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

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

9.4 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 61600 sq ft

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Explore the area

View in a 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

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
Our prices include all fees. No hidden fees.

Add dates for prices

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  • Kitchen
  • Washing machine
  • Dryer
9.4 out of 10, Exceptional, (11 reviews)
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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

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 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
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.

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 Fish Hole Adventure Golf 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 - 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
  • ‪The Old Salty Dog - ‬8 min drive
  • ‪Dry Dock Waterfront Grill - ‬6 min drive
  • ‪Tarpon Bay Grill & Tiki Bar - ‬23 min drive
  • ‪Chart House Restaurant - ‬7 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 11 Apr 2026, prices found for a 1-night stay for 2 adults at Winter’s Overrated. Longboat Key Isn’t. — 2BR w/ Beach Access on 4 Jul 2026 start from £214, 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

9.4

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. 26 out of 36 reviews
Rating 8 - Good. 9 out of 36 reviews
Rating 6 - Okay. 1 out of 36 reviews
Rating 4 - Poor. 0 out of 36 reviews
Rating 2 - Terrible. 0 out of 36 reviews

9.8/10

Cleanliness

9.8/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Kimberlee

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location
Stayed 3 nights in Feb 2026
Verified

8/10 Good

dennis r.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very clean and very friendly staff.perfect location great activity amenities.great hot tub and pool
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

jacqueline k.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Pool was lovely and the bay view was great. Staff were very helpful
Stayed 14 nights in Feb 2026
Verified

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
Response from VrboOwner on 5 Feb 2026
Thank you so much for the wonderful review, Nancy! We're really glad you love staying here — the location, pool, and tennis/pickleball courts truly make it a fun spot. It’s great to hear the condo felt spacious and well equipped for your vacation. We’d be happy to welcome you back anytime.
Verified

10/10 Excellent

Jennifer M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was perfect for our family of four. There are bikes, pool noodles, umbrellas, and chairs available to use. Kitchen tools are available but bring all of your own oils and seasonings - this isn’t the type of place where you’ll find leftovers from previous guests. The beach is directly across the street and super convenient. We had a corner two bedroom that had gulf and bay views. Definitely recommend!
Stayed 3 nights in Mar 2026
Verified

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
Response from VrboOwner on 13 Jan 2026
Thank you so much for sharing your experience, Dana. We're delighted to hear you enjoyed the spacious condo, the amenities, and the easy access to the beach — those are some of our favorite features too. We appreciate your note about the furniture and are glad the recent updates made a positive difference. Your recommendation means a lot, and we’d be happy to welcome you back anytime.
Verified

8/10 Good

Diane N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Every one was pleasant. Clean.
Stayed 8 nights in Jan 2026
Verified

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
Response from VrboOwner on 18 Jul 2025
Sean Thank you so much for your review! We’re glad to hear you still had a great stay despite the bit of ongoing post-hurricane construction at the property. We appreciate your understanding and patience as improvements are completed, and we hope to welcome you back again soon!
Verified

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
Response from VrboOwner on 2 Jun 2025
Thank you so much, Nathan! We're thrilled to hear you loved your stay on the key and enjoyed the condo. It's especially great to know our staff helped make your visit even more enjoyable. We'd love to welcome you back anytime!
Verified

10/10 Excellent

Mark S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Staff is awesome!
Stayed 3 nights in Jul 2025
Response from VrboOwner on 3 Aug 2025
"Thank you so much for your kind words! We’re thrilled to hear that you had such a positive experience with our team. We’ll be sure to pass along your feedback to them—they’ll be so happy to hear it. We can’t wait to welcome you back soon!
Verified

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
Response from VrboOwner on 14 Jul 2025
Thank you so much for the wonderful 5/5 review! We’re delighted to hear you enjoyed the clean, spacious condo and that our staff helped make your stay pleasant. We’d love to welcome you back anytime!
Verified

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
Response from VrboOwner on 6 Jul 2025
Hi Mark We’re honored to hear that, after vacationing at LBK for years, this was one of the best stays you’ve had. We're so glad you enjoyed both the ocean and bay views—it's a special combination that really makes the location unique. We truly appreciate you choosing to stay with us and hope to welcome you back for another memorable visit in the future! Warm regards,
Verified

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
Response from VrboOwner on 4 Sept 2025
Thank you so much for your kind review! We are delighted to hear you enjoyed the spacious condo, the views, and the easy walk to the beach. We are also glad you were able to make use of the beach chairs, umbrellas, and bikes—it is wonderful to know they added to your stay. And thank you for sharing your beautiful sunset pictures with us, they truly capture the charm of the area. We would love to welcome you back again soon!
Verified

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
Response from VrboOwner on 2 Jun 2025
Thank you for the thoughtful review, David! We're so glad you enjoyed the spacious, well-equipped condo and the peaceful atmosphere. It's great to hear the nearby crosswalk made beach access safe and easy-that convenience makes all the difference. We hope to welcome you back soon!
Verified

10/10 Excellent

NANCY N.

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
Response from VrboOwner on 5 Feb 2024
Thank you for your great review! It was a pleasure hosting you. We hope to host you again in the future.
Verified

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
Response from VrboOwner on 23 Jun 2025
Thank you so much for your kind review! We're glad to hear the unit provided plenty of space for your group and that you enjoyed the well-equipped kitchen. It's great to know the beach access and included chairs and umbrellas were a bonus, and that you had time to relax by the pool. Spotting manatees in the bay is always a special treat—we’re so happy you got to experience that! We hope to welcome you back again soon.
Verified

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
Response from VrboOwner on 2 Jun 2025
Thank you for the fantastic review, Susan! We're so glad you loved the condo and its peaceful location. It's great to hear the spaciousness, well - kept grounds, and especially Geri at the front office made your stay even better. We hope to welcome you back soon for another relaxing getaway.
Verified

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
Response from VrboOwner on 2 Jun 2025
Thank you, Andy! We're glad you found it to be a good value and enjoyed your stay. Sometimes simple and comfortable is just what you need - we'd love to have you back anytime!
Verified

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
Response from VrboOwner on 2 Jun 2025
Thank you for your feedback, Gary! We're glad to hear you and your family enjoyed the stay, found everything clean, and appreciated the friendly staff and the convenient beach access. We understand your thoughts on pricing and truly appreciate your honesty. It means a lot that you'd choose to stay with us again - we'd love to welcome you back!
Verified

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
Response from VrboOwner on 2 Jun 2025
Hi Mark, Thank you for the kind words! We're so glad you enjoyed the relaxing atmosphere, spacious accommodations, and beautiful view. It's wonderful to hear our staff made a positive impact on your stay - we'd love to welcome you back anytime!
Verified

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
Response from VrboOwner on 21 Jul 2024
Hi Joshua, Thanks for the review and allowing us to host you. We appreciate the feedback. We are delighted that you enjoyed your stay. Come back to see us soon!
Verified

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
Response from VrboOwner on 2 Jun 2025
Thank you for your feedback, Bryan. We're glad you enjoyed the location, but we're sorry to hear the furniture and mattresses didn't meet your expectations. We truly appreciate you bringing this to our attention, and we'll be sure to pass it along o improvements can be made. Your comfort is important to us, and we hope to have the chance to provide a better experience in the future.
Verified

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
Response from VrboOwner on 2 Jun 2025
Thank you for your feedback, Janis! We're glad everything met your expectations. We appreciate the suggestion about adding more TV viewing options like Netflix - that's definitely something we'll consider making future stays even better. Hope to host you again soon!
Verified

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
Response from VrboOwner on 2 Jun 2025
Thank you for the wonderful review, Phil! We're so glad you enjoyed the convenient location, spacious condo, and quiet surroundings. It's great to hear everything worked smoothly and that our team was responsive during your stay. We truly appreciate the recommendations and would love to host you again!
Verified

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
Response from VrboOwner on 23 Jun 2025
Hi Patrick; Thank you for sharing your feedback. We’re very sorry to hear that the twin beds were uncomfortable and disruptive to your stay. We will have our team inspect the mattresses and address any replacements needed. Your comments about the interior and guest bathroom door are also appreciated, and we’re glad our maintenance team was able to resolve the latch issue during your visit. On a positive note, we're happy to hear you found the kitchen well stocked, the air conditioning and TV in good working order, and our staff friendly. We value your input and will use it to help improve the guest experience.

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!

Languages:

English

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