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

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A heated pool
Smart TV
Dining
Fridge, microwave, oven, stovetop
5 bedrooms, iron/ironing board, free WiFi, bed sheets

Reviews

9.4 out of 10
Exceptional

Entire home

5 bedrooms3 bathroomsSleeps 10211 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Explore the area

View map
Sarasota, FL
  • Place, Coconuts Family Entertainment Center
    ‪15 min walk‬
  • Place, The Landings
    ‪4 min drive‬
  • Place, Lido Beach
    ‪18 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪21 min drive‬

Room options

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  • Parking included
  • Free Wi-Fi
4.6 out of 5, Wonderful, 1,003 reviews
The price is NZ$347
includes taxes & fees
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About the area

Sarasota

With a stay at this vacation home, you'll be centrally located in Sarasota, a 2-minute drive from Sarasota Memorial Hospital and 7 minutes from Siesta Key Beach. .This vacation home is 6.8 mi (10.9 km) from Lido Beach and 5.1 mi (8.2 km) from St. Armands Circle.
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What's nearby

  • Coconuts Family Entertainment Center - 15 min walk - 1.3 km
  • The Landings - 4 min drive - 2.8 km
  • St. Armands Circle - 17 min drive - 11.2 km
  • Lido Beach - 18 min drive - 11.8 km
  • Mall at University Town Center - 22 min drive - 23.8 km

Getting around

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

Restaurants

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

🌴 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.
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. Complimentary wireless internet access is available to keep you connected.
Enjoy recreational amenities such as a water park and a hot tub.
Guests will find features like wireless internet access and onsite parking.

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Heated pool
  • Hot tub
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Onsite parking options include a garage

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Freezer
  • Hob
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 3 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room
  • Separate dining area

Entertainment

  • Smart TV with cable/satellite channels

Outdoor areas

  • Fenced yard
  • Gas grill
  • Lanai

Laundry

  • Laundry facilities
  • Washer/dryer

Comfort

  • Air conditioning
  • Fan
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a village
  • In the city centre
  • Near a hospital
  • Near a zoo
  • Near an outlet shopping centre
  • Near the bay
  • Near the marina
  • Near the sea

Things to do

  • Heated pool
  • Optional golf privileges
  • Water park
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Horseback riding nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkelling nearby
  • Swimming nearby
  • Wildlife walks nearby
  • Windsurfing nearby
  • Winery tours nearby

Safety features

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

General

  • Unit size: 2,269 square feet

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
Information provided by the property may be translated using automated translation tools

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 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
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. 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

Reviews

10/10 Excellent

Sara L.

Liked: Cleanliness

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

10/10 Excellent

Mike G.

Liked: Cleanliness

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

8/10 Good

Mark M.

Liked: Cleanliness

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

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