Siesta Key, Florida, is perhaps one of the most well-kept secrets of the state. With its stunning white-sand beaches, unique shopping, fresh seafood, and incredible culture, Siesta Key brings everything you love about Florida without the crowds you’ll find in the major tourist attractions like Orlando and Miami. When you’re vacationing with a group, however, it can be tough to find a rental home to keep everyone comfortable. Luckily, we offer an abundance of Siesta Key vacation homes for rent perfect for groups of all sizes.
Sunset Splash – 95 Messina
This 8-bed, 7.5-bath home can fit up to 24 people to suit large groups. The ground-level home forms a U-shape to give everyone some privacy. You’ll have access to free parking and WiFi, as well as beach equipment rentals available from Tropical Breeze’s Adventure Tiki. Enjoy our Professional Linen Service Program, a full kitchen, washer/dryer, BBQ grill, and so much more.
Salty Dog – 515 Canal A
Sleep up to 17 people in this 6-bed, 4.5-bath home. You’re just a two-minute walk from the beach and a seven-minute walk from the village. You’ll have TVs and WiFi throughout the home, as well as a large kitchen and dining room. The covered patio and pool area bring the luxury outdoors, too!
Summer House – 99 Messina
This home is perfect for 22 people with its 6 bedrooms and 6 bathrooms. You’re less than two minutes from the beach and the village, perfect for getting out the door in a hurry. Entertain outdoors at the pool or grill, or stay in with the WiFi and HDTV. You’ll also have a washer/dryer in the home, a covered porch, and other fantastic amenities.
Surf View – 303 Calle
Bring everyone to this 8-bed, 8.5-bath home that sleeps up to 22. Special features here include a game room, private heated pool, and multiple balconies with unbelievable views of Siesta Village. You’ll also enjoy our complimentary Professional Linen Service Program and Property Manager Program.
Dry Dock – 515 Canal B
This 6-bed, 6.5-bath home sleeps 18 and comes equipped with all the luxury amenities you need. You will have our Professional Linen Service Program, equipment rentals with Tropical Breeze, a full kitchen, and a shared dock, among other great features.
The Pool House – 98 Messina
16 people can fit comfortably in this 5-bed, 4-bath home. The beach is just a block away, and the village is even closer! There is a washer/dryer in the home, as well as a large backyard, private pool, and more.
Island House – 344 Canal
This brand-new home features 7 bedrooms and 6 bathrooms to suit up to 23 people. The lock-out apartment suite gives more privacy, and you can enjoy the stunning views of the Gulf from multiple spots throughout the home. There is a canal right across the street for you to fish and kayak.
Siesta Palooza – 322 De Mayo
Your party of 25 will love this 8-bed, 8-bath home that’s just a short distance to Siesta Key Village, making it one of the top Lido Key vacation rentals. You’ll have access to beach equipment and a large pool featuring a dry bar and sun deck. Plus, you’re tucked away in a quiet neighborhood for maximum privacy. This home is certainly one of our best Siesta Key vacation rentals for large groups.
Aloft on Canal – 542 Canal
Groups of 22 fit comfortably in this 8-bed, 6-bath home. The property features an elevator with access to every floor and a pool area with space to entertain. Use the private dock across the street to park your boat or enjoy some time fishing the canal.
Sunset Gulf – 551 Beach Rd
This 8-bed, 5-bath home is ideal for groups of 25. This property is steps from the beach and just a quick stroll or bike ride from the variety of shops and restaurants in Siesta Key Village. This property participates in our Professional Linen Program, so you are sure to get a quality night’s rest and have plenty of towels for all of your group’s time in the large, luxurious pool.
