Spa, Near Siesta Key!?

Check-out is at 10:00 AM.

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

Located in South Poinsettia, this vacation home is within 2 mi (3 km) of Sarasota Memorial Hospital, The Landings, and Shell Beach. Marie Selby Botanical Gardens and Sarasota Art Museum are also within 3 mi (5 km).

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 26 out of 32 reviews
Rating 8 - Good. 3 out of 32 reviews
Rating 6 - Okay. 2 out of 32 reviews
Rating 4 - Poor. 0 out of 32 reviews
Rating 2 - Terrible. 1 out of 32 reviews

9.4/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

9.2/10

Location

9.2/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Mitch M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Mike G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fun family getaway

House was comfortable and had everything we needed. Enjoyed breakfast on the covered patio. Beach towels, chairs, umbrellas and toys made daily beach trips easy.
Stayed 7 nights in May 2025
Verified

10/10 Excellent

Carrie H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

judith s.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Thanksgiving visit

Fabulous!
Stayed 7 nights in Nov 2023
Verified

10/10 Excellent

Lydia D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Abir T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Verified traveler

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Nancy R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Jim C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

William H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

flora p.

Liked: Cleanliness, check-in, communication, location, listing accuracy

2023 holiday

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

8/10 Good

Mark M.

Liked: Cleanliness, check-in, communication, listing accuracy

Nice property for family

Very nice home. Wonderful kitchen and good flow. In need of a little upkeep. Marble floors chipped in a number of places is hazardous (cut toe). Roofers stopped by (cold call) every day looking to give a bid to repair roof - visible from the road.
Stayed 7 nights in Apr 2025
Verified

10/10 Excellent

Bettina K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

xxxx

Beautiful house, perfect setup of the rooms. We enjoyed the possibilities of being able to spread out or sit all together. The tiki bar and the pool with spa were amazing!! Plenty of towels, pillows and blankets, nice and clean washer and dryer. We really appreciated the warm welcome in the house. Thank you!
Stayed 14 nights in Dec 2023
Verified

10/10 Excellent

Natasha S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing Experience

Our group of 9 stayed at the Casamigos for Thanksgiving week. The house is spacious, well equipped, all appliances are new and top of the line, plenty of towels, quality bedding, many nice details throughout. The service is top-notch, we felt very pampered with the attention to our needs. It is like staying at a fancy hotel, only better because of space and privacy. Both kids and adults enjoyed the heated pool and the tiki bar. It was a lovely time and we hope to be back soon.
Stayed 9 nights in Nov 2020
Verified

6/10 Okay

Terri E.

Liked: Cleanliness, check-in, communication, listing accuracy

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
Verified

10/10 Excellent

Lois D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Reaper

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Sonya G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Sara L.

Liked: Cleanliness, check-in, communication, listing accuracy

Casamigos

The property was beautifully laid out. We went with one other couple. We each had a king size bed with private bath. We had an amazing chef’s dream kitchen. Loved the pool and Tiki bar. More than enough linens were supplied. The management was called a couple of times for small issues which were fixed within minutes of our phone call. Our only 3 star rating was for the location. Located near a very busy and at times loud intersection. However, we were still within a short drive to Siesta Key beach, local tourist area and grocery stores and pharmacy. We generally eat out every night on vacation but because the house, pool and kitchen were so inviting, we ate in a couple of nights.
Stayed 7 nights in May 2025
Verified

10/10 Excellent

Denise S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

6/10 Okay

Cara F.

Liked: Cleanliness, check-in, communication

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
Verified

8/10 Good

Jack F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice home but in need it of a few touchups

We enjoyed our stay a lot however there are a few things that people should be aware of. The hot water takes a long time to get to the showers. The hot tub does not heat up because it is run on the same pump as the pool. Many of the light switches were in need of repair in the master bedroom As well. many of the walls were scuffed up. I would recommend putting some carpeting near the entryways where people come in from the pool as it’s slippery when wet
Stayed 7 nights in May 2021
Verified

10/10 Excellent

Tony T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

Mimi S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified

10/10 Excellent

mike l.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome vacation

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

About the host

Hosted by The Cottages on the Key, Inc.

Host profile image

What makes this property unique

Welcome to Casamigos, one of Siesta Key's newest luxury homes with private heated pool! Minutes to world famous Siesta Key Beach and Village!

Languages:

English, French, German, Dutch

Premier Host

They consistently provide great experiences for their guests
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