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Longboat Key Vacation Rentals & Apartments - 17 Rentals Available

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17 Vacation rentals

1 / 28

Longboat Key Condo

  • 1
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

from $156 / night

(57)

1 / 13

Longboat Key House

  • 4
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
“Great family vacation in a spacious and clean home with kids in their own rooms, full kitchen and close to the beach and to restaurants and activities. The January weather was awesome, 75-80 each day without rain.Likely return next year.Resort has...”
- Review left on 01/22/2017

$200

Very Good (57 reviews)

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from $200 / night

(2)

1 / 20

Longboat Key Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“The Longboat Beach Club was a beautiful vacation location! The hotel room was the best I ever had. The beach was picture perfect, the food was excellent and the weather could not have been better. I thought I was vacationing in heaven! Thank you!...”
- Review left on 10/05/2015

$300

Very Good (2 reviews)

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from $300 / night

(15)

1 / 72

Longboat Key Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
“The two balconies and lanai overlooking the fabulous Gulf of Mexico provid a beautiful and ever-changing view of Nature's best work. Condo is large, clean and comfortably furnished with wifi and 3 TV's. Every convenience has been thought of, from...”
- Review left on 04/07/2015

$115

Excellent (15 reviews)

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from $115 / night

(1)

1 / 25

Longboat Key Apartment

  • 2
  • 4
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“The condo is much larger and much more upscale then the pictures actually show. The location on the resort site makes for an excellent vacation, no noise, close to pool and fitness Center. The direction left by the owner re everything was exact and...”
- Review left on 01/04/2015

$59

Excellent (1 reviews)

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from $59 / night

(1)

1 / 22

Longboat Key Condo

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“This was a family holiday including 2 grandchildren, who loved every minute of the holiday and did not want to leave. Lovely 3 bedrooms condo in garden grounds, which lead to the beach, family swimming pool and adult pool and spa. 8 tennis courts....”
- Review left on 01/26/2017

$215

Very Good (1 reviews)

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from $215 / night

(12)

1 / 13

Longboat Key Condo

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“Saubere, sehr gut ausgestattete und geschmackvoll eingerichtete Wohnung mit allem was man benötigt und noch vielem mehr. Im 2. Stock (= 3rd Floor in USA) gelegen, über eine Außentreppe direkt neben dem zur Wohnung gehörenden Parkplatz oder per...”
- Review left on 10/06/2016

$180

Very Good (12 reviews)

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from $180 / night

1 / 16

Longboat Key Condo

  • 3
  • 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

from $257 / night

(8)

1 / 24

Longboat Key Condo

  • 1
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“Enjoyed a 7 night stay in this well furnished 1 bedroom condominium. The owner provided everything to make our stay very comfortable in a very well kept unit. The pool area and grounds are all well maintained We were in walking distance to the...”
- Review left on 12/29/2016

$120

Excellent (8 reviews)

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from $120 / night

(1)

1 / 49

Longboat Key House

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Our Stay at the Conrad Cabana on Longboat Key was more than we had wished for. The moment we entered the home we knew that we would be very comfortable and we were. Throughout the rental process everything went smoothly and when we arrived we were...”
- Review left on 02/21/2016

$400

Excellent (1 reviews)

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from $400 / night

1 / 23

Longboat Key Condo

  • 2
  • 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$93

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from $93 / night

(1)

1 / 24

Longboat Key Apartment

  • 2
  • 5
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This was our first time to Longboat Key,Florida. This condo was adorable and in a great location! We arrived at night and once we unlocked the door were so relieved. It is a quaint 2 bedroom 1 bath condo that was so clean and lovely furnishings. We...”
- Review left on 04/11/2016

$136

Very Good (1 reviews)

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from $136 / night

(5)

1 / 44

Longboat Key House

  • 5
  • 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“The house is stunning, but that is nothing compared to the location! Right on the beach, beautiful views! Kids loved the pool while the adults loved the relaxation. I can't think of anything negative to say...we truly enjoyed our time at the house...”
- Review left on 02/09/2017

$800

Excellent (5 reviews)

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from $800 / night

(9)

1 / 12

Longboat Key Cottage

  • 3
  • 6
  • Min stay varies
  • Ask about children
  • Air conditioning
“It was a pleasure to stay here. The neighborhood is quiet and peaceful, and there's a really nice beach that's a few minutes walk -- a few others that aren't much further. The house was clean and everything was set and prepared for our stay. The...”
- Review left on 01/08/2017

$91

Excellent (9 reviews)

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from $91 / night

1 / 10

Longboat Key Townhouse

  • 3
  • 7
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $334 / night

1 / 26

Longboat Key Townhouse

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$100

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from $100 / night

1 / 14

Longboat Key Condo

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $84 / night

Your search has been expanded 7.7 miles to include more rentals

1 / 11

Sarasota House - 4.3 miles away

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

from $240 / night

1 / 12

Bradenton House - 5.5 miles away

  • 3
  • 6
  • Min stay varies
  • Nearest beach 15 mi
  • Swimming pool
  • Child friendly

$200

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from $200 / night

(6)

1 / 4

Bradenton Apartment - 5.7 miles away

  • 1
  • 2
  • 1 night min
  • Ask about children
  • Air conditioning
  • Pet friendly
“Hi stayed at trailer park just across from the rental homes it was a nice clean park with friendly people most were from Canada, I would stay again , Sonja at the park was very accommodating thank you for your help with our site. Dave”
- Review left on 01/05/2017

from $60 / night

(2)

1 / 21

Bradenton Condo - 5.7 miles away

  • 2
  • 4
  • Min stay varies
  • Ask about children
  • Air conditioning
“I recently spent a week at this lovely condo in Shorewalk Vacation Villas. It was very nice. Kitchen and living area were quite modern and well stocked and decorated. The bedrooms and bathrooms were a little dates but very clean and comfortable. The...”
- Review left on 10/19/2016

$111

Very Good (2 reviews)

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from $111 / night

1 / 70

Anna Maria Island Condo - 6.5 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

from $215 / night

(4)

1 / 46

Bradenton Beach Condo - 6.8 miles away

  • 2
  • 4
  • 3 nights min
  • Ask about children
  • Air conditioning
“My family and I spent a week at this beautiful place. You never need to leave the island, it has everything. Trolleys and buses, but most everything is within walking distance. There are so many things to do, swimming, shelling, fishing, bike...”
- Review left on 07/06/2012

$171

Excellent (4 reviews)

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from $171 / night

(4)

1 / 29

Bradenton Beach Condo - 6.9 miles away

  • 1
  • 2
  • 3 nights min
  • Ask about children
  • Air conditioning
“This condo was delightful! Everything was clean, clean, clean. The full kitchen was well stocked with pots, pans, untensils, coffee maker. The bed was vey comfortable. My son slept well on the fold out couch. Just steps from the most beautiful...”
- Review left on 07/08/2012

$171

Excellent (4 reviews)

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from $171 / night

(4)

1 / 5

Bradenton Condo - 7 miles away

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“Michelle was so helpful and willing to meet all our our expectations and needs. The location of her condo is so convenient. It is close the YMCA, Publix, Walmart, Home Depot, excellent restaurants, and many more. We would consider staying there...”
- Review left on 03/05/2017

$96

Very Good (4 reviews)

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from $96 / night

1 / 14

Bradenton Beach Townhouse - 7.1 miles away

  • 2
  • 4
  • Min stay varies
  • Ask about children
  • Air conditioning

$220

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from $220 / night

1 / 4

Bradenton Beach Apartment - 7.2 miles away

  • 1
  • 5
  • 1 night min
  • Air conditioning

$205

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from $205 / night

1 / 20

Bradenton Beach Condo - 7.2 miles away

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$344

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from $344 / night

(2)

1 / 24

Bradenton Condo - 7.3 miles away

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$111

Excellent (2 reviews)

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from $111 / night

1 / 9

Cortez Townhouse - 7.4 miles away

  • 4
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$296

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from $296 / night

1 / 16

Bradenton Villa - 7.4 miles away

  • 2
  • 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$100

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from $100 / night

(2)

1 / 4

Cortez Cottage - 7.4 miles away

  • 2
  • 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Air conditioning
  • Pet friendly
“This apartment had a beautiful open concept, nicely decorated. The place was supplied with nice quality furniture and cooking apparatus. Quiet and right on the canal, close to everything. Owners were above and beyond for help, and just a click...”
- Review left on 01/02/2015

$92

Very Good (2 reviews)

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from $92 / night

1 / 24

Bradenton Beach House - 7.5 miles away

  • 6
  • 13
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $500 / night

(2)

1 / 24

Bradenton Beach House - 7.5 miles away

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“My family and friends and I rented this property to celebrate my bachelorette weekend and we picked the most perfect house possible! The layout of the house was ideal for accommodating a large number of guests in addition to providing comfortable...”
- Review left on 09/06/2016

$400

Excellent (2 reviews)

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from $400 / night

(5)

1 / 93

Anna Maria Island House - 7.7 miles away

  • 4
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“We enjoyed our stay at this property. The home is well decorated and all rooms are very spacious. The master bedroom is enormous with jacuzzi and large walk-in shower. The other bedrooms are very spacious too. Our manager resolved a few minor...”
- Review left on 08/10/2016

$351

Excellent (5 reviews)

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from $351 / night

(6)

1 / 41

Bradenton Beach Condo - 7.7 miles away

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“Mark, the owner, is very responsive in communications. He told us to just bring yourselves and everything is there, beach towel, beach chairs, towels, etc. Sure enough everything is there and in great condition. This condo complex has private...”
- Review left on 01/25/2016

$151

Excellent (6 reviews)

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from $151 / night

(10)

1 / 22

Bradenton House - 7.7 miles away

  • 3
  • 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
“The location of this property is a perfect area. Just as described by the owner. House is fully equipped including a hand mixer. We enjoyed watching the water sports on the bay from the patio. Lots of parks and popular beaches within 5 mile...”
- Review left on 04/07/2017

$129

Very Good (10 reviews)

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from $129 / night

1 / 28

Bradenton Beach Condo - 7.7 miles away

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

from $115 / night

(7)

1 / 72

Anna Maria Island Condo - 7.7 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Hidden Oasis is a lovely property - nicely decorated, very clean, very well-kept, and equipped with pretty much everything you might need or want. It also has a fantastic view of the gulf and the beach; and this view is visible from the living room...”
- Review left on 03/16/2017

$251

Excellent (7 reviews)

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from $251 / night

(28)

1 / 97

Bradenton Beach Condo - 7.7 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“It was a great experience. The condo was close to perfect. It was a great spot close to the beach and many restuarants and shops. The Island was perfect with free trolly service and very clean roads and ammenities. The Ocean views and the white...”
- Review left on 06/05/2016

$251

Very Good (28 reviews)

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from $251 / night

About Longboat Key

With endless white sand beaches and unobstructed views of the Gulf of Mexico, it’s no surprise that Longboat Key is a vacation hotspot. Book the perfect seaside Longboat Key condos for you and your family, and get ready for a vacation you won’t forget.

Introduction to Longboat Key

Located just off the Gulf Coast of Florida, Longboat Key is a barrier island that includes just four square miles of land and about 12 square miles of water. With such an expansive waterfront, Longboat Key is a true beach community. Many residents live here only in the winter, which means there are numerous vacation homes available throughout the warmer months.

Longboat Key Climate

Like many Gulf Coast communities, Longboat Key welcomes hot, humid summers and warm winters. The highs in July and August average about 90 degrees, while December and January days typically top out around 60 degrees. Longboat Key welcomes over 250 sunny days, and though the area receives an above average amount of rain, it’s extremely rare to spot snow along the coast.

How to Get Around Longboat Key

West Florida is a car lover’s paradise, with Gulf of Mexico Drive as the single main road that extends along the length of the key. Most Longboat Key condos are just a short drive away from both the main drag and the waterfront, so be sure to rent a car if you’re flying into Sarasota Bradenton International Airport.

Hit the Beaches

Longboat Key Beach faces the Gulf of Mexico and boasts clear, calm water and soft, white sand. You won’t find buzzing boardwalks or massive crowds here, but you will find plenty of space to swim and sunbathe. There are several public beach access points along the key, but arrive early to take advantage of limited parking.
At the northern edge of the key, Beer Can Island offers a secluded spot to swim, fish, and gather with friends. Since this beach is only accessible by boat, plan to rent a boat or charter a boat trip.

Explore the Gulf

One of the most popular ways to explore offshore is renting a boat. Outfitters like Cannons Marina and CB’s Saltwater Outfitters rent boats by the half day, full day, or week. Depending on what you want to do and the size of your group, you can rent a three-person motorboat for fishing, a six-person speedboat for cruising along the coast, or a 14-person pontoon that’s perfect for spending the day at sea. Be sure your group’s driver has a driver’s license and some boating experience under his or her belt.

Go Golfing

If you're a landlubber, rest assured there's plenty to do back on shore. Harbourside Course offers three different courses and 27 holes of golf. Play in the midst of flora like palmettos and palms, and enjoy the sparkling gulf views and refreshing breeze.

With easy beach access, activities on and offshore, and numerous Longboat Key condos for rent, this spot makes the perfect beach vacation.

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Longboat Key Travel Tips

If you are looking for a vacation destination that includes white sandy beaches and a great mix of activities for the whole family to enjoy, make plans now to visit Longboat Key, FL. With the Gulf of Mexico on one side and Sarasota Bay on the other, there are miles of beach to be explored. The neighboring attractions in Sarasota, Bradenton, and Anna Maria Island offer more opportunity to explore the area while enjoying the Caribbean-like beaches of Longboat Key. Plan your family vacation today with VacationHomeRentals.com and enjoy your visit from any of the many Longboat Key rentals on the island. 

Longboat Key Attractions

While it is no secret that the main attraction of Longboat Key is the easy access to many popular beaches, you can find many family centered adventures within nearby parks. Longboat Key offers plenty of opportunities to enjoy first class shopping and dining. Continental cuisine, fresh seafood, coffeehouses, and more are all available. Enjoy shopping at Longboat Key's Avenue of Flowers shopping area, the specialty boutiques at The Centre Shops or explore the galleries and shops at St. Armand Circle. If you are a collector of beautiful antiques you will want to be sure and visit the Soma District, located a short drive from Longboat Key.
The entire island is only 11 miles long but includes easy access to some of the most beautiful beaches in the state. While it may be hard to decide on a favorite beach during your first visit, you can find Longboat Key vacation rentals to choose from that provide you with the ideal starting point for access to one or several of the following beaches.
  • Greer Island
  • Cortez Beach
  • Holmes Beach
  • Manatee County Beach
  • Ann Marie Beach
  • Coquina Beach
  • Lido Key
Enjoy local dining and attractions such as these:

South Lido Park

South Lido Park a beautiful park covers 100 acres and offers attractive views of the Gulf of Mexico and the city of Sarasota. The whole family will enjoy kayaking, picnics, cookouts, nature trails, and many more seasonal outdoor activities. 

Blind Pass Beach

Blind Pass Beach may be one of the best kept secrets in the Longboat Key area. Located approximately 12 miles from Longboat Key this beach is a bit isolated, but offers the seclusion you might expect to find on a Caribbean vacation! Plan a day to enjoy the water, free parking, playground equipment to keep the younger family members busy and much more. You and your family can wander along the nature trail that includes dunes, rent a canoe or kayak to launch from the beach, or try your luck at fishing.
Other attractions you and your family may enjoy while relaxing in Longboat Key include Quick Point Nature Preserve and Islandside Golf Club. Additionally, you and your family are sure to enjoy are the Chartered Fish Tours and Ringling Bros. Barnum & Bailey Circus. The circus winter headquarters are in Bradenton which is a short drive from Longboat Key. Kids and adults alike will enjoy a tour of the museum and an opportunity to tour the grounds and enjoy regularly scheduled shows and exhibits.

Longboat Key Events

As a small town, Longboat key doesn't have a lot of events aside from their annual Holiday Night of Lights which features Christmas carol sing-alongs and a parade, but neighboring cities such as Bradenton provide ample entertainment and opportunities. Every Sunday you can enjoy Jazz Brunch on the Beach in Anna Maria. On New Year's Eve, a big celebration happens on Main Street in Bradenton.
Plan your family vacation travel today with VacationHomeRentals.com and see for yourself why so many families like yours return to Longboat Key every year!
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