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Longboat Key Vacation Rentals & Apartments - 401 Rentals Available

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401 Vacation rentals

1 / 17

Longboat Key House

  • 6
  • 20
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

$1,100.00

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from $1,100.00 / night

(2)

1 / 22

Longboat Key Condo

  • 3
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
“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

$215.00

Very Good (2 reviews)

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from $215.00 / night

1 / 24

Longboat Key House

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly

$150.00

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from $150.00 / night

1 / 26

Longboat Key Condo

  • 2
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children

$150.00

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from $150.00 / night

1 / 24

Longboat Key House

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly

$217.00

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from $217.00 / night

1 / 20

Longboat Key Apartment

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children

$84.00

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from $84.00 / night

1 / 34

Longboat Key House

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly

$166.00

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from $166.00 / night

1 / 28

Longboat Key Apartment

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children

$600.00

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from $600.00 / night

1 / 24

Longboat Key House

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children

$501.00

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from $501.00 / night

1 / 47

Longboat Key Apartment

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children

$84.00

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from $84.00 / night

1 / 27

Longboat Key Apartment

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children

$134.00

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from $134.00 / night

1 / 21

Longboat Key House

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly

$133.00

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from $133.00 / night

1 / 14

Longboat Key House

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly

$166.00

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from $166.00 / night

Your search has been expanded 14.4 miles to include more rentals

(38)

1 / 24

Siesta Key Condo - 9.7 miles away

  • 2
  • 4
  • 7 nights min
  • Nearest beach 0.25 mi
  • Swimming pool
  • Child friendly
“Excellent property with lot of parking, laundy on site and warm water in the pool, which was really appreciated on the cooler dates, speacially by the kids. Close walk to a white sandy beach was on asset. Condo was very spacious and full equipped. We...”
- Review left on 01/02/2013

$85.00

Excellent (38 reviews)

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from $85.00 / night

(26)

1 / 24

Siesta Key Condo - 9.8 miles away

  • 2
  • 6
  • 7 nights min
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly
“This was our first trip to Siesta Key, but not our last! We are already booking another stay at Siesta Breakers for next year. It is a great location on the Beach and great access to the mainland...”
- Review left on 07/14/2014

$147.00

Excellent (26 reviews)

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from $147.00 / night

1 / 24

Sarasota Cottage - 12.4 miles away

  • 2
  • 6
  • min stay varies
  • Ask about children
  • Air conditioning

$190.00

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from $190.00 / night

1 / 13

Bradenton Cottage - 10.3 miles away

  • 1
  • 2
  • min stay varies
  • Air conditioning

$132.00

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from $132.00 / night

(25)

1 / 24

Bradenton House - 11.1 miles away

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 15 mi
  • Swimming pool

Responds fast! Avg. 1 hour 35 minutes

“The location of this house is really outstanding. We enjoyed being on the river, watching the beautiful sunsets daily, watching birds come and go into the inlets. It is a private place within a lovely subdivision with lakes and riverfront. We also...”
- Review left on 02/02/2017

$150.00

Excellent (25 reviews)

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from $150.00 / night

(25)

1 / 24

Sarasota Condo - 8.5 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Not only is the location perfect, but the condo is more then perfect! Everything we needed for a week at the beach including beach chairs... towels etc! Couldn't have been a better vacation! Can't wait to book again... THANKYOU STEVE...”
- Review left on 10/17/2017

$128.00

Excellent (25 reviews)

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from $128.00 / night

(2)

1 / 16

Siesta Key Condo - 9.5 miles away

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“Siesta Key is the best beach I ever been so far and this place that Jack and Darlene provide is a dream. Everything is clean and in perfect working condition. The beach is very nice (and I have visited many being a South Floridian), crystal clear and...”
- Review left on 09/19/2016

$193.00

Excellent (2 reviews)

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from $193.00 / night

(3)

1 / 33

Bradenton Beach Cottage - 8.4 miles away

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
“My husband and I spent the weekend in this cottage to celebrate his milestone birthday. We found it to be very comfortable and welcoming. I especially love the sunroom for my morning coffee and yoga. We were pleasantly surprised at how comfortable...”
- Review left on 11/23/2017

$150.00

Very Good (3 reviews)

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from $150.00 / night

1 / 12

Ellenton Apartment - 14.4 miles away

  • 1
  • 2
  • min stay varies
  • Ask about children
  • Air conditioning

$95.00

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from $95.00 / night

1 / 26

Bradenton House - 9.6 miles away

  • 4
  • 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$158.00

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from $158.00 / night

(7)

1 / 55

Sarasota House - 10.9 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Ask about children
“This is our fourth or fifth year that we have come to the villa in December we absolutely love it . There is so much to do there are tennis courts & communal pool, there is a mall around the corner plenty of publix & a short drive to the beach. The...”
- Review left on 12/29/2016

$93.00

Very Good (7 reviews)

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from $93.00 / night

(2)

1 / 25

Holmes Beach Townhouse - 12.2 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$299.00

Excellent (2 reviews)

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from $299.00 / night

(6)

1 / 22

Siesta Key Condo - 7.5 miles away

  • 1
  • 4
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 1 hour 59 minutes

“We stayed for a week and had the best time ever. The accommodations are top notch, locals are very friendly, food delicious and breathtaking beaches. Definitely looking forward to coming back”
- Review left on 12/15/2015

$127.00

Excellent (6 reviews)

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from $127.00 / night

(16)

Certificate of Excellence

1 / 26

Anna Maria Island House - 8.9 miles away

  • 4
  • 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 12 minutes

Certificate of Excellence

“Gorgeous, beautiful home away from home. This home has everything you and your family will need. The granite kitchen is fully equipped and beautiful. I was able to make a full Thanksgiving dinner with everything that was supplied in the home! Our...”
- Review left on 11/30/2016

$450.00

Excellent (16 reviews)

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from $450.00 / night

(2)

1 / 18

Sarasota Villa - 12 miles away

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 48 minutes

“The condo was perfect for our stay. Plenty of room to spread out and everyone had their own space. Highly recommend...”
- Review left on 07/22/2015

$85.00

Excellent (2 reviews)

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from $85.00 / night

(6)

1 / 21

Siesta Key Condo - 9.2 miles away

  • 1
  • 3
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“We actually stayed in unit #113 and it was simple but clean with updated kitchen. The grounds, pool, and amenities were well maintained and clean. The Gulf view was amazing! We have visited many beaches but this was the most beautiful with a quiet...”
- Review left on 07/07/2016

$200.00

Excellent (6 reviews)

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from $200.00 / night

1 / 20

Bradenton Beach Condo - 8 miles away

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$572.00

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from $572.00 / night

(3)

1 / 16

Bradenton House - 10.4 miles away

  • 3
  • 6
  • min stay varies
  • Nearest beach 20 mi
  • Swimming pool
  • Child friendly
“we rented this home for a week in July, the home is beautiful, it is equipped with every thing you could possibly need. the pool area was very relaxing and enjoyable. we loved the hone and would rent again...”
- Review left on 07/13/2014

$126.00

Excellent (3 reviews)

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from $126.00 / night

1 / 16

Lakewood Ranch Villa - 11.9 miles away

  • 3
  • 6
  • 30 nights min
  • Nearest beach 19 mi
  • Swimming pool
  • Ask about children

Responds fast! Avg. 3 hours 42 minutes

$167.00

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from $167.00 / night

(2)

1 / 41

Siesta Key Condo - 8.3 miles away

  • 2
  • 5
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“Our stay at Siesta Palms was great. The condo was very clean and up to date. We enjoyed the beautiful pool and proximity to the beach. The owners couldn't have been kinder or more accommodating. I highly recommend this condo...”
- Review left on 04/15/2016

$257.00

Excellent (2 reviews)

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from $257.00 / night

(2)

1 / 36

Bradenton Beach Cottage - 8.4 miles away

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$150.00

Excellent (2 reviews)

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from $150.00 / night

1 / 38

Sarasota Condo - 10.1 miles away

  • 2
  • 6
  • min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 42 minutes

$170.00

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from $170.00 / night

1 / 54

Sarasota House - 10.2 miles away

  • 4
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 42 minutes

$380.00

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from $380.00 / night

(21)

1 / 20

Sarasota Condo - 8.2 miles away

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“Found this property on the website and I'm glad I did. Ms Kathy is great! The property was beautiful. From the minute we walked in, the place is very nice and relaxing. Everything you need in the comfort of your home including beach equipments. Felt...”
- Review left on 07/20/2016

$105.00

Excellent (21 reviews)

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from $105.00 / night

(1)

1 / 49

Holmes Beach House - 11.5 miles away

  • 6
  • 12
  • min stay varies
  • Nearest beach 0.01 mi
  • Swimming pool
  • Child friendly

$599.00

Excellent (1 reviews)

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from $599.00 / night

1 / 29

Siesta Key House - 7.4 miles away

  • 4
  • 13
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 42 minutes

$270.00

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from $270.00 / night

(2)

1 / 56

Siesta Key Villa - 7.9 miles away

  • 4
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 42 minutes

$310.00

Average (2 reviews)

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from $310.00 / 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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