Luxury Vacation Rentals in Longboat Key

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

$590

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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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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2 BR | 2 BA | Sleeps 4 | Quick View

$491

avg/night

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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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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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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
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

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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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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3 BR | 3 BA | Sleeps 8 | Quick View

$395

avg/night

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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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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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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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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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$319

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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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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1 BR | 1 BA | Sleeps 4 | Quick View

1

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

$315

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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1 BR | 1 BA | Sleeps 6 | Quick View

$306

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

$303

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 Condo

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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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2 BR | 2 BA | Sleeps 4 | Quick View

$300

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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Key Amenities

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

About this property

New new new! More photos coming. Charmingly remodeled bungalow blocks from Whitney Beach & a block from bay. Open layout w/high ceilings, stainless appliances w/ gas stove. Heated swimming pool & hot tub. Relax & listen to breezy palms smack up against each other in this gorgeous landscaping! ...

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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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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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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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1 BR | 1 BA | Sleeps 6 | Quick View

10
last minute deal
LAST MINUTE DEAL 3/26 - 4/9: 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

2 BR | 2 BA | Sleeps 4 | Quick View

$256

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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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Situated on Longboat Key, this secured and gated 1st floor condo boasts water views throughout, 2 spacious lanai, each with own walk-down steps to water and pool, across the street to private beach with cabanas, grills, restrooms, etc. Great room, fully equipped kitchen (including microwave, dishwasher, ...

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

$247

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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Key Amenities

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

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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Property Type

Longboat Key Apartment

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3 BR | 2 BA | Sleeps 6 | Quick View

2
owner special
Owner special: January 2025 is available, please contact owners for special discounts.

Distance to beach: 200 yards to Private Deeded Beach Access

$240

avg/night

View Details

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 canal home that is well stocked and as a bonus is pet friendly"

We thoroughly enjoyed or stay. It is in a great location on a quiet street with a very short stroll to the beach. The house is clean, comfortable, and well stocked with all the essential items you need ...

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Key Amenities

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

About this property

Beautiful beachfront unit on the 3rd floor with lake view and Gulf views. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. Very popular unit. This unit has large beds in both bedrooms. Great for 2 couples. Kitchen recently remodeled and all new windows and doors.The online ...

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Property Type

Longboat Key Condo

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Inquire for rates

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Key Amenities

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

About this property

2 bedroom/ 2 bath This newly renovated condo is the closest unit to the beach. It is located on the 2nd floor with elevator access. It has amazing ocean views from the living area, master bedroom, and covered patio. We often see dolphins from the patio. The master bedroom is located upstairs in the ...

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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

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
  • 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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$223

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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2 BR | 2 BA | Sleeps 5 | Quick View

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

$214

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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$213

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

$212

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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2 BR | 2 BA | Sleeps 4 | Quick View

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

$209

avg/night

View Details

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
  • 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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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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1 BR | 1 BA | Sleeps 4 | Quick View

1

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

"Would absolutely recommend!"

This condo is wonderful. The condo itself is very spacious for a 1 bedroom. And it's decorated beautifully. Modern and clean, clean, clean! Also, it's well stocked to get you started when you arrive (paper ...

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Longboat Key Vacation Rentals