10 Beach Homes Perfect for Groups on Siesta Key & Lido Key

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.

Beautiful pool and patio outdoor area at large vacation rental in Siesta Key

Summer 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.

Large Siesta Key vacation home with covered patio and pool

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!

Vacation rental home for large group with amazing outdoor entertainment area

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.

Open floor plan in Siesta Key vacation rental

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.

Canal front vacation rental home in Siesta Key

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.

Beachfront vacation home with amazing back yard in Siesta Key

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.

siesta key rental homes

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.

A top Lido Key vacation rental home with a large entertainment area outside

Lido Key Retreat – 1406 Westway

Your party of 17 will love this 7-bed, 5-bath home that’s just a short distance to St. Armand’s Circle, making it one of the top Lido Key vacation rentals. You’ll have access to beach equipment and a large entertainment area outside, and you’re tucked away in a quiet neighborhood for maximum privacy.

Amazing luxurious vacation rental home in Siesta Key

John Ringling House – 76 S Wash

Groups of 10 fit comfortably in this 3-bed, 2-bath home. You can easily access tons of sites like City Island Boat Ramp and Bird Key Park, or travel a short 2.3 miles to downtown Sarasota. Enjoy your complimentary beach equipment for use during your stay, our Professional Linen Service Program, and our Property Manager Program to make the most of your vacation.

Well-decorated vacation home in Siesta Key

Ringling Manor – 112 Fillmore

This 4-bed, 3-bath home is ideal for groups of 8. Head to nearby Lido Key Beach, St. Armand’s Circle, or downtown Sarasota, or stay in and enjoy the privacy of the quiet neighbordhood. Inside, enjoy amenities like our Concierge Service, free WiFi, large living and dining rooms, and more.
Our Siesta Key vacation rental homes make it easy to plan your group’s getaway, whether you’re traveling with eight people or 25. Browse our website to review all our rentals for large groups, or contact us for more information.


Siesta Key Luxury Rental Properties
5111 Ocean Blvd. Suite B, C & D
Siesta Key, Florida USA 34242
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