Vacation Rentals By Owner In Oak Bluffs, MA

Showing 308 Of 308 Vacation Rentals

$506.69

Bright old-world cottage with two porches & large yard - walk to town & beaches

Oak Bluffs, Massachusetts, United States

Oak Bluffs CottagebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrSavor the old-world charms of Oak Bluffs Cottage, an ideally situated Martha's Vineyard getaway with a two-level porch to enjoy quiet island mornings and evenings! Take advantage of the provided beach chairs as you spend fun summer days in the sun and come home from the beach to prepare meals for the whole family in the full kitchen, or opt for an outdoor barbecue with the provided grill, the spacious yard, and the shaded deck. Don't worry about the heat, as there are new ductless mini-split air-conditioning units in the common areas and all three bedrooms.brbrWhat's nearby: brThis home is conveniently located on the edge of downtown Oak Bluffs, just over half a mile west of the ferry terminal. You'll be within easy walking distance of great restaurants, a market, coffee shops, incredible seafood, and the historic Flying Horses Carousel. The home is also only three-quarters of a mile from Inkwell Beach, Oak Bluffs Town Beach, Ocean Park, and the marina.brbrThings to know:brbrParking notes: There is free parking available for 1 vehicle.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

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Bath

Sleeps

Exceptional(6)

$967.54

/ Nightly

Private Vacation Home

Charming home with private hot tub, firepit, deck, grill, outdoor shower, AC

Oak Bluffs, Massachusetts, United States

Tiffany's TreasurebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThis two-story home will be just the perfect place to bring the whole family for an unforgettable vacation to Oak Bluffs! Nestled in the woods on a beautiful 1.58-acre lot and adjacent to the Trailhead Southern trails, this private home away from home is the perfect retreat if you are searching for endless peace of mind. brbrYou will be close to great local attractions, including Martha’s Vineyard Performing Arts Center, Oak Bluffs Town Beach/Inkwell Beach, Oak Bluffs downtown/ferry, Flying Horses Carousel, Joseph Sylvia State Beach, downtown Edgartown, and Lighthouse Beach.brbrThis charming home is all about outdoor living with an extensive deck offering the perfect spot to unwind and create everlasting memories! Treat yourself to soothing baths in the private hot tub or gather around the firepit for some storytelling while roasting marshmallows. Grab your favorite book and head over to the hammock in the woods for a relaxing time. There is an outdoor dining area and a gas grill should you feel like surprising your friends with delicious grilled treats. In addition, you will find an outdoor shower that is perfect for rinsing off!brbrInside, discover a bright great room with vaulted ceilings and skylights. There is a plethora of entertaining books if you are more of a bookworm. The large kitchen area is appointed with all modern appliances and essentials needed to prepare culinary masterpieces. This floor also houses two bedrooms with access to the deck. Upstairs are two main suites with en suite bathrooms, and one of them also enjoys a private balcony.brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brbrParking notes: There is free parking available for 4 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

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Exceptional(79)

$454.62

/ Nightly

Private Vacation Home

Comfortable Island Home, Easy Access to Beaches and Town

Oak Bluffs, Massachusetts, United States

Salt Box style Log Home with open floor plan built by my family with a country feel, located on a wooded lot in the down island town of Oak Bluffs. Central Air and easy walk to local beach that is used by families of the Lagoon Heights area. Beautiful town and state beaches close by. Charter fishing, golf, great restaurants and ample shopping for the occasional rainy day. Many local attractions to visit, gingerbread homes, tabernacle, oldest functioning carrousel, walking/ bike trails and nature preserves to keep one busy while enjoying the the Vineyard's laid back, casual nature. First floor bedroom has queen bed, upstairs has the full bed. Loft area has three twin beds. Screened porch has wicker furniture, two couches and two comfortable chairs. The home provides a comfortable retreat for those that prefer to be away from crowds, yet only a short trip to town and the beaches.br*If not able to bring your own linens, they can be provided for an additional fee that is dealt with at the time of arrival. I will discuss with the guests prior to arrival. brbrKeywords: Log home, deck, screened porch, grill, outside shower, quiet neighborhood, walk to local beach, 1.1 miles to town, restaurants, shopping and fishing. Golf close by at Farm Neck and a 10-15 minute ride to Mink Meadows Golf Club in Vineyard, Haven.brbrCheck in time generally around noon on day of arrival. Varies according to departure of party leaving. Check out time is generally 10 am to provide sufficient time for turnover(terminal cleaning) before next parties arrival.brbrOwner does not break up a prime summer week, therefore all bookings need to be for seven nights. In addition, the weeks need to run Saturday to Saturday, as the turnover day with support with cleaning is on Saturday during prime time. All other dates can book a minimum of two nights at anytime.

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Bath

Sleeps

Exceptional(14)

$3725.2

/ Nightly

Private Vacation Home

Oak Bluffs Retreat. NEW PRIVATE POOL

Oak Bluffs, Massachusetts, United States

Large beautifully appointed three bedroom, 2 1/2 bath house, with a den perfect for space for everyone to enjoy themselves. The enormous living room is sun drenched as it is flanked by floor to ceiling windows and has two sitting areas -- one for nights gathered around the TV and the other which is great for conversation. The living room leads to a large wrap around deck with a gas grill, family size outdoor dining table, and love seat and chairs. There is an open kitchen and dining room that is perfect for entertaining. In the mornings sit and sip coffee or read a book in the cozy sitting room off of the kitchen. brbrWhile the inside of the home is inviting, you will be undoubtedly drawn to its outside. There is a large black bottom pool, appointed with lounge chairs for each house quest. The fire pit is the perfect setting for late night chats with friends after a perfect meal together on the large deck off of the living room. brbrThe three bedrooms are on the second floor. The large master with a California king bed is an oasis with an en suite bath and a private terrace. The two amply sized guest bedrooms share a bath and have their own balcony, which is shared between them. One guest bedroom has a queen size bed the other room has two twin beds. On the third floor is a den -- or man cave -- with a sofa, TV.brbrWhile the inside of the home is inviting, you will be undoubtedly drawn to its outside. The house sits on 1 1/2 acres with beautiful landscaped gardens. There is a large black bottom pool, appointed with lounge chairs for each house quest. The fire pit is the perfect setting for late night chats with friends after a perfect meal together on the large deck equipped with oval dining table off of the living room. If solitude is more your desire, treat yourself to the private deck off of the master bedroom and a shared deck between the two quest bedrooms. brbr The location is ideal no matter how you choose to spend your day. Its central location is just minutes from the heart of Oak Bluffs, Edgartown, Vineyard Haven and many beaches! The house sits right off of the bike path and is just a short walk to YMCA and all of its amenities -- including its incredible gym facilities and heated pool. The home is equipped with WiFi, two large screen smart TVs, and gas grill,

Bed

Bath

Sleeps

Exceptional(3)

$758.93

/ Nightly

Private Vacation Home

House with guest studio close to town and beach with grill, games, AC & patio

Oak Bluffs, Massachusetts, United States

Sankofa Martha's VineyardbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrNestled in the historic Vineyard Highlands at the beginning of the African American Heritage Trail, this charming home with included studio offers a unique and inviting retreat for your vacation. The newly renovated cottage-style house is located in the sought-after East Chop area of Oak Bluffs, providing a perfect blend of tranquility and convenience. Step onto the fabulous front porch for some people-watching or enjoy a private backyard oasis, ideal for al fresco dining.brbrWith 4 bedrooms, 2 baths, and the ability to comfortably sleep 9 guests, this home is perfect for families or groups of friends looking to explore the beauty of Oak Bluffs. Just a short walk away from Circuit Ave, Oak Bluffs Harbor, the beach, and the iconic East Chop Lighthouse, you'll have easy access to all the town's attractions while still enjoying a peaceful setting. Parking is included for two cars in the driveway.brbrThe amenities at this vacation home are designed to enhance your stay and provide all the comforts of home. From a washer/dryer and gas fireplace to a fully equipped kitchen with modern appliances, you'll have everything you need for a relaxing getaway. Enjoy the outdoor firepit, patio, and gas grill for memorable evenings under the stars. The property also includes Sankofa Studio, a fabulous studio apartment for additional space and privacy.brbrExplore the area's natural beauty and attractions, from the nearby beaches to the historic sites and lively town center. Whether you're interested in water activities like kayaking and jet skiing or prefer hiking and cycling adventures, Oak Bluffs offers something for everyone. After a day of exploration, unwind in the comfortable living spaces, play board games, or stream your favorite shows.brbrDon't miss the chance to experience the best of Oak Bluffs from this exceptional vacation rental. Book your stay today and create lasting memories in this picturesque seaside town on Martha's Vineyard.brbrPlease note that Martha's Vineyard, while beautiful with an abundance of natural landscapes, does have ticks in grassy and wooded areas, so we recommend checking yourself after outdoor activities and taking appropriate precautions to ensure your stay remains enjoyable.brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brbrParking notes: There is free parking available for 3 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

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Sleeps

Exceptional(63)

$921.53

/ Nightly

Guest House

Carriage House, Swimming, Boating, Kayaking, just steps from your door...

Oak Bluffs, Massachusetts, United States

WELCOME TO PARADISE!!! we sanitize!!!!! We have implemented a system so you are able to check in and out without and person to person contact. We care about safty.brThis beautiful new Carriage House is located in Prestigious Fresh Pond Estates. It sits tucked away in the woods off the main roads, Plenty of privacy in a quiet neighborhood. Yet has easy access to beaches, bike paths and town, Fresh water pond in your back yard. (3 two person kayaks available plus 2 single kayaks for your use, with life jackets). (THEY EACH SEAT 2 PEOPLE) Fresh water swimming offers calm waters which makes it great for the kids.brbrWe sanitize the entire place in-between each tenant. We wash all comforters each time someone new comes in, we bleach all surfaces and alcohol all door handles, toilet, air out the place for 24 hrs...brbrJust 2 miles from the HEART of Oak Bluffs & Circuit Avenue activities. brOak Bluffs center offers, restaurants, movies, the nation's first carousel, shopping, and more beaches. brJust 500 feet from bike path, This property is centrally located a 5 minute drive to Edgartown or Vineyard Haven. brNo need to bring anything, high chair, toys, video games, books, DVD collection, beach toys, towels, house is fully equipped. Crib upon request..brLots of extras available on this wonderful property Amenities include Air Conditioning, Wifi, TVs & Laundry Facilities. The large, modern windows accentuate the view. The kitchen opens onto Living area.Great Location for visitors with or without a vehicle. Public Transportation close by.Tour the beautiful island of Martha's Vineyard. Stay in comfort. Shops, restaurants & galleries are a short drive away. Ideal Retreat for Groups and friends traveling together.brHome is located just 100 yards from the pond which is a wonderful spot to enjoy a beautiful sunset or sunrise or your morning coffee. The house is bright and airy with an open floor plan and cathedral ceilings. The well equipped kitchen has everything needed . This exceptional property has a park-like setting with wildlife and gardens , apple trees, raspberries, grapes,- excellent for walking, biking, running and water sports. Take the nearby bike path to many Vineyard towns and beaches. A vacation to remember!brbrHistory of Oak Bluffs: Oak Bluffs is the quintessential old fashioned summer resort. Lively & upbeat, Circuit Avenue offers galleries, retail shops - clothing, crafts & jewelry, a variety of casual & upscale restaurants, ice cream parlors, pubs w/music, bicycle rentals, lodging & a harbor w/cafes & water-sports available. Ocean Park faces the water & is home to summer concerts & events. The gingerbread cottages dating back to the 1800s in the campgrounds surround the open air Tabernacle which offers services, community sings, art shows, high profile professional performing artists & political forums. Union Chapel bustles w/activity. Dancers, authors, artists. Just a mile from the property is Farm Neck is a world class 18 hole golf course frequented by presidents, visitors & locals alike. Music & Aromas fill the air. Walk to the Beach on Nantucket Sound. Walk to everything in town. Island ferries come into the harbor on a seasonal basis. Buses are available to all island towns. Plenty of street parkingbrbrThe island truly offers something for everyone and a vacation experience that won't soon be forgotten.brThis house is located on an acre and a half of beautifully landscaped grounds with lots of trees. brJust a two minute walk to a pond and, a one minute ride to the bike trail, and 2 mile's to town. WIFI included and as well as all Smart TVsbr. Farm Neck Golf Course and the OB Library nearby. You'll never want to leave!brWe welcome you to our tastefully decorated home with all the charm and amenities that is all “Vineyard.” With all new appliances and furniture and hard wood floors, the house has a family-friendly open floor plan. With two bedrooms, One with a new Comfy mattress, the house comfortably sleeps 5 adults.brThis meticulously maintained charming Carriage house offers a great atmosphere with all the amenities for a perfect vacation. Quiet, end of the road location yet really close to town. Wooded backyard with lots of beautiful landscaping.brChildren's toys for all ages,

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Sleeps

Exceptional(18)

$654.98

/ Nightly

Private Vacation Home

Family friendly, walking distance to town, harbor, shops, restaurants, beaches

Oak Bluffs, Massachusetts, United States

Canary CottagebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrExperience the Martha's Vineyard of yesteryear at this beautifully updated historical home, ideally located near the heart of Oak Bluffs. The ferry terminal, the Flying Horses Carousel, Oak Bluffs Town Beach - it's all within a half-mile stroll. This two-story home has stood on Brunswick Avenue since 1870, with a classic, covered front porch where you can relax in the afternoons. It's a wonderful location for walking to dinner, visiting the East Chop Lighthouse, and spending your days on Inkwell Beach or Joseph Sylvia State Beach. brbrBegin and end each day outside on the porch, which offers plentiful space for sipping morning coffee, playing board games in the afternoons, and sharing alfresco dinners with your loved ones. The interior has been thoughtfully updated with modern comforts while preserving the home's 150-year-old character. White walls and ceilings reflect the natural sunlight, two living rooms offer TVs with cable and streaming capability, and the eat-in kitchen is equipped with stainless steel appliances. Find a stacked washer/dryer for your swimsuits and towels, complimentary WiFi throughout the house, and uncluttered bedrooms to provide a restful night's sleep.brbrTHINGS TO KNOWbr Upstairs bathroom has a small showerbrStreaming services are available, but guests must log in using their accounts.brAir-conditioning is comprised of window units which are only available in the living area and three bedrooms.brbrParking notes: There is free parking available for 2 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

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Bath

Sleeps

Exceptional(2)

$543.57

/ Nightly

Apartment

Private suite with roof deck, near golf, bus stop, shops, and trails

Oak Bluffs, Massachusetts, United States

Garage SuitebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWelcome to our cozy one-bedroom suite, a perfect retreat for couples or solo travelers seeking a peaceful getaway in Oak Bluffs, MA. Nestled privately above our garage, this newly built suite offers a serene escape just one mile from the Oak Bluffs ferry, beautiful beaches, charming shops, and the picturesque harbor. For golf enthusiasts, the renowned Farm Neck Golf Course is less than a mile away, while Niantic Park and Tradewinds Field Preserve are just a short stroll from your door.brbrAs you enter the suite, you'll find a welcoming kitchen and dining area that sets the tone for a relaxing stay. The hallway leads you to a modern bathroom with a stand-up shower, and at the end of the hall, a comfortable bedroom awaits, featuring a queen bed designed for restful nights. With central AC and all the essential amenities, including a fridge, microwave, and coffee maker, you’ll feel right at home.brbrEnjoy the fresh air on the roof deck or unwind in the side yard, both accessible from your suite. Please note that the backyard is not available for use, and we kindly ask that you refrain from smoking on the roof deck or stairs to maintain the integrity of the property. brbrWith free parking for one car and a bus stop conveniently located in front of the property (VTA route #7), exploring the area is a breeze. Whether you're interested in beachcombing, whale watching, or simply soaking in the local culture, our suite serves as the ideal base for your adventures. Book your stay today and experience the charm of Oak Bluffs!brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brbrParking notes: There is free parking available for 1 vehicle.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

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Most popular vacation rentals in Oak Bluffs

Exceptional(2)

$2204.99

/ Nightly

Private vacation home

Amazing Gem with Guest House and Private Sandy Beach on Lagoon Pond

Oak Bluffs, Massachusetts, United States

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Exceptional(2)

$2226.16

/ Nightly

Private vacation home

Soulas Martha's Vineyard, Walk to Inkwell Beach & Town

Oak Bluffs, Massachusetts, United States

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Exceptional(2)

$2960.05

/ Nightly

Private vacation home

Best Kept Secret Retreat for Adults with Water & Golf Course Views!

Oak Bluffs, Massachusetts, United States

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Exceptional(2)

$3015.90

/ Nightly

Private vacation home

Grand Coastal-Style Estate In The Preserve

Oak Bluffs, Massachusetts, United States

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Sleeps

Exceptional(2)

$3248.61

/ Nightly

Private vacation home

Maison Calme/Peaceful Home

Oak Bluffs, Massachusetts, United States

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Bath

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Exceptional(2)

$3591.16

/ Nightly

Private vacation home

Spacious 9-bedroom house with Waterview, WiFi, AC in delightful Oak Bluffs

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$3725.20

/ Nightly

Private vacation home

Oak Bluffs Retreat. NEW PRIVATE POOL

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$1108.69

/ Nightly

Private vacation home

Indulge in the ultimate vacation experience at this exquisite custom log home.

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$1076.68

/ Nightly

Private vacation home

AMENITIES GALORE IN OAK BLUFFS PRIVATE COMMUNITY, DOCK, TENNIS, CENTRAL AC

Oak Bluffs, Massachusetts, United States

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Bath

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Exceptional(2)

$1076.81

/ Nightly

Apartment

Perfect location! Beach, Harbor & Town. Beautiful 1st Floor Apartment Oasis

Oak Bluffs, Massachusetts, United States

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Bath

Sleeps

Vacation Rentals By Owner In Oak Bluffs, MA

$506.69

$967.54

$454.62

$3725.2

$758.93

$921.53

$654.98

$543.57

Rent a place that suits your needs

Most popular vacation rentals in Oak Bluffs

$2204.99

$2226.16

$2960.05

$3015.90

$3248.61

$3591.16

$3725.20

$1108.69

$1076.68

$1076.81

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