15 Fabulous Siesta Key Vacation Rentals For Your Florida Beach Getaway

We saved the best for last! This seven-bedroom vacation rental will set you back a pretty penny, but you can split it with up to 17 other people. Offering over 3,000 square feet of outdoor space, this vacation home features a heated pool with a waterslide and beach entry, sun shelf, and hot tub. Views of the gulf can be seen from multiple levels, including the rooftop deck. It even has an elevator!

Located in the heart of Siesta Key Village, this house is just a few houses down from the beach. Beach towels and beach chairs are included, as is parking for up to four cars. Everything — including the beach, restaurants, and shops — is just a quick one-minute walk from this awesome place. It can even be pet-friendly for an additional fee.

Situated on the beautiful canal system, this Siesta Key vacation rental is perfect for those who plan on bringing or renting a boat, as you can pull it right up to the house. This five-bedroom house also features a heated pool. Both Siesta Village and the beach are within walking distance, but if you prefer to drive to the beach, the host has a parking spot on the beach for guests. Two tenants share the property and parking area but do not have access to the yard, pool, house, or canal.

Just steps from Siesta Key Beach, this four-bedroom vacation home can be found on historic Cape Leyte Drive. Watch the sun go down from the pool and hot tub. For those traveling with little ones, this rental provides a crib, stroller, toys, books, board games, a child-size bike with training wheels, and helmets. There’s also a beach wagon, fishing poles, and a bike trailer.

Situated in a quiet neighborhood just off the beaten path from the Village and beach, this Siesta Key vacation rental can be found on the corner of two canals. It offers direct access to the Gulf, which is nice since it comes with a tandem kayak for guest use. Watch boats come in and out from the pool area and keep an eye out for osprey and great white egrets that roam the property’s lush landscape. Walk down the street to see the sun go down over the Gulf, then walk to a restaurant for dinner.

Not only does this townhome boast a private pool, but it’s also less than a five-minute walk to Siesta Key Beach and Siesta Key Village. Beach towels and chairs are provided. Between the garages and driveway, there’s parking for up to four cars. Take the tip-only shuttle service around the Key. Rental discounts on bikes, kayaks, paddleboards, and boat tours are also provided.

Just a block and a half from the powdery white sand and turquoise Gulf of Mexico waters of Siesta Key Beach, this spacious four-bedroom house sleeps 11. Off the main bedroom, a balcony offers a partial view of the ocean — the perfect place to sip a margarita and watch the sun go down over the water. Lounge by the heated saltwater pool, complete with waterfall. An outside shower makes it easy to rinse the beach off you. Plus, Siesta Key Village is just a few blocks away.

Casa De Siesta is perfect for a pair of families traveling together as it is a combination of two units that can accommodate a total of 12 guests. One up-to-25-pound dog is permitted for a fee, too. Out back, there’s everything your group needs for fun in the south Florida sun, including a pool, hot tub, outdoor dining table, grill, and lounge chairs. The rental also includes everything you’ll need for a day at the beach: a cooler, beach towels, caddy, and beach chairs, which is nice since the beach is just a short walk away. Siesta Key Village is also within walking distance.

We don’t know what’s better, the fact that this house has a private pool and jacuzzi, that it’s located on the Grand Canal, or that it’s within two blocks of the world-famous powdery white beaches of Siesta Key. Oh, and it’s within walking distance of Siesta Key Village!

Rent a boat or jet ski and pull right up to the back of this dream vacation home. It also offers easy access to beautiful areas to walk, run, or ride your bike. Take in views of the pool and Grand Canal from two of its three balconies. Plenty of parking is available, too.

Nestled amongst 100-year-old oak trees, this three-bedroom vacation rental lies across the street from a private school in a safe, quiet neighborhood. This peaceful retreat features a heated, saltwater pool in a screened-in patio. Siesta Key Village is within walking distance. Note: The home can only be rented one time per 30 days due to zoning restrictions.

Situated along the canal in a quiet, high-end neighborhood, this four-bedroom vacation rental features a private splash pool in an enclosed lanai. Plenty of parking is provided in the garage and driveway. There’s also a private area to launch a kayak. Siesta Key Beach is within walking distance, and Siesta Key Village is about 15 minutes away on foot.

Situated on the Grand Canal, this four-bedroom vacation rental can be found on a quiet street in a very nice neighborhood. Spend your time lounging by the private, secluded pool, or take a short walk to the beach. Several bikes, a couple of beach chairs, beach umbrellas, a cooler, lots of beach toys, and plenty of beach towels are provided. Siesta Key Village is just minutes away.

Nestled in the heart of Siesta Key Village just one street off of Ocean Boulevard, this two-bedroom apartment is part of the Village West complex. Community amenities include a heated pool and one reserved parking space. The beach is just a minute away on foot. You don’t even have to pack any beach chairs — they’re already waiting for you at the beach! A beach wagon and cooler are provided. Catch the free trolley or one of the “tips only” golf cart shuttles to experience top-notch restaurants, shopping, and nightlife in the village.

This centrally located condo is just a block from Siesta Key Village and the beach is within walking distance as well. Its fun, colorful pool area features tiki bars. This pet-friendly place is perfect for people who want to pack their pup along.

This two-bedroom condo is nestled in the gated community of Crescent Arms, which can be found on the Gulf of Mexico just north of the Stickney Point bridge. The sugar-white sands of Crescent Beach can be seen from its enclosed lanai.

This first-floor condo is part of the gated Gulf & Bay Club Bayside community on the side of Siesta Key that faces Florida. The unit features an enclosed patio that looks out onto a pond. Community amenities include two heated pools, two tennis courts, a fishing dock, and a clubhouse with a dry sauna and gym. Enjoy access to the large private beach, which is just a five-minute walk across the street. Beach chairs, toys, towels, an umbrella, and a wagon are provided. Parking is also provided in the attached garage.