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Longboat Key Vacation Rentals

(77 rentals)
Longboat Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Updated top-floor 2 Bedroom + Den with a pullout sleeper with stunning water views from nearly every room. Enjoy the private beach just steps away, featuring 750’ of Gulf frontage and renowned sugary white sand. The open concept layout is perfect for coastal vacationing, complemented by two spacious...

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$234
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • WiFi

About this property

Seaplace is a gulf-front community that sits on 42 acres. Enjoy a half mile of beachfront and 1-mile walking trail in addition to two heated pools and three Har-Tru tennis courts.This home located in the sought after Seaplace community has a very personal feel to it and the beach is steps away from...

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$182
avg per night
Longboat Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
2 reviews

Distance to beach: 0.0 miles to Longboat Key Beach - Condo is on the beach!

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

The Beachcomber building and heated pool are located directly on the white sandy beach of Longboat Key! Suite 501 has an island view of Longboat Key with a partial view of Sarasota Bay from the 5th floor. Unit 501 is located ten steps to the elevator and 10 steps to the heated pool located directly on...

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Featured review

"Great vacation"

Great location and staff,very clean and comfortable.Being on beach store was across street.Very quite at night so glad we didn't stay at Anna Marie Island to busy.Staff very professional, getting back to...

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$293
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

For those who do not know Beachplace, it is more of a resort than it is a gated condo community. During the winter there are plenty of planned activities including a movie night once a week, a book club, pot luck dinners, tennis, pickle ball and more. This beautiful 5th floor corner unit has amazing...

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Featured review

"Amazing Place"

Arrived on the 1st of May what amazing place the Beachplace is right on the Gulf of Mexico the beach and the water was amazing. So many restaurants to visit and a Publix just down the road . Can’t recommend...

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$203
avg per night
Longboat Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
3 reviews

Distance to beach: 0.1 miles to Private beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

This WATERFRONT condo is very spacious, beautifully updated. Perfectly located within a minute of a private sandy beach and right along the waters edge of a salt water canal and intra coastal waterway. Enjoy the great water views that span the full width of the ground floor condo. Fishing, kayaking,...

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Featured review

"Comfort & Convenience"

Spent a full month and it truly felt like a home away from home. The condo had everything you needed for the beach, umbrellas, beach cart, great beach towels & even kids toys. The kitchen was exceptionally...

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$234
avg per night

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Longboat Key Condo
Sleeps 6, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

This property is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. There is a full kitchen, living area with a queen size sleeper sofa, and a bedroom with two queen size beds. It is part of the Zilli Collection.Each with the Zilli touch of amazing view, decor, (not typical...

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$348
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

This is a Walkdown level fully remodeled condo. On the soft white sand beaches of Longboat Key, Beach Place offers 31 luxury acres and 1450 linear feet of beach. Resort Style Amenities include large community pool and exercise facility.New Listing! Perfect beach view elevated walkdown level fully...

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$362
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Exquisite beach and Gulf view unit on the 3rd floor of building 3. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. New owner has upgraded unit including tiling, furniture replacement, painting, new kitchen appliances, new linen, TV's and more. This condo also has new windows...

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$294
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • WiFi

About this property

Experience Coastal Elegance at Beachplace PenthouseWelcome to your dream beachfront retreat, where coastal living meets luxury at its finest. Nestled on the coveted sixth-floor Beachfront corner of Beachplace building 8, this beautiful penthouse offers an unparalleled living experience with breathtaking...

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$404
avg per night
Longboat Key Apartment
Sleeps 6, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

This property is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. It is part of the Zilli Collection. Each with the Zilli touch of amazing view, decor, (not typical wicker furniture, silly beach artifacts, 40 year old flooring, one SIZE fits all, etc.). We call it...

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$361
avg per night
Longboat Key Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 100 yards to Whitney Beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Discover this 3-bedroom gem in Longboat Key.Wake up to the sound of waves and enjoy direct beach access just a few feet from your door. This bright and inviting first-floor 3-bedroom, 2-bathroom condo on Longboat Key offers 1,500 square feet of comfort, convenience, and coastal charm, the ideal place...

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$465
avg per night
Longboat Key Condo
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • WiFi

About this property

Short Term Stays available Imagine waking up to a breathtaking panorama of the Gulf of Mexico,. This completely remodeled condo, the largest in the community, offers unobstructed, 8th-floor views that will take your breath away. Picture yourself stepping onto the expansive terrace and feeling the cool...

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$823
avg per night
Longboat Key Apartment
Sleeps 6, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

This property is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. There is a full kitchen, living area with a queen size sleeper sofa, and a bedroom with a king size bed. It is part of the Zilli Collection. Each with the Zilli touch of amazing view, decor, (not typical...

View all property information

Featured review

"Great Rental"

Zilli 202 was the best rental! It had an absolutely gorgeous view. My husband and I went for our 35th anniversary. We could not have asked for a better place. Jim was a great host. He was very informative...

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$384
avg per night
Longboat Key Villa
Sleeps 8, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Welcome to the Zilli family Villa beach house on Longboat Key. After using this 2,000 sf home for their own family vacations, the house was completely redecorated and stocked to offer all the comforts of home to our guests. A cool, beachy palette welcomes you to sit back and relax.Make plans now to...

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Featured review

"Spacious luxury right on the beach"

The owner is attentive to details and is there for you if you need him. Large, contemporary furnishings, private, full of amenities you desire and often don't get at a resort. Don't hesitate to rent this...

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$600
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Penthouse level fully renovated 2 bedroom condo offers modern luxury. It is paradise within paradise. This is a very rare find.Beachplace is one of Longboat Key's premier vacation rental locations on the island! With amazing direct Oceanfront views, this top floor unit boasts a double balcony....

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$428
avg per night
Longboat Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

7th floor corner unit with balcony offering wide, sweeping view of the beach and Gulf. Both bedrooms offer clear view of Bay and downtown Sarasota. The unit has been newly updated and professionally decorated complete with tile floors, quartz countertops, high end furnishings and remote blinds. Living...

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$293
avg per night
Longboat Key Apartment
Sleeps 6, 1 bedroom, 1 bathroom
3 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

This property is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. There is a full kitchen, living area with a queen size sleeper sofa, and a bedroom with two queen size beds. It is part of the Zilli Collection.Each with the Zilli touch of amazing view, decor, (not typical...

View all property information

Featured review

"Amazing sunsets!"

This condo is absolutely beautiful! We had everything we needed and more! The condo is so roomy and very comfortable. And the views are breathtaking. The owner is amazing, with great communication and...

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$341
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Paradise is not lost. Beachplace is a private gated Gulf front community with 24 hour security located on the famous Longboat Key. Steps away from the longest stretch of private beach on Longboat Key and located on 30 acres of manicured grounds, Beachplace is one of the island’s most beautiful...

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$333
avg per night
Longboat Key Condo
Sleeps 4, 1 bedroom, 1 bathroom

Distance to beach: 0.0 miles to Whitney Beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Step into coastal luxury with this beautifully renovated, ground-floor 1-bedroom condo mere steps from the sparkling shoreline of Longboat Key. From the moment you enter, the panoramic beach view draws you in like a wave—open the sliding glass doors to feel the gulf breeze, hear the soothing rhythm...

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$220
avg per night
Longboat Key Villa
Sleeps 2, 1 bedroom, 1 bathroom
6 reviews

Distance to beach: 150 yards to Gulf Of Mexico

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Ground Floor Condo- 1 Bedroom- Sleeps 2 - walk a block and a half across the street to the beach.Beautiful end unit attached villa in the charming community of St. Judes on Longboat Key. Just a short walk to the private beach access and to the 32 acre Joan Durante Park FULL of fabulous tropical walking...

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Featured review

"Lovely place!"

This adorable rental was the perfect size for 2. It was very clean. I was so impressed how close we were to the beach

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$140
avg per night
Longboat Key Villa
Sleeps 4, 2 bedrooms, 1 bathroom
6 reviews

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Escape to a sparkly clean and relaxing beach getaway in this beautifully updated 2-bedroom, 1-bath condo, perfectly located in the heart of Longboat Key. Just a short stroll to the beach, local restaurants, grocery stores, and more, this unit is ideal for couples or families seeking comfort and convenience.The...

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Featured review

"Post Hurricane Milton review"

This is not so much a review as it is an update for people concerned about the aftermath of Hurricane Milton. The city of Longboat Key has done an impressive job at cleaning up the hurricane’s mess....

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$197
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

2 Bedrooms, 2 bathroom, gulf front, private beach, white sand, elevators. The condo is located directly on the beach waters of the Gulf of Mexico. The unit features a fully equipped kitchen, a dining room, a living room with sleeper sofa and 3 chairs, primary bedroom with king size bed with office...

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$169
avg per night
Longboat Key Villa
Sleeps 5, 2 bedrooms, 1 bathroom
2 reviews

Distance to beach: 500 yards to Gulf of Mexico

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Little Palm on the bay in Longboat Key, Florida, a place to go when you want to relax and enjoy! Sunbathing, fishing, and boating right at your backdoor with the beach and pool only a short walk away!  BOATERS, you can bring your boat or rent a boat to be available right out your back door. Don’t...

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Featured review

"Nice trip"

I loved my month here. I would never have 5 people though. It is 600 sq. ft and 1 bath. There were two of us and it was fine. Lovely back area on a canal. Very quiet and nice people around. There...

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$160
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

PENTHOUSE, DOUBLE BALCONIES, breathtaking wide sweeping straight on views of the Gulf and Bay make our Beachplace condo a true paradise on Longboat Key. This sought after resort is gated on the south end of the island close to the famous Saint Armands Circle, Publix’s and many highly rated restaurants....

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$519
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner

About this property

Views from every window 2 Bedroom/2 Bathroom (no one living above) corner end unit with access to a rooftop deck directly above this sunny and bright unobstructed panoramic view of Sarasota Bay with deeded beach access to one of the most pristine stretches of pearly white Gulf of Mexico sand directly...

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Featured review

"HBC"

Lovely place with a great view of the bay. Well set up with all of the things you need. Owner very accomodating

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$200
avg per night
Longboat Key Condo
Sleeps 2, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Newly renovated & furnished 1/1 second floor condo with wonderful view of Bishops Bayou on the uncrowded north end of Longboat Key. Whitney Beach has a beautiful natural stretch of beach as well as many amenities including tennis / pickleball courts, swimming pools, shuffleboard & boat docks...

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$150
avg per night
Longboat Key House
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Distance to beach: 0.5 miles to Longboat

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Completely renovated Island home located 4 houses off Tarawitt point on a large 90x125ft lot. Coveted lifestyle and location on a deep water canal in the heart of Longboat Key. This waterfront home has 125ft of seawall docking for a boat up to 30 ft. boat plus a jet ski lift and room for other water toys....

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Longboat Key House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Beach Paradise by Beach Retreats Vacation RentalsLongboat Key, FL 3 Bedrooms | 3 Bathrooms | Sleeps 6 | Steps to Beach | Community Pool Views | 30-Night Minimum StayYour Longboat Key Retreat Welcome to Beach Paradise, a spacious 3-bedroom, 3-bath home perfectly situated just steps from the...

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$513
avg per night
Last Minute Deal
Longboat Key Condo
Sleeps 6, 1 bedroom, 1 bathroom
12 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Spectacular Gulf Views and Breathtaking Sunsets – Renovated Beachfront Condo.Relax and unwind at our newly renovated 1-bedroom, 1-bath condo on the pristine beaches of Longboat Key. With sweeping 180° Gulf views, modern upgrades, and easy beach access, this is one of the best values on the...

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Featured review

"Wonderful place!!"

This is an absolute must stay!! You have your own private beach, and everything is so close. The view from the balcony is breathtaking., by far the best place to have your coffee in the morning! The host...

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$307
avg per night
Longboat Key Condo
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

  • Pet friendly
  • Private pool

About this property

NEW LISTING! Welcome to Bay Dream Believer, your luxurious bayfront escape on beautiful Longboat Key! This bright and beautifully upgraded condo offers breathtaking views of Sarasota Bay through massive picture windows and an enclosed patio that lets you soak in the scenery year-round. Located just across...

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$310
avg per night
Longboat Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Distance to beach: 5 feet to Just outside your door & window

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Magnificent Condo directly on the Gulf of Mexico! Right on the beach! Every sunset is unique and beautiful! Located in very well-maintained and updated Longboat Harbor Towers.The barrier isle Longboat Key is a quiet, non-touristy location voted one of North America's top islands by Conde Nast...

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Featured review

"Happy in Longboat Key"

We enjoyed our stay & owners were very helpful for helping us when needed! Beautiful view of the Gulf! Unit was sparkling clean & well equipped & comfortable. We are returning next year as well. The property...

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$133
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

2 Bedroom and 2 Bath condo located in the resort community of Beachplace. Faces the golf course with limited Gulf view and has access to the boardwalks to the Beach. Beachplace sets up chairs and umbrellas daily on the beach to make access very simple and inviting. All NEW furnishings throughout this...

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$242
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Great beach and Gulf views are breathtaking from your balcony, living room, kitchen and dining room of the Penthouse condo located on the 15th floor of Islands West Complex. You will love the beach views and fast Wi-Fi. Master bedroom with King bed has amazing views of the Bay and the Sarasota Downtown...

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$269
avg per night
Longboat Key House
Sleeps 7, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Charming Sarasota Retreat with pool and putting green in Gulf Gate Welcome to your perfect Sarasota getaway! Nestled in the desirable Gulf Gate neighborhood, 2921 Captiva Dr. offers a relaxing retreat just minutes from world-famous Siesta Key Beach. This beautifully appointed vacation rental features...

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$256
avg per night
Longboat Key House
Sleeps 2, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Charming one-bedroom guest house featuring floor-to-ceiling windows, high vaulted ceilings, & an open kitchen. Balcony enclosed with heavy curtains, perfect for peaceful mornings & nights. Kick back, relax, in this calm, stylish space, capturing the essence of Old Florida. Experience peaceful...

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Featured review

"Amazing Location"

This place is amazing. The location could not be more perfect. The beach and three amazing restaurants are all within five minutes walking distance. The grounds are impeccably kept and the owner is very...

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Longboat Key Condo
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

This fabulous, 2000-square-foot, fourth story, corner, direct beachfront, condominium features spectacular views of the gulf and bay. Hear the waves from the master suite and enjoy a dinner on the screened lanai while viewing one of Longboat's incredible sunsets. Sip a morning coffee on the back...

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$533
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Penthouse unit on the top floor of building 3 at Beachplace. Top floor units enjoy a double balcony with access from the living room and Master bedroom. Amazing views of Beach, Pool, Pond and downtown Sarasota.This is a very popular floorplan at Beachplace. You have spectacular views of the beach and...

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$313
avg per night
Longboat Key Studio
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Looking for a vacation in warm sunny Florida in a condo where you walk directly out onto the deck and onto the beach. Stay in this 2 bedroom (2 king beds), 2 bath condo . It is on the Gulf Side. Right on the Beach with amazing views. Condo is beautiful and in excellent condition

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$405
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Beautiful beachfront unit on the 2nd floor with lake view and partial Gulf. This is a beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. It just feels like home. It was decorated by Anne Folsom Smith. It has many custom features, including hand crafted furniture, unique kitchen backsplash...

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$216
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

2 bedroom + Den and 3 bathrooms with views of the Beach of Longboat Key. Prestigious entrance to the Pierre through the lobby with a concierge doorman to great your guests as they arrive to visit. This unit offers 2 balconies to relax on and enjoy the view of the sunset or calm waters of the Gulf of Mexico....

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$353
avg per night
Longboat Key House
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

Discover this newly rebuilt hurricane-resistant home at 701 Broadway St, Longboat Key, FL 34228 . Perfect for couples or small families seeking a serene vibe.Property Features2 bedrooms, 2 bathrooms. 1 bedroom guest house above garage, just one flight up. Fully gated backyard with swimming...

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Featured review

"Super Cute Long Boat Key Cottage!"

Absolutely loved our stay at this Longboat Key cottage! It’s perfect if you work from home — fast, reliable Wi-Fi and a dreamy window seat made it easy (and enjoyable) to stay productive. The location...

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$750
avg per night
New
Longboat Key House
Sleeps 12, 4 bedrooms, 3 bathrooms

Distance to beach: 0.5 miles to Deeded Beach Access

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Luxury and Coastal Elegance! This Stunning Turnkey Canal-Front Pool Home was Built in 2015. Situated on the Highly Desired North End of Longboat Key. Featuring 120 Feet of Beautiful Canal Frontage, A 10,000lbs Boat Lift and Deeded Beach Access only Steps Away! Truly A Boater's Paradise! At Almost...

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$650
avg per night
Longboat Key House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

Looking to step back in time to enjoy the "Old Florida Lifestyle?" Located in the quaint historic village of Longbeach is this cozy one-family house with two queen bedrooms and a third private space that sleeps two more. Two fulls baths accommodates all. Kitchen includes microwave, coffee...

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$232
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to Longboat Key - you've stumbled on a unique hidden gem tucked away on the upper Gulf Coast of Florida. Small, private, and quiet - the key vacation that really makes you get away from it all. Our condominium in Bayport Beach and Tennis Club is a beautiful private retreat with unobstructed...

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$340
avg per night
Longboat Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 400 yards to Gulf Beach - Private Owner Beach Pavilion

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

This beautiful ground floor modern quiet condo offers direct views of Sarasota Bay and just steps from the stunning gulf beach. Inside you will find a modern, renovated interior. The living space boasts abundant natural light. The kitchen is bright with up to date appliances, and a breakfast bar that's...

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$85
avg per night
Longboat Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
5 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

This ground floor waterfront condo located in a gated community of Longboat Harbour and is one of Longboat Keys most desirable social communities. This one bedroom, one bathroom, first floor unit has walkout access to Sarasota Bay where you often see dolphins and manatees from your lanai. This unit is...

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Featured review

"Grreat stay atLong Boat Harbour"

What a beautiful development Long Boat Harbour is! My wife and I stayed in unit E104 for 2 months. Haley is a very gracious host to allow us to stay in her home. We had such a wonderful time, we did...

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$157
avg per night
Longboat Key Condo
Sleeps 4, 0 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

This sublime oceanfront studio (We own two more in the same building, plus one down the road - email for more info!) is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located on the second floor, overlooking the heated pool and ocean,...

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$323
avg per night
Longboat Key Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • WiFi

About this property

On the soft white sand beaches of Longboat Key, Beachplace offers 31 luxury acres and 1450 linear feet of beach. More beachfront than any other condo on Longboat Key. Resort Style Amenities include large community pool and exercise facility.Beautiful beachview unit on the 2nd floor with lake view...

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$299
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Come enjoy the Beach - Private parking included. Beautiful beachview unit on the 3rd floor with a Beach and Lake view. Beachplace Building 3 unit 304. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. A sought after unit with shiplap wall in living room and master bedroom, great...

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$247
avg per night
Longboat Key House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Rental located directly on a Canal with a boat lift available for use. This is a single family home that contains 2,192 sq ft and contains 3 bedrooms and 3 bathrooms and a private swimming pool. Dining room has views to the water. Canal connects directly to the Bay and the neighborhood is located on the...

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$319
avg per night
Full map
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Longboat Key Weather

 | 

7222°  5111°
JANUARY
Ocean 6418°
7423°  5312°
FEBRUARY
Ocean 6518°
7725°  5714°
MARCH
Ocean 6719°
8228°  6016°
APRIL
Ocean 7323°
8731°  6518°
MAY
Ocean 7826°
9032°  7122°
JUNE
Ocean 8228°
9133°  7323°
JULY
Ocean 8530°
9133°  7323°
AUGUST
Ocean 8730°
9032°  7222°
SEPTEMBER
Ocean 8529°
8529°  6518°
OCTOBER
Ocean 8228°
8027°  5915°
NOVEMBER
Ocean 7524°
7423°  5312°
DECEMBER
Ocean 6921°

FAQ

How many vacation rentals are there in/around Longboat Key?

There are 77 Longboat Key vacation rentals available on FloridaRentals.com. From condo rentals to house rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Longboat Key?

There are vacation rentals available in Longboat Key for as low as $85 per night with an average price per night of $282.

Can I find a vacation rental in Longboat Key?

Yes, you can find vacation rentals in Longboat Key close to Coquina Beach, Durante Community Park, and Longboat Key. Don't forget to stop in to Quick Point Nature Reserve or Bayfront Park.

Do any vacation rentals in Longboat Key have a pool?

Yes, there are 8 vacation rentals with a pool in Longboat Key on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Longboat Key vacation rentals on the ocean?

There are 20 oceanfront rentals in Longboat Key available on FloridaRentals.com. Use our filters to search and book yours today!