Welcome to this luxury Key West style home by the sea! It is your place in the sun to makememories and unwind! Get ready to make memories at Crosswinds Cottage!Your home away from home This home has been professionally decorated and recently renovated, including luxury vinyl flooring throughout.Sleeping & BathroomsTotal bedrooms: 3 Bedroom 1 (primary suite): King-sized bedBedroom 2: King-sized bedBedroom 3: King-sized bed and a twin-sized bunk bed with a pull-out twin-sized trundle (3 twin-sized beds total) for plenty of sleeping optionsTotal bathrooms: 2.5 Bathroom 1 (primary suite): Separate walk-in shower, a jet tub, a toilet room, double vanity, and hair dryerBathroom 2: Powder room on main levelBathroom 3: ...

Welcome to this luxury Key West style home by the sea! It is your place in the sun to make

memories and unwind! Get ready to make memories at Crosswinds Cottage!

Your home away from home 

This home has been professionally decorated and recently renovated, including luxury vinyl flooring throughout.

Sleeping & Bathrooms

Total bedrooms: 3 

Bedroom 1 (primary suite): King-sized bed

Bedroom 2: King-sized bed

Bedroom 3: King-sized bed and a twin-sized bunk bed with a pull-out twin-sized trundle (3 twin-sized beds total) for plenty of sleeping options

Total bathrooms: 2.5 

Bathroom 1 (primary suite): Separate walk-in shower, a jet tub, a toilet room, double vanity, and hair dryer

Bathroom 2: Powder room on main level

Bathroom 3: Shower-tub combo, generous vanity, and hair dryer 

Amenities 

Elevator: Access to all levels

Private Pool: Heated pool with in-pool bench seating 

Private Yard: Fully fenced yard with full-sized palm trees and professional, tropical landscaping, poolside recliners and Adirondack chairs

Covered Patio: Grill and six-person dining table 

Grilling: Grill and grilling tools (located under covered patio) 

Game Room: Foosball, basketball game, giant Connect-Four game, comfortable sitting area, and TV. 

Balconies: A private balcony off the primary suite with chairs, and a second balcony off the living space with a dining table and four oversized wicker-style chairs 

TVs: Five flat screen TVs throughout the house with Smart TVs in the living room, game room, and large upstairs bedroom; all bedrooms, family room, and the game room have flat screen TVs

Internet: Free, high-speed wireless internet

Appliances: Extra-large sized washer and dryer; and all new, full-sized stainless steel kitchen appliances - fridge, dishwasher, garbage disposal, stove & oven, microwave, coffee maker, Keurig, blender.  The kitchen is fully equipped for any cooking need.

Beach supplies: 2 adult bikes, beach wagon, and beach towels 

Central air-conditioning and ceiling fans in each room 

Professional linen cleaning service   

Access

There is an elevator that serves all floors to accommodate guests and help with luggage.

**Please keep in mind that the elevator is not ADA certified and if it becomes inoperable due to any reason, the stairs will be the only form of transportation to and from the unit**

Pets

Guests are allowed up to 2 dogs. Crosswinds Cottage also has a fully fenced backyard, and the local dog park is a very short walk.   Please see booking terms and conditions. 

Layout 

Crosswinds Cottage is a three-story, Key West style home with elevator access to all levels. 

Ground level: Includes a converted garage game room that offers the best of indoor-outdoor living and access to the private pool and grill. 

Main level: The main level includes the primary suite with a king-sized bed, large walk-in closet, work desk, and private balcony as well as a spacious bathroom with separate shower, a jet tub, toilet room, and double vanity

The kitchen (with island and stainless steel, full-sized appliances), dining room, living room, and shared balcony are also on this level.  The balcony comfortably accommodates 4 for outside relaxing and dining.

Powder Room for guest access.

Laundry area with oversized washer and dryer.

Third level: Two bedrooms and full bathroom with tub located between the two bedrooms. The first bedroom has a king-sized bed. The second bedroom provides you with various sleeping options. It includes a king-sized bed, and a bunk bed comprised of a twin over twin with a pull-out twin trundle.  

Things to do 

Perfectly located to provide privacy and relaxation, Crosswinds Cottage is just a short walk to the beautiful white sand Anna Maria beaches.  Just a few minutes' walk the city park with a children's playground, a skate park, pickle ball court, tennis courts, an open field, and enclosed dog park. 

Easily walk to locally operated restaurants and boutiques with delicious local food and quaint island themed gifts just around the corner. The location of Crosswinds Cottage, in the heart of Holmes Beach, has something for everyone. 

With two adult bikes available for your convenience, you can easily explore the rest of

the island without a car. There is a free public Island Trolley Service is also available to inspire your adventure!  Also, try out the Monkey Bus for point-to-point service. 

Head to the beach, go parasailing, or take a sunset cruise or paddleboard on the crystal-clear blue waters in the Gulf!

Beach

Crosswinds Cottage is just a short five-minute walk to Anna Maria Island's world-renowned white sandy beaches!   

Guests can enjoy the supplied 2 adult bikes, beach wagon, and beach towels. 

Dining

Crosswinds Cottage is close to several dining options. We recommend checking out restaurants like the Waterfront, Chateau Anna Maria, Ugly-Grouper, grab burgers at Skinny's or Harry's, or watch the sunset at the Sandbar or Beach House. 

A local favorite is The Doctors Office for craft cocktails and plates - and only about a five-minute walk from Crosswinds Cottage. 

Shopping

Crosswinds Cottage is about a five-minute walk to nearby boutique shopping - such as Original Sand Dollar and several clothing and beachy boutiques.  You can walk a bit further or take the free trolley to the other shopping hot-spots on Anna Maria Island.  And don't forget the wonderful fresh seafood at local purveyors.  

Transportation

Take the free trolley around Anna Maria - with easy access to Bean Point, historic Bridge Street, and more. 

Why we love it here

Crosswinds Cottage offers a fantastic location that is ideal for your Anna Maria Island getaway. It is close to local shops and restaurants, and it is only a short stroll to the pristine Gulf beaches to enjoy during the day and watch gorgeous sunsets in the evening.  

Crosswinds Cottage is fully outfitted to be your home away from home!

Crosswinds Cottage has a private heated pool with a covered lanai and mature tropical landscaping for your relaxation. Enjoy quality time outdoors around the pool, grill up a delicious home cooked meal or simply try out some of the delicious local seafood--this home offers it all!

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Bringing your dogs?  

Guests are allowed up to 2 dogs. Provided they are housebroken and must be friendly with other dogs and people. Pet must be disclosed up front at the time of inquiring/booking and a one-time non-refundable fee of $150 will be due at the time of booking to accommodate for extra cleaning/pet sanitation. 

Should we receive complaints from neighbors of barking/disruption we reserve the right to ask you to remove the pet immediately. Undeclared pets will be charged $500, and you will be required to vacate the property. By booking this property you are agreeing to the terms and fees associated with bringing an approved pet. We closely monitor all properties.

You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After that time, or for reservations made or less than 60 days in advance of check-in, your reservation is non-refundable.

Written notice is required to cancel a reservation; an email from the address associated with the reservation is acceptable as written notice.

For canceled reservations with a check-in date equal to or less than 60 days away: We will open the property back up to the rental market and if the property re-rents we will refund the guests the rental rate minus the $495 processing fee and any price differential.

If Guest needs to shorten their stay or change to a different property, the normal cancellation policy applies. No changes are permitted during the stay.

You are vacationing in a residential area.  Please be a good neighbor by keeping the noise to a respectful level during the day and night.  Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. Quiet hours on the island are recognized from 10pm-7am.

Rentals typically run Saturday to Saturday, If you are looking for a stay that is not a 7-night rental or would like to begin your vacation on a day other than Saturday please send us an email to [email protected] as we can sometimes accommodate alternate reservations.