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Longboat Key Vacation Rentals & Apartments - 259 Rentals Available

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259 Vacation rentals

(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

(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

$224.00

Very Good (57 reviews)

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from $224.00 / 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

$88.00

Excellent (38 reviews)

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from $88.00 / night

(9)

1 / 13

Ellenton House - 14.2 miles away

  • 2
  • 4
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning

Responds fast! Avg. 3 hours 54 minutes

“Lovely house great setting 5 minute walk to the pool. Quiet complex friendly people. 5 minute drive to 301 for start of shops k Mart, Public, Brand name outlets and Wal-Mart, Post Office and Banks. Many restaurants on door step too. Beach approx 40...”
- Review left on 11/11/2016

$115.00

Excellent (9 reviews)

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from $115.00 / night

(12)

1 / 23

Bradenton House - 14.1 miles away

  • 3
  • 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“My stay was from July 2- July 16 and I absolutely loved it. The rooms and bathrooms were super clean. Kitchen has all the appliances you needed it, home came with shower towels and amazing air conditioning through the vents. The neighborhood was...”
- Review left on 07/17/2016

$279.00

Excellent (12 reviews)

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from $279.00 / night

(4)

1 / 19

Bradenton Villa - 14.4 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“House was a great location for our Needs. Very Clean and spacious. Heated Pool was a great asset.. Would have liked a bigger more useable grill...”
- Review left on 02/23/2017

$180.00

Excellent (4 reviews)

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from $180.00 / night

1 / 25

Sarasota House - 10.9 miles away

  • 3
  • 6
  • 7 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning

$197.00

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from $197.00 / 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

1 / 19

Palma Sola House - 10 miles away

  • 4
  • 8
  • 7 nights min
  • Child friendly

$158.00

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from $158.00 / night

1 / 33

Siesta Key Condo - 10.1 miles away

  • 1
  • 4
  • min stay varies
  • Nearest beach 0.09 mi
  • Swimming pool
  • Ask about children

$228.00

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from $228.00 / night

(1)

1 / 28

Sarasota House - 7.4 miles away

  • 3
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 21 minutes

“The Beach House was exactly what we anticipated: clean, comfortable, cute and perfectly located on the beach. The lawn, fire ring, hammocks, children's play area and lawn furniture were extras that added a lot. The kitchen was large enough for...”
- Review left on 03/06/2014

$584.00

Excellent (1 reviews)

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from $584.00 / 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

1 / 7

Sarasota Condo - 12.6 miles away

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

Responds fast! Avg. 3 hours 18 minutes

$204.00

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from $204.00 / night

(10)

1 / 42

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

$100.00

Very Good (10 reviews)

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from $100.00 / night

(23)

1 / 23

Anna Maria Island Cottage - 11.4 miles away

  • 2
  • 5
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden

Responds fast! Avg. 1 hour 26 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

$104.00

Excellent (23 reviews)

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from $104.00 / night

1 / 16

Oneco Cottage - 6.5 miles away

  • 1
  • 2
  • min stay varies
  • Air conditioning
  • Pet friendly

$64.00

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from $64.00 / night

(2)

1 / 16

Sarasota Condo - 4.4 miles away

  • 2
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool
“We rented this two bedroom listed as a Condo, it is really two adjoining hotel rooms with kitchenettes. Nice accommodations, however the shower heads could be a little higher not convenient for taller people. Great view, right on Marina, close to the...”
- Review left on 01/23/2015

$114.00

Very Good (2 reviews)

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from $114.00 / 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 11 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

$516.00

Excellent (16 reviews)

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from $516.00 / night

1 / 14

Anna Maria House - 13.6 miles away

  • 2
  • 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

Responds fast! Avg. 1 hour 15 minutes

$573.00

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from $573.00 / night

1 / 70

Anna Maria Island Condo - 7.5 miles away

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

Responds fast! Avg. 2 hours 27 minutes

$344.00

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from $344.00 / night

(7)

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. 3 hours 20 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

$147.00

Excellent (7 reviews)

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from $147.00 / night

(5)

1 / 24

Siesta Key Condo - 8.3 miles away

  • 1
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“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

$228.00

Excellent (5 reviews)

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from $228.00 / night

(2)

1 / 34

Bradenton Condo - 10.5 miles away

  • 2
  • 6
  • min stay varies
  • Nearest beach 12 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 9 minutes

$144.00

Excellent (2 reviews)

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from $144.00 / night

(1)

1 / 33

Anna Maria Island Villa - 7.9 miles away

  • 2
  • 3
  • min stay varies
  • Child friendly

Responds fast! Avg. 3 hours 56 minutes

$201.00

Excellent (1 reviews)

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from $201.00 / night

(3)

1 / 21

Bradenton Condo - 4.5 miles away

  • 2
  • 3
  • min stay varies
  • Nearest beach 10 mi
  • Child friendly
  • 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

$115.00

Average (3 reviews)

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from $115.00 / night

1 / 16

Lakewood Ranch Villa - 11.9 miles away

  • 3
  • 6
  • min stay varies
  • Nearest beach 19 mi
  • Swimming pool
  • Ask about children

Responds fast! Avg. 3 hours 42 minutes

$153.00

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from $153.00 / night

1 / 28

Siesta Key Apartment - 7.4 miles away

  • 2
  • 8
  • min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning

Responds fast! Avg. 2 hours 21 minutes

$602.00

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from $602.00 / night

(10)

1 / 18

Siesta Key Condo - 7.6 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly
“Great property, beautiful pool, super close to the beach and the village - will totally be back! Awesome property management as well...”
- Review left on 06/13/2016

$144.00

Excellent (10 reviews)

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from $144.00 / night

1 / 14

Siesta Key Apartment - 7.3 miles away

  • 1
  • 4
  • min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning

Responds fast! Avg. 2 hours 21 minutes

$258.00

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from $258.00 / night

1 / 79

Bradenton Beach Condo - 8.5 miles away

  • 2
  • 6
  • min stay varies
  • Child friendly

Responds fast! Avg. 3 hours 29 minutes

$189.00

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from $189.00 / night

(3)

1 / 18

Sarasota Condo - 10.3 miles away

  • 2
  • 6
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool

Responds fast! Avg. 3 hours 13 minutes

“We came to Sarasota for the first time in June and couldn't have picked a better condo! Location is great, condo was clean and spacious, and parking was easy. Overall very pleased and would definitely stay again...”
- Review left on 08/24/2017

$98.00

Very Good (3 reviews)

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from $98.00 / night

1 / 19

Holmes Beach Townhouse - 11.8 miles away

  • 3
  • 8
  • 4 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$500.00

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from $500.00 / 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

$311.00

Excellent (2 reviews)

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from $311.00 / night

1 / 13

Anna Maria Island Apartment - 7.9 miles away

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

$252.00

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from $252.00 / night

1 / 9

Gulf Gate Branch Condo - 9.8 miles away

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

$126.00

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from $126.00 / night

(21)

1 / 27

Sarasota Villa - 12.1 miles away

  • 2
  • 6
  • min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 26 minutes

“We really like this place. The beaches are the best ever!!! We had great time in family. 5 min walk to Costco and other store. House very clean, good for a familly of 6. We appreciate having a pool near the house for an evening activity after the...”
- Review left on 09/14/2016

$107.00

Excellent (21 reviews)

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from $107.00 / night

(6)

1 / 40

Bradenton House - 13.5 miles away

  • 3
  • 6
  • 30 nights min
  • Nearest beach 25 mi
  • Swimming pool
  • Child friendly
“As soon as I unlocked the door to this property and looked in, I turned to my wife and said, "you're definitely going to be impressed" and needless to say she was!The home was by far the best we ever rented and I would have even rated it higher than...”
- Review left on 06/17/2016

$137.00

Excellent (6 reviews)

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from $137.00 / night

1 / 15

Sarasota Apartment - 6.9 miles away

  • 3
  • 3
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$115.00

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from $115.00 / night

(1)

1 / 26

Sarasota House - 10 miles away

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“My wife, two boys and I stayed here for a week for my wife and sons birthday. We had a great time and everything was as advertised. The pool and beach are right there, the house was cozy and everything was great. We even had cupcakes waiting upon our...”
- Review left on 05/23/2016

$185.00

Excellent (1 reviews)

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from $185.00 / night

(3)

1 / 24

Sarasota Townhouse - 8.1 miles away

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“The house was nice but a little out dated. A few things went wrong, but the owner really helped out immediately to rectify all the problems. It had all the things you wanted for the beach except an umbrella, which if we had one, we would have...”
- Review left on 06/04/2013

$409.00

Very Good (3 reviews)

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from $409.00 / 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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