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Gertrude Rentals Want a vacation? Call 888-5SIESTA.

Rated “Excellent” for a reason!

Whether you’re planning a trip in sandals or snow boots you can find the perfect fit quickly and book it with confidence at Gertrude Rentals. We don’t have AI bots or crazy Airbnb fees. We have a flexible-straightforward inquiry process that allows you to book independently online or call and email for hand-picked recommendations from an expert rental matchmaker. Booking a Gertrude rental is going to be easy just like a vacation should be! Contact us and book a vacation getaway now!

All Siesta Key

Siesta Village

Siesta's Crescent Beach

Siesta Key Resorts

Vermont Mountains

We’re Gertrude Vacation Rentals

Top Locations

Hundreds of units only in great locations, a perfect fit for every group and budget.

Highly Rated

Thousands of guests agree our stays earn 5-stars for location, adventure, service, and more!

Gertrude Is

We’re natives, transplants, visitors, and locals each with one thing in common, we understand your vacation time is precious and love what we do.

Guest Testimonials

Gregory B.

Guest

I have nothing but good things to say about Gertrude’s. Every house has been clean, beautiful, and Dan makes it so easy for us. Thank you for all the good times!

Pat M.

Guest

Definitely be back Dan! Can’t wait to do it again. Easiest Airbnb and best Siesta Key experience yet!

Kathy S.

Guest

Another fabulous (4th) time. The condo was well stocked with everything we needed both for cooking and for days at the beach. Dan and the staff are always so easy to work with. It makes all our family trips a piece of cake. -

Sara D.

Guest

Thanks again guys! I was nervous about doing a rental property, but it was so simple and the close proximity to everything yet in a well stocked house made it feel like 3 days were 30!