Gertrude Rentals

Vacation Rentals

Hours:

Open - 7:00 AM to 10:00 PM, 365 days

Driving Directions:

Gertrude is in all the top locations, including - Siesta Village, Siesta Key Beach, and Crescent Beach!

About Us

Find your perfect Siesta Key getaway with Gertrude Rentals!

Choose from 80+ professionally managed vacation rentals in Siesta Key's most desirable locations. From spacious 8-bedroom luxury homes to budget-friendly studios, we have the perfect stay for couples, families, and groups of all sizes.

Every property features thoughtfully selected amenities, outstanding guest reviews, and convenient access to Siesta Key's world-famous beaches, plus the island's best shopping, dining, and entertainment.

Book with confidence through Gertrude Rentals—no AI bots, no hidden fees, just friendly local experts providing personalized service and seamless booking from start to finish.

Reserve your stay online today, or call or email us for personalized recommendations from a real person who knows and loves Siesta Key.

Highlights

The Beaches – walk to Siesta Key’s whitest sand and calmest water.
Pool Properties – heated with sun-shelves, chaises, dining, and grills.
Ocean View Properties – enjoy views of the Gulf beaches and sunsets from comfort of your rental.
Dining and Entertainment – a short walk or trolley ride to Siesta's top entertainment.
Price – traveler focused pricing and always direct and at the guaranteed lowest cost.