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

Condo in Longboat Key with kitchen and balcony

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

Aerial View
Pool and Crane's Bay
Living area
Room
Room

Reviews

9.6 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 6148.6 sq m

Popular amenities

  • Pool
  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

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, Lido Beach
    ‪8 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪22 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

1 Double Sofa Bed

Guest Bedroom

2 Single Beds

Main Bedroom

1 King Bed

2 bathrooms

Guest Bath

Toilet · Shower only

Main Bath

Bathtub or shower · Toilet · Jetted bathtub

Spaces

Kitchen
Balcony
Dining area

About this property

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

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washing machine
Dryer
Free WiFi

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House Rules

Check in after 4:00 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

No 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 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

We should mention

A car is recommended for transport to and from this property

About the area

Longboat Key

Located in Longboat Key, this condo is by the sea. 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 Lido Beach and Bradenton Beach. Mote Marine Laboratory & Aquarium and Marie Selby Botanical Gardens are also worth visiting. Take the opportunity to explore the area for water adventures such as power boating and other activities like wildlife walks.
Map
Longboat Key, FL

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 - 8 min drive - 8.8 km
  • St. Armands Circle - 9 min drive - 10.2 km
  • Siesta Key Beach - 27 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

Frequently asked questions

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

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

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

As of 1 February 2026, prices found for a 1-night stay for 2 adults at Winter’s Overrated. Longboat Key Isn’t. — 2BR w/ Beach Access on 9 February 2026 start from NZ$1,051.83, 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 Winter’s Overrated. Longboat Key Isn’t. — 2BR w/ Beach Access pet-friendly?

No, pets are not allowed at this property.

How much is parking at Winter’s Overrated. Longboat Key Isn’t. — 2BR w/ Beach Access?

On-site parking is available at the property.

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

Check-in begins at 4:00 PM.

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

Checkout is at 10:00 AM.

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

Situated by the sea, this condo building is within 1 mile (2 km) of Longboat Key Beaches and Longboat Key Public Tennis Center. Lido Beach and St. Armands Circle are also within 6 miles (10 km).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 21 out of 28 reviews
Rating 8 - Good. 6 out of 28 reviews
Rating 6 - Okay. 1 out of 28 reviews
Rating 4 - Poor. 0 out of 28 reviews
Rating 2 - Terrible. 0 out of 28 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

8/10 Good

NANCY N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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, check-in, communication, location, listing accuracy
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

8/10 Good

Sean P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Nathan P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Mark S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Staff is awesome!
Stayed 3 nights in Jul 2025

10/10 Excellent

Theresa G.

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

10/10 Excellent

Mark B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Lori D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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

David S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Heather P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

10/10 Excellent

NANCY N., Lakeland, FL

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location!

My family loved being so close to the pool, and just a short walk to the beach. We will definitely book this condo again.
Stayed 4 nights in Dec 2023

10/10 Excellent

Susan F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

10/10 Excellent

Andy L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

good value!

nothing extra fancy but nice place.
Stayed 3 nights in Jan 2025

8/10 Good

Gary D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Mark S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxing

Laid-back and a ton of space with beautiful view. Staff was incredibly helpful.
Stayed 7 nights in Nov 2024

10/10 Excellent

Joshua K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Property

Excellent property and as advertised! The condo is larger than most in its class!
Stayed 7 nights in Mar 2024

8/10 Good

Janis Y.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Met our expectations

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

8/10 Good

Bryan B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice location. Old furniture

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

10/10 Excellent

Phil L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

6/10 Okay

Patrick C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

chris s.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Best Longboat Key Location, Great Condo

2 BR Condo exceeded expectations. On-site manager made check-in/out easy. Maintenance staff handled one small issue regarding a bath nozzle quickly and in a friendly fashion. Condo was more spacious than the pictures show. Immaculately clean. Publix very close. Tennis facilities very close. Was the for a USTA tournament and it was ideal.
Stayed 5 nights in Nov 2023

10/10 Excellent

Wendy S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

10/10 Excellent

Karen O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Longboat Key Condo

Spacious condo and appreciated the layout for privacy between the MBR and the twin bedroom. Enjoyed the porch access off the MBR and the FR. Spacious/ updated kitchen also with another separate balcony and breakfast table. Incredibly private and quiet. Perfect walk across the street to the beach ( no life guard beach but you have several public beaches within 15 mins either in Anna Marie island or at Lido beach). The pool is clean and warm. So loved the evening entertainment with the pod of manatees in the back bay. Accommodated with beach chairs/ umbrellas etc. Great coffee shop next door to condo and grocery store was 5 min by car. Overall great trip and can’t wait to return with more family members !
Stayed 5 nights in Mar 2024

10/10 Excellent

Chris H.

Stayed 3 nights in Jun 2025

10/10 Excellent

Mary H.

Stayed 3 nights in May 2025

About the host

Hosted by Rich, Elisabeth, Adele, Angie and Sheri

Host profile image
Some of our best memories come from childhood family vacations. It's our vision to help other families find accommodations in places that are easily reached, provide attractions, and are affordable. Each of our properties provide unique environments, but they are all family friendly. We are here to answer your questions and help you find the right destination for creating vacation memories.

Why they chose this property

We have come to love Longboat Key for the relaxed "no fuss" atmosphere.  The Gulf of Mexico is famous for gorgeous blue water and white sand beaches.  We love the quiet and carefree pace that comes with the absence of high-rise buildings.  We hope you do too!

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English

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