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Gertrude Rentals Siesta Key Rentals - Beach Village or Lagoon

Experience Siesta Key!

Soak up Siesta Key with a stay in one of our beach vacation rentals! Choose between a variety of different communities including the Siesta Key Village, Crescent Beach, and Siesta’s resort area. Our vacation rentals feature cozy, coastal décor as well as proximity to Siesta Key’s gorgeous, white sand beaches and activities. Browse our Siesta Key short-term rentals and start planning a vacation at North Americas best beach! Looking to swap out the beach for the ski slopes? We also feature properties in Vermont’s Green Mountains. Check out our Vermont vacation rentals when you want a cozy home for Vermont’s ski season! You can contact us for more information 888-5SIESTA or email us at gertrude.rentals@gmail.com

We’re Gertrude Vacation Rentals

Top Locations

Over 60 units, only the best 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.

Booking Siesta Key Getaways with Gertrude

No hidden fees, markups, expenses, or resort charges, and no cleaning requirement. Single point of contact and unparalleled knowledge, service, and dependability. Choose from over 45 top properties in all Siesta Keys best locations. Instant confirmation and always at the guaranteed lowest rate!

Contact Us

Over 45 Different Siesta Key Properties Available

North America's best white sand beaches. Walking distance to world famous shopping, dining, and entertainment. Units with private pools, ocean-views, lagoon front decks, lazy hammocks and tiki-huts, and rooftop sun-decks. Call or email now and we’ll help find the perfect fit for you and your group. Always human and never a bot.

Find Your Rental

Guest Testimonials

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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!

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Pat M.

Guest

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

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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. -

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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!

Gertrude Rentals Property Managment

Give Us A Call At:

(888) 574-3782

Gertrude Rentals Property Managment

Give Us A Call At:

(888) 574-3782

Free Rental Evaluation

Discover Your Property’s True Potential


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