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Longboat Key Vacation Rentals & Apartments - 155 Rentals Available

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155 Vacation rentals

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(2)

1 / 22

Siesta Key House - 8 miles away

  • 3
  • 7
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“My husband and I stayed at Tiffany Sands for the months of February and March 2016. We loved the proximity to the beach and Siesta Key Village. The townhouse is well appointed and had nearly everything we needed for a comfortable 2 month stay. The...”
- Review left on 04/28/2016

$373.00

Very Good (2 reviews)

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from $373.00 / night

(11)

1 / 20

Bradenton House - 7.7 miles away

  • 3
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“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 radius...”
- Review left on 04/07/2017

$287.00

Very Good (11 reviews)

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from $287.00 / night

(1)

1 / 16

Bradenton Condo - 8.9 miles away

  • 3
  • 6
  • 120 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
“We vacationed at this villa during February and March 2011. It is spacious and quite nicely furnished. We especially enjoyed the setting - the view from every window is of trees and shrubs with no other dwellings visible. One minor drawback of its...”
- Review left on 04/28/2011

$107.00

Very Good (1 reviews)

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from $107.00 / night

(4)

1 / 12

Bradenton House - 16.5 miles away

  • 3
  • 3
  • 13 nights min
  • Beach/lakeside relaxation
  • Nearest beach 30 mi
  • Swimming pool
“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

(6)

1 / 24

Holmes Beach Condo - 10 miles away

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“My Husband ,Son & I had a wonderful time at the Condo,it was clean ,comfortable & near the beach ,shops & the bus stops.I could not ask for anything better ,will be looking to rent again in the future”
- Review left on 09/01/2015

$155.00

Excellent (6 reviews)

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from $155.00 / night

1 / 8

Sarasota Condo - 4.4 miles away

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

Responds fast! Avg. 3 hours 43 minutes

$57.00

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from $57.00 / night

(9)

1 / 31

Siesta Key House - 8.1 miles away

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
“House was newly renovated, nicely funnies and clean. Short walk to Siesta Key Beach and 1 mile to town. Very sweet neighborhood...”
- Review left on 03/05/2017

$567.00

Excellent (9 reviews)

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from $567.00 / night

(7)

1 / 16

Holmes Beach Villa - 10.7 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Five of us and two dogs spent last week of July here, Great location, 8 iron golf shot to the beach from front yard, fantastic pool in back yard complete with all the toys you need for the beach or pool in garage, also refrigerator in garage to save...”
- Review left on 08/27/2015

$458.00

Very Good (7 reviews)

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from $458.00 / night

(3)

1 / 34

Bradenton Condo - 10.5 miles away

  • 2
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Swimming pool

$144.00

Excellent (3 reviews)

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from $144.00 / night

(4)

1 / 25

Siesta Key Condo - 10.1 miles away

  • 1
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This place is absolutely great. Me and my girlfriend spent two nights over the weekend at this condo. First of all this place has more stuff that we could imagine. It literally includes everything you need for having a pleasant and comfortable stay....”
- Review left on 07/26/2016

$161.00

Very Good (4 reviews)

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from $161.00 / 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

(2)

1 / 10

Siesta Key Condo - 8.6 miles away

  • 1
  • 4
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“FIVE STARS!!!!! Terry the owner is a great guy that insured our stay in his condo went well. The condo has a great location just a couple of blocks from the Siesta Key Beach. The condo has everything you need for a great beach experience. The...”
- Review left on 01/24/2017

$104.00

Excellent (2 reviews)

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from $104.00 / night

(1)

1 / 23

Siesta Key Condo - 9.1 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$352.00

Excellent (1 reviews)

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from $352.00 / night

(1)

1 / 26

Sarasota Cottage - 5.1 miles away

  • 1
  • 3
  • 7 nights min
  • Beach/lakeside relaxation
  • Air conditioning
  • Private garden

$149.00

Excellent (1 reviews)

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from $149.00 / night

(3)

1 / 11

Sarasota Condo - 8.7 miles away

  • 2
  • 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 20 mi
  • Swimming pool

Responds fast! Avg. 3 hours 30 minutes

“This condo was extremely well appointed and had everything that we needed. We stayed 3 months and enjoyed every minute. The owners were gracious and responsive to every question. The view was outstanding. How much did we like it -we are renting it...”
- Review left on 03/30/2015

$115.00

Excellent (3 reviews)

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from $115.00 / night

1 / 26

Bradenton Beach Villa - 9.1 miles away

  • 4
  • 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$458.00

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from $458.00 / night

(14)

1 / 41

Siesta Key Condo - 7.6 miles away

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

$199.00

Excellent (14 reviews)

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from $199.00 / night

(15)

1 / 24

Siesta Key House - 8.3 miles away

  • 5
  • 13
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$610.00

Very Good (15 reviews)

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from $610.00 / night

1 / 37

Sarasota Condo - 10.3 miles away

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

$172.00

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from $172.00 / 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 / 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

1 / 35

Siesta Key Condo - 10.2 miles away

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.09 mi
  • Swimming pool

$491.00

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from $491.00 / night

1 / 21

Bradenton Apartment - 6.3 miles away

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

$148.00

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from $148.00 / night

(21)

1 / 20

Sarasota Condo - 8.2 miles away

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • 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

$114.00

Excellent (21 reviews)

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from $114.00 / night

(5)

1 / 29

Bradenton Condo - 6.4 miles away

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$138.00

Very Good (5 reviews)

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from $138.00 / night

1 / 24

Bradenton Villa - 6.4 miles away

  • 2
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$138.00

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from $138.00 / night

(22)

1 / 31

Siesta Key Condo - 9.4 miles away

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“My wife and I spent 2 weeks at this well kept and wonderfully located condominium. We loved that it is a garden style complex and not a high rise building. This unit being on the 1st floor makes it even better. Being able to walk right out to the...”
- Review left on 02/05/2021

$258.00

Excellent (22 reviews)

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from $258.00 / night

(6)

1 / 53

Siesta Key House - 8 miles away

  • 3
  • 9
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

$682.00

Excellent (6 reviews)

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from $682.00 / night

(3)

1 / 36

Bradenton Beach Cottage - 8.4 miles away

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

$327.00

Excellent (3 reviews)

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from $327.00 / night

(25)

1 / 42

Sarasota Condo - 8.5 miles away

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“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

(31)

1 / 24

Anna Maria Island Cottage - 11.4 miles away

  • 2
  • 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 51 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

$98.00

Excellent (31 reviews)

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from $98.00 / night

(1)

1 / 16

Bradenton House - 4.6 miles away

  • 3
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool

$201.00

Excellent (1 reviews)

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from $201.00 / night

1 / 16

Siesta Key Condo - 10.2 miles away

  • 1
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.09 mi
  • Swimming pool

$400.00

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from $400.00 / night

(40)

1 / 16

Sarasota Guest house - 4.7 miles away

  • 1
  • 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary
“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

$180.00

Excellent (40 reviews)

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from $180.00 / night

(6)

1 / 40

Siesta Key Condo - 8.3 miles away

  • 1
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.09 mi
  • Swimming pool
“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

$400.00

Excellent (6 reviews)

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from $400.00 / night

(2)

1 / 25

Siesta Key Condo - 8.3 miles away

  • 2
  • 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.09 mi
  • Swimming pool
“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

$491.00

Excellent (2 reviews)

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from $491.00 / night

1 / 30

Bradenton Villa - 6.4 miles away

  • 2
  • 7
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$138.00

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from $138.00 / night

(1)

1 / 18

Bradenton Apartment - 6.5 miles away

  • 2
  • 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$149.00

Excellent (1 reviews)

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from $149.00 / night

1 / 19

Bradenton Beach Cottage - 12.7 miles away

  • 1
  • 3
  • 2 nights min
  • Car not necessary
  • Air conditioning

$229.00

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from $229.00 / night

(5)

1 / 26

Bradenton Beach Apartment - 8 miles away

  • 1
  • 5
  • 2 nights min
  • Air conditioning

$338.00

Excellent (5 reviews)

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from $338.00 / 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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