Longboat Key Vacation Rentals

(56 rentals)
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2 BR | 2 BA | Sleeps 8 | Quick View

$562

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

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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Property Type

Longboat Key Villa

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1 BR | 1 BA | Sleeps 4 | Quick View

1
owner special
Owner special: PRIME VACATION WEEKS IN MARCH 2025 ARE NOW AVAILABLE!

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

$232

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

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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Property Type

Longboat Key Condo

"Fabulous location; wonderful, clean condo. Everything needed was provided. Wonderful staff from check in to maintenance."

Location was wonderful. Midway between Anna Maria Island and the pier to Sarasota and a more city vibe. Restaurants on Longboat were terrific (make reservations) Lazy Lobster; Shore;Salty Dog; Dry Dock; ...

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1 BR | 1 BA | Sleeps 6 | Quick View

$282

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

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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Property Type

Longboat Key Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

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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Property Type

Longboat Key Condo

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2 BR | 2 BA | Sleeps 4 | Quick View

$363

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool

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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Property Type

Longboat Key Condo

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1 BR | 1 BA | Sleeps 6 | Quick View

$299

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

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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Property Type

Longboat Key Apartment

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1 BR | 1 BA | Sleeps 6 | Quick View

$284

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

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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Property Type

Longboat Key Apartment

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1 BR | 1 BA | Sleeps 6 | Quick View

1

$279

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

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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Property Type

Longboat Key Apartment

"We did not book this trip so I'm giving them a great review"

We are giving them a great review, because obviously you are not on top of this as we did not book this trip!!

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1 BR | 1 BA | Sleeps 2 | Quick View

3

Distance to beach: 150 yards to Gulf Of Mexico

$137

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Ground Floor Villa Condo- 1 Bedroom- Sleeps 2 - walk 4 min to beachAdorable end unit attached villa in the charming walkable community of St Judes on Longboat Key just a short 4 minute walk to the private beach access (see photo) and 3 minute walk to the neighboring 32 acre Durante Park FULL of fabulous ...

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Property Type

Longboat Key Villa

"Slice of paradise"

This place was clean and had everything you would need. The bed was the most comfortable bed I have ever slept in. The beautiful beach was just a short walk away and they provided beach chairs too. The ...

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2 BR | 2 BA | Sleeps 5 | Quick View

Distance to beach: 0.1 miles to 3355 Gulf of Mexico Drive

$200

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

Charming condo on Gulf of Mexico Drive, the beach access is across the street from our parking lot, literally steps away to the Gulf. Located in the "Dock on the Bay", we enjoy the benefits of a smaller association. The landscaping and property reflect what all of Florida once looked like. We ...

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Property Type

Longboat Key Condo

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$317

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

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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Property Type

Longboat Key Condo

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2 BR | 2 BA | Sleeps 4 | Quick View

$455

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

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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Property Type

Longboat Key Condo

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2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 0.1 miles to Across Gulf of Mexico Dr

$179

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

TOTAL FULL DIRECT BAY VIEW in the front and Canal view in the back!!!! This 2 BR 2 BATH comfortable coastal beachy condo will delight and impress both inside and out. The primary bedroom has a king bed and en-suite and the 2nd bedroom has a queen size bed. Previous reviews have all been 5 star on other ...

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Property Type

Longboat Key Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Gulf side paradise with hundreds feet of beautiful beach. This one bedroom condo on the fourth floor with a private balcony is the place to enjoy the sound of the rolling waves and some of the most spectacular sunsets on Longboat Key. Take the elevator and you’re just steps away from the heated ...

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Property Type

Longboat Key Condo

"Turtle Crawl Inn Resort Unit 402"

The unit was comfortable and the beach front view was spectacular. The property was also clean and very quiet. The office manager, Rebecca, was friendly and helpful. My husband and I would be delighted ...

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2 BR | 1 BA | Sleeps 5 | Quick View

2

Distance to beach: 500 yards to Gulf of Mexico

$142

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Rentals by owner

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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Property Type

Longboat Key Villa

"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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$151

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Rentals by owner

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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Property Type

Longboat Key Condo

"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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$173

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pet friendly

About this property

Surrounded by tropical landscaping & fruit trees on a corner lot, this cozy 3 bed/2 bath home features an open floor plan w/new kitchen & remodeled baths. Those who enjoy a quiet retreat will enjoy the pond with lilly pads & fire pit. LBK's historic fisherman's village combines rich ...

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Property Type

Longboat Key House

"The property we stayed at was very nice."

First off, we didn't stay at the property listed above. We stayed in Big Pine Key on E. Cahill street. The property was very nice as well as the property manager, Dave. Nothing bad to say except that our ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • 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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Property Type

Longboat Key Condo

"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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3 BR | 2 BA | Sleeps 6 | Quick View

7

Distance to beach: 0.2 miles to Whitney Beach

$200

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

3 bedroom, 2 bath cottage close to Gulf and Bay Great 3 bedroom, 2 bath house with pool on the north end of Longboat Key. Longbeach Village is a neighborhood with 'Old Florida Charm' unlike most of LBK. You will be two houses from the bay (boat launch and pier), and 3 blocks from a fabulous ...

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Property Type

Longboat Key House

"Paradise"

Wonderful location in quiet neighbor. Walking distance beach and fishing pier. We enjoyed our stay!

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3 BR | 3 BA | Sleeps 8 | Quick View

$489

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

We have a private laneway to our own piece of beautiful sugar sand, longboat key beach. We adjoin 35 acres of park and walk trails and bay lookouts nearby. EASY ACCESS VIA a new, fully enclosed ELEVATOR, beside the GARAGE TO ALL THE LIVING AREAS! Over an acre of lawns joining to 35 acres of park ...

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Property Type

Longboat Key House

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3 BR | 2 BA | Sleeps 6 | Quick View

4

Distance to beach: 200 yards to Private Deeded Beach Access

$231

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

*** CONTACT OWNER FOR: - Discount for off season months July-October 2024 & & Discount for multi months rentals. ***A lovely pet and family friendly private home, located on a private deep water canal with direct access to Sarasota Bay and only a short 3 minutes walk (200 meters) away from ...

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Property Type

Longboat Key House

"Great house on LBK"

I have been coming to LBK for over 20 years. This was the best month I’ve spent on the island. The canal house is in a great location mid island with a short stroll to the beach. A variety of restaurants ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Nestled in a serene enclave, this charming one-bedroom cottage is the perfect island oasis. Combining timeless elegance with modern amenities, it features high vaulted ceilings, a contemporary kitchen, & cutting-edge conveniences including high-speed internet, a reverse osmosis water system, & ...

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Property Type

Longboat Key Cottage

"Cozy Coastal Cottage with EVERYTHING you need"

We had an unforgettable time in Longboat Key! The cottage we stayed in was perfect for what we were looking for. It’s located directly in between the bay and the gulf where we could easily walk from ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

Newly renovated 2 bedroom, 2 bath condo. Open kitchen, spacious living room and an integrated dining room. Bonus room which can serve as an office or extra sleeping quarter. Master bedroom features a private balcony to enjoy the ocean and spectacular sunsets. Laundry room with full size washer and dryer. ...

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Property Type

Longboat Key Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Rentals by owner

About this property

Newly remodeled charming 2 bed/ 1 bath beach condo located 5 min walk from beach, restaurants, groceries and more. Perfect place for a relaxing beach getaway!Nestled in a quiet residential complex and centrally located in Longboat key, condo features a fully equipped renewed kitchen with upgraded ...

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Property Type

Longboat Key Villa

"Little bit of paradise"

This is a darling condo, that looks exactly as it is pictured, with all the needed items for cooking and beaching and enjoying a a very relaxing vacation. August is not the best month in Florida but the ...

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1 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 50 yards to Our own private beach!

$306

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Relax in this privately owned, Old Florida Charm, “coastal themed” ground floor condo located on the Southern Gulf side of Florida. The condo offers views of the Sarasota Bay, a community heated pool, hot tub, boat dock, and a three minute walk to the private beach with turquoise waters on ...

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Property Type

Longboat Key Condo

"Fantastic rental"

Our stay at the Beach Castle was beyond what we had expected. Everything was freshly remodeled and clean. It included everything we needed for a great stay. You can’t beat the close distance to the beach. ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

About this property

SCHILLER - 2 Bedrooms, 2.0 Baths (Sleeps 4)Minimum 1 month lease. Please see COVID 19 AND STANDARD CANCELLATION POLICY BELOW - it is different from VRBO policy options as are payment options. Arrivals prior to 90 days are to be paid in fullCharming, waterfront Longboat Key surprise! This 2 bedroom ...

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Property Type

Longboat Key House

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1 BR | 1 BA | Sleeps 6 | Quick View

10
last minute deal
LAST MINUTE DEAL 4/10 - 4/24: Beachfront. No street crossing. Incredible Panoramic Gulf View. Have two more condos, same resort.

$275

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

GULF FRONT - ON THE SAND. SPECTACULAR GULF VIEWS AND SUNSET VISTAS.RATES ARE SUBJECT TO CHANGE WITHOUT UPDATING ON THIS PLATFORM. CAN BE LOWER OR HIGHER. PLEASE REQUEST. AVAILABLITY ON CALENDAR MIGHT NOT BE SYNCRONIZED. PLEASE SEND INQUIRY.Also I have garden view one-bedroom #64 and Studio #63 ...

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Property Type

Longboat Key Condo

"Wonderful!! We’ll be back!"

Our unit was equipped with everything we needed! Liked the full kitchen as we’d stay home some nights and have dinner on the balcony as we watched the beautiful sunsets. Very clean and comfortable beds. ...

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DEAL

$177

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Newly decorated and all new furnishings, beautiful unit, with stunning, really stunning views from every room. Wake up and watch the pelicans soar by and fish breaking water. Private, beautiful sandy beach with bathrooms, showers and tables. Kayak launch, clubhouse, two gorgeous pools, one right on the ...

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Property Type

Longboat Key Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

We have one more Mexican Gulf View unit 403 and garden one-bedroom #64 and Studio #63 units in this resort. Units 64 and 63 can be rented as 2-bedroom apartments.Welcome to Paradise! Unit 301 with 180 degrees unobstructed Mexican Gulf View. See my site for more info: LongboatKeyParadise The unit ...

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Property Type

Longboat Key Apartment

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Discover a unique, remodeled 1920s bungalow near Whitney Beach and the bay, offering an open layout with high ceilings and modern appliances. This home features a heated pool, hot tub, and lush, private landscaping. Originally a post office, it has historical charm with a fully fenced yard, boat parking. ...

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Property Type

Longboat Key House

"Beautiful accommodations"

After my first great experience at the landlord’s other property, I booked this one. Again, the landlord was fabulous and met all our needs. The furnishings were beautiful and very clean. The beds are ...

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$237

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Pool

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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Property Type

Longboat Key Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

About this property

This 7th floor Islander Club condo was completely rebuilt in 2016 by the project of renowned Boston designer. Modern kitchen with stainless steel brand new appliances opens to spacious living room/dining area with oversized sofa and 55-inch HDTV. Master bedroom with king size bed offers beautiful view ...

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Property Type

Longboat Key Apartment

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3 BR | 3 BA | Sleeps 8 | Quick View

$372

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

New construction 3 Br/3 bath house perfectly located on a quiet street just steps from the beach and the bay. Amenities include: pool with sun deck, poolside outdoor covered sitting area and natural gas grill, large screened in lanai, garage, elevator, 2 en suites, fenced back yard, washer/dryer, fully ...

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Property Type

Longboat Key House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Rentals by owner

About this property

Our canal front condo is avaialble for rent December 2024 - March 2025. Cedars East (0.6 mile walk) offers monthly memberships for tennis/pool/fitness center. The kitchen and bathrooms have been completely remodeled this year. Appliances, cabinets, sectional sofa with sleeper and Roku TV are all new. ...

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Property Type

Longboat Key Townhome

"Highly recommend!!"

We just spent 2 months at Tim’s condo and can’t speak highly enough about it! The location is perfect, mid island, walk to beach, on the canal which is just beautiful!! It’s great to have 2 floors ...

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1 BR | 1 BA | Sleeps 4 | Quick View

2

Distance to beach: 0.1 miles to Private beach

$200

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

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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Property Type

Longboat Key Condo

"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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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool

About this property

**New Vacation Rental!** Welcome to your amazing beachfront Longboat Key at Sunset Beach vacation. Sunset Beach is a 3 building complex located directly on Gulf of Mexico with it's powdery sandy beach and perfect sunset views. Guests will find a large gulf front pool, spa, community room for social ...

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Property Type

Longboat Key Condo

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2 BR | 2 BA | Sleeps 4 | Quick View

$234

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool

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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Property Type

Longboat Key Condo

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1 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 500 yards to Whitney Beach

$156

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

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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Property Type

Longboat Key House

"Location"

What a location! Walk to beach and local restaurants. Beautiful little cottage! Plan to return in 2024. Love that it pet friendly.

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$219

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Rentals by owner

About this property

***CANAL VIEW HOME/WALK TO THE BEACH/NEWLY FURNISHED***Dreamed of living on an island? Look no further! Nice and quiet residential street in beautiful Longboat Key. This 2 bedroom, 1.5 bathroom sits on a water canal. Newly furnished with a farmhouse coastal decor offering two bedrooms on the second ...

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Property Type

Longboat Key Condo

"Six Weeks In Paradise"

We spent the holidays and January in this wonderful and well-appointed condo on LBK. Our daughter from St. Pete joined us for Christmas and a few other weekends. We couldn’t have been more comfortable. ...

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1 BR | 1 BA | Sleeps 4 | Quick View

$199

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

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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Property Type

Longboat Key Condo

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

WALK 0.3 mi to Whitney Beach! Charmingly Renovated cottage nestled away on the back corner of large gated lot. Perfect for two lovebirds, & also sleeps two separately w/queen tempurpedic sofa (no mattress bars) & daybed for a friend! Every window is fully covered so you may enjoy sleeping! Pin-drop ...

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Property Type

Longboat Key Cottage

"Best Ideal Situation I could Have Hoped For"

I traveled cross country from Oregon and had no idea anything about Florida! I booked this place randomly without ever having been to this area or the East coast. Thank god it turned out the way it did! ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Live life on the beach---Private parking included!Beachplace is one of Longboat Key's premier vacation rental locations on the island!With amazing direct Gulf-front views, this sophisticated and chic 4th floor condo with balcony has it all!This condo has modern updates throughout including ...

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Property Type

Longboat Key Condo

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1 BR | 1 BA | Sleeps 4 | Quick View

1

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

$133

avg/night

View Details

Key Amenities

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

About this property

Magnificent Condo directly on the Gulf of Mexico! Right on the beach! Every sunset is unique and beautiful!No need to fight any traffic or an overcrowded public beach. Beautiful view of the turquoise waters of the Gulf of Mexico. It is very private and peaceful. The ideal spot for a relaxing getaway ...

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Property Type

Longboat Key Condo

"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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$216

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Pool

About this property

60 Day Minimum Required. Beachfront Condo offers great views to the gulf from the 7th floor living room and bedroom. This unit is freshly remodeled. Enjoy the oversized balcony with two ceiling fans as you relax and watch the full beauty of nature.Association requires a minimum of 60 days. Direct ...

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Property Type

Longboat Key Condo

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Welcome to Bayport Beach and Tennis Club!Available for minimum one month rentals beginning JUNE 1, 2024.DISCOUNT GIVEN FOR 6+ MONTH RENTAL. 6 MONTH RENTAL IS NOT SUBJECT TO STATE/COUNTY TAX.Bayport Beach and Tennis Club is a beach to bay tropical oasis situated on 27 lushly landscaped acres ...

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Property Type

Longboat Key Condo

"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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Key Amenities

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

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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Property Type

Longboat Key Condo

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Key Amenities

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

About this property

You will be captivated by the majestic ocean views the moment you step foot into the unit. Step out of this 1st floor unit and in just over 100 steps you be dipping your toes in the water. Whitney beach is pristine and private with wonderful people who own and rent. Enjoy the beachside pool and 4 ...

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Property Type

Longboat Key Condo

"Great place"

Wonderful. Great location. Great facilities. Well equipped. Wonderful for families. Beach is gorgeous.

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2 BR | 2 BA | Sleeps 4 | Quick View

$350

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

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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Property Type

Longboat Key Condo

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2 BR | 1.5 BA | Sleeps 4 | Quick View

Distance to beach: 0.3 miles to Gulf Of Mexico

$112

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly

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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Property Type

Longboat Key Townhome

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1 BR | 1 BA | Sleeps 4 | Quick View

4

$130

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

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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Property Type

Longboat Key Condo

"Excellent Stay"

We had such a great time in this condo. It was convenient to pool and beach. Also some great restaurants close by. We enjoyed the manatees from the pool. We look forward to returning. What a great ...

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Longboat Key Vacation Rentals

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°

Escape to the Stunning Southwest Florida Shores with Longboat Key Condos for Rent


If you’re looking for some rest and relaxation after a tough few months at work or a long school year, Longboat Key vacation rentals are where it's at! As soon as your feet hit the sand and you feel the sun on your skin, the stress will begin to melt away.

Southwest Florida is home to so many unique and scenic beach towns. Some of them are small and sleepy, others are lively and energetic, and many more have an inviting mix of both. Are you unsure of where along the Florida coast to book your next vacation? As you deliberate, make sure to keep Longboat Key on your radar.

Longboat Key is a small, tight-knit community located on one of western Florida’s many barrier islands. To the east of Longboat Key is Sarasota Bay, and to the west is the expansive Gulf of Mexico. Thus, no matter where you are on Longboat Key, you’re sure to have a gorgeous view of the water and a short walk to the beach.

As you’re planning your beachside vacation in Longboat Key, you might be wondering whether to book a hotel for your lodging or choose something a bit more special. At FloridaRentals, we know firsthand how much more memorable staying in a rental home can make any vacation when compared to overbooked and noisy hotels.

When you book a Longboat Key rental for your trip, you’ll be able to rest easy knowing that your lodging is fully private and you’re guaranteed some much-needed peace and quiet. What’s more: our listings include homes of all sizes and locations, so finding the right rental home for you and your family is quick and easy.

Booking only takes a few minutes. After that, you’ll be one step closer to an incredible vacation in Longboat Key.

Best Restaurants Near Longboat Key Vacation Rentals


Love an ocean view when you’re dining? In Longboat Key, the closeness of the Gulf of Mexico and Sarasota Bay on either side means that nearly every restaurant in town has a view of the water.

Perhaps you’re looking for an upscale romantic establishment for date night or a casual spot for a quick lunch or dinner with family. No matter what sort of cuisine you desire, Longboat Key’s many eateries are sure to satisfy.

If you’re on a romantic getaway to Longboat Key with your significant other, you should consider making reservations at Euphemia Haye Restaurant. You’re guaranteed to have a memorable date night at this fine dining establishment.

Housed in one of the Key’s historic beachside cottages, the menu features a varied list of global dishes and plenty of fine wines. And once you’ve finished your dinner, you can head upstairs to The Haye Loft to enjoy a nightcap and a decadent dessert crafted by the incredible in-house chefs.

It wouldn’t be a proper trip to the Florida coast without some authentic and delicious seafood. The Lazy Lobster is the perfect spot to get just that, and it is only a few steps away from the shores of Sarasota Bay.

Each dish at The Lazy Lobster is crafted with only the freshest seafood and other locally sourced ingredients. Add in a varied list of unique cocktails and craft beers and you’ve got yourself a lively and delicious lunch or dinner.

If you’re ever in need of some coffee to fuel your long day of outdoor exploration, Turtle Coffee Bar is a local favorite for coffee and tea drinks of all kinds. Only adding to the magic is the fact that you can walk straight from the establishment to the beach in minutes by crossing Gulf of Mexico Drive.

Traveling to Longboat Key


If you’re flying into Florida to visit Longboat Key, the most convenient airport to use is Sarasota Bradenton International Airport. From there, it is recommended that you rent a car rather than use public transit so that you can visit the many destinations available and take your time along your route. A rental car also allows you to travel up and down Longboat Key with ease.

The drive from Sarasota Bradenton International Airport to Longboat Key is roughly 14 miles, which usually takes fewer than 30 minutes to complete. If you’re traveling into town from elsewhere in Florida, you’ll likely use routes like U.S. Highway 301 (north to south) and State Roads 72 or 70 (east to west) to reach Longboat Key.

Longboat Key Activities for Every Lifestyle


Though Longboat Key has a sleepy vibe perfect for slow-paced living and plenty of relaxation, there is no shortage of activities to explore. Whether you’re looking for an adventure or some calming pastimes to enjoy on your vacation, Longboat Key has it all.

For some fun in the sun, Bayfront Park is a popular destination. This public park is located right on the shore of Sarasota Bay, providing stunning ocean views as well as direct beach access.

Some other amenities that visitors can use at Bayfront Park include plenty of sports courts and open fields, a large play structure for kids, and picnic tables perfect for a casual lunch by the water.

Just south of Longboat Key on Lido Shores is the Mote Marine Laboratory & Aquarium. Here, visitors can learn all about the local marine life surrounding Longboat Key and beyond and gain a new appreciation for native wildlife. There are also plenty of hands-on exhibits and activities for kids and visitors of all ages to enjoy.

When you visit Longboat Key, you can explore many different beaches, all of which feature glistening white sand and warm turquoise waters. However, Little Beach is one of the town’s most popular lookouts and beaches. Protected by pieces of land, the waters at Little Beach are very calm and inviting for visitors of all ages.

Your perfect vacation in Longboat Key is waiting for you. Get started by perusing all of our rental homes on FloridaRentals today.


FAQ

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

There are 56 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 $92 per night with an average price per night of $232.

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 10 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 18 oceanfront rentals in Longboat Key available on FloridaRentals.com. Use our filters to search and book yours today!