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Longboat Key holiday rentals

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Best Longboat Key holiday rentals

These are the best prices for 1-2 Oct.
Siesta Key Beachside Villas - Siesta Key - Outdoor view
Siesta Key Beachside Villas
Siesta Key, FL, United States
8.7Very Good(902)
Villa
£223+
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The Ringling Beach House - Siesta Key - Bedroom
The Ringling Beach House
Siesta Key, FL, United States
8.3Very Good(810)
Apartment
£228+
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Siesta Key Island Rentals - Siesta Key - Living room
Siesta Key Island Rentals
Siesta Key, FL, United States
9.2Wonderful(58)
House
£259+
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Haley's at Anna Maria Island Inn - Holmes Beach - Outdoor view
Haley's at Anna Maria Island Inn
Holmes Beach, FL, United States
7.9Good(484)
Apartment
£192+
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Tropical Beach Cottage-Steps to the Beach-Short Walk to Siesta Key Village - Siesta Key
Tropical Beach Cottage-Steps to the Beach-Short Walk to Siesta Key Village
Siesta Key, FL, United States
9.1Wonderful(533)
Cottage
£262+
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Stunning 1-Bedroom Apartment Overlooking Pool, steps to Siesta Beach - Siesta Key - Pool
Stunning 1-Bedroom Apartment Overlooking Pool, steps to Siesta Beach
Siesta Key, FL, United States
9.6Wonderful(42)
Apartment
£355+
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Hidden Paradise on Lakefront Property Among Tropical Landscape on Siesta Key - Siesta Key - Patio
Hidden Paradise on Lakefront Property Among Tropical Landscape on Siesta Key
Siesta Key, FL, United States
8.5Very Good(16)
Condo
£161+
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Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway - Siesta Key - Living room
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
Siesta Key, FL, United States
9.2Wonderful(25)
Condo
£201+
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Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool - Siesta Key - Pool
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool
Siesta Key, FL, United States
9.2Wonderful(17)
Condo
£177+
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5 Star Quiet, Comfy Home, Pets Ok, Walk Dtwn, Trolley to Beach ,bike Legacy Trl - Sarasota - Living room
5 Star Quiet, Comfy Home, Pets Ok, Walk Dtwn, Trolley to Beach ,bike Legacy Trl
Sarasota, FL, United States
9.9Wonderful(60)
House
£149+
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Siesta Key Beachside Getaway Cottage Walking Distance To Beach And Village - Siesta Key - Beach
Siesta Key Beachside Getaway Cottage Walking Distance To Beach And Village
Siesta Key, FL, United States
9.3Wonderful(32)
Cottage
£234+
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Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More - Siesta Key - Balcony
Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More
Siesta Key, FL, United States
8.8Very Good(18)
Apartment
£203+
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Fully Renovated Beachside Getaway With Heated Pool Walk to Restaurants - Siesta Key - Pool
Fully Renovated Beachside Getaway With Heated Pool Walk to Restaurants
Siesta Key, FL, United States
9.5Wonderful(19)
Condo
£244+
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Beautiful property on Siesta Key - Siesta Key
Beautiful property on Siesta Key
Siesta Key, FL, United States
8.4Very Good(83)
Villa
£166+
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Modern & Fresh - Less than 3 miles to the Beach! - Sarasota
Modern & Fresh - Less than 3 miles to the Beach!
Sarasota, FL, United States
9.3Wonderful(19)
House
£154+
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One Ocean - A 1101 - Siesta Key
One Ocean - A 1101
Siesta Key, FL, United States
9.8Wonderful(18)
Apartment
£166+
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Booking Insights

KAYAK’s insights for holiday rentals in Longboat Key

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Longboat Key with confidence.

What is the cheapest day of the week to book a vacation rental in Longboat Key?

Sunday offers the lowest rates in Longboat Key, with an average nightly price of £238. The highest prices are found on Saturday, with average rates at £338.

How much is a vacation rental in Longboat Key for tonight by property type?

The best deal for a vacation rental in Longboat Key found by KAYAK users in the last 5 days was £194 in a Condo. Apartment prices start at £585.

How much is a vacation rental in Longboat Key for this weekend by property type?

The best deal for a vacation rental in Longboat Key found by KAYAK users for the upcoming weekend was £189 in a House. Apartments prices start at £401 and Condos at £426.

How early should you book a vacation rental in Longboat Key?

Book at least 71 days before your stay begins to get the best price for your Longboat Key vacation rental.

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Good to know

Low season

High season

September
March
Cheapest month to stay with an average 34% drop in price.
Most expensive month to stay with an average 19% rise in price.

KAYAK's top tips for finding Longboat Key holiday rental deals

  • Longboat Key, Florida, boasts several beachfront vacation rentals with fantastic ocean views. You can check into Beachcomber unit 204, a 2-bedroom condo facing the Gulf of Mexico with a great beach and pool view. The vacation home has a private beach, a balcony, cable TV, and a fully-equipped kitchen. You can also check into Silver Sands Gulf Beach Resort, a 1-bedroom unit with sea views, a full-sized kitchen, and beach access.
  • For pet-friendly Longboat Key vacation rentals, you can book The Beach Nest. The 3-bedroom vacation home welcomes dogs of any size at no fee. Cats are accepted upon request. You can also check into Blue Heron House, which welcomes dogs of any size for no extra fee. Cats are allowed upon request. Your pets will have access to a spacious playing area and a pet-relief area.
  • The Beach on Longboat Key #105 offers an ideal vacation home for those traveling to Longboat Key as a group. This Gulf-front condominium complex, which can accommodate up to 8 guests, features 3 bedrooms, 3 bathrooms, a heated pool, a full-sized kitchen, daily housekeeping service, and laundry facilities. You will also enjoy the best beachfront view and easy beach access.
  • Visitors looking for Longboat Key vacation rentals with free parking can check into Beach Castle #18. The 1-bedroom unit with free and private parking features family rooms, a well-fitted kitchen, a heated pool, and a hot tub. You can also check into Cabana Beach Club #5, which offers free parking, air-conditioned rooms, and a well-fitted kitchen.
  • For family-friendly Longboat Key house rentals, you can check into Island Paradise, a 3-bedroom vacation home along 1210 Bogey Lane. The vacation home features family rooms, an outdoor playing area for kids, a full-sized kitchen, laundry facilities, and access to Cedars Tennis Club. It is a 10- to 15-minute walk to several Longboat Key beaches.
  • Beachfront, air-conditioned, pool, and pet friendly are the most popular holiday rental property amenities in Longboat Key
  • Holiday rentals in Longboat Key are around 510% cheaper than hotels on average. Search here to compare prices for all accommodation types in Longboat Key.
  • The best holiday rental properties in Longboat Key are Quiet Tropical Dtwn 5 Star Home Nearsarasota Legacy Bike Trl & Trolley to Beach (10.0, 50 reviews), 5 Star Quiet, Comfy Home, Pets Ok, Walk Dtwn, Trolley to Beach ,bike Legacy Trl (9.9, 60), and Stunning 1-Bedroom Apartment Overlooking Pool, steps to Siesta Beach (9.6, 42), based on ratings and reviews from real travellers.
  • If you’re looking for a cheap holiday rental in Longboat Key, you should consider visiting during the low season. The cheapest holiday homes in Longboat Key can be found in September and April.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Longboat Key for 10 days.

FAQs when booking a holiday home in Longboat Key

  • How much is a holiday rental for a week in Longboat Key?

    The average price for a weekly Longboat Key holiday rental found by KAYAK users in the last 2 weeks is £2,299.

  • How much is a holiday rental for a month in Longboat Key?

    The average price for a monthly Longboat Key holiday rental found by KAYAK users in the last 2 weeks is £9,853.

  • What types of holiday rentals are available in Longboat Key?

    There are loads of different property types that you can make your holiday home in Longboat Key. You’ll find apartments, condos, cottages, houses and villas.

  • Are there any pet-friendly holiday rentals in Longboat Key?

    There are a number of dog and pet-friendly Longboat Key holiday rentals, with around 8% allowing you to bring your pet along with you.

  • How much is a holiday rental in Longboat Key for tonight?

    In the last 72 hours, users have found Longboat Key holiday rentals for tonight for as low as £194. Search here for similar prices

  • How can I find holiday rentals near me in Longboat Key?

    Take a look at our holiday rentals map to find the best holiday rental homes near you.

  • What vacation rentals in Longboat Key have barbecue facilities?

    To host a barbecue party with family or friends while on vacation in Longboat Key, you can check into Boathouse II. The 2-bedroom vacation has a garden with an outdoor grill, picnic tables, and a swimming pool. You can also check into Willow Bay, which has a terrace with a grill and an outdoor dining area with a garden view.

  • What are the best vacation rentals for couples in Longboat Key?

    For the perfect romantic getaway in Longboat Key, consider booking Sea Club I. The vacation home features an outdoor pool, a well-equipped kitchen, and a patio with an ocean view. You can also check into Lyons Lane, which has a hot tub and an outdoor pool. It is a 5-minute walk to the beach.

  • What vacation rentals in Longboat Key are close to Bayfront Park Recreational Center?

    If you’re looking for Longboat Key vacation rentals close to the recreational center, you can book LaPlaya 106A, less than a mile away. The entire apartment unit features 2 spacious bedrooms, a well-fitted kitchen, and a seating area. You can also book Pelican Harbour MH1, 0.4 miles from the recreational park. The entire house unit has 2 bedrooms and 2 bathrooms and can host up to 4 guests.

  • What vacation rentals in Longboat Key are close to Sarasota Bradenton International Airport?

    You can book Gulf and Beach View Apartment 403, 14 miles from Sarasota Bradenton International Airport. The 1-bedroom vacation home features a fully-equipped kitchen, a dining area, a tennis court, and a balcony with sea views.

Where to stay in Longboat Key?

Our map will help you find the perfect place to stay in Longboat Key by showing you the exact location of each holiday rental.

More options for your stay in Longboat Key

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