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Winter’s Overrated. Longboat Key Isn’t. — 2BR w/ Beach Access

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Beach
Outdoor dining
A heated pool
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Fridge, microwave, oven, stovetop

Reviews

9.4 out of 10
Exceptional

Entire condo

2 bedrooms2 bathroomsSleeps 6149 sq m

Popular amenities

  • Pool
  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
The current price is AU$1,125
includes taxes & fees
3 Apr - 4 Apr

Explore the area

View map
Longboat Key, FL
  • Place, Longboat Key Beaches
    ‪1 min walk‬
  • Place, Longboat Key Public Tennis Center
    ‪11 min walk‬
  • Place, Siesta Key Beach
    ‪29 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪24 min drive‬

Room options

About the area

Longboat Key

This condo places you steps from Longboat Key Beaches and within a 20-minute stroll of Longboat Key Public Tennis Center. .Condo features a washer/dryer, free WiFi and 2 bathrooms. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A balcony, in-room jetted baths and a sofa bed are also available. .This smoke-free condo building offers barbecues, a picnic area and a lift. Added amenities include a hot tub and laundry facilities.
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What's nearby

  • Longboat Key Beaches - 1 min walk - 0.0 km
  • Longboat Key Public Tennis Center - 11 min walk - 0.9 km
  • Lido Beach - 7 min drive - 8.8 km
  • St. Armands Circle - 9 min drive - 10.2 km
  • Siesta Key Beach - 29 min drive - 25.0 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 21 min drive

Restaurants

  • ‪McDonald's - ‬21 min drive
  • ‪Dry Dock Waterfront Grill - ‬6 min drive
  • ‪The Old Salty Dog - ‬8 min drive
  • ‪New Pass Grill & Bait Shop - ‬7 min drive
  • ‪Tarpon Bay Grill & Tiki Bar - ‬23 min drive

About this property

Entire place

You'll have the entire condo to yourself and will only share it with other guests in your party.

Winter’s Overrated. Longboat Key Isn’t. — 2BR w/ Beach Access

Looking for a winter glow-up? Welcome to Longboat Key—where sandy beaches, soft breezes, and that “I could really get used to this” island vibe turn even the coldest months into sunshine season. Your home base: a spacious 1600+ sq. ft. 2BR condo perched right over Crane’s Bay with front-row seats to postcard-perfect views (and the occasional surprise manatee cameo).

Inside, you’ll find all the comforts of home—only sunnier.
Main Bedroom: King bed + private bath with a jetted tub worthy of vacation-level bubble baths
Guest Room: Two twin beds (aka the cozy kid zone or bestie bunk room)
Living Room: Sleeper sofa for extra guests
Second Bathroom: Easy access for everyone—no vacation “line for the shower” chaos

A Kitchen Built for Vacation Mode
Fully equipped with full-size appliances, roomy countertops, a breakfast nook made for slow mornings, and all the essentials—dishes, pots, pans, toaster, coffee pot, and utensils.
Plus, in-unit washer + dryer to keep swimsuits fresh and sandy footprints in check.

Resort Perks to Keep the Good Times Rolling
Heated Outdoor Pool & Whirlpool (Dawn to Dusk)
Perfect for cold-weather refugees and sunset soakers.
Tennis & Pickleball Courts
Serve up some friendly competition—or just look sporty, no judgment.
Beach + Gear Access
Ask at check-in for our limited supply of beach chairs, umbrellas, bikes, helmets, tennis gear, and fishing equipment.
(First come, first sun-kissed.)
Picnic & BBQ Area
Grill, chill, and dine under the Florida sky.
Lobby Entertainment
Books, games, and videos—because even paradise has cozy indoor days.

Before You Book, A Few Helpful Notes

Parking: No campers, motorhomes, or trailers. (We’ve got storage options—call us.)
Smoking: Allowed only on balconies or designated areas. Not inside.
Pets: We love them too, but this property is pet-free.
Occupancy: Max of 6 guests, kiddos included.
House Rules: No pets, no smoking/vaping inside, no parties.
Views: your view may vary.
Age Requirement: 21+ to rent and check in.
Maintenance: If anything pops up, our team is quick on the fix.

On-Site Office Hours
Mon–Fri: 8 AM – 4 PM
Sat: 9 AM – 5 PM

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Property amenities

Pool/Spa

  • Communal pool
  • Heated pool
  • Hot tub

Internet

  • Available in the condo: Free WiFi

Parking and transport

  • Car recommended
  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Jetted bathtub
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Books
  • Games

Outdoor areas

  • Balcony
  • Barbecue grill
  • Dock
  • Picnic area

Laundry

  • Laundry facilities
  • Washer/dryer

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Lift
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near the bay
  • Near the marina
  • Near the sea

Things to do

  • Bicycles
  • Heated pool
  • Tennis
  • Motor boating nearby
  • Wildlife walks nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Bicycles
  • Unit size: 1,600 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 21

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events allowed

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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher and a smoke detector in all accommodation.

Property is also known as

409

Frequently asked questions

Are there any beaches close to Winter’s Overrated. Longboat Key Isn’t. — 2BR w/ Beach Access?

Yep, Winter’s Overrated. Longboat Key Isn’t. — 2BR w/ Beach Access is a short 1-minute walk from Longboat Key Beaches.

How much does it cost to stay at Winter’s Overrated. Longboat Key Isn’t. — 2BR w/ Beach Access?

As of 24 Mar 2026, prices found for a 1-night stay for 2 adults at Winter’s Overrated. Longboat Key Isn’t. — 2BR w/ Beach Access on 3 Apr 2026 start from AU$1,125, 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.

Does Winter’s Overrated. Longboat Key Isn’t. — 2BR w/ Beach Access have a pool?

Take your pick from a heated pool, a pool and a communal pool.

What luxury perks are available at Winter’s Overrated. Longboat Key Isn’t. — 2BR w/ Beach Access?

This property features a heated pool, as well as a jetted bath and a living room.

What makes Winter’s Overrated. Longboat Key Isn’t. — 2BR w/ Beach Access a romantic place to stay?

1 hot tub, Jetted bath, and private balconies all help set the scene for a sizzling getaway at Winter’s Overrated. Longboat Key Isn’t. — 2BR w/ Beach Access.

Is there a private hot tub at Winter’s Overrated. Longboat Key Isn’t. — 2BR w/ Beach Access?

Yep, there is a hot tub.

Is there a free airport shuttle available at Winter’s Overrated. Longboat Key Isn’t. — 2BR w/ Beach Access?

No, Winter’s Overrated. Longboat Key Isn’t. — 2BR w/ Beach Access does not offer an airport shuttle service.

What time are check-in & check-out at Winter’s Overrated. Longboat Key Isn’t. — 2BR w/ Beach Access?

Check-in begins at 4:00 PM. Check-out time is 10:00 AM.

Are pets allowed at Winter’s Overrated. Longboat Key Isn’t. — 2BR w/ Beach Access?

No, pets are not allowed.

Winter’s Overrated. Longboat Key Isn’t. — 2BR w/ Beach Access Reviews

Reviews

9.4

Exceptional

Rating 10 - Excellent. 24 out of 34 reviews
Rating 8 - Good. 9 out of 34 reviews
Rating 6 - Okay. 1 out of 34 reviews
Rating 4 - Poor. 0 out of 34 reviews
Rating 2 - Terrible. 0 out of 34 reviews

9.8/10

Cleanliness

Reviews

10/10 Excellent

jacqueline k.

Liked: Cleanliness
Pool was lovely and the bay view was great. Staff were very helpful
Stayed 14 nights in Feb 2026

8/10 Good

dennis r.

Liked: Cleanliness
Very clean and very friendly staff.perfect location great activity amenities.great hot tub and pool
Stayed 3 nights in Feb 2026

10/10 Excellent

Kimberlee

Liked: Cleanliness
Great location
Stayed 3 nights in Feb 2026

8/10 Good

Diane N.

Liked: Cleanliness
Every one was pleasant. Clean.
Stayed 8 nights in Jan 2026

10/10 Excellent

La Belle P.

Liked: Cleanliness
Stayed 5 nights in Jan 2026

8/10 Good

Theresa B.

Stayed 5 nights in Dec 2025

8/10 Good

NANCY N., Lakeland, FL

Liked: Cleanliness
We love staying here! The location is ideal, and we love the pool and tennis/pickleball court. The condo is very spacious and well appointed with everything needed for a wonderful vacation. We will definitely be back!
Stayed 5 nights in Dec 2025

10/10 Excellent

Dana O.

Liked: Cleanliness
We enjoyed the large condo, amenities of the complex and how close it was to the beach. While the furniture makes it seem older, it definitely has had some updates and we would recommend it.
Stayed 3 nights in Dec 2025

10/10 Excellent

Lori D.

Liked: Cleanliness
Loved how spacious the condo was, along with the great views. Walk to the beach was easy. So nice to have beach chairs, umbrellas, and bikes available for guests.
Stayed 2 nights in Aug 2025

10/10 Excellent

Mark S.

Liked: Cleanliness
Staff is awesome!
Stayed 3 nights in Jul 2025

10/10 Excellent

Chris H.

Stayed 3 nights in Jun 2025

8/10 Good

Sean P.

Liked: Cleanliness

Great stay!

While still a bit of post hurricane construction was going on at the property, it didn’t ruin our stay.
Stayed 4 nights in Jul 2025

10/10 Excellent

Theresa G.

Liked: Cleanliness
Lovely condo, clean and spacious. Staff was very nice...would definitely book again.
Stayed 4 nights in Jul 2025

10/10 Excellent

Mark B., Hendersonville

Liked: Cleanliness

June trip

We have vacationed at LBK for years.This was one of the best offerings Ocean views and bay views.
Stayed 10 nights in May 2025

10/10 Excellent

Heather P.

Liked: Cleanliness

Great stay

Lots of space in the unit for 4 adults. Well equipped kitchen that we enjoyed using. The beach is across the street with a bonus of having chairs and umbrellas to use. Nice pool. Loved seeing the manatees in the bay.
Stayed 6 nights in May 2025

6/10 Okay

Patrick C., Orlando, Florida

Liked: Cleanliness

Came up a bit short.

Twin beds were unacceptable, very noisy and crunchy loud sounds at every move. Twin mattresses need to be replaced. Overall needs some attention to detail on the unit interior. Could use a “refresh “ to look more current. Guest bathroom door would not latch closed until the maintenance man fixed it. Kitchen was well stocked, air works well, TV works fine. Staff very friendly.
Stayed 3 nights in Jun 2025

10/10 Excellent

Mary H.

Stayed 3 nights in May 2025

8/10 Good

Janis Y.

Liked: Cleanliness

Met our expectations

All we expected , only suggestion would be more TV viewing options esp Netflix
Stayed 3 nights in May 2025

10/10 Excellent

Nathan P.

Liked: Cleanliness

What a great place to stay

We loved staying on the Key and the place was great. What an awesome condo. We had a great time and the staff was the best.
Stayed 5 nights in Apr 2025

10/10 Excellent

Wendy S.

Liked: Cleanliness

Bay view with Manatees

Our visit was brief but we certainly enjoyed our stay! Seeing manatees from the balcony was a nice treat along with having beach access directly across the street. The condo was spacious and the kitchen was well equipped though we didn't cook or have a need for the guest bedroom. The view is very nice from the living room and master bedroom. This unit is located on the corner and also by the stairs if needed. It was nice to have beach chairs, toys and an umbrella available down at the parking garage. There's a nice tennis court and Bayside pool. Also, there were two gas grills on the property. The management is onsite and accessable if needed. Very nice place. It's clean and well managed. It definitely shows when people care!
Stayed 3 nights in May 2025

8/10 Good

Bryan B.

Liked: Cleanliness

Nice location. Old furniture

Mattresses were old and squeeked.
Stayed 14 nights in Feb 2025

8/10 Good

Gary D., holland MI

Liked: Cleanliness

Great family place

Nice and clean, staff was very friendly. Beach access was across the road but there is a crosswalk, with flashing lights, right there which made it easy. I think it was a little pricey for what you get but I would stay there again.
Stayed 5 nights in Feb 2025

10/10 Excellent

David S.

Liked: Cleanliness

Wonderful stay

The condo was very spacious and well equipped. Most notably, it was very quiet and we had a cross-walk so we could safely cross GMD to walk on the beach.
Stayed 5 nights in Feb 2025

10/10 Excellent

Phil L.

Liked: Cleanliness

Great Location

Across the street from the beach. Large condo was as represented. Quiet building . No problems with the unit appliances. Short drive to Publix and CVS. St Armands Ciricle is about 15 minutes away. Very responsive management. We would definitely recommend!
Stayed 4 nights in Feb 2025

10/10 Excellent

Susan F.

Liked: Cleanliness

Wonderful condo in a wonderful location!

Loved the spaciousness of the condo we rented, the front office (Geri!) was fabulous, grounds are well maintained. The bonus was how quiet - bay facing but just across the street from the Gulf.
Stayed 4 nights in Feb 2025