Longboat Key holiday rentals

We found 11,806 holiday rentals — enter your dates for availability
Discover a selection of 20 homes, 17 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:13 Nov - 20 Nov

Living area
Pool
Exterior
Outdoor dining
Exceptional
(136 reviews)

6 Bedrooms - Waterfront,pool, dock, great for families. Big yard, lots of room.

Bradenton

8% off
S$10,039
for 7 nights, 1 home
S$1,434 per night
includes taxes & fees
6 Bedrooms - Waterfront,pool, dock, great for families. Big yard, lots of room.
Interior
Interior
Dining
Private kitchen
Exceptional
(42 reviews)

KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE

Sarasota

7% off
S$3,064
for 7 nights, 1 home
S$438 per night
includes taxes & fees
KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE
Private kitchen
Marina
Pool
Property grounds
Exceptional
(72 reviews)

Relaxing Lakefront Home: 3BR/2BA, Heated Pool, Near Siesta Key Beach

Sarasota

7% off
S$2,730
for 7 nights, 1 home
S$390 per night
includes taxes & fees
Relaxing Lakefront Home: 3BR/2BA, Heated Pool, Near Siesta Key Beach
Living area
Private kitchen
Interior
Interior
Exceptional
(64 reviews)

Waterfront/Kayak with Manatees/Heated Pool/Bikes/Firepit/Fish/close to Beaches

Bradenton

7% off
S$4,133
for 7 nights, 1 home
S$590 per night
includes taxes & fees
Waterfront/Kayak with Manatees/Heated Pool/Bikes/Firepit/Fish/close to Beaches
Stop by the local market and use our well-equipped kitchen for dining in.
Eat your grilled catch of the day poolside in our new outdoor dining set for 8.
It's cocktail hour!
Living area
Exceptional
(120 reviews)

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

Holmes Beach

7% off
S$6,800
for 7 nights, 1 home
S$971 per night
includes taxes & fees
Sunset Landing AMI Beach House. 6BR/4.5BA. Private pool. 2 blks to beach.
Terrace/patio
Property grounds
Living area
Exterior detail
Exceptional
(101 reviews)

Sarasota Cozy & Clean, Near #1 Beach Siesta in SouthGate Neighborhood

Sarasota

8% off
S$1,188
for 7 nights, 1 apartment
S$170 per night
includes taxes & fees
Sarasota Cozy & Clean, Near #1 Beach Siesta in SouthGate Neighborhood
Marina
Outdoor dining
Waterfront restaurant on premisis with live music
Fitness facility
Very good
(164 reviews)

SARASOTA Waterfront hotel Room KING BED # 215 ON SARA BAY 7150 N Tamiami Trail

Sarasota

7% off
S$881
for 7 nights, 1 room
S$126 per night
includes taxes & fees
SARASOTA Waterfront hotel Room KING BED # 215 ON SARA BAY 7150 N Tamiami Trail
Fitness facility
Pool
Outdoor dining
Property grounds
Excellent
(155 reviews)

Right on the Waterfront Marina - Suite 117 - 7150 N Tamiami Tail, Sarasota FL

Sarasota

8% off
S$1,083
for 7 nights, 1 room
S$155 per night
includes taxes & fees
Right on the Waterfront Marina - Suite 117 - 7150 N Tamiami Tail, Sarasota FL
Large dinning room
Desk/office space
Living area
Pool
Exceptional
(61 reviews)

Amazing heated pool & spa just minutes from Anna Maria Island

Bradenton

7% off
S$2,990
for 7 nights, 1 home
S$427 per night
includes taxes & fees
Amazing heated pool & spa just minutes from Anna Maria Island
exercise room in main building
Kitchen renovated Fall 2013/Spring 2014
Room
activity area in main building
Exceptional
(107 reviews)

Palm Bay Club - Bayfront Large 2/2 Condo - Reasonable Price

Siesta Key

6% off
S$3,193
for 7 nights, 1 apartment
S$456 per night
includes taxes & fees
Palm Bay Club - Bayfront Large 2/2 Condo - Reasonable Price
living room
private rooftop deck
Dining area
Exterior
Exceptional
(82 reviews)

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

Bradenton Beach

7% off
S$3,786
for 7 nights, 1 apartment
S$541 per night
includes taxes & fees
Anna Maria Sunrise on the Bay, Sunsets on the beach.Luxury 3BR with Rooftop Deck
Beach
Interior
Interior
Living area
Exceptional
(30 reviews)

Beach front paradise located in a Condo Building Beach front Penthouse!

Siesta Key

8% off
S$5,912
for 7 nights, 1 home
S$845 per night
includes taxes & fees
Beach front paradise located in a Condo Building Beach front Penthouse!
Living area
Bookcases open to let in more sunlight from the bedroom.
Open kitchen with eat-at-island and drop-leaf table for additional dining.
A great place to watch beach goers on their way to Bean Point.
Exceptional
(202 reviews)

Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!

Anna Maria

7% off
S$4,775
for 7 nights, 1 home
S$682 per night
includes taxes & fees
Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!
Interior
Sports court
Interior
Private kitchen
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$2,029
for 7 nights, 1 home
S$290 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
Private kitchen
Island Time! Bridge St.
Perfect private outdoor space rain or shine.
Interior
Exceptional
(196 reviews)

2 BR 2 Full BA on Anna Maria Island just steps to Beach!

Bradenton Beach

8% off
S$3,225
for 7 nights, 1 home
S$461 per night
includes taxes & fees
2 BR 2 Full BA on Anna Maria Island just steps to Beach!
Children’s area
Room
Dining
Room
Exceptional
(24 reviews)

Villa & Garden in Downtown Sarasota ~ Walkable to downtown, 5 Minutes to Beaches

Sarasota

7% off
S$2,801
for 7 nights, 1 villa
S$400 per night
includes taxes & fees
Villa & Garden in Downtown Sarasota ~ Walkable to downtown, 5 Minutes to Beaches
Private kitchen
Interior
Dining
Living area
Exceptional
(43 reviews)

3 Minute walk to beautiful AMI beach! Old Florida Charm with a Modern Flair!

Holmes Beach

7% off
S$1,743
for 7 nights, 1 apartment
S$249 per night
includes taxes & fees
3 Minute walk to beautiful AMI beach! Old Florida Charm with a Modern Flair!
Interior
Sports court
Terrace/patio
Exterior
Exceptional
(181 reviews)

Amazing 1 Br/1 Ba Condo at Casa Mar

Siesta Key

7% off
S$3,008
for 7 nights, 1 apartment
S$430 per night
includes taxes & fees
Amazing 1 Br/1 Ba Condo at Casa Mar
Guest bedroom downstairs with a queen bed.
Fully stocked kitchen perfect for eating at home.
Screened in patio seats 8 at the table. 
Love seat and two swiveled chairs.
Dining room seats 8
Exceptional
(68 reviews)

Ingram House 2

Sarasota

5% off
S$2,670
for 7 nights, 1 home
S$381 per night
includes taxes & fees
Ingram House 2
Boat/Fishing Deck
Quiet and safe neighborhood for families to swim, walk, bike, and fish
Front Entrance
View of spacious main pool and clubhouse.  Dry sauna and gym inside.
Exceptional
(101 reviews)

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

Siesta Key

5% off
S$3,293
for 7 nights, 1 apartment
S$470 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)
  • Fort De Soto Park (15.8 mi / 25.4 km)
  • Tampa Bay (25.2 mi / 40.6 km)
  • Jewfish Key (2.5 mi / 3.9 km)
  • Longboat Key Beaches (2.8 mi / 4.6 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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