Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!

Photo gallery for Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!

Aerial view of Siesta Key's sandbar and turquoise waters.
Colorful Siesta Key dockside charm.
A pathway lined with palm trees and covered structures, leading towards a building.
A swimming pool with a curved edge, surrounded by lounge chairs and umbrellas, with a view of the water and palm trees.
Sunset view from balcony.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • Private garden
    A rare find — relax in the peaceful, private garden space.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Close to Siesta Key Beach
Sleeps 62 bedrooms4 beds

Popular amenities

  • Heated pool
  • Hot tub on site
  • Onsite parking available
  • Kitchen
  • Laundry room
  • Air-conditioning

Explore the area

View in a map
Siesta Key, FL
  • Place, Siesta Key Beach
    ‪6 min walk‬
  • Place, Siesta Key Beach Playground
    ‪15 min walk‬
  • Place, Crescent Beach
    ‪3 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪31 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

2 Double Beds

Common Space

1 Double Sofa Bed

2 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Office
Balcony
Separate dining area
Garden
Dining area

About this property

Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!

The Bayside Unit
Top floor bayside Siesta Key vacation rental with 40-foot balcony, tennis/pickleball courts, elevator, private beach and complimentary beach chaises, two heated pools, bay-front lounging area, hot tub, causeway on inter-coastal, boat moors, fitness center, fishing pier, and beautifully manicured grounds stretching from Beach to Bay. Enjoy resort amenities in the heart of Siesta Key. Book a getaway now!

What Guests Love
∙ Resort Amenities – heated pools, jacuzzi, gym, pickle, tennis, and boat moors
∙ The Balcony – royal palm views from balcony connecting bedrooms and living area
∙ The Grounds – fishing causeway, private bay and Siesta Key beach access, lined by royal palms
∙ Private Beach – 4-min walk to private beach and Siesta Key's widest whitest sands
∙ Restaurants – 2-min walk to free trolley to all Siesta's shopping dining and entertainment
∙ Sunsets –walk 4-min to best sunsets in America or just enjoy from your balcony
∙ Activities – scooter, golf cart, bike and kayak rentals nearby
∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conch
∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donuts
∙ The Memories – perfect fit for all with resort amenities and trolley to all top attractions
∙ Price - this Siesta Key vacation rental listing is direct with the manager and is the guaranteed lowest cost


The Beach
Our beach is a private Siesta Key beach with the widest whitest sands, free chaise lounges, and umbrella rentals. The water is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing.

The Location
With so many amenities, and all of it free of charge, a 3-night stay here will feel like a two-week getaway. If you get the most from a vacation when you don't have search or worry about anything, this unit is not a plus for you it's a must! Although you could easily take a free trolley 1-mile any direction to dozens of shops and restaurants, you can also satisfy every vacation desire without ever putting on your shoes or leaving this resort. You can swim in pools or in the Gulf, fish the inter-coastal, exercise in the gym, sleep in the sun, explore Siesta Key's best beach, make Sandcastles, and even sightsee all in a safe environment and right on your property. The beach here has the whitest sand on the island, but some of the best moments are watching boats and dolphins pass from the private balcony or nearby bay-front pool.

Bedroom Details
This is a 3rd-floor (top) unit with an elevator. This two-bedroom unit has a king bedroom, a bedroom with two fulls, and a sofa in the living room. You can sleep up to 6. If you need more space, I can get an additional unit nearby.

Beach Gear Provided
We provide beach towels, and the resort provides free chaise loungers and umbrella rentals. If you have any issues just reach out and we will do whatever we can. Correction for Air-b-n-b listings this location doesn't provide "snorkeling gear" but this and anything you need can be rented or purchased nearby.

Important Resort Limits
1) Expect a special experience where each visitor's peaceful enjoyment is respected. The minimum age for visitors not accompanied by a parent or guardian is 25 years. Stay up as late as you want, but the “quiet neighbor times” begin 10 PM. After 10 PM relocate the party to nearby Siesta Village or the Crescent Beach area. 2) Just one parking space per unit. However, cars are not necessary and an additional "emergency parking space" is available 1 mile away. If any of these limits are not a fit for you, please let me know, I have other properties available.

Household Items Provided
This vacation rental comes with bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.

What to Bring
Siesta Key is a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.

Post Booking Support
We understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time.

Travel Insurance
If you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.

Terms
Payments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.
Our prices include all fees. No hidden fees.

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House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 20069708
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock

About the area

Siesta Key

Located in Siesta Key, this condo is near theme parks and on the waterfront. St. Armands Circle and Mall at University Town Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Siesta Key Beach and Crescent Beach. Travelling with kids? Consider Mote Marine Laboratory & Aquarium, or check out an event or a game at Ed Smith Stadium. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with ecotours and cycling.
Map
Siesta Key, FL

What's nearby

  • Siesta Key Beach - 6 min walk - 0.6 km
  • St. Boniface Episcopal Church Labyrinth - 14 min walk - 1.2 km
  • Siesta Key Beach Playground - 15 min walk - 1.3 km
  • Safe Harbor Siesta Key - 2 min drive - 1.8 km
  • Crescent Beach - 3 min drive - 2.1 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 31 min drive

Restaurants

  • ‪Panera Bread - ‬4 min drive
  • ‪Captain Curt's Crab & Oyster Bar - ‬18 min walk
  • ‪Hooters - ‬4 min drive
  • ‪Five Guys - ‬4 min drive
  • ‪Starbucks - ‬6 min drive

Frequently asked questions

Does Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! have a pool?

Yes, this property has a pool. Pool types include heated pools.

How much does it cost to stay at Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!?

As of 21 Aug 2026, prices found for a 1-night stay for 2 adults at Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! on 7 Aug 2027 start from £1,392, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! pet-friendly?

No, pets are not allowed at this property.

How much is parking at Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!?

On-site parking is available at the property.

What time is check-in at Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!?

Check-in begins at 3:00 PM.

What time is check-out at Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!?

Checkout is at 10:00 AM.

Where is Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis! located?

This family-friendly Siesta Key condo building is located on the waterfront, within 1 mi (2 km) of St. Boniface Episcopal Church Labyrinth, Siesta Key Beach and Crescent Beach. Siesta Key Beach Playground and Safe Harbor Siesta Key are also within 1 mile (2 km).

About the host

Hosted by Gertrude Rentals 888-5SIESTA

Host profile image
Dan Jones, "owner" Gertrude Rentals
Phone: (888) 5-SIESTA
Email: gertrude.rentals@gmail.com
Website: gertruderentals.com

Languages:

English, French

Premier Host

They consistently provide great experiences for their guests
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