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Longboat Key Condos & Vacation Rentals

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  2. United States of America
  3. Florida
  4. Longboat Key

Our Favorite Vacation Rentals in Longboat Key

  • Beach Getaway Mi to Siesta Key
     Country House
    Booking.com
    From
    $361
  • The Spurge Mansion - Sleeps 20
     5br Country House
    HolidayLettings
    From
    $2,000
  • BeachPoint Cottages
     Home/Apartment
    Booking.com
    From
    $419
  • Dream Lover Boat & Breakfast on Anna Maria Island
    Excellent2br Boat
    HolidayLettings
    From
    $335
  • Beach Escape with Heated Pool - Sleeps 20
     3br Home/Apartment
    HolidayLettings
    From
    $1,566
  • BIG HOUSE 5br/2bth/Playground walk DOWNTOWN,Beach
     5br Home/Apartment
    HolidayLettings
    From
    $278
  • Luxury Waterview Mansion
     5br Country House
    HolidayLettings
    From
    $1,652
  • Tropical Beach Vacation - Sleeps 16
     4br Home/Apartment
    HolidayLettings
    From
    $662
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Check prices for these upcoming dates

Longboat Key Vacation Rentals with a Pool

  • Unforgettable Longboat Key Vacation Rental | Private Beach | Heated Pool | Outdoor Spa | Waterfront | Boat Dock| Sleeps 10
     4br Home/Apartment
    Airbnb
    From
    $1,397
  • Stunning Waterviews Beach Escape - Sleeps 8
     3br Home/Apartment
    Airbnb
    From
    $1,397
  • Tropical Beach Escape - 13 Min to beach- Sleeps 12
     4br Home/Apartment
    Airbnb
    From
    $1,242
  • Tropical Waterfront Escape - Anna Maria Vacation Rental - Sleeps 10
     4br Home/Apartment
    Airbnb
    From
    $2,033
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Longboat Key Vacation Rentals with Wi-Fi

  • 2 private rooms,close to the beaches and IMG
    Excellent2br Home/Apartment
    Airbnb
    From
    $154
  • Bungalow Beach Resort: The Mermaid
     Studio
    Airbnb
    From
    $496
  • Luxury Tropical Waterfront House - Sleeps 12
     5br Home/Apartment
    Airbnb
    From
    $2,033
  • Tropical Beach Paradise - 10 Minutes to the beach - Sleeps 14
     5br Home/Apartment
    Airbnb
    From
    $2,033
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Longboat Key Pet-Friendly Vacation Rentals

  • Amazing Hacienda Style Villa - Very Close To Siesta
     3br Country House
    HolidayLettings
    From
    $663
  • Share Mediterranean Home...Historic River District
     2br Home/Apartment
    Airbnb
    From
    $153
  • Bay Breeze Cottages #2
    ExcellentHome/Apartment
    Airbnb
    From
    $337
  • Tropical Waterfront Oasis Near Siesta Key Beach - Sleeps 12
     3br Home/Apartment
    Airbnb
    From
    $1,423
Show all

Longboat Key Travel Guide

For a tropical island getaway without venturing too far out from Florida mainland, Longboat Key is the perfect place to visit. With deserted white sandy beaches, translucent turquoise waters and swimming and snorkeling opportunities at every turn, its appeal is undisputed.

Things to Do in Longboat Key

The best things to do in Longboat Key are to enjoy the beaches. Not only are these beautiful places to relax, they often have no-one else around! Coquina Beach and the beaches over at Beer Can Island are among the best in the area. The Joan M Durante Community Park offers interesting trails through wetlands for when you get bored of laying on the beaches.

Best Time to Visit Longboat Key

The spring and fall months are the best times to visit Longboat Key. At this time, temperatures are still hot but not quite as humid as the summer.

A Local's Guide to Longboat Key

Longboat Key in Florida is the perfect waterfront location for a relaxing stay away. With beachfront condos, revered white sand beaches, fine dining and a luxury golf club, it is hardly surprising that Longboat Key is such a popular destination for travelers all over the globe. Its stunning beaches extend for 12 miles, and this, coupled with a number of cultural activities, makes it a hotspot for a number of vacation rentals in Longboat.

A holiday in Longboat Key is perfect for those looking for a tropical island adventure, without straying too far from Florida mainland. The most popular activity is making use of the sandy beaches and surrounding barrier islands, however just a short drive away there are many other towns that are well worth exploring too. St Armands Circle is nestled between the turquoise waters of Sarasota Bay and the Gulf of Mexico and is renowned for being a continental market place that makes shopping a calming and enjoyable experience. St Armands is a charming synthesis of past and present and is within easy reach of a number of Longboat Key vacation rentals.

Longboat Key offers a mix of luxury and budget condo rentals, making it a popular destination for a range of travelers. Located north of St Armands Key and Lido Key, many shopping and dining experiences are within easy reach of the town’s main residential area, where the island starts to widen, and this is where much of the Longboat Key accommodation is located. In addition to standard apartments, BnBs, hotels and villas, the area is also host to some more unique properties, many of which are pet friendly. By using rentals in Longboat Key, visitors are also in easy reach of Downtown Sarasota, known as Florida’s cultural coast, home to a symphony of ballet, opera and art galleries. Additionally, Siesta Key is also just a short drive away, and enjoys its reputation of being home to one of America’s best beaches.

If you are looking for a relaxing beachfront holiday with access to great shopping and dining facilities, then look no further than rentals in Longboat Key, where you are likely to find your perfect vacation home.

Condos in Longboat Key

There is no shortage of vacation rentals and beachfront condos in Longboat Key, all of which make the perfect home away from home during a vacation here. The town is divided between Sarasota and Manatees counties, and borders the beautiful Gulf of Mexico. Its 12 miles of white sand beaches have helped to make this town a desirable play to stay. People come from miles around to enjoy the warm climate, the excellent golfing facilities, and the tennis club. Just a short drive away, visitors can go shopping at Downtown Sarasota or learn more about art and circus history in the unique Ringling Museum. For some family fun, the Sarasota Jungle Gardens allow people to get up-close to a range of majestic animals.

With so much to see and do, Longboat Key condo rentals are in high demand, but with a range of rental options to suit your preferences and budget, finding the perfect spot isn't a huge task.

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Price and Availability in Longboat Key

Most expensive
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The cheapest day to stay at a vacation rental in Longboat Key tends to be Thursday, while the most expensive day tends to be Friday. Vacation homes in Longboat Key tend to be busiest on Fridays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Longboat Key is in February, while the cheapest month is in May. The most popular time to book a vacation rental in Longboat Key is in the high season in March. Longboat Key has its low season in September, when less people are visiting and the vacation home occupancy rate drops.
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The Weather in Longboat Key

Rainy days
84° 40°
3
87° 46°
2
86° 45°
1
94° 56°
2
97° 67°
2
99° 73°
6
94° 71°
14
96° 72°
13
96° 69°
2
94° 71°
3
91° 51°
1
84° 48°
3
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Longboat Key. The warmest months in Longboat Key are July and August, when temperatures reach 99 ˚F. The coolest month is December, when temperatures drop to 40 ˚F. The wettest month in Longboat Key is June with 13.92 inches of rain, while the driest month is February with 0.53 inches of rain.

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What Expert Travelers Think

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    Jeff Campbell
    Jeff CampbellMiddle Class Dad
    Middle Class Dad

  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

    Becky
    BeckyKid World Citizen
    Kid World Citizen

  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School
    LTL Mandarin School

Vacation Rentals in Longboat Key

Pick the perfect accommodation for your trip at AllTheRooms.com. We aggregate Airbnb, RedAwning, Priceline and others. Longboat Key has 1,835 hotels, vacation rentals and other special places to stay, with prices to suit careful travellers, luxury travelers and everything in between. A vacation in Longboat Key can be budget-friendly - our cheapest price rental is available at $25 per night. In general, an accommodation in Longboat Key will cost you $620 per night.

Those needing to get some work finished during their trip to Longboat Key can choose from 443 places to stay that provide WiFi. We have 12 accommodations that include a breakfast included. Fitness fanatics can get a workout in during their stay by choosing from 86 accommodations that have gym facilities. If you are driving to Longboat Key, you'll want to pick from 434 places to stay that provide parking. 404 hotels and vacation rentals have a a pool or jacuzzi

AllTheRooms has 47 pet-friendly places to stay in Longboat Key, so if you're traveling with your pet you won't have any problems.

We combine a wide variety of Longboat Key accommodations including vacation rentals, home stays, hostels and other unique places to stay into one easy search. We show results from more than 4 providers, including 417 places to stay from Airbnb, 23 accommodations from RedAwning and 11 places to stay from Priceline.

725 accommodations in Longboat Key have been reviewed; 40% are rated highly. 835 accommodations allow instant booking.

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