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Longboat Key Vacation Rentals

(76 rentals)
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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$359
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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$142
avg per night
Longboat Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
2 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

"Absolutely wonderful - wish we could go back!!"

First, we have vacationed on Longboat for the past 5 years. Longboat is a special place where you feel relaxed, enjoy the gorgeous beach and the laid back feel compared to more touristy places in Florida....

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$234
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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$606
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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$370
avg per night

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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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$255
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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$445
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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$862
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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$385
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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$300
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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$314
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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$357
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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$391
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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$346
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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$166
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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$186
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 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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$428
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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$221
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, 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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$214
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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$178
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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$199
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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$542
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 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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$312
avg per night
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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$542
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 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
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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$317
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, 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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$341
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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$252
avg per night
Longboat Key Townhome
Sleeps 4, 2 bedrooms, 1.5 bathrooms

Distance to beach: 0.3 miles to Gulf Of Mexico

Key Amenities

  • Air conditioning
  • WiFi

About this property

Bring your boat or just enjoy the view of the canal in this coastal townhome! It’s on the North end of LBK on a deep water canal with quick access to Sarasota Bay and the Gulf of Mexico. The location is ideal near Harry’s Restaurant and Store and just steps from the Deeded Beach Front, Durante...

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$138
avg per night
Longboat Key Villa
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Recently updated 2-bedroom, 2-bath canal-front villa on Longboat Key. This home offers modern finishes, water views, and easy access to the beach just a short walk away. Located in a quiet residential area in a small 2-unit coastal home (duplex).Features:Updated kitchen with new appliances Hurricane-impact...

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Longboat Key Condo
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

The unit is a 1 bedroom 5th floor condo directly on the beach in beautiful Longboat Key. There is beachfront pool as well as a gas grill for barbecuing at the beach. The unit has a partial water view of Sarasota Bay. Walking distance to restaurants and shops including a Publix and CVS.

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$286
avg per night
Longboat Key House
Sleeps 4, 1 bedroom, 1 bathroom
2 reviews

Distance to beach: 500 yards to Whitney Beach

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 on the northernmost end, is a lovely cottage steps from Sarasota Bay and 2 1/2 blocks from Gulf of Mexico with its own relaxing courtyard surrounded by beautiful lush...

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Featured review

"cozy cottage"

The cottage is in a great location on Longboat Key. It is small but having the outside patio was nice extra space to use. Quick walk and view of the bay, and not a long walk to the beach.

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$153
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Amazing Direct Beach views from your balcony, living room, kitchen, dining room and bedroom in this Islands West Condo. The sunsets are breathtaking. You will love the beach views and fast Wi-Fi. This is a luxury rental. Condo has a single unit washer/dryer in one. There is a Islands West is the ideal...

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$350
avg per night
Longboat Key Apartment
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Enjoy seeing sunrise from the lanai or on the dock, and also enjoy sunset on the beach, directly across the street. The unit is completely renovated, nicely furnished, and well stocked - designed for those who love to cook. This 2 bedroom, 2 bath first floor unit with fantastic bayou views its located...

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$252
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 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
Longboat Key Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Beautiful beachfront unit on the 5th floor with lake view and partial Gulf. Beautifully appointed 3 bedroom, 2 bath unit with a real feel of home. King Bed in Master, Queen Bed in 2nd Bedroom and 2 twins in 3rd bedroom.RRR-00586.2023Come stay a month or more! The well-maintained and gorgeous...

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$315
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Spacious 2 bedroom condo in Beachplace gated complex. King in Master bedroom. Come enjoy your time at the Beach. This is a great condo for you to call home for a month or more. Condo is meticulously clean and well cared for. Owners have upgraded the furnishings including large smart TV's One month...

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$302
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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$279
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 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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$407
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to Bayport Beach and Tennis Club!Available for minimum one month rentals beginning OCTOBER 1, 2025.Bayport Beach and Tennis Club is a beach to bay tropical oasis situated on 27 lushly landscaped acres on Longboat Key, FL. The grounds are meticulously maintained and provide a tranquil...

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Featured review

"Home Away From Home"

The property owners are terrific. The apartment was impeccable and met all needs and beyond. Would definitely return

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$203
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Beautiful beachfront unit on the 5th floor with pool view and partial Gulf. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades.The well-maintained and gorgeous grounds include the following amenities: • 24 hour manned guard gate. • Private beach access with chairs...

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$303
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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$334
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Beautiful Beachplace beachfront unit on the 3rd floor spectacular Gulf and beach view. Has brand new windows and doors and is an end unit in building 3 with glass sliding doors on 2 walls of the living room. This is the closest building to the pool. It has 2 parking spaces. One is covered. Beautifully...

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$293
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 76 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 $302.

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!