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Gertrude's Siesta | Private Patios, Beach & Village, 100 steps to Best Views on Siesta Key!

Family-friendly holiday home in Siesta Key with a water park

Photo gallery for Gertrude's Siesta | Private Patios, Beach & Village, 100 steps to Best Views on Siesta Key!

Spacious open floor plan with full kitchen, island seating, and cozy dining area—perfect for relaxing or entertaining.
Bright open space with full kitchen, dining for six, and lots of natural light.
Comfortable seating, smart layout, and direct access to the private patio.
Private patio (one of two), Siesta Key 3BR
Amazing water views and fishing 100-steps away, Siesta Key 3BR

Reviews

9.8 out of 10
Exceptional
3 bedrooms3 bathroomsSleeps 10

Popular amenities

  • Beach view
  • Parking available
  • Air conditioning
  • Dryer
  • Washer

Explore the area

View in a map
Siesta Key, FL
  • Place, Siesta Key Beach
    ‪12 min walk‬
  • Place, Crescent Beach
    ‪7 min drive‬
  • Place, Lido Beach
    ‪18 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪20 min drive‬

Rooms & beds

3 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

2 Single Bunk Beds

Common Space

1 Single Bed and 1 Double Sofa Bed

3 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Spaces

Kitchen
Office
Separate dining area
Dining area

About this property

Gertrude's Siesta | Private Patios, Beach & Village, 100 steps to Best Views on Siesta Key!

Casa Tranquilla
Spacious luxury home, 100% private, just 100ft from best views on Siesta Key. Impeccable 2025 remodel and array of amenities and features ensure a comfortable island getaway. Great for families with plenty of space onsite, three dining areas, large bedrooms, two patios, and easy access to beaches dining and entertainment! Just 100 feet to water-views, 5-minute walk to the Siesta Village, and 15-minute walk to top beaches. Book Casa Tranquilla today! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiesta


What Guests Love
∙ Nearby Views – 100ft to the best views on the island and world-class fishing
∙ The Village – 5-min walk to shopping dining and entertainment of Siesta Village
∙ Beaches – 15-min walk to Siesta Key's best beaches
∙ Relaxing – two private patios and spacious interiors
∙ Sunsets – 100ft walk to best sunsets in America & 180-degree water views
∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conch
∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donuts
∙ Activities – bikes, paddleboards, scooter and golf cart rentals nearby
∙ Island Trolleys – take them from the village, free of charge, up and down the island
∙ The Memories – walk to all siesta key is top attractions and guaranteed fun for all

The Beach
Your nearest beach is a pleasant 15-minute walk on Ocean Blvd through the shopping and dining of the village. We like to walk to breakfast in the village then head straight to the beach at Access 7 or Sunset Pier. Leaving the beach, we stop off for lunch, dinner or happy hour. The beaches here are the widest, have panoramic views of the gulf to the North-West-and-South, and are the top spot in North America for sunsets. You can swim or wade to Sand Dollar Island, a naturally occurring white sand cay popular with dolphin sand-dollars and “occasionally” manatee and giant-conch. The water is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing.
*Special note - Siesta Key Access 4 is just 100 feet from the house and, although not a swimming spot, it delivers the best views on the island, and is an amazing pick for morning coffee, evening drinks, and sunsets on the water. It's also pet friendly, boasts world class fishing, and you could get picked up here by a hired tour boat.

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The Home
Large 3BR home fully remodeled in 2025. Impeccable décor and amenities throughout. Out-door grilling and dining, open floor plan perfect for bigger groups, surrounded by palms. Set on the Northern edge of Siesta Village just 5-min walk to restaurants and the best fresh oysters, seafood, tropical drinks, ice cream, entertainment, and even gourmet donuts on the island.

Bedroom Details
It's a large 3BR and all ground floor. This home has two king bedrooms, and a queen bedroom with additional twin over twin bunk bed, and a sofa in the living room and master. You can sleep up to 10 people. If you need more space, we can get you Tempur-pedic rollaways or an additional unit nearby.

Beach Gear Provided
We provide beach towels, chairs, carts, and umbrellas. If you don't have what you need, just reach out and we can usually get it for you. 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.

Household Items Provided
We provide 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
It's 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.

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.

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.

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Amenities

Kitchen
Washing machine
Dryer
Pet-friendly
Air conditioning
Beach view

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House Rules

Check in after 3:00 PM
Minimum age to rent: 21
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

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

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 Bailey Hall, a neighbourhood in Siesta Key, this holiday home is near theme parks and near the beach. 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 Coconuts Family Entertainment Center and Marie Selby Botanical Gardens. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Siesta Key, FL

What's nearby

  • Siesta Key Beach - 12 min walk - 1.1 km
  • Shell Beach - 2 min drive - 2.1 km
  • Crescent Beach - 7 min drive - 6.2 km
  • St. Armands Circle - 16 min drive - 14.6 km
  • Lido Beach - 18 min drive - 16.6 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 29 min drive

Restaurants

  • ‪Circle K - ‬9 min walk
  • ‪Gilligan's Island Bar & Grill - ‬13 min walk
  • ‪Siesta Key Oyster Bar - ‬13 min walk
  • ‪Sun Garden Cafe - ‬11 min walk
  • ‪The Big Tiki Lounge - ‬15 min walk

Frequently asked questions

Is Gertrude's Siesta | Private Patios, Beach & Village, 100 steps to Best Views on Siesta Key! pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at Gertrude's Siesta | Private Patios, Beach & Village, 100 steps to Best Views on Siesta Key!?

Check-in begins at 3:00 PM.

What time is check-out at Gertrude's Siesta | Private Patios, Beach & Village, 100 steps to Best Views on Siesta Key!?

Checkout is at 10:00 AM.

Where is Gertrude's Siesta | Private Patios, Beach & Village, 100 steps to Best Views on Siesta Key! located?

This family-friendly Siesta Key holiday home is located by the sea, within a 15-minute walk of Siesta Key Farmers Market and Siesta Key Beach. Irma Beach and Shell Beach 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