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Anna Maria vacation rentals

We found 4,786 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Anna Maria by choosing from 453 houses, 31 condos, and other vacation rentals. Whether you’re staying in a vacation home with friends, family, or just with your pet, you'll have the amenities you expect and more, including WiFi and parking. Whatever you're looking for, you're sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Anna Maria

Showing deals for:May 15 - May 22

Image gallery for Beach across the road, pool a few steps out the door of this charming cottage.

Terrace/patio
10 out of 10, Exceptional, (81 reviews)
Exceptional
(81 reviews)

Beach across the road, pool a few steps out the door of this charming cottage.

Bradenton Beach

13% off
Price is $315
$2,206 for 7 nights
All fees included
Beach across the road, pool a few steps out the door of this charming cottage.

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Find out more about Anna Maria

Why visit Anna Maria

  • Beautiful beaches: Enjoy the pristine sandy shores and stunning sunsets at Anna Maria's picturesque beaches.
  • Rich cultural experiences: Discover local history at charming museums and engage with the vibrant arts scene.
  • Outdoor activities: Participate in various outdoor adventures, including kayaking, fishing, and biking along scenic trails.
  • Family-friendly atmosphere: Experience a welcoming environment perfect for families, with activities for all ages.
  • Luxurious accommodations: Stay in cozy vacation rentals, from beachfront condos to spacious private homes.

Popular types of accommodation in Anna Maria

Discover the perfect getaway with our Anna Maria vacation rentals. Whether you're seeking a cozy condo, a spacious private vacation home, or a charming apartment, we have options to suit every traveler's needs. With a variety of Anna Maria Island rentals available, you can enjoy the beautiful beaches and vibrant local culture in comfort. Explore our selection of Anna Maria Island vacation homes and find your ideal retreat today.

  • Condos: Renowned for their modern amenities, condos are the top choice for vacationers seeking comfort and a stunning view of Anna Maria.
  • Houses: Ideal for families and groups, these spacious homes offer a home-like atmosphere and privacy during your stay.
  • Apartments: Perfect for couples or solo travelers, apartments provide a cozy and convenient base for exploring the island.
  • Cottages: Charming and quaint, cottages deliver a unique, rustic experience, often just steps from the beach.
  • Villas: Luxurious and spacious, villas offer upscale accommodations with exquisite designs and amenities.**

Top attractions in and around Anna Maria

Anna Maria, Florida, is perfect for beach lovers and outdoor enthusiasts seeking scenic beauty and cultural experiences. With attractions like stunning beaches, fascinating history museums, and vibrant marinas, visitors can enjoy a variety of activities. This charming destination offers a delightful blend of relaxation and exploration, making it an ideal spot for a memorable vacation.

  • Anna Maria Beach: A stunning beach located 0.7 miles from Anna Maria, this spot offers a tranquil atmosphere with soft sands and beautiful sunsets. Perfect for relaxing, sunbathing, and enjoying the gentle waves.
  • Bean Point Beach: Situated within Anna Maria, this picturesque cape features stunning scenery and a serene beach vibe. It's an ideal location for peaceful walks and breathtaking views of the Gulf.
  • IMG Academy: Located 10 miles away, IMG Academy is renowned for its sports training programs and athletic facilities, making it a unique destination for sports enthusiasts and aspiring athletes.

Things to do recommended for couples

For a romantic getaway in Anna Maria, indulge in a soothing treatment at Aluna Wellness Center & Spa, just 4 miles away. For an adventure, try paddleboarding with AMI Paddleboard Adventures, 3 miles away. End your day with some fun at Fish Hole Adventure Golf, located 5 miles from the island.

Things to do recommended for families

Families can enjoy a game at LECOM Park, explore ice skating at Ellenton Ice and Sports Complex, or unwind at Maximo Park for a relaxing day outdoors. Each location offers unique experiences perfect for creating lasting memories together.

Things to do recommended for groups

Enjoy a night out at the Island Players theater for a cultural experience, shop for unique items at the West Coast Surf Shop just 3 miles away, and explore Bridge Street's family-friendly atmosphere 5 miles from Anna Maria for a perfect blend of entertainment and shopping.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Anna Maria

When traveling with a group, family, pets, or planning an extended stay, it's important to prioritize the right features. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Anna Maria with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Anna Maria with young kids: Traveling with young kids can be a bit tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, think about how close you are to family-friendly attractions to make the trip more enjoyable.
  • Taking your pets with you to Anna Maria: For many families, a vacation isn't truly fulfilling without their furry companion joining in. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Anna Maria: If you're in search of vacation rentals that offer great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search to enhance your experience.

Where to stay near Anna Maria

Anna Maria, Florida, is a charming beach destination perfect for outdoor enthusiasts and families alike. Explore stunning beaches, indulge in luxury vacation properties, and immerse yourself in the friendly atmosphere of this quaint city. Nearby, you can discover vibrant neighborhoods offering excursions and budget-friendly options, making it an ideal getaway for all types of travelers. Experience the best of island life and create lasting memories in this picturesque coastal paradise.

  • Anna Maria Island: Nestled just 2 miles from the vibrant town of Anna Maria, this picturesque island boasts stunning beaches and a relaxed atmosphere perfect for families and outdoor enthusiasts. Visitors will find an array of resorts and recreational areas, making it an ideal spot for beach activities and relaxation. The local attractions include beautiful family beaches and a nearby theme park, offering fun for all ages. Explore charming shops and indulge in delicious dining options while soaking in the breathtaking coastal views.
  • St. Pete Beach: Located 15 miles away, St. Pete Beach is a lively city known for its beautiful sandy shores and family-friendly atmosphere. This destination is perfect for those seeking outdoor adventures and relaxation by the sea. St. Pete Beach offers a variety of resorts and shopping areas, ensuring a delightful experience for visitors. Enjoy the stunning local beaches and discover the unique charm of the town’s neighborhoods, where you can find dining, shopping, and entertainment options that cater to all tastes.
  • Holmes Beach: Just 3 miles from Anna Maria, Holmes Beach is a charming city that embodies the quintessential beach getaway. With its family-friendly vibe and outdoor activities, it’s an excellent choice for travelers seeking sun and fun. Highlights include a selection of resorts and shopping mall centers, as well as access to beautiful beaches and scenic recreational areas. Visitors can also explore the nearby cape, making it a perfect location for those who want to enjoy the natural beauty and laid-back lifestyle of Florida’s Gulf Coast.

Best time to go to Anna Maria

If you're planning a trip to Anna Maria, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from May to July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January62.4°F (16.9°C)Light RainMostly SunnyAverageSlightly Low
February64.8°F (18.2°C)No Rain (Dry)Mostly SunnyAverageAverage
March67.8°F (19.9°C)No Rain (Dry)Mostly SunnyAverageSlightly High
April73.0°F (22.8°C)Light RainSunnyAverageSlightly High
May77.5°F (25.3°C)Light RainMostly SunnyHighAverage
June81.7°F (27.6°C)Light RainMostly SunnyHighAverage
July83.1°F (28.4°C)Light RainMostly SunnyHighSlightly High
August83.7°F (28.7°C)Light RainMostly SunnyAverageAverage
September81.7°F (27.6°C)Light RainMostly SunnyAverageSlightly Low
October77.2°F (25.1°C)Light RainMostly SunnyLowSlightly Low
November70.5°F (21.4°C)Light RainMostly SunnyLowAverage
December66.4°F (19.1°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming travel plans? Being open to adjusting your travel dates can really help, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to narrow down options by price, location, and type of vacation rental.

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you’ll receive OneKeyCash on the full booking amount. It's certainly rewarding to be the planner. Become a part of our One Key rewards program to unlock exclusive savings for members and earn OneKeyCash on eligible stays. Sign up today and start reaping the benefits.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or easily view and organize your travel plans. You can find properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

With beaches and fun activities, you’ll love Anna Maria

Visitors to Anna Maria Island always find a fun vacation haven, perfect for kayaking and experiencing island life. Tucked away on Anna Maria’s north end is Bean Point Beach, ideal for those seeking an island paradise with an Old Florida vibe. Anna Maria Bayfront Park offers sweeping views of Tampa Bay, and in addition to its beaches is also home to numerous restaurants. Spend your afternoons with your toes in the sand or shopping till you drop—either way, your Anna Maria vacation rental gives you access to a getaway the whole family will enjoy.

Immerse yourself in the Anna Maria experience

The beaches are just one reason to book an Anna Maria vacation rental. The island boasts museums as well as restaurants serving everything from fresh seafood to specialty cupcakes and donuts. Take a stroll on the pier—or down Pine Avenue with its colorful, eclectic shops. It’s not every day you get to soar hundreds of feet over the ocean, so if you’re feeling brave, try parasailing. If staying in the water is more your speed, check out Bean Point, and keep an eye open for manatees, which are known to mingle with human swimmers.

Pack the sunscreen—there’s lots to do in Anna Maria

Anna Maria vacation rentals are perfect if you love the beach. There are endless entertainment options for those who love the sun, sand, and water. Rent Segways for the family and tour the island in style. Go on a sightseeing dolphin cruise, or have some high-powered fun on a jet ski. Spend hours relaxing on the beach, or keep things active and sign up for a kayak lesson or tour. Paddleboard rentals, boat trips, fishing excursions and more are yours for the taking when you book a vacation rental in Anna Maria.

Expect pleasant weather any time of the year

Anna Maria has sun, sand, beautiful beaches, and exceptional weather. The climate is warm and temperate with plentiful rainfall, and when it does rain, it’s often short-lived before the clear blue skies return. Most of the year sees abundant sunshine, and in the heart of summer, the average high is a pleasant 88 degrees. Winter is mild with an average January low of 52. The best time to book a vacation rental in Anna Maria depends on what you’d like to do, but even winter is typically comfortable enough for outdoor activities.

Exploring the natural features in Anna Maria

Travelers enjoy Anna Maria for its island views, beaches and sunrises. Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Anna Maria is a great spot to appreciate mother nature. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Lido Beach (18.2 mi / 29.3 km)
  • Bean Point Beach (0.6 mi / 1 km)
  • Anna Maria Beach (0.9 mi / 1.4 km)
  • Manatee Public Beach (2.6 mi / 4.2 km)
  • Brandenton Beach (4.2 mi / 6.8 km)
  • Cortez Beach (5.2 mi / 8.4 km)

Transportation to and around Anna Maria

The nearest airport is in Tampa Intl. Airport (TPA), located 33.2 mi (53.5 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Sarasota-Bradenton Intl. Airport (SRQ), which is 14.8 mi (23.9 km) away.

Frequently asked questions

What is the best area to stay in Anna Maria, Florida, United States of America when booking a vacation rental?
A great area to consider when booking a vacation rental in Anna Maria, Florida, is the northern part of the island. This charming neighborhood is known for its laid-back atmosphere and beautiful beachfront, making it an ideal spot for families and couples looking to unwind. With a range of properties available, from cozy cottages to spacious beachfront homes, you'll find options that cater to different preferences and budgets.

One of the top attractions in this area is the stunning Anna Maria Island Beaches, where you can soak up the sun, enjoy swimming, or take leisurely strolls along the shore. Another highlight is the Anna Maria Island Historical Museum, which offers insights into the island's rich history and culture, making it a great stop for those interested in local heritage.
How much does it cost to rent a vacation home in Anna Maria?
Prices for vacation rentals in Anna Maria vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Anna Maria to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Anna Maria vacation house rentals?
You can find great discounts on house rentals in Anna Maria on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Anna Maria?
For renting a beach house in Anna Maria, the area along the Gulf of Mexico is particularly appealing. The northern part of the island offers a tranquil atmosphere with beautiful sandy beaches, making it ideal for families and couples seeking a relaxing getaway. Properties here often feature amenities such as private pools, outdoor dining areas, and direct beach access, allowing guests to fully enjoy the coastal experience.

The vicinity near Anna Maria Island City Pier is another attractive option, where you'll find charming cottages and larger homes that cater to various group sizes. Many of these rentals come equipped with modern kitchens, spacious living areas, and porches or balconies that provide stunning views of the sunset over the water. The area is also close to local shops and restaurants, adding convenience for travelers looking to explore the local culinary scene.

Additionally, the southern end of the island near Coquina Beach offers a more laid-back vibe, with beach houses surrounded by lush tropical landscapes. Here, visitors can expect properties with outdoor showers, beach gear, and easy access to the nature trails in the nearby Leffis Key Preserve.
What is the most popular type of vacation rental accomodation in Anna Maria?
In Anna Maria, vacation houses are the most popular type of rental, with about 727 available throughout the area. These houses are often located near the beach and local attractions, offering spacious living areas, multiple bedrooms, and fully equipped kitchens, ideal for families or groups. Many also feature private outdoor spaces, such as gardens or patios, superb for enjoying the warm Florida weather. Additionally, there are around 40 condos, which typically provide amenities like pools and fitness centers, while 28 cottages and 18 apartments offer a cozier, more intimate setting.
Are there any family house rentals in Anna Maria?
In Anna Maria, Florida, families will find a wealth of rental options—approximately 638 homes available throughout the area. The charming neighborhoods like Anna Maria City and Holmes Beach are particularly popular among families, offering a variety of spacious rooms. Many of these properties come equipped with full kitchens, allowing for convenient meal preparation, as well as comfortable living areas for family gatherings.

Visitors can enjoy amenities such as private pools, outdoor patios for barbecues, and even game rooms to keep the kids entertained. Proximity to beautiful beaches, such as Bean Point and Manatee Public Beach, ensures that families can easily access sandy shores and water activities. Additionally, local attractions like the Anna Maria Island Historical Society and the nearby Coquina Beach make for great day trips.
Can I rent a vacation home with a pool or hot tub in Anna Maria?
In Anna Maria, there are many vacation homes available for rent that feature pools and hot tubs, with around 683 options to choose from. This picturesque island community is known for its stunning beaches and charming atmosphere, making it a popular destination for travelers seeking relaxation.

You can find these properties throughout various neighborhoods on the island, including the tranquil areas near Bean Point and the bustling spots close to Anna Maria City Pier. Many rentals come equipped with private swimming pools, hot tubs, and spacious outdoor patios, ideal for enjoying the warm Florida weather. Additionally, amenities like fully equipped kitchens, laundry facilities, and Wi-Fi are commonly available, ensuring a comfortable stay for families and groups.
Can I find long-stay vacation rentals in Anna Maria?
A long-stay vacation rental in Anna Maria is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Anna Maria?
In Anna Maria, there are a number of pet-friendly house rentals available, with a total of 274 options for travelers looking to bring their furry friends along. Many of these rentals are located close to the stunning beaches and picturesque waterfront, providing both comfort and convenience for guests. Expect amenities such as spacious backyards, outdoor seating areas, and fully equipped kitchens, making these homes great for families or groups looking to enjoy a relaxed beach vacation with their pets.

The Anna Maria Island area itself is renowned for its charming atmosphere and access to pet-friendly parks and beaches. The nearby Anna Maria City Pier offers scenic views and is a great spot for leisurely walks with pets. Additionally, several local restaurants and cafes welcome pets, allowing for enjoyable outings throughout the trip.
Are there any remote work vacation rentals in Anna Maria?
In Anna Maria, Florida, there are numerous vacation rentals suitable for remote work, with around 808 options available. This charming coastal destination offers a variety of properties that cater to those looking to balance work and leisure. Many of these rentals come equipped with high-speed internet access, ensuring a reliable connection for remote work needs. You can expect amenities such as dedicated workspaces, Wi-Fi, and comfortable living areas that allow for productive work sessions.

The island is known for its beautiful beaches, quaint shops, and local dining experiences, providing plenty of opportunities to unwind after a day of work. Properties often feature outdoor spaces like patios or balconies, superb for enjoying the warm Florida weather. Additionally, being close to points of interest such as the Anna Maria City Pier and the scenic beaches makes it an ideal location for a workation. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Anna Maria vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Anna Maria with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Anna Maria?
In Anna Maria, popular vacation rental amenities include fully equipped kitchens, allowing guests to prepare their own meals and enjoy home-cooked dining. Onsite parking is commonly available, which is convenient for those traveling with vehicles. Many rentals feature decks or patios, providing outdoor spaces to relax and enjoy the pleasant Florida weather. Additionally, coffee and tea makers are standard in most units, suiting guests' morning routines. Furthermore, many properties are located near the beach, offering easy access for sunbathing and water activities.
When is the best time to visit Anna Maria for a vacation rental?
The best time to book a vacation rental in Anna Maria is during the peak season, which runs from May to July. This vibrant period attracts families and beach enthusiasts eager to soak up the sun on the island's stunning sandy shores. With warm temperatures averaging in the mid-80s Fahrenheit, this season is great for outdoor activities, from swimming and snorkeling to kayaking in the gentle waves of the Gulf.

June stands out as a particularly popular month, offering a lively option with plenty of events and local festivals that highlight the island's charm. Visitors can enjoy leisurely strolls along the beach, explore quaint shops, and indulge in fresh seafood at local eateries, all while basking in the delightful coastal climate.

For travelers seeking more budget-friendly options, consider visiting in November. This month provides a peaceful retreat, allowing guests to enjoy the natural beauty of Anna Maria without the bustling crowds. The weather remains pleasant, with temperatures typically in the low 70s Fahrenheit, making it ideal for beachcombing and scenic bike rides along the picturesque coastline.

Ultimately, whether you prefer the vibrant energy of the peak season or the tranquility of the shoulder months, Anna Maria offers a delightful experience year-round.
How early should I book a Anna Maria vacation rental?
Book your Anna Maria vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Anna Maria, Florida, United States of America?
In Anna Maria, Florida, visitors can enjoy a variety of attractions that highlight the area's natural beauty and relaxed coastal charm. The Anna Maria Island Historic Green Village offers a glimpse into the area's history with its eco-friendly shops and educational exhibits. The beautiful beaches along the island, particularly in the Holmes Beach area, are great for sunbathing and swimming, with soft sandy shores and clear waters.

For outdoor enthusiasts, the Anna Maria City Pier is a popular spot for fishing and enjoying stunning views of the Gulf of Mexico, while nearby Tampa Bay offers opportunities for kayaking and paddleboarding. Additionally, the island features the picturesque Bean Point Beach, renowned for its tranquility and breathtaking sunsets.

Visitors can also explore the local dining scene, with many waterfront restaurants serving fresh seafood and providing a laid-back atmosphere. The charming shops and galleries in the Pine Avenue area offer unique local crafts and art, making it a delightful area to stroll and shop.
Can I change or cancel my Anna Maria home rental booking on Vrbo?
To find Anna Maria vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Anna Maria vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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