When you start planning a Florida vacation, you are going to find a sea of vacation rentals run by an equally large number of vacation property management companies located up and down the entire length of the Sunshine State, offering a staggering array of choices that may add confusion to the feelings you have about your upcoming trip. The good news is RentTheKeys can help narrow your choices, providing quality rentals that aren’t just located in one town but are spread out over a pretty large section of Florida, offering homes and condos from Anna Maria Island all the way to Siesta Key. The even better news? Today, with the help of our Florida Keys vacation guide, we are going to take you on a tour of the towns, islands, and Keys in which our homes are located, giving travelers a peek into what makes each area stand out and the realization that RentTheKeys is the only company you will want to rent from!

Florida Keys Vacation Guide to Anna Maria Island

A is for amazing, awe inspiring, and of course, Anna Maria Island, the first stop on our tour. Known for its classic old Florida vibe, it is also a popular sea turtle nesting grounds with nearly 200 of these endangered species crawling up to the white sand beaches and depositing their eggs in holes in the sand every year. The properties we offer in Anna Maria Island are condos, providing one or two bedrooms, with many also providing stunning views of the sea. Access to community amenities can include pools and community grilling areas.

Rod & Reel Pier, 875 N Shore Drive, Open Daily from 8AM-9PM

The beaches of Anna Maria Island are white sand, and its downtown area is filled with cute shops and delicious restaurants, with one of the most notable restaurants being the Rod & Reel Pier. Offering a traditional Florida dining experience, the hand painted sign found at the entrance of the pier adds a rustic charm to your adventures at this restaurant that has sat on this pier since 1947 and its menu includes classic surf and turf dishes that will bring a smile to your tastebuds.

Pine Avenue

This historic main street is often the center of the fun you can have while staying on AMI, offering charming cottages, shops, and the historic Old City Jail, a structure built in 1927 to hold rowdy beachgoers, but is now just another opportunity for a selfie. Offering no bars, no doors, or even a roof, your social media sites will be enhanced with the selfies you take here.


Founded in the 1840s and offering humble beginnings as a lumber and turpentine industry, today Bradenton holds a huge part of our hearts and it is rumored that Scott Baio from the hit television shows of the 70s and 80s (Happy Days and Charles in Charge) likes to call this all-American town home. The beaches of Bradenton are popular ones, and LECOM Park is the Spring Training home of the Pittsburgh Pirates. Our Bradenton escapes are standalone homes, offering screened-in patios anchored by crystal-clear pools, providing an idyllic vacation experience for families and moderately sized traveling groups.

Bradenton Blues Festival, Waterside Park, December

We often find that attending local festivals is the best way of experiencing an authentic feel of the town you are visiting, and the Bradenton Blues Festival is truly a cool and exciting experience. Coming to new digs in Waterside Park in December and offering an exciting lineup of the best blues performers from all over the country, visitors can also expect to enjoy delicious food and drinks as the food trucks are expected to converge upon this musical festival.

Red Barn Flea Market, 1707 1st Street, Open Wednesdays, Fridays, and Saturdays 9AM-4PM

Today’s travelers are finding that the best souvenirs can be found at flea markets, antique stores, and thrift stores, and Red Barn Flea Market offers the best of the best. Offering 600 booths in 80,000 square feet of air-conditioned space, it’s also a form of farmers’ market, providing fresh produce and other tasty foods.

Cape Coral

Cape Coral is most famous for its 400 miles of canals, and many of our RentTheKeys Sunshine State sanctuaries can be found on those canals. The town itself is a great place to explore, especially if you enjoy natural adventures such as hiking, boating, or just meandering through nature preserves that are beautiful and serene. Our Cape Coral homes tend to be standalone structures, filled with comfortable furnishings and modern conveniences, with many offering incredible views of the canals that snake through our town.

Four Mile Cove Ecological Preserve, 2500 SE 34th Street, Open Daily 7AM-8PM

Offering a walking trail, visitor’s center, and a patriotic Veteran’s Memorial Area, Four Mile Cove Ecological Preserve is home to an extensive variety of local wildlife and is a popular birdwatching park where eagles, ibis, herons, and migratory birds are often spotted doing their thing. Also offering picnic areas and restrooms, the preserve is charming in its simplicity.

Longboat Key

Longboat Key is a barrier island that lies between two more towns in which RentTheKeys offers vacation homes, Bradenton and Sarasota, and is thought to have earned its name from the Spanish longboats that were once noticed in the region. Rock star celebrity Joe Perry has a home on Longboat Key, and water activities such as kayaking, surfing, SUP, and sailing are popular with locals and travelers. Our Longboat Key escapes will be cozy and comfortable condos, often offering sea views and sleek and modern decors, and they also include access to community amenities.

Longboat Key Paddleboard and Kayak, 4134 Gulf of Mexico Drive

The waters surrounding Longboat Key will be teeming with watersport enthusiasts, and if you are a fan of SUP or kayaking, Longboat Key Paddleboard and Kayak offers rentals of boards and Kayaks as well as providing some fantastic tours of the area. Providing a private launching spot which is much more relaxing for visitors learning a new sport, they include lessons on how to use their equipment with the cost of rentals or tours.

Euphemia Haye Restaurant & the Haye Loft, 5540 Gulf of Mexico Drive, Closed Mondays

The beautiful cottage in which the Euphemia Haye Restaurant is located adds an extra layer of wonderful to your fine dining experience in a restaurant that has been a local tradition for over 40 years. Their menus are an international fusion of flavor, including Thai, Indian, and even Italian specialties and the Haye Loft is a lounge space providing a truly authentic Florida experience.

North Port

North Port is known for being the only town in the state that features an entire state forest within its city boundaries and is a popular vacation spot for outdoor enthusiasts. Although not as extensive as the canal system in Cape Coral, North Port offers 80 miles of canals and the serene and beautiful Mayaka River flows through town, with some of our RentTheKeys sanctuaries residing on its banks. The cottages we offer in this charming Florida town are cozy and comfortable and are a reflection of the golden days of our home state.

Warm Mineral Springs, 12200 San Servando Avenue

Known as the “Miracle Lake,” the warm waters of Warm Mineral Springs are often filled with people seeking to find healing for their aches and pains, and although there is no medical proof that the springs can help, we feel that it is impossible to feel bad after time spent soaking in the 85 degree waters that have a history that dates back 30,000 years.

Cool Today Park, 18800 W Villages Parkway

Spring Training for Major League Baseball is a big deal here in Florida, home to the Grapefruit League with 15 teams migrating here for the spring season, including the Atlanta Braves. Based out of Cool Today Park in February and March, there is no greater treat than spending a beautiful day out on the ball field watching your favorite teams play and enjoying a taste of the south served at the concession stands.

Port Charlotte

Billed as “Florida’s Gateway to Fun and Adventure,” you may not have heard of Port Charlotte before sitting down to this article, but after today, we think you will never forget our coastal town. Established in the 1950s, many of the homes in town are mid-century modern marvels, but its history dates back thousands of years to a time when the Paleo-Indians lived off the wooly mammoths they chased, utilizing the hairy creatures for food, clothing, and shelter. Our homes in Port Charlotte are charming and beautiful, often offering hot tubs or firepits in their backyards.

Port Charlotte Beach Park, 4500 Harbor Boulevard

Offering white sand beaches, a boardwalk and fishing pier, sports courts, horseshoe pits, playgrounds, and picnic areas, Port Charlotte Beach Park promises to be an adventure that will take more than one visit to conquer.

The Grill at 1951, 1951 Tamiami Trail, Closed Sundays

Special occasions deserve special occasion restaurants, and the Grill at 1951 falls easily into this delicious category. Offering live music and an elevated menu that is surf and turf based and although everything tasted here is fantastic, we highly recommend visitors save room for dessert. Their Chocolate Ganache Cake for Two encourages sharing, romance, and falling in love with its sweet taste.


Sarasota is nicknamed Circus City, due to one of its more famous residents, John Ringling, and the compound he built there, but is also home to pristine white sand beaches, a sophisticated nightlife, and some of our very best RentTheKeys vacation havens. Our Sarasota properties are a blend of homes and condos and may be located on Sarasota Bay or in family neighborhoods that travelers always feel comfortable staying, and many will offer private pools or at the very least access to community pools.

Mote Marine Laboratory & Aquarium, 1600 Ken Thompson Parkway, Open Daily from 9:30-5

Since 1955, Mote Marine Laboratory & Aquarium has concentrated on being a place of Sanctuary for our sea creature friends, as well as being a premier research laboratory and animal hospital. Want an up close and personal peek at a manatee, one of the friendliest and also most endangered creatures of the sea? Buffett the manatee is an animal ambassador who helps spread the word about the plight of these charming animals.

Original Word of Mouth, 6604 Gateway Avenue, Open Daily 8AM-2PM

As you frolic in the surf, explore the aquarium at Mote Laboratory, and discover all the reasons Sarasota is destined to be your favorite vacation destination, starting each day with a hearty breakfast at Original Word of Mouth café will ensure you have the energy to keep going.

Siesta Key

Taking up just 3.5 square miles, Siesta Key, the last spot on our tour of wonderful, is a small key with a big heart and the whitest sand beaches in the state. Our Siesta Key escapes are a blend of condos, cottages, stand alone homes, and townhomes, with many located within sight of our beautiful white sand beaches.

Go to the Beach

There are three beaches on Siesta Key—Siesta Beach, Crescent Beach, and Turtle Beach, and if you don’t spend a good portion of your time building sandcastles, relaxing in the Florida sun, or swimming in the warm and clear waters of the Gulf of Mexico, can you really consider this an excellent vacation? Also, take the time to watch the sunset. You can thank us later!

The Beach Club, 5151 Ocean Boulevard, Open Noon to 2AM Daily

If you still have the energy for a night out on the town after your long days on Siesta Key, the Beach Club is our most popular night spot, staying open until the week hours of the morning and providing live music 7 nights a week. Offering trivia nights, rotating DJs, and the hottest time on the coolest Key, go ahead and check out what they have to offer; you can always sleep in the day after.

Reserve your favorite RentTheKeys eternal summer sanctuary today!