NEW LISTING! | Ocean-views, Walk 1-Min Beach & Village, Private Balconies Hot-tub Deck & Elevator!

Siesta Key, Florida
$1144 avg/night
Bed 3

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 10

Max Sleeps

Serious Leisure is a new listing by Gertrude Rentals

NEW LISTING! Serious Leisure is an ocean-view unit just 1-min walk to all Siesta's top attractions! Large 3BR boasts 4 balconies, ocean-views, elevator, and 100% private outdoor areas including swim-spa, deck and alfresco dining area. In heart of Siesta Village. Just 1-minute walk to Siesta's best Beach and the shopping dining and entertainment of the village! Spacious, bright, airy, and surrounded by palms. Experience Siesta Key's top attractions without sacrificing space and comfort. Book a getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiesta

What Guests Love
SERIOUS LEISURE “AT A GLANCE”
∙ Wonderful new listing! Gertrude Rentals Siesta Key has thousands of 5-star reviews!
∙ Private Balconies and Deck – beautiful views from 4 balconies plus deck in the palms
∙ Private Swim-spa – large outdoor heated swim-spa and deck
∙ The Beaches – 1-minute to Siesta Key's top beaches with white sand and calm clear water
∙ Restaurants – 1-minute walk to the shopping dining and entertainment of the Siesta Village
∙ Gulf Breezes – 5 balconies and westerly windows means catching sea breezes day and night
∙ Relaxing – 3 baths, elevator, and a balcony off every bedroom and kitchen
∙ Sunsets –walk 1-minute to best sunsets or just enjoy from private deck or balconies
∙ Alfresco Dining – large kitchen, 2 grill areas and 2 private al-fresco dining areas
∙ 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 – walk to all siesta key is top attractions and guaranteed fun for all


The Beach
Our beach is the widest, has panoramic views of the gulf to the North-West-and-South, and is 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. You can go from the water to lunch or dinner and back to the sand without putting on your shoes.


The Location
You aren't planning one vacation, you're planning vacations for every individual in your party. Whether it's solitude or activities, this property will deliver what they need. It's just steps to the top attractions on the island including 4 beach accesses, and 20 bars and restaurants. Walk right 450ft to the best beaches in America or left 450ft to the world-famous shopping dining and entertainment of the Siesta Key Village. This area has - ice-cream, tide pools, daiquiris, dolphins, fresh oysters, white-quartz-sand, big breakfast, sunsets, amazing seafood, white lagoons, craft beer, sand dollars, live music, shopping, and gourmet donuts. Back at the house, you'll enjoy private swim-spa, two alfresco, dining areas, four balconies, and a sundeck. When you'd prefer to relax, you'll find lots of bright and airy out the way rooms and terraces for quiet decompressing.


Bedroom Details
This is a huge 3BR, you can sleep up to 11 family style. The master suite (huge) has a ocean-views, King bed, balcony, en-suite bath with shower and spa-tub, comfy chaise lounger, and enough room for pack-n-plays and rollaway beds. *Note master bedroom has ocean views are from the balcony, bathroom, and bedroom windows! Bedroom #2 has two full beds and balcony with obstructed ocean-views. Bedroom #3 has two twin beds and balcony with westerly exposure and a sliver of an ocean view. The living area has large sectional sofa big enough for two children:) If you need additional space we can offer more bedrooms nearby.


Beach Gear Provided
We provide beach towels, chairs, carts, umbrellas, bikes and paddle boards. 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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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly
  • BEACH

    Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 2600 Sq Ft (242 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    Free WiFi, With Speed Of 100+ Mbps (good For 1–2 People Or Up To 6 Devices)
  • OUTDOORS

    Balcony Barbecue Grill
  • POOL/SPA

    Hot Tub
  • BATHROOMS

    3 Bathrooms Bathtub Or Shower Hair Dryer Towels Provided
  • WORKSPACES

    Desk Chair
  • LANGS SPOKEN

    English French
  • THINGS TO DO

    Cycling Nearby Fishing Nearby Kayaking Nearby Marina Nearby Snorkeling Nearby Surfing/body Boarding Nearby Swimming Nearby Theme Parks Nearby Water Park Wildlife And Game Walks Nearby
  • ENTERTAINMENT

    TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Highchair Travel Crib
  • LOCATION HIGHLIGHTS

    In A Village In The City Center Near A Hospital Near A Zoo Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Elevator If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. Smoke-free Property Wheelchair Accessible

CheckIn Check-in : 03:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 10

Map Map

School District Rates & Availability

Review Review

  • Thomas H.

    Submitted Oct 17, 2025

    Stayed Oct 4, 2025

    The location allows easy access to the beach in one block and the village in about the same distance. The homes amenities provided plenty of space for multiple groups and beautiful beach views from upper floors. Daniel, as always, is available to whatever question you have.

  • Christine B.

    Submitted Sep 14, 2025

    Stayed Sep 9, 2025

    Place was clean, steps away from the beautiful sand and great accommodations and perks. Will definitely book with this property again.

  • Submitted Aug 18, 2025

    Stayed Aug 14, 2025

    Our stay in Siesta Key was absolutely incredible! The location truly couldn’t be better — just a quick 2-minute walk to the beach, which made it effortless to catch the sunrise in the morning and stroll back for unforgettable sunsets at night. To make things even better, the home is situated only 30 seconds from bars, restaurants, and shopping, so we had dining and entertainment right at our fingertips without ever needing to get in the car.The house itself is a four-story gem. Every level was thoughtfully designed, clean, and beautiful, with plenty of space for everyone to spread out yet still come together for meals and evenings on the patio and massive jacuzzi. It felt both luxurious and welcoming — the perfect balance of a vacation retreat and a comfortable home.Another highlight was Daniel the host.  He was responsive and very attentive. Anytime we had a question or small request, they replied immediately and were genuinely invested in making sure our stay was perfect. That level of communication and care really set this experience apart.If you’re looking for a place in Siesta Key that combines location, comfort, and hospitality, this property is a dream. We left with amazing memories and can’t wait to return!

  • Hannah s.

    Submitted Aug 11, 2025

    Stayed Aug 6, 2025

    This was a great location close to beach and village all within walking distance. The beach cart was a huge help for all our needs! Paddleboards were an extra perk ❤️ The house was very spacious and would definitely stay here again. Dan and his team were awesome and very responsive. Thank you for a great stay and easy check in and out!

  • Heather Y.

    Submitted Aug 5, 2025

    Stayed Aug 1, 2025

    Lovely house with a perfect location on Siesta Key. Short walk to both the beach and the village.

  • Brian G.

    Submitted Jun 9, 2025

    Stayed Jun 6, 2025

    This property was amazing, from the amenities to the location. Steps from the beach and steps from the village. The views from the balcony were amazing and the convivence of the elevator was fantastic. I would love to stay there again.

  • Brian W.

    Submitted May 27, 2025

    Stayed May 11, 2025

    The team was incredibly responsive and attentive throughout our stay. The location couldn't have been better—just minutes from the beach and close to great restaurants and shops. The home had plenty of space for our family, and everything was clean and comfortable. We had a wonderful experience and would definitely stay again. Highly recommend!

  • Kade H.

    Submitted May 27, 2025

    Stayed May 19, 2025

    You really can't find a better location in Siesta Key. It's a short walk to beach accesses 3 and 4, and a short walk to the village. The condo is tall enough to offer multiple spots to view the ocean! It's a family friendly home - my 4 kids loved having a floor to themselves. The elevator worked consistently, which was key considering the number of floors. The place was tidy, stocked, and spacious. I should also mention that it was well cooled because outside was very hot! The top floor bathroom was huge and pure luxury. There is a mid floor bathroom with a large stone shower - it's really cool. There are large closets throughout the house. The appliances are updated and clean. And with a large family, the washer and dryer were very helpful - K

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Total

Includes taxes and fees
$1,144+
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