Longboat Key holiday rentals

We found 11,784 holiday rentals — enter your dates for availability
Discover a selection of 21 homes, 19 apartments and other holiday rentals in Longboat Key that are perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a hot tub. No matter what you're looking for, you'll be sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Longboat Key

Showing deals for:4 Dec - 11 Dec

Living area
Pool
Private kitchen
Dining
Exceptional
(288 reviews)

Immaculate, 3 bedroom, 2 bath Close to Siesta Beach, with secluded HEATED POOL

Sarasota

7% off
S$2,248
for 7 nights, 1 home
S$321 per night
includes taxes & fees
Immaculate, 3 bedroom, 2 bath Close to Siesta Beach, with secluded HEATED POOL
Terrace/patio
Private kitchen
Room
Exterior detail
Exceptional
(84 reviews)

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Sarasota

8% off
S$2,409
for 7 nights, 1 home
S$344 per night
includes taxes & fees
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Room
Room
Outdoor shower (yes there is one inside also)
Private kitchen
Exceptional
(30 reviews)

Adorable 1 Bedroom, 1 Bath guesthouse < 1block to Lido Beach

Sarasota

5% off
S$2,746
for 7 nights, 1 room
S$392 per night
includes taxes & fees
Adorable 1 Bedroom, 1 Bath guesthouse < 1block to Lido Beach
Pool
Eat your grilled catch of the day poolside in our new outdoor dining set for 8.
It's cocktail hour!
Living area
Exceptional
(121 reviews)

Sunset Landing AMI Beach House. 6BR/4.5BA. Private pool. 2 blks to beach.

Holmes Beach

7% off
S$6,753
for 7 nights, 1 home
S$965 per night
includes taxes & fees
Sunset Landing AMI Beach House. 6BR/4.5BA. Private pool. 2 blks to beach.
Private kitchen
Pool
Terrace/patio
Property grounds
Exceptional
(189 reviews)

LAKEFRONT 2bed/2bath with Heated POOL house, JUST 5 min away SIESTA KEY BEACH!

Sarasota

7% off
S$2,051
for 7 nights, 1 home
S$293 per night
includes taxes & fees
LAKEFRONT 2bed/2bath with Heated POOL house, JUST 5 min away SIESTA KEY BEACH!
Private Swimming Pool & Relaxing Area.
Longboat Pass
Beachfront Local Restaurant. Perfect For Sunset on The Beach.
Take An Incredible Stroll Through The Ringling Museum In Sarasota!
Exceptional
(83 reviews)

Heated Pool~Massive Spanish Home~Water Views~Sunset Deck~Grill~WIFI~Near Beaches

Bradenton

8% off
S$6,302
for 7 nights, 1 home
S$900 per night
includes taxes & fees
Heated Pool~Massive Spanish Home~Water Views~Sunset Deck~Grill~WIFI~Near Beaches
Exterior
Private kitchen
Dining
Living area
Exceptional
(12 reviews)

Siesta Vista, Spacious Waterfront Home. One Block to Beach & Village. Roof Deck!

Siesta Key

7% off
S$10,508
for 7 nights, 1 home
S$1,501 per night
includes taxes & fees
Siesta Vista, Spacious Waterfront Home. One Block to Beach & Village. Roof Deck!
Property grounds
Pool
Exterior
Private kitchen
Exceptional
(39 reviews)

6 BR/5.5 Bth-Huge Heated Pool/Spa/Water Slide...Short -1 Min Walk to Beach

Holmes Beach

27% off
S$9,887
for 7 nights, 1 home
S$1,412 per night
includes taxes & fees
6 BR/5.5 Bth-Huge Heated Pool/Spa/Water Slide...Short -1 Min Walk to Beach
Bedroom3
Sitting Area
Bedroom4
Swimming Pool
Exceptional
(16 reviews)

Waterfront, Boat Dock, Kayaks, Fishing, Pool, Spa. 4BR / 9Beds / Sleeps14

Palmetto

7% off
S$5,080
for 7 nights, 1 home
S$726 per night
includes taxes & fees
Waterfront, Boat Dock, Kayaks, Fishing, Pool, Spa. 4BR / 9Beds / Sleeps14
Bathroom
Terrace/patio
Bedroom #2- Queen mattress
Private kitchen
Exceptional
(20 reviews)

Charming 2-bedroom house in the heart of Sarasota—A quaint nature escape

Sarasota

8% off
S$1,538
for 7 nights, 1 home
S$220 per night
includes taxes & fees
Charming 2-bedroom house in the heart of Sarasota—A quaint nature escape
Front Yard
Dining Room
Full Kitchen
Living Room by Front Door
Exceptional
(42 reviews)

Downtown Sarasota, Casa de Zara

Sarasota

8% off
S$2,410
for 7 nights, 1 home
S$344 per night
includes taxes & fees
Downtown Sarasota, Casa de Zara
fenced in backyard
Terrace/patio
back bedroom, king size bed
Private kitchen
Exceptional
(325 reviews)

Charming cottage in quiet area, close to beach & bay.

Anna Maria

8% off
S$3,235
for 7 nights, 1 cottage
S$462 per night
includes taxes & fees
Charming cottage in quiet area, close to beach & bay.
Private kitchen
Interior
Living area
Living area
Exceptional
(18 reviews)

5BR with New Heated Pool ! 6mi from AMI Beach & IMG Academy! Spring Break Sales

Bradenton

11% off
S$3,962
for 7 nights, 1 home
S$566 per night
includes taxes & fees
5BR with New Heated Pool ! 6mi from AMI Beach & IMG Academy! Spring Break Sales
Dining
Pool
Interior
Dining
Exceptional
(22 reviews)

Southside Bungalow - Sleeps 8 - Pool, Spa & Putting Green

Sarasota

8% off
S$6,430
for 7 nights, 1 home
S$919 per night
includes taxes & fees
Southside Bungalow - Sleeps 8 - Pool, Spa & Putting Green
Living area
Private kitchen
Terrace/patio
Room
Exceptional
(110 reviews)

75 ft Canal Front Anna Maria House, Great for Boaters, Newly Renovated

Anna Maria

8% off
S$4,299
for 7 nights, 1 home
S$614 per night
includes taxes & fees
75 ft Canal Front Anna Maria House, Great for Boaters, Newly Renovated
Terrace/patio
Sports court
Private kitchen
Interior
Exceptional
(45 reviews)

Beautiful Blue Beach House Kids & Pets OK Aug, Sept, Oct, Nov, Dec DISCOUNTS! Beautiful Blue Beach House/AMIsland White Sand Beaches

Bradenton

6% off
S$2,119
for 7 nights, 1 home
S$303 per night
includes taxes & fees
Beautiful Blue Beach House Kids & Pets OK Aug, Sept, Oct, Nov, Dec DISCOUNTS! Beautiful Blue Beach House/AMIsland White Sand Beaches
Exterior
Beach
Property grounds
Property grounds
Exceptional
(97 reviews)

Resort Gem

Bradenton

7% off
S$1,634
for 7 nights, 1 apartment
S$233 per night
includes taxes & fees
Resort Gem
living room
private rooftop deck
Private dock for residents and guests
Dining area
Exceptional
(82 reviews)

Anna Maria Sunrise on the Bay, Sunsets on the beach.Luxury 3BR with Rooftop Deck

Bradenton Beach

7% off
S$3,592
for 7 nights, 1 apartment
S$513 per night
includes taxes & fees
Anna Maria Sunrise on the Bay, Sunsets on the beach.Luxury 3BR with Rooftop Deck
King bedroom
Screened porch
BBQ and Outdoor patio space
Fully stocked kitchen
Exceptional
(44 reviews)

Island House Resort - Waterfront 2-bedroom condo directly on Siesta Key Beach!

Siesta Key

6% off
S$3,588
for 7 nights, 1 room
S$513 per night
includes taxes & fees
Island House Resort - Waterfront 2-bedroom condo directly on Siesta Key Beach!
Exterior
Marina
Private kitchen
Living area
Exceptional
(39 reviews)

Siesta Key Beachside Condo-direct beach access

Siesta Key

8% off
S$3,520
for 7 nights, 1 apartment
S$503 per night
includes taxes & fees
Siesta Key Beachside Condo-direct beach access
Property grounds
Interior
Living area
Interior
Exceptional
(43 reviews)

Luxury condo located directly on Siesta Key Beach

Siesta Key

7% off
S$2,747
for 7 nights, 1 apartment
S$392 per night
includes taxes & fees
Luxury condo located directly on Siesta Key Beach
Private kitchen
Beach
Room
Outdoor dining
Exceptional
(102 reviews)

Low Rider - Bottom Unit -

Bradenton Beach

8% off
S$4,542
for 7 nights, 1 home
S$649 per night
includes taxes & fees
Low Rider - Bottom Unit -
Private kitchen
Living area
Pool
Terrace/patio
Exceptional
(13 reviews)

Hometown Paradise- Canalfront home with dock and heated pool

Bradenton

8% off
S$4,095
for 7 nights, 1 home
S$585 per night
includes taxes & fees
Hometown Paradise- Canalfront home with dock and heated pool
View of spacious main pool and clubhouse.  Dry sauna and gym inside.
Quiet and safe neighborhood for families to swim, walk, bike, and fish
Enclosed patio brand new furniture (purchased June 2024)
Front Entrance
Exceptional
(102 reviews)

Gulf & Bay Club Bayside, 1st Floor, CLEAN, 5 STARS & EXCELLENT REVIEWS!

Siesta Key

5% off
S$4,416
for 7 nights, 1 apartment
S$631 per night
includes taxes & fees
Gulf & Bay Club Bayside, 1st Floor, CLEAN, 5 STARS & EXCELLENT REVIEWS!
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Relaxing Longboat Key will entice you

Enjoy the monuments and other features of Longboat Key. This relaxing city is known for its beaches, bird watching and seaside. Siesta Key Beach and Lido Beach are just a couple of the must-see attractions in the area. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Longboat Key

Are you hoping to find things to do during your stay? Venture out of your cosy holiday rental and experience everything that Longboat Key has to offer. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Sarasota Jungle Gardens (7.1 mi / 11.4 km)
  • Mote Marine Laboratory & Aquarium (7.4 mi / 12 km)
  • Premier Sports Campus at Lakewood Ranch (16.9 mi / 27.3 km)
  • Aluna Wellness Center & Spa (5.3 mi / 8.6 km)
  • Harborside Golf Course at Longboat Key Club (6.9 mi / 11.2 km)
  • Links on Longboat (7 mi / 11.2 km)

Exploring the beaches and other natural features in Longboat Key

Travellers enjoy Longboat Key for its sunsets and seaside. Whether you're an adventurous traveller or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Longboat Key. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Siesta Key Beach (12 mi / 19.4 km)
  • Lido Beach (8.8 mi / 14.2 km)
  • Tampa Bay (25.2 mi / 40.6 km)
  • Longboat Key Beaches (2.8 mi / 4.6 km)
  • Coquina Beach (3.2 mi / 5.2 km)
  • Cortez Beach (4.2 mi / 6.7 km)

Seasonal weather averages in Longboat Key

Travellers enjoy Longboat Key for its boating. If you're hoping to enjoy some warm-weather activities on your holiday, August, July, June and September are the hottest months to visit, when temperatures average 28°C.

How to get to and around Longboat Key

The nearest airport is in Sarasota, FL (SRQ-Sarasota-Bradenton Intl.), located 6.7 mi (10.8 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to St. Petersburg, FL (SPG-Albert Whitted), which is 24.4 mi (39.2 km) away.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Longboat Key?
Condos are the most popular type of holiday rental in Longboat Key, according to our data. Even if you have a different idea about what you want, Vrbo has holiday homes in a variety of shapes and sizes. Take a look at our options to find your ideal match.
How much does it cost to rent a holiday rental in Longboat Key?
Length of stay, season and property type are some things that can determine the price of a holiday home. Simply enter your dates of travel to find your ideal match. From comfy cabins to expansive luxury villas, all Vrbo holiday rentals offer incredible value.
How much does it cost to rent a beach house in Longboat Key?
Prices for beach houses in Longboat Key differ depending on the size and type of the property and time of year you're travelling. Just enter your travel dates into Vrbo and how many guests to view your rental options and prices. From there you can use our filters to narrow your search by amenities, ratings, nearby activities and more.
What are popular rental amenities in Longboat Key?
A sauna, a beach view and tennis rank as the most popular rental amenities in Longboat Key. Whether you plan to go as a party of one, with your sweetheart or as a family group, Vrbo will help you find a holiday rental that suits your tastes with all the conveniences you're looking for.
What are the top attractions for families in Longboat Key?
There are loads of cool things to do and see with the family in Longboat Key, including:
  • Coquina Beach
  • Cortez Beach
  • Manatee Public Beach
Can I find two-bedroom holiday rentals in Longboat Key?
Longboat Key has 135 two-bedroom holiday rentals that you can choose from. Discover a holiday home with all the comfort and privacy you want at a price you'll love on Vrbo.
Are there holiday rentals with WiFi in Longboat Key?
You can pick from 94 holiday rentals with WiFi in Longboat Key. If you want to disconnect from daily life while on holiday, but still want to be connected to the web, these getaways have just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How old do you have to be to rent a holiday rental in Longboat Key?
The age limit can vary across properties on Vrbo, so be sure to check the rules of the holiday rental in Longboat Key you want to book. But normally, it's 16, 18 or 21.
How long can I rent a holiday rental in Longboat Key for?
How long you can book a holiday rental in Longboat Key depends on the property. Just enter your desired travel dates to look at a list of options offering extended stays. With plenty of amenities such as air conditioning and kitchens, as well as some offering weekly or monthly discounts, you're sure to get someplace just right to call your home away from home in Longboat Key.

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