The seasons do not change all that much when you spend them in the Florida Keys. With the exception of a few stormy days and a couple of cooler nights, every day in paradise is the best day of your vacation! The sun is usually shining, the temperatures are generally balmy, and your summer or fall vacation to the Keys promises to be one you will never forget, especially when you choose RentTheKeys for your vacation escape! Offering a generous selection of homes and condos filled with all the comforts of home, it is the luxuries found inside that will bring your getaway to the next level of wonderful! This guide to our properties and all the good times you can have during your seasonal vacation will ensure that every minute of your stay will be filled with fun, comfort, and relaxation!

Vacation Dreams Can Come True

The best way we know to make your vacation dreams come true is by offering our guests the vacation home of their dreams! Choose a condo on Siesta Key decorated with sunny walls and plush furnishings and relax happily knowing the beach is within walking distance or choose a condo with beach views that will keep you from having to miss out on a single moment of the beach experience. Fully equipped kitchens with updated appliances and cheerful ambience help bring back the joy in cooking. Dining areas located just steps away from the kitchen offer the perfect spaces to play board games, devour meals, or chat with family and friends. Cozy, warm, and welcoming, our condos are the perfect size for couples or smaller families, offering access to community amenities, free Wi-Fi, and state of the art electronics that ensure every moment of your time away from home will be filled with fun!

We also feature private homes, larger in size but still offering the warmth found in our smaller condos. Located where you want to be, on your favorite Key overlooking the waters of the Gulf or closer to town where the shops, restaurants, and necessary places are all within walking distance, our seasonal homes may end up being the highlight of an already fabulous Florida getaway! Sit out on patios by the pool, sipping mojitos and watching the sun sink over the horizon in a fiery explosion of color. Watch the big game on the big screen television in living rooms that serve multiple purposes or gather round the dining room table and show your kids how playing board games can be more fun than the video games they are used to playing! Every day promises to be better than last as you play, sleep, and learn anew what it means to relax, making you wonder, “Why didn’t I think of doing this sooner?”

Falling for Fall

School vacations have changed over the years, and many schools offer fall breaks that can last as long as two weeks, making it the perfect time to get away! As fall is a quieter time on the Keys, your vacation will be even more relaxing as you build sandcastles at water’s edge, sip the night away at local hot spots, or just enjoy the natural beauty of your home away from home!

Take a walk on the wild side with a visit to the Big Cat Habitat & Gulf Coast Sanctuary, located just off Siesta Key in Sarasota. Home to the big three—lions, tigers, and bears—this beautiful place is a sanctuary for primates, birds, and more than a few domestic animals that make their home in the petting zoo found here. Visitors can get up close and personal with sloths, silver foxes, ruffled lemurs, and wallabies, or can enjoy a virtual encounter with a variety of other animals, without even having to leave the comfort of their home away from home.Tiger at the Big Cat Habit & Gulf Coast Sanctuary

Lido Key is home to the Ted Sperling Park, where kayaking through the mangrove tunnels is a beautiful way to spend a few hours of your Florida Keys fall break. Kayaking SRQ offers guided tours through the mangrove tunnels, lasting two hours and offering a magic that never fails to charm, and because the manatees are out in force from spring through early winter, you may have the opportunity to meet one of our favorite friendly beasts as you quietly paddle your way under the trees. Alligators aren’t known for living in these areas and their peak season is in May, so when your tour guide pulls over to a secluded beach, feel free to swim and play and search for shells to your heart’s content!

Speaking of gators, for some reason travelers often actually WANT to see a real live alligator, and although you can have a virtual encounter at the Big Cat Habitat, the airboat tours offered aboard the Gator Gal in Myakka River State Park will give you the opportunity to run across one in person while staying safe! This activity is destined to be your favorite wildlife adventure as you explore one of the most beautiful areas in the state on your Florida Keys fall vacation.

This Way to the Beach

Beach time is an activity that can be enjoyed year-round in the Keys, and because the fall months are not extremely busy, it may even feel as if the beaches were created just for you and your family! The three beaches on Siesta Key offer distinctly different vibes and include Siesta Beach with its concession stands, lifeguards, and Sunday evening Drum Circles that celebrate the setting of the sun. Crescent Beach is where the snorkelers will love to explore the waters off Point of Rock, and Turtle Beach is a fun spot to play volleyball, horseshoes, or simply hang out at the shaded playground watching your littles play! Lido Beach on Lido Key has a history of being slightly naughty, having once been a nude beach, but today visitors behave and keep all their clothes on! The beaches on Casey Key (found just south of Siesta Key) are incredible places to go shell hunting, and if you are hungry but don’t want to leave the sugary white sands, The Crows Nest (in nearby Venice) offers fresh seafood, delicious views, and ice-cold beverages that will wet your whistle and warm your soul. Finally, Longboat Key offers more than just awesome beaches and warm waters, and as you devour Grouper Sandwiches at the Salty Dog, kayak or swim with the locals at the Cove (located behind the Chart House) and watch the wonderful shows put on by Ski-a-Rees, a free waterskiing show that has been performing on the waters of Longboat Key since 1947, your tour of the beaches may be complete (for the moment!) but there is still so much more to see and do that you may feel the need to come back during your next vacation in the summer!

The Long and Lazy Days of a Florida Keys Summer

As the earth continues its tour round the sun, the long and lazy days of summer bring about new joys for travelers visiting the Florida Keys. This is the season of fun on the Keys, and as you enjoy your time at the beaches we discussed earlier, there will be times when you hope to stay inside, reveling in the chill of the air conditioning blowing down your neck.

A visit to the Sarasota Art Museum is first up on our list of Florida Keys summer excitement, and as you amble throughout the structure that was once a high school, if you listen closely, you may hear the whispered echoes of high school cheers, locker doors slamming shut, and laughter ringing through the halls. Explore the exhibits on display, demonstrating the talents of the nation’s most creative artists, marveling at the use of colors and the beauty of the subject matter, the fun you have here can go on for hours and although you may be tempted to return, you must remember there is still more to do!

Shopping on St. Armand’s Circle (the shape of the circle was built to resemble the rings of a circus) will keep you cool, especially when you catch sight of the “ice” you can purchase at Armel Jewelers! For over 50 years this specialty jewelry store has witnessed the beginning of young couple’s forevers, the celebrations of dreams realized, and the joyful tears of patrons who have accomplished something so important it deserves to be commemorated with something shiny! When the skies darken and the storms come rolling in, young families may find that their favorite adventure is the simplest one of all: a trip to the movies, where imagination reins supreme and popcorn is the treat of the day! From the Regal Hollywood in Sarasota with its multiple screens to the CMX CineBistro on Siesta Key where viewers can eat, drink, and lose themselves in the fantasies playing on the big screen to the Burns Court Cinema where independent films and foreign movies can enjoy their time in the sun, a trip to the movies has never been this fun!

The rich Florida landscape is green and luxuriant, the moist weather making it easy to grow a garden, and while we don’t expect you to grow your own garden during your stay, walking along the paths of the Marie Selby Botanical Gardens is a peaceful and enjoyable experience! Located in Sarasota, this 45-acre plant sanctuary offers flowers, plants, waterfalls, and art, bringing beauty to its guests in every way. Because it is dedicated to the study of orchids, the large selection of delicate blooms will amaze!

When the Dinner Bell Rings

Our favorite part of any vacation in any season is being able to enjoy a taste of the town, and as you take part in your own culinary exploration of the Keys, the restaurants we list here will be the tastiest part of your getaway! Keep it simple with a visit to Captain Curt’s Crab & Oyster Bar, 1200 Old Stickney Point Road, where the crab is fresh, the clam chowder is memorable, and any of their seafood dishes will be the highlight of your day. When the thirst for something sweet, frosty, and dangerous hits, there is no better place to sate your thirst than Daquiri Deck in Siesta Key Village! Offering a legendary Happy Hour from 3 to 7 PM, daily, the live music and sweet seafood offer the perfect way to celebrate another day in paradise, but it is those daquiris you will dream about for years to come.
Enjoy a daiquiri on the beach for your next Florida Keys vacation
The lifestyle in the Keys is a casual one, but when you want something a little more formal (perhaps you have something special to celebrate!) Euphemia Haye Restaurant & The Haye Loft is the direction you will want to turn your rental car towards! Located on Longboat Key in a charming cottage just across the street from the water, this extra special restaurant will turn an ordinary Tuesday into an event you will never want to forget! Costing a little more than most of the restaurants you will visit, it is the perfect example of you get what you pay for because every item on its menu is amazing.

Finally, enjoy a taste of Florida history with a visit to the Columbia Restaurant on Lido Key. We often say that the longest running businesses stick around for a reason and the Columbia, which has been open since 1905, is a perfect example, and even though the Lido Key expansion of the original Tampa one is newer, the food is just as great! This popular place is well loved, so reservations are definitely recommended!

RentTheKeys Is the Best Choice

Contact us and Reserve your seasonal sanctuary today and you too can experience a vacation that is absolutely unforgettable!