Monthly Rentals in Longboat Key

(46 rentals)
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Longboat Key Townhome
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1.5 bathrooms
1 review

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Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Cedars East (0.6 mile walk) offers monthly memberships for tennis/pool/fitness center. The kitchen and bathrooms were remodeled in 2023. Appliances, cabinets, sectional sofa with sleeper and Roku TV's are all new (2023). The living area, kitchen and half bathroom are downstaris. Upstairs is the ...

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Property Type

Longboat Key Townhome

Featured review

"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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Longboat Key Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$449

avg/night

$449
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Longboat Key Condo

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Longboat Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$322

avg/night

$322
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

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

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Property Type

Longboat Key Condo

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Longboat Key Villa
2 BR | 1 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 1 bathroom
5 reviews

$197

avg/night

$197
avg per night
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Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

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

Featured review

"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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Longboat Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$461

avg/night

$461
avg per night
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Key Amenities

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

About this property

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

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Property Type

Longboat Key Condo

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Longboat Key Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$388

avg/night

$388
avg per night
View Details

Key Amenities

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

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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Longboat Key Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$442

avg/night

$442
avg per night
View Details

Key Amenities

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

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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Longboat Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
4 reviews

Distance to beach: 200 yards to Private Deeded Beach Access

$292

avg/night

$292
avg per night
View Details

Key Amenities

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

About this property

*** CONTACT OWNER FOR: - rates are now reduced for off season months August -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) ...

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Property Type

Longboat Key House

Featured review

"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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Longboat Key Condo | On the beach
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

$265

avg/night

$265
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

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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Longboat Key Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$649

avg/night

$649
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Longboat Key Condo

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Longboat Key Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$404

avg/night

$404
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Longboat Key Condo

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Longboat Key Condo | On the beach
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$394

avg/night

$394
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Longboat Key Condo

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Longboat Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$402

avg/night

$402
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Longboat Key Condo

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Longboat Key Villa
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
3 reviews

Distance to beach: 150 yards to Gulf Of Mexico

$143

avg/night

$143
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Ground Floor Villa Condo- 1 Bedroom- Sleeps 2 - walk 4 min to beachBeautiful 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 and a 3 minute walk to the 32 acre Joan Durante Park FULL of fabulous tropical ...

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Property Type

Longboat Key Villa

Featured review

"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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Longboat Key Villa
2 BR | 1 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 1 bathroom
2 reviews

Distance to beach: 500 yards to Gulf of Mexico

$194

avg/night

$194
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

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

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Property Type

Longboat Key Villa

Featured review

"Nice trip"

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

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Longboat Key Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

$261

avg/night

$261
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Longboat Key Condo

Featured review

"Amazing Place"

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

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Longboat Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

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

$232

avg/night

$232
avg per night
View Details

Key Amenities

  • Air conditioning

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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Longboat Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
8 reviews

Distance to beach: 0.2 miles to Whitney Beach

$232

avg/night

$232
avg per night
View Details

Key Amenities

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

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

Featured review

"Sunny Beaches"

Quiet place, close to beaches and restaurants. …..

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Longboat Key Condo | On the beach
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$277

avg/night

$277
avg per night
View Details

Key Amenities

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

About this property

Newly renovated 3 bedroom, 2 bath condo. Open kitchen, spacious living room and an integrated dining room. Office den, ideal for working or relaxing. Master bedroom features a private balcony to enjoy the ocean and spectacular sunsets. Laundry room with full size washer and dryer. Two oceanfront balconies ...

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Property Type

Longboat Key Condo

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Longboat Key House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms

$526

avg/night

$526
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

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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Longboat Key Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$313

avg/night

$313
avg per night
View Details

Key Amenities

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

About this property

This Spectacular beachfront condo on Longboat Key is a 2 bedroom, 2 bath unit on the 6th floor of the Arbomar Condominium. An open concept floor plan includes a galley kitchen with SubZero appliances, dining room, and living room that exits to a spacious lanai overlooking the Gulf of Mexico. Take in ...

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Property Type

Longboat Key Condo

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Longboat Key Cottage
1 BR | 1 BA | Sleeps 1 | Quick View
Sleeps 1, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

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

Featured review

"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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Longboat Key House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$566

avg/night

$566
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool

About this property

Charming, waterfront Longboat Key surprise! This 2 bedroom 2 bath house is sure to impress. Total renovation will bring you delight upon entering. Fun, chic, beach inspired decorating with the fun, splattered octopus theme to bring a smile to anyone. Plenty of dishware, gadgets, cooking equipment for ...

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Property Type

Longboat Key House

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Longboat Key Apartment
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

Distance to beach: 500 feet to Private access

$179

avg/night

$179
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Private BEACH Access! [2 Units Available Turquoise Gem and Turtle Walk CONTACT ME Turtle Walk MAY BE AVAILABLE] *Designer Renovation* Single level, 4 minute Walk to Bright White Quartz Sand, Welcome to UPGRADED BEACH PARADISE Featuring - NEW Full Stainless-Steel Kitchen, NEW Cabinets and Granite Countertops. ...

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Property Type

Longboat Key Apartment

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Longboat Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

$200

avg/night

$200
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner

About this property

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

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Property Type

Longboat Key Condo

Featured review

"HBC"

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

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Longboat Key Cottage
Studio | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 0 bedrooms, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Last minute fall getaway special!Just a short 0.3-mile stroll to Whitney Beach! This charmingly renovated cottage is tucked away in the back corner of a spacious, gated lot. Ideal for a romantic getaway for two: queen Tempurpedic sofa (no uncomfortable mattress bars!) and a cozy daybed to also accommodate ...

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Property Type

Longboat Key Cottage

Featured review

"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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Longboat Key Condo
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1.5 bathrooms
2 reviews

$238

avg/night

$238
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

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

Featured review

"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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Longboat Key House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms

Distance to beach: 0.5 miles to Longboat

$1155

avg/night

$1,155
avg per night
View Details

Key Amenities

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

About this property

Imagine waking up to dolphins playing just beyond your window. This exquisitely renovated Longboat Key luxury waterfront home offers breathtaking "Big Bayfront" views and unparalleled access to the Gulf of Mexico. Boater's Dream: • Direct access to the Gulf for fishing or cruising • Private ...

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Property Type

Longboat Key House

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Longboat Key Condo | On the beach
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
1 review

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

$267

avg/night

$267
avg per night
View Details

Key Amenities

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

About this property

Magnificent Condo directly on the Gulf of Mexico! Right on the beach! Every sunset is unique and beautiful!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

Featured review

"Happy in Longboat Key"

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

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Longboat Key House
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Distance to beach: 500 yards to Whitney Beach

$177

avg/night

$177
avg per night
View Details

Key Amenities

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

About this property

Looking to step back in time to enjoy the "Old Florida Lifestyle''? Located in the quaint historic village of Longbeach on the northernmost end, is a lovely cottage steps from Sarasota Bay and 2 1/2 blocks from Gulf of Mexico with its own relaxing courtyard surrounded by beautiful lush ...

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Property Type

Longboat Key House

Featured review

"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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Longboat Key House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$268

avg/night

$268
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Longboat Key House

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Longboat Key Condo
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom

$118

avg/night

$118
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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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Longboat Key House
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
1 review

$192

avg/night

$192
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

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

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Property Type

Longboat Key House

Featured review

"Amazing Location"

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

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Longboat Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

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

Featured review

"Mini Paradise on LBK"

We stayed at this gem for 6 weeks while renovating our home and it was fabulous!!! The location is amazing, literally 3 blocks from Whitney Beach, fabulous dining options literally across the street (Mar ...

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Longboat Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

$298

avg/night

$298
avg per night
View Details

Key Amenities

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

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

Featured review

"Great place"

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

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Longboat Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$350

avg/night

$350
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

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

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Property Type

Longboat Key Condo

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Longboat Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

$266

avg/night

$266
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to Bayport Beach and Tennis Club!Available for minimum one month rentals beginning JUNE 6, 2024.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 ...

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Property Type

Longboat Key Condo

Featured review

"Home Away From Home"

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

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Longboat Key Townhome
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1.5 bathrooms

Distance to beach: 0.3 miles to Gulf Of Mexico

$189

avg/night

$189
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

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

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Property Type

Longboat Key Townhome

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Longboat Key Apartment | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$283

avg/night

$283
avg per night
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Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

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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Longboat Key Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
2 reviews

Distance to beach: 0.1 miles to Private beach

$234

avg/night

$234
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

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

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Property Type

Longboat Key Condo

Featured review

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

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

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Longboat Key Condo | On the beach
3 BR | 2.5 BA | Sleeps 5 | Quick View
Sleeps 5, 3 bedrooms, 2.5 bathrooms

$450

avg/night

$450
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Longboat Key Condo

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Longboat Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$308

avg/night

$308
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool

About this property

Welcome to your amazing beachfront vacation. The apartment has a fully appointed updated kitchen with plenty of storage and counter space. Renovations include freshly painted in 2023, new high impact windows and sliders, plantation shutters, tiled flooring, closet organizers, new living and dining room ...

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Property Type

Longboat Key Condo

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Longboat Key Apartment
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$275

avg/night

$275
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

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

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Property Type

Longboat Key Apartment

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Longboat Key Apartment
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$167

avg/night

$167
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Available now! Beautiful. Newly remodeled condo with spectacular views of Sarasota Bay and private access to the white sand beaches across the street (few steps away). Second floor, end unit located in Pelican Harbour Condominium and Beach Club in Longboat Key. An extensive remodel was just completed ...

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Property Type

Longboat Key Apartment

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Longboat Key Mobile home
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

$100

avg/night

$100
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Great beach house on Longboat Key. Over 55 community two person occupancy limit with allowances for guests, no pets, parking for one vehicle.Next availability. July, August, September 2025, January 2026Tropical paradise awaits you on Longboat Key. The folks at Twin Shores call this The Green ...

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Property Type

Longboat Key Mobile Home

Featured review

"Slice of Beach Paradise - Immaculate and beautifully restored 1950's trailer"

I rented this adorable beach tiny house for 2 years during the season. Dec 2022-Apr 2023 & Nov 2023-Apr 2024. I cannot say enough about the house, location, community and the landlord. 2 Bed, 2 BA (1 ...

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Longboat Key Condo
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

$300

avg/night

$300
avg per night
View Details

Key Amenities

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

About this property

Situated on Longboat Key, this secured and gated 1st floor NEWLY RENOVATED 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, ...

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Property Type

Longboat Key Condo

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