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Longboat Key Vacation Rentals & Apartments - 200 Rentals Available

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200 Vacation rentals

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(2)

1 / 72

Anna Maria House - 13.1 miles away

  • 2
  • 6
  • 2 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

Responds fast! Avg. 3 hours 17 minutes

$418.00

Excellent (2 reviews)

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from $418.00 / night

(5)

1 / 18

Siesta Key Condo - 8.3 miles away

  • 1
  • 4
  • min stay varies
  • Nearest beach 0.09 mi
  • Swimming pool
  • Child friendly
“Thank you for a wonderful week! The room was beautiful and Mary Ann and staff were all so accommodating to anything that you may need! We would highly recommend Siesta Palms to everyone! We are looking forward to coming back as soon as possible,...”
- Review left on 07/13/2016

$263.00

Excellent (5 reviews)

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from $263.00 / night

(3)

1 / 36

Bradenton Beach Cottage - 8.4 miles away

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

Responds fast! Avg. 3 hours 17 minutes

$189.00

Excellent (3 reviews)

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from $189.00 / night

1 / 16

Siesta Key Condo - 10.1 miles away

  • 2
  • 5
  • 7 nights min
  • Nearest beach 0.09 mi
  • Swimming pool
  • Child friendly

$304.00

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from $304.00 / night

(8)

1 / 23

Siesta Key House - 8.2 miles away

  • 4
  • 10
  • 7 nights min
  • Nearest beach 0.2 mi
  • Swimming pool
  • Child friendly

$880.00

Excellent (8 reviews)

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from $880.00 / night

1 / 16

Siesta Key Condo - 10.1 miles away

  • 3
  • 6
  • 7 nights min
  • Nearest beach 0.09 mi
  • Swimming pool
  • Child friendly

$338.00

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from $338.00 / night

(2)

1 / 18

Sarasota Villa - 12 miles away

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

Responds fast! Avg. 59 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

$274.00

Excellent (2 reviews)

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from $274.00 / night

(5)

1 / 26

Bradenton Beach Apartment - 8 miles away

  • 1
  • 5
  • min stay varies
  • Air conditioning

Responds fast! Avg. 3 hours 17 minutes

$338.00

Excellent (5 reviews)

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from $338.00 / night

1 / 21

Bradenton Apartment - 6.3 miles away

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

$149.00

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from $149.00 / night

(12)

1 / 40

Siesta Key Condo - 8.6 miles away

  • 2
  • 6
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Great place! Everything was wonderful,beach was a short walk away. Love all the new addition to public beach. Pool was heated,we went swimming every day. Unit was very clean and comfortable,couldn't ask for a better place. Took the free taxi to...”
- Review left on 01/06/2017

$89.00

Excellent (12 reviews)

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from $89.00 / night

(13)

1 / 16

Siesta Key Condo - 8.3 miles away

  • 1
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 29 minutes

“We stayed in Crescent Royale #409. Condo was extremely clean and well supplied. We had flown in and was thrillled to see beach chairs, umbrellas, towels and etc. that we couldn't bring along. The property was peaceful and quiet. Only problem was RED...”
- Review left on 10/04/2016

$159.00

Very Good (13 reviews)

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from $159.00 / night

(2)

1 / 25

Siesta Key Condo - 8.3 miles away

  • 2
  • 5
  • 7 nights min
  • Nearest beach 0.09 mi
  • Swimming pool
  • Ask about children
“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

$304.00

Excellent (2 reviews)

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from $304.00 / night

1 / 63

Sarasota Condo - 12.6 miles away

  • 2
  • 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

Responds fast! Avg. 2 hours 6 minutes

$153.00

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from $153.00 / night

(5)

1 / 29

Bradenton Condo - 6.4 miles away

  • 2
  • 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 1 hour 26 minutes

$138.00

Very Good (5 reviews)

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from $138.00 / night

1 / 16

Bradenton House - 4.6 miles away

  • 3
  • 4
  • min stay varies
  • Nearest beach 10 mi
  • Swimming pool
  • Air conditioning

$189.00

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from $189.00 / night

(1)

1 / 23

Siesta Key Condo - 9.1 miles away

  • 3
  • 6
  • 7 nights min
  • Child friendly
  • Air conditioning

$352.00

Excellent (1 reviews)

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from $352.00 / night

1 / 33

Bradenton House - 8.1 miles away

  • 3
  • 6
  • 2 nights min
  • Child friendly
  • Air conditioning

Responds fast! Avg. 54 minutes

$138.00

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from $138.00 / 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

$243.00

Excellent (2 reviews)

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from $243.00 / night

(21)

1 / 17

Holmes Beach Townhouse - 10.1 miles away

  • 2
  • 6
  • 7 nights min
  • Nearest beach 0.05 mi
  • Swimming pool
  • Child friendly
“This was my family's first visit to Anna Maria Island and it won't be our last. We loved the beaches, restaurants, and amazing sunsets. The Gulf View Townhouse was clean and centrally located, and it was an added bonus to have a pool on the...”
- Review left on 07/19/2016

$184.00

Very Good (21 reviews)

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from $184.00 / night

(7)

1 / 24

Siesta Key Condo - 9.7 miles away

  • 2
  • 4
  • 7 nights min
  • Nearest beach 0.25 mi
  • Swimming pool
  • Child friendly
“Had an excellent time! Unit was clean and precisely as described. Great location on Siesta Key with a short walk for Groceries, Food and Libations. Beach was a 5min walk across the street (using the signaled crosswalk) through the beachside section...”
- Review left on 03/13/2017

$107.00

Excellent (7 reviews)

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from $107.00 / night

1 / 16

Siesta Key Condo - 10.2 miles away

  • 1
  • 4
  • min stay varies
  • Nearest beach 0.09 mi
  • Swimming pool
  • Child friendly

$258.00

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from $258.00 / night

(8)

1 / 22

Siesta Key Condo - 7.5 miles away

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

$147.00

Excellent (8 reviews)

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from $147.00 / night

(3)

1 / 5

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

$144.00

Excellent (3 reviews)

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from $144.00 / night

(9)

1 / 41

Siesta Key Condo - 7.6 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly

$175.00

Excellent (9 reviews)

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from $175.00 / night

(9)

1 / 17

Sarasota Condo - 8.3 miles away

  • 2
  • 5
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We had such a wonderful trip to Siesta Key! The condo was very nice. Beautifully decorated, very clean, and great location! Everything from booking it to checking out was very easy. Everything we needed was available to us, and more! Everybody...”
- Review left on 08/02/2016

$152.00

Excellent (9 reviews)

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from $152.00 / night

1 / 14

Siesta Key Condo - 9.7 miles away

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

$138.00

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from $138.00 / night

1 / 20

Siesta Key Condo - 10.2 miles away

  • 2
  • 4
  • 7 nights min
  • Nearest beach 0.09 mi
  • Swimming pool
  • Child friendly

$287.00

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from $287.00 / night

1 / 12

Siesta Key Condo - 10.1 miles away

  • 1
  • 4
  • min stay varies
  • Nearest beach 0.09 mi
  • Swimming pool
  • Child friendly

$258.00

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from $258.00 / night

(2)

1 / 8

Sarasota Condo - 4.4 miles away

  • 1
  • 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 9 mi
  • Swimming pool

Responds fast! Avg. 2 hours 4 minutes

$63.00

Average (2 reviews)

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from $63.00 / night

(4)

1 / 12

Bradenton House - 16.5 miles away

  • 3
  • 5
  • min stay varies
  • Nearest beach 30 mi
  • Swimming pool
  • Child friendly
“We enjoyed this house, and it was the warmest December on record! Went to the beach 3 times and the ocean was warm enough to swim in this year! Look forward to more trips to Florida...”
- Review left on 01/08/2016

$167.00

Excellent (4 reviews)

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from $167.00 / night

(23)

Certificate of Excellence

1 / 44

Anna Maria Island House - 8.9 miles away

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

Responds fast! Avg. 2 hours 1 minutes

Travelers’ Choice award

“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

$487.00

Excellent (23 reviews)

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from $487.00 / night

(1)

1 / 15

Sarasota House - 12.6 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning

$68.00

Average (1 reviews)

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from $68.00 / night

1 / 19

Siesta Key Condo - 10.2 miles away

  • 2
  • 5
  • 7 nights min
  • Nearest beach 0.09 mi
  • Swimming pool
  • Child friendly

$304.00

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from $304.00 / night

1 / 26

Bradenton House - 9.6 miles away

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

$165.00

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from $165.00 / night

(25)

1 / 42

Sarasota Condo - 8.5 miles away

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 22 minutes

“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

$172.00

Excellent (25 reviews)

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from $172.00 / night

1 / 32

Bradenton Villa - 6.4 miles away

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

$149.00

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from $149.00 / night

(7)

1 / 15

Bradenton Apartment - 11.3 miles away

  • 1
  • 2
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Air conditioning

Responds fast! Avg. 3 hours 10 minutes

“What a fantastic place. We had the pleasure of staying in Bob?s studio. Bob thought of everything to make our stay as close to home as possible. We couldn?t have asked for more. The surroundings are pure Florida. The grounds near the studio were well...”
- Review left on 11/19/2016

$144.00

Very Good (7 reviews)

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from $144.00 / night

(28)

1 / 21

Anna Maria Island Cottage - 11.4 miles away

  • 2
  • 5
  • min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

Responds fast! Avg. 1 hour 9 minutes

“Songbird is a little slice of heaven with everything we needed to have a comfortable stay. We stayed for one week. Joel, the owner, is very thoughtful, and accommodating, and he makes it known that he is there for you if you need him. Which is so...”
- Review left on 05/20/2017

$218.00

Excellent (28 reviews)

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from $218.00 / night

(35)

Certificate of Excellence

1 / 16

Sarasota Guest house - 4.7 miles away

  • 1
  • 2
  • 7 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning

Travelers’ Choice award

“My husband and I stayed in Joyce and Jeff's beautiful guest apartment for two weeks. Everything was perfect inside and out. The property was immaculate and the owners included extra touches that went above and beyond. While we spent most of our time...”
- Review left on 08/09/2017

$131.00

Excellent (35 reviews)

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from $131.00 / night

(3)

1 / 34

Bradenton Condo - 10.5 miles away

  • 2
  • 6
  • 3 nights min
  • Nearest beach 12 mi
  • Swimming pool
  • Child friendly

$144.00

Excellent (3 reviews)

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from $144.00 / 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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