Longboat Key Rentals by Owner

(33 rentals)
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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Available May 2023 - September 2023 only. Luxury, bayfront condo. Newly remodeled condo with spectacular views of Sarasota Bay and private access to the white sand beaches across the street. Second floor, end unit located in Pelican Harbour Condominium and Beach Club in Longboat Key. An extensive remodel ...

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Property Type

Longboat Key Apartment

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2 BR | 2 BA | Sleeps 4 | Quick View

LAST MINUTE DEAL 6/16 - 7/15: Summer special $3500.00 for a 30 day rental, available 6/16

$128

avg/night

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Key Amenities

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

About this property

This gorgeous 2 Bedroom / 2 Bath spacious, bright condo located in the beautifully maintained association of Whitney Beach on Longboat Key. You can have it all- Gulf and Bay access! Natural light floods the open floor plan, which features a breakfast bar, dining area with bar area, living room and lanai ...

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Property Type

Longboat Key Condo

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DEAL

1 BR | 1 BA | Sleeps 4 | Quick View

1
Owner special: SUMMER VACATION ON THE BEACH! ENJOY LONGBOAT KEY with a 20% SAVINGS PRICE REDUCTION!

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

$180

avg/night

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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

Beautiful, peaceful one bedroom / one bath condo on Longboat Key. Amazing view and breeze from the lanai. Private friendly gated community with great amenities. Four pools, tennis court, BBQ girls, shuffleboard, work out facilities, game room. Private beach access across the street with private bathrooms ...

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Property Type

Longboat Key Condo

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Key Amenities

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

About this property

Welcome to the Pet Friendly Tropical Paradise House. Once you drop your suitcases, you’re a short 3-minute walk to sugar soft white sand on your own private beach.  Bring your favorite bottle of wine, while you admire the beautiful orange warm Florida sunset from your own gazebo (complete with ...

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Property Type

Longboat Key House

"Perfect Quiet Location"

Loved how close the beach was to the house, very quiet and relaxing neighborhood. House very spacious.

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4 BR | 2 BA | Sleeps 2 | Quick View

LAST MINUTE DEAL 5/24 - 7/5: Available now for that needed week or weekend getaway for 2. Enjoy the beach, or private pool.

$393

avg/night

View Details

Key Amenities

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

About this property

Enjoy this serene property and location...and while this home is spacious and just steps from the sandy white beach and the beautiful Gulf of Mexico waters on Longboat Key...it is being offered as a rental for 2 people to embrace their vacation time. This home and its large inviting pool area, with ...

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Property Type

Longboat Key House

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DEAL

1 BR | 1 BA | Sleeps 2 | Quick View

3

Distance to beach: 150 yards to Gulf Of Mexico

$136

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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$267

avg/night

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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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$140

avg/night

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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

"Best decision I ever made!"

My first trip to the Sarasota area but certainly not my last! I stayed in this condo for approximately 2 months and it was the best two months I've had in a very long time! The condo is clean, attractively ...

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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

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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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Key Amenities

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

About this property

Sprawling ranch pool house ( 3 bed, 2 bath, one car garage) in one of the best neighborhoods in Sarasota (please note, this house is in Granada Sarasota, NOT Longboat Key), 5 minutes from the gorgeous beaches of Siesta Key Beach and 7 minutes from downtown Sarasota as well as 5 minutes from the best ...

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Property Type

Longboat Key House

"Great tropical retreat"

Great location, beautiful neighborhood. The house is spacious, comfortable, kitchen has everything you need. The outdoor patio with a pergola and fan, surrounded and covered by a magnificent tropical jungle ...

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3 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 200 yards to Private Deeded Beach Access

$208

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 CURRENT AVAILABILITY ***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 the quiet white sand beach perfect for morning beach-combing and end of day amazing ...

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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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$249

avg/night

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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 2 | Quick View

1

Distance to beach: 50 feet to Beach Access Directly Across the Street

$125

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Come enjoy sunsets of the Gulf of Mexico's turquoise waters. Located directly across the street from one of the nicest secluded beach accesses in the area. This second floor unit is just steps across from a beautiful beach access on Longboat Key, Florida. Turnkey furnished 1 bedroom, 1 bathroom vacation ...

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Property Type

Longboat Key Condo

"Beautiful Unit and Amazing Location"

This is a beautiful unit, and such a peaceful, perfect location. Short walk to the beach and short walk to grocery store . Very private! Denise is an amazing host and very accommodating! I would highly ...

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2 BR | 1 BA | Sleeps 5 | Quick View

5

$200

avg/night

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Key Amenities

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

About this property

NEW LISTING! Newly remodeled charming 2 bed/ 1 bath condo 5 min walk from beach entrance and shops. Nestled in a quiet area, our place is perfect to relax and enjoy beach style leaving.Fully equipped kitchen with upgraded stainless steel appliances (dishwasher included) beautiful new quartz counter ...

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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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4 BR | 4 BA | Sleeps 8 | Quick View

1
Owner special: Summer Savings! Up to $1,000 off summer months. Inquire for dates and details.

$357

avg/night

View Details

Key Amenities

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

About this property

Welcome to Peacock Paradise, a tropical oasis nestled within the historic Longbeach Village at the north end of Longboat Key. Perfectly situated between gulf and bay, enjoy a quick walk to the beach, bay, boat launch, and several amazing restaurants like Shore, Mar Vista, Whitney’s, and more. Make ...

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Property Type

Longboat Key House

"Incredible Beach House Rental on Longboat Key"

My family rented this property from NYE till the week following of 2023 and it was truly an amazing experience from start to finish (it was my me, my husband and our toddler daughter + small dog). The host ...

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$196

avg/night

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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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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 stretch of ...

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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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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Enjoy being located in heart of LongBeach, a historical fishing village on Longboat.This is a compound that may be leased separately as a 3 bed/2 bath main house + two 1bed/1 bath guest cottages, all remodeled/newly furnished + smart TV's. High vaulted ceilings in cottages. Brand new & updated ...

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Property Type

Longboat Key Estate

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1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 500 yards to Whitney Beach

$153

avg/night

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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 tropical landscaping. ...

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Property Type

Longboat Key House

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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 recently 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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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 lanai ...

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Property Type

Longboat Key Condo

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Key Amenities

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

About this property

*****The home is rented January, February and March of 2023***** Our home has everything needed for a wonderful Florida vacation! Located in Country Club Shores on the southern end of Longboat Key the beach is just a quick stroll away. This 3 bedroom 2 bath canal home with updated kitchen & baths, ...

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Property Type

Longboat Key House

"Exceptional"

This home was absolutely beautiful. The decorations, cleanliness and amenities were above par. In the 8 years I have been coming to Longboat Key , this home was by far the best. I definitely will rent ...

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3 BR | 3 BA | Sleeps 8 | Quick View

$489

avg/night

View Details

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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2 BR | 2 BA | Sleeps 4 | Quick View

$200

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
  • 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

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Welcome to Bayport Beach and Tennis Club!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 and inviting atmosphere. Enjoy sunrises over the bay, sunsets on the ...

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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
  • 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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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

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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

3

$93

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

"Snowbird perfect"

This was a perfectly cozy and comfortable January retreat. The unit delivered on everything promised and the condo complex amenities could be among the best that LB Key has to offer. Truly great access ...

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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
  • 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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Longboat Key Vacation Rentals