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Longboat Key Vacation Rentals & Apartments - 282 Rentals Available

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282 Vacation rentals

1 / 17

Longboat Key House

  • 6
  • 20
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

$802.00

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from $802.00 / night

(57)

1 / 13

Longboat Key House

  • 4
  • 10
  • 2 nights min
  • 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

$228.00

Very Good (57 reviews)

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from $228.00 / night

Your search has been expanded 14.4 miles to include more rentals

(6)

1 / 40

Bradenton House - 13.5 miles away

  • 3
  • 6
  • min stay varies
  • Nearest beach 25 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 24 minutes

“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

$111.00

Excellent (6 reviews)

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from $111.00 / 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 0 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

(22)

1 / 15

Bradenton Condo - 9.4 miles away

  • 2
  • 6
  • 6 nights min
  • Nearest beach 8 mi
  • Swimming pool
  • Child friendly
“Anita and Joe were great hosts and wonderful people! The condo is in a secure location close to lots of entertainment, attractions, and shopping. The neighborhood was quiet and friendly with lots of exercise walkers and dog walkers. We spent most...”
- Review left on 02/02/2017

$144.00

Very Good (22 reviews)

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from $144.00 / night

1 / 19

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

(33)

1 / 16

Sarasota Guest house - 4.7 miles away

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

$132.00

Excellent (33 reviews)

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from $132.00 / 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 / 13

Siesta Key Condo - 10.1 miles away

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

$228.00

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from $228.00 / night

(5)

1 / 29

Bradenton Condo - 6.4 miles away

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

Responds fast! Avg. 57 minutes

$138.00

Very Good (5 reviews)

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from $138.00 / 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. 3 hours 2 minutes

$573.00

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from $573.00 / 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

$172.00

Very Good (21 reviews)

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from $172.00 / night

1 / 33

Bradenton House - 8.1 miles away

  • 3
  • 6
  • min stay varies
  • Child friendly
  • Air conditioning

Responds fast! Avg. 57 minutes

$138.00

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from $138.00 / night

(3)

1 / 36

Bradenton Beach Cottage - 8.4 miles away

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

$189.00

Excellent (3 reviews)

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from $189.00 / night

(2)

1 / 22

Siesta Key House - 8 miles away

  • 3
  • 7
  • 14 nights min
  • 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

$344.00

Very Good (2 reviews)

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from $344.00 / night

1 / 17

Siesta Key Condo - 10.2 miles away

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

$228.00

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from $228.00 / 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

$207.00

Excellent (4 reviews)

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from $207.00 / night

(8)

1 / 22

Siesta Key Condo - 7.5 miles away

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

Responds fast! Avg. 3 hours 47 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 (8 reviews)

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from $147.00 / night

(1)

1 / 16

Bradenton Condo - 8.9 miles away

  • 3
  • 6
  • min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
“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

(9)

1 / 15

Sarasota Condo - 8 miles away

  • 2
  • 6
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning
“I can't say enough good things about this property. The location was great, close to the beach and an easy walk into the village. I don't think I have ever stayed anywhere that was so clean! They have every amenity available. We stayed for an...”
- Review left on 02/25/2015

$245.00

Excellent (9 reviews)

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from $245.00 / 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

(9)

1 / 31

Siesta Key Condo - 9.4 miles away

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“This condo is beautifully decorated with top notch fixtures and is very clean. It is a 2 minute walk from the beach, and even though the pool and hot tub are a 30 second walk from the patio, we were never bothered by any noise from the pool. The...”
- Review left on 04/26/2019

$236.00

Excellent (9 reviews)

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from $236.00 / night

1 / 19

Palma Sola House - 9.6 miles away

  • 6
  • 18
  • 7 nights min
  • Child friendly

$293.00

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from $293.00 / night

1 / 21

Bradenton Apartment - 6.3 miles away

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

Responds fast! Avg. 57 minutes

$149.00

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from $149.00 / 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 / 20

Bradenton Beach Condo - 8 miles away

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

$655.00

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from $655.00 / night

1 / 24

Bradenton Beach Condo - 8.3 miles away

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

$344.00

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from $344.00 / night

1 / 13

Siesta Key Condo - 10.1 miles away

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

$228.00

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from $228.00 / night

(1)

1 / 26

Sarasota House - 10 miles away

  • 2
  • 4
  • 4 nights min
  • 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

$300.00

Excellent (1 reviews)

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from $300.00 / night

(7)

1 / 23

Siesta Key House - 8.2 miles away

  • 4
  • 12
  • 7 nights min
  • Nearest beach 0.2 mi
  • Swimming pool
  • Child friendly

$682.00

Excellent (7 reviews)

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from $682.00 / night

1 / 19

Bradenton Beach Cottage - 12.7 miles away

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

$155.00

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from $155.00 / 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. 3 hours 2 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 Beach Villa - 9.1 miles away

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

$262.00

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from $262.00 / night

1 / 18

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

(6)

1 / 21

Siesta Key Condo - 9.2 miles away

  • 1
  • 3
  • 14 nights min
  • 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

$272.00

Excellent (6 reviews)

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from $272.00 / night

(1)

1 / 13

Lakewood Ranch House - 10.7 miles away

  • 2
  • 4
  • 14 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

$279.00

Average (1 reviews)

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from $279.00 / night

(11)

1 / 20

Bradenton House - 7.7 miles away

  • 3
  • 6
  • min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
“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

$167.00

Very Good (11 reviews)

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from $167.00 / night

(22)

Certificate of Excellence

1 / 44

Anna Maria Island House - 8.9 miles away

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 59 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

$205.00

Excellent (22 reviews)

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from $205.00 / night

1 / 16

Oneco Cottage - 6.5 miles away

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

$67.00

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from $67.00 / 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. 2 hours 41 minutes

$57.00

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from $57.00 / 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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