Well, it’s official. You survived another holiday season without totally going insane, and even if it was close, now that you have crossed the bridge from 2023 to 2024, it is time to start planning a vacation that will kick off the new year the right way, perhaps with a getaway to the white sand beaches of Siesta Key. If your early winter journey has you visiting our island paradise and staying in our Rent Siesta Key escapes, this guide to doing it right will help you make the happiest of memories during your 2024 in Siesta Key!

Sunrise, Sunset

Mother Nature has perfected at least two things over the millennia, and here in Florida, those two items are, of course, the sunrise and the sunset. If your visit lasts through an entire weekend, we invite you to explore the Sunday evening Siesta Key Drum Circle, celebrating the beauty of a Siesta Key sunset with music, companionship, and love. We’ve talked about the Drum Circle many times over the years, so we won’t go into much detail other than to say it starts about an hour before sunset, and it is an experience you will never forget. The sunrise, however, is one of those things that while equally worthy, may take a little more convincing due to the early hour, but we have just one thing to say about that: Go back to bed after the sun has completed its morning journey and dream happy dreams about the fiery colors that took over the sky!

Siesta Key Wine Bar, 5138 Ocean Boulevard Suite C

Believe it or not, the peace you are feeling from leaving the chaos of the holidays behind and waking up every day in the comfort of our Rent Siesta Key seasonal sanctuaries can be enhanced quite easily with a visit to the Siesta Key Wine Bar. Offering wines from all over the world, it is difficult to find a more relaxing, more soul soothing activity than by sitting at the wood tables on a cool winter’s night, (it’s open until 10 every night except Sundays and Wednesdays) sipping silky wines and savoring the company of your favorite traveling partner. Offering wine flights for sampling, the Siesta Key Wine Bar focuses on relaxation. Can you think of anything you need more?

Take a Tour of the Key

The beauty of Siesta Key will never let you down and with the weather in the winter months being so wonderful, enjoying a tour of the Key aboard a Segway will bring a new awareness of all that the area has to offer. Robin Hood Rentals, located at 5255 Ocean Boulevard, is easily found in downtown Siesta Key Village and offers one- and two-hour tours by Segway. Also offering pretty much everything you need to have a great time, including scooters, golf carts, bicycles, kayaks and paddleboards, this one stop shop for fun may bring you your favorite memories of your trip.

Work on Your Tan

With temperatures rarely dropping below 71 degrees in the daytime, a day at the beach may actually be at the top of your itinerary, especially for those who visit from some of our coldest states. In many of our sanctuaries, guests will find all the gear they need to enjoy a day at the beach, including towels, chairs, umbrellas, and even a cooler that just needs to be stocked with your favorite food and drink. Choose the beach you want to visit, (There are three on Siesta Key: Siesta, Crescent, and Turtle) pack your gear and spoil yourself with a day of sun, surf, and white sand.

Sarasota Seafood & Music Festival, January 26-28, JD Hamel Park in Sarasota

Siesta Key isn’t all that large, just over three square miles in size, but that’s ok; it only makes it easier to explore the towns located just off the key. Sarasota, for example, is home to one of our favorite and most delicious festivals, the Sarasota Seafood & Music Festival, taking place the last weekend of the month. Your kick off to 2024 doesn’t have to start at the final strike of the clock at midnight, and if you wait until the end of January to make your journey, you will experience the sweetest seafood, hottest music, and a chance to explore the talents of local artists and crafts people who will be displaying their work for your purchasing pleasure!

Spoil Yourself at Home

After the chaos of the holidays, you may find that your favorite moments on Siesta Key are the ones spent at home, enjoying the luxury amenities and quiet relaxation that come standard in our seasonal sanctuaries. Binge watch your favorite streaming shows on Smart TVs, enjoy a cozy meal prepared in our fully equipped kitchens and devoured in our dining rooms, and experience deep sleep and happy dreams in cloud soft beds anchoring our tranquil bedrooms.

Reserve your favorite escape today and feel pampered, spoiled, and completely at home during your time on Siesta Key!

The year-round sun and warmth of Florida make it an ideal destination any time of year. No matter where you choose to go in the Sunshine State, there is plenty to see and do. Choosing the sunny, sandy shores of the keys adds another layer of rest and relaxation to your Florida vacation. This winter, take an island vacation on Siesta Key. To make sure everything goes as planned for your winter 2022 Siesta Key getaway, you’ll want to start planning well in advance. Starting now means you’ll have your pick of everything that will make your vacation great, including reservations, rentals, activities, and most importantly: where you’ll stay.

Priority

First come, first served. Many businesses use it to attract more customers earlier. Being the early bird often comes with perks like guaranteed admission, lower entry fees, and other special treatment only available to those who get there first. The same can be true for vacation rentals. Booking your 2022 winter getaway to Siesta Key with Rent Siesta Key now gives you your choice of vacation rental homes, so you can reserve the one that will enhance your island experience the best.

Discounts

Experienced travelers know that booking travel necessities like airfare, admission to popular attractions, and accommodations secure you some of the best of the best items at the lowest price. Last-minute bookings often come with a premium, as well as missing out on what’s just right for you – including rental properties, while those who plan in advance can take advantage of lower prices on the most sought-after homes on Siesta Key.

Peace of Mind

Booking your 2022 winter vacation now and securing reservations for your preferred vacation home on Siesta Key means you don’t have to worry about a major part of your trip as you count down the days to your arrival. Once you’ve secured the vacation home of your dreams, you can focus on booking the other activities and attractions that will make your winter 2022 island adventure one to remember for years to come.

Get Everyone Ready for the Siesta Key Getaway

Planning your winter 2022 trip to Siesta Key now means there’s plenty of time to get everyone prepared for the trip. New bathing suits or clothes, luggage, and other large purchases can be made with plenty of time to spare. You can create personalized lists of the items needed for the duration of the trip and purchase or pack the items in advance rather than having to toss them in carelessly at the last minute, making them easy to locate when you arrive. You’ll also have plenty of time to secure the valuables and deal with other practical matters.

Organization

Booking your vacation rental with Rent Siesta Key for your 2022 winter getaway not only means you can focus on other trip planning to-do’s, but it also means you have more time to prepare every last detail. If you’ve never been to Siesta Key, use the extra time and peace of mind to download maps of the area around your rental, as well as the best routes to all the fun on your must-do list during your trip. Gather the things you’ll need for your trip of a lifetime and store them somewhere easily accessible so all you’ll have to do is pack the car and head to the airport!

Time to Save

With everything booked, down payments, secured, and everything else for your perfect winter vacation on Siesta Key in place, you’ll have plenty of time to save some extra spending cash. No matter how you save your pennies, with the extra time you’ve given yourself you’ll have plenty of extra sets aside for a comfortable, fun trip. There are bound to be impromptu adventures that require admission fees, groceries during your stay, other items not provided at your vacation rental, other incidentals, as well as some fun souvenirs to bring home.

Book Early For 2022 Winter Island Fun

When you book your winter 2022 getaway with Rent Siesta Key, you won’t be short on fun activities to fill your time while you’re here. You’ll be able to design a getaway that is uniquely yours with memories to last a lifetime. Relax and unwind after a fun-filled island day with loved ones. Enjoy a one-bedroom for your small family or sweetheart getaway, all the way up to six bedrooms for a larger group. Prepare a meal in the fully equipped kitchen and enjoy it in the dining area, or in a private outdoor space like a patio or balcony. At the end of the day, relax in a private bedroom. Opt for a premium unit for perks like double ovens, stainless steel appliances, flat-screen TVs, a private pool, and more. Include everyone this winter by asking about select rentals that allow your fur babies to stay.

Contact us today to book your winter 2022 getaway in Siesta Key!

The year-round sun and warmth of Florida makes it an ideal destination any time of year. No matter where you choose to go in the Sunshine State, there is plenty to see and do. Choose the sunny, sandy shores of the keys adds another layer of rest and relaxation to your Florida vacation. This summer, take an island vacation. To make sure everything goes as planned for your summer 2022 island retreat, you’ll want to start planning well in advance. Starting now means you’ll have your pick of everything that will make your vacation great, including reservations, rentals, activities, and most importantly: where you’ll stay.

Discounts

Experienced travelers know that booking travel necessities like airfare, accommodations, and admission to popular attractions secures you some of the best of the best items at the lowest price. Last-minute bookings often come with a premium, as well as missing out on the rental property that’s right for you, while those who plan in advance can take advantage of lower prices on the most sought-after homes on Siesta Key. Lower costs may apply to other aspects of your trip. Airfare, vehicle rentals, attraction admission, and popular activities offer discounts to travelers who think ahead and book now.

Priority

First come, first served is a saying popular with businesses that want to attract more customers. Arriving early often comes with perks like guaranteed admission, lower entry fees, and other special treatment only available for a limited time. The same can be true for vacation rentals. Booking your 2022 summer, Siesta Key getaway with Rent Siesta Key now means you’ll have your choice of vacation rental homes so you can reserve the one that will enhance your island experience however you like.

Peace of Mind

Booking your 2022 summer vacation now and securing reservations for your preferred vacation home on Siesta Key means you don’t have to worry about a major part of your trip as the days go by. Once you’ve secured the vacation home of your dreams, you can focus on booking the other activities and attractions that will make your summer 2022 island adventure one to remember for years to come.

Organization

Booking your vacation rental with Rent Siesta Key for your 2022 summer getaway not only means you can focus on other trip planning to-dos, but it also means you have more time to prepare every last detail. If you’ve never been to Siesta Key, use the extra time and peace of mind to download maps of the area around your rental as well as the best routes to all the fun places on your must-do list during your trip. Gather the things you’ll need for your trip of a lifetime and store them somewhere easily accessible so all you’ll have to do is pack the car and head to the airport.

Time to Save

With everything booked, down payments secured, and everything else for your perfect summer vacation on Siesta Key in place, you’ll have plenty of time to save extra spending cash. Save your change from regular purchases in a jar or move money each week to an account opened especially for vacation expenses. There are bound to be impromptu adventures that require admission fees, groceries during your stay, other items not provided at your vacation rental, other incidentals, as well as some fun souvenirs to bring home.

Rentals

Travelers who book early not only have secured exactly what they want, they may end up getting a little more. Rather than having to rent, or even purchase items you won’t be taking home with you – bikes, beach equipment or sand toys, and items not traditionally offered to renters may be included in your fees at no extra charge.

Get Everyone Prepared

Planning your summer 2022 trip to Siesta Key well in advance means there’s plenty of time to get everyone prepared for the journey. New bathing suits or summer clothes, luggage, and other large purchases can be made. You can create personalized lists of the items needed for the duration of the trip can be figured out and purchased or packed in advance rather than being tossed in carelessly at the last minute. You’ll also have plenty of time to secure the valuables you’re not taking with you.

Book Early for 2022 Summer Siesta Key Fun

When you book your summer 2022 getaway with Rent Siesta Key, you won’t be short on fun activities to fill your time while you’re here. You’ll be able to design a getaway that is uniquely yours with memories to last a lifetime. Relax and unwind after a fun-filled day with your group. Enjoy a one-bedroom for your small family or sweetheart getaway, all the way up to six bedrooms for a larger group. Prepare a meal in the fully equipped kitchen and enjoy it in the dining area, or in a private outdoor space like a patio or balcony. At the end of the day, relax in a private bedroom. Opt for a premium unit for perks like double ovens, stainless steel appliances, flat screen TVs, a private pool, and more. Include everyone this summer by asking about select rentals that allow your fur babies to stay.

Contact us today to book your summer 2022 getaway in Siesta Key!