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Longboat Key Vacation Rentals

(80 rentals)
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

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

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$225
avg per night
Longboat Key Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

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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$220
avg per night
Longboat Key Condo
Sleeps 4, 0 bedrooms, 1 bathroom

Key Amenities

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

About this property

This sublime oceanfront studio (We own two more in the same building, plus one down the road - email for more info!) is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located on the second floor, overlooking the heated pool and ocean,...

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$292
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

**Welcome to our beachfront Longboat Key condo!If you’re looking for a special two-bedroom, two-bathroom retreat with beautiful waterfront gulf and sunset views, white sandy beach, palm trees and resort style community pool, this may be the place for you! We invite you to look at our photos...

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$265
avg per night
Longboat Key Apartment
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

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

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$212
avg per night

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Longboat Key Villa
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

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

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Longboat Key Condo
Sleeps 6, 3 bedrooms, 2.5 bathrooms

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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$493
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Imagine waking up to breathtaking views of the Gulf and the Sarasota skyline - every single room boasts this incredible panorama! This luxurious condo offers a king-size master bedroom with stunning bay and skyline views, and a comfortable second bedroom with a queen bed.The open-concept kitchen,...

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$465
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

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

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$333
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Beach and Tennis resort style facility with an adult pool and a family pool. This is an excellent top floor modern feeling condo in a beautiful setting.This unit is two levels with an entrance on both floors. Ground Floor Access and building elevator to 2nd floor access. Also has an internal stairway. Main...

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$131
avg per night
Longboat Key Townhome
Sleeps 4, 2 bedrooms, 1.5 bathrooms
1 review

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 living area, kitchen and half bathroom are downstaris. Upstairs is the master bedroom with king bed and guest bedroom with 2 twins. Beach chairs, umbrella, wagon, treager grill all included. 60 day minimum during...

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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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$136
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Penthouse unit on the top floor of building 3 at Beachplace. Top floor units enjoy a double balcony with access from the living room and Master bedroom. Amazing views of Beach, Pool, Pond and downtown Sarasota.This is a very popular floorplan at Beachplace. You have spectacular views of the beach and...

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$230
avg per night
Longboat Key House
Sleeps 6, 2 bedrooms, 2 bathrooms

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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$211
avg per night
Longboat Key House
Sleeps 4, 1 bedroom, 1 bathroom
2 reviews

Distance to beach: 500 yards to Whitney Beach

Key Amenities

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

About this property

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

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Featured review

"cozy cottage"

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

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$142
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

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

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Featured review

"Home Away From Home"

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

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$156
avg per night
Longboat Key House
Sleeps 5, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • WiFi

About this property

Looking for a month vacation in warm sunny Florida in a home where you walk directly out onto the deck directly onto the beach? Stay in this 3 bedroom (2 king beds/1 queen), 2 bath condo in Salty Acres with 2 covered parking spaces. It is on the Gulf Side with amazing views. Condo is beautiful and recently...

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$470
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Beautiful beachview 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 system...

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$188
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Come enjoy the Beach - Private parking included. Beautiful beachview unit on the 3rd floor with a Beach and Lake view. Beachplace Building 3 unit 304. Beautifully appointed 2 bedroom, 2 bath unit with many modern upgrades. A sought after unit with shiplap wall in living room and master bedroom, great...

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$146
avg per night
Longboat Key Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Private pool
  • WiFi

About this property

Beach views from kitchen through living room and master bedroom, 3 bedroom, 2 bathroom condo on beautiful Longboat Key. Second floor unit in 3 floor complex, easy access within complex and beach, walking distance to great dining. Complex complete with pool, beach chairs, barbeque grill and tennis / pickleball...

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$265
avg per night
Longboat Key House
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

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

About this property

Discover this newly rebuilt hurricane-resistant home at 701 Broadway St, Longboat Key, FL 34228 . Perfect for couples or small families seeking a serene vibe.Property Features2 bedrooms, 2 bathrooms. 1 bedroom guest house above garage, just one flight up. Fully gated backyard with swimming...

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Featured review

"Super Cute Long Boat Key Cottage!"

Absolutely loved our stay at this Longboat Key cottage! It’s perfect if you work from home — fast, reliable Wi-Fi and a dreamy window seat made it easy (and enjoyable) to stay productive. The location...

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Longboat Key Condo
Sleeps 8, 3 bedrooms, 2 bathrooms

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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$252
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

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

About this property

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

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Featured review

"Amazing Place"

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

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$167
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

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

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$199
avg per night
Longboat Key Condo
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

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

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$259
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

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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$285
avg per night
Longboat Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
1 review

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

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! Located in very well-maintained and updated Longboat Harbor Towers.The barrier isle Longboat Key is a quiet, non-touristy location voted one of North America's top islands by Conde Nast...

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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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$133
avg per night
Longboat Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

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

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$311
avg per night
Longboat Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
5 reviews

Key Amenities

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

About this property

This ground floor waterfront condo located in a gated community of Longboat Harbour and is one of Longboat Keys most desirable social communities. This one bedroom, one bathroom, first floor unit has walkout access to Sarasota Bay where you often see dolphins and manatees from your lanai. This unit is...

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Featured review

"Grreat stay atLong Boat Harbour"

What a beautiful development Long Boat Harbour is! My wife and I stayed in unit E104 for 2 months. Haley is a very gracious host to allow us to stay in her home. We had such a wonderful time, we did...

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New
Longboat Key Villa
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

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

About this property

Bright, fully updated and exceptionally well appointed villa with a large private lanai, pool and hot tub awaits you, your pet* and your guests! King, queen and twin bedrooms sleep six. Linens, and a wide selection of kitchen equipment and entertainment supplies are included. Attached garage houses...

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$312
avg per night
New
Longboat Key Villa
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Welcome to Sapphire Palms on the Canal, a beautifully renovated waterfront villa on Longboat Key designed in crisp whites and calming sapphire blues.Natural light fills the open living space, where sliding glass doors frame peaceful canal views and swaying palms. The interior blends clean coastal...

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Full map
Map

Longboat Key Weather

 | 

7222°  5111°
JANUARY
Ocean 6418°
7423°  5312°
FEBRUARY
Ocean 6518°
7725°  5714°
MARCH
Ocean 6719°
8228°  6016°
APRIL
Ocean 7323°
8731°  6518°
MAY
Ocean 7826°
9032°  7122°
JUNE
Ocean 8228°
9133°  7323°
JULY
Ocean 8530°
9133°  7323°
AUGUST
Ocean 8730°
9032°  7222°
SEPTEMBER
Ocean 8529°
8529°  6518°
OCTOBER
Ocean 8228°
8027°  5915°
NOVEMBER
Ocean 7524°
7423°  5312°
DECEMBER
Ocean 6921°

FAQ

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

There are 80 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 $53 per night with an average price per night of $216.

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 9 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 19 oceanfront rentals in Longboat Key available on FloridaRentals.com. Use our filters to search and book yours today!