Longboat Key holiday rentals

We found 11,907 holiday rentals — enter your dates for availability
Discover a selection of 16 homes, 15 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:25 Dec - 1 Jan

Have your morning coffee on the lanai.
Quiet spot in paradise
French doors to the lanai and 60 inch TV on the wall.
Gumbo tree in front yard
Exceptional
(92 reviews)

Quiet cozy home near Anna Maria Island, Robinson Preserve, DeSoto Nt’l Monument

Bradenton

8% off
S$2,175
for 7 nights, 1 home
S$311 per night
includes taxes & fees
Quiet cozy home near Anna Maria Island, Robinson Preserve, DeSoto Nt’l Monument
Rainbow at The Cut House
Kitchen
Manatee River with 120 ft dock
View of River from house
Exceptional
(64 reviews)

Snead Island Cut Home - Oceanfront near Anna Maria , Boat docking, pet friendly

Palmetto

8% off
S$4,052
for 7 nights, 1 home
S$579 per night
includes taxes & fees
Snead Island Cut Home - Oceanfront near Anna Maria , Boat docking, pet friendly
Pool
Anna Maria, Florida's ocean is your ultimate fun zone!
Living, lounging, cooking—our space does it all.
Shopping on Anna Maria Island is like discovering hidden gems!
Exceptional
(56 reviews)

Luxury Family Escape: Spacious 4BR, Pool, Close to AMI, Dining & Attractions!

Bradenton

8% off
S$10,035
for 7 nights, 1 home
S$1,434 per night
includes taxes & fees
Luxury Family Escape: Spacious 4BR, Pool, Close to AMI, Dining & Attractions!
Exterior detail
Private kitchen
Terrace/patio
Room
Exceptional
(84 reviews)

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

Sarasota

8% off
S$2,379
for 7 nights, 1 home
S$340 per night
includes taxes & fees
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Dining
Living area
Private kitchen
Living area
Exceptional
(212 reviews)

Exceptional Five Star Sarasota Cottage Old Florida Charm Dogs Stay Free

Sarasota

8% off
S$2,166
for 7 nights, 1 home
S$309 per night
includes taxes & fees
Exceptional Five Star Sarasota Cottage Old Florida Charm Dogs Stay Free
Property grounds
Pool
Fitness facility
Room
Excellent
(156 reviews)

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

Sarasota

8% off
S$1,077
for 7 nights, 1 room
S$154 per night
includes taxes & fees
Right on the Waterfront Marina - Suite 117 - 7150 N Tamiami Tail, Sarasota FL
Heated waterfront pool
Outdoor dining
Waterfront restaurant on premisis with live music
Marina
Very good
(164 reviews)

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

Sarasota

8% off
S$1,065
for 7 nights, 1 room
S$152 per night
includes taxes & fees
SARASOTA Waterfront hotel Room KING BED # 215 ON SARA BAY 7150 N Tamiami Trail
Arial view of the building - right on the beach!
Beach
Living area
Interior
Exceptional
(24 reviews)

Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6

Siesta Key

8% off
S$4,773
for 7 nights, 1 apartment
S$682 per night
includes taxes & fees
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6
Interior
Private kitchen
Living area
Exterior
Exceptional
(63 reviews)

Charming Beach home sits amongst huge Banyan Trees, walk to beach’s & Pine Ave.

Anna Maria

8% off
S$4,350
for 7 nights, 1 home
S$621 per night
includes taxes & fees
Charming Beach home sits amongst huge Banyan Trees, walk to beach’s & Pine Ave.
Beach
Room
Interior
Living area
Exceptional
(6 reviews)

Private Suite w/ Lounge & Private Patio

Bradenton

8% off
S$852
for 7 nights, 1 apartment
S$122 per night
includes taxes & fees
Private Suite w/ Lounge & Private Patio
Local artist painted bar seats
Unit 6 with vegetation no longer there
Cable tv
Salt Bar and Table
Exceptional
(42 reviews)

Gulf Front • Steps to Sand • Sunset View • Balcony

Bradenton Beach

8% off
S$6,550
for 7 nights, 1 apartment
S$936 per night
includes taxes & fees
Gulf Front • Steps to Sand • Sunset View • Balcony
Room
Property grounds
Beach
Pool
Exceptional
(36 reviews)

Perfect 1-bedroom condo with AC in Bradenton Beach

Bradenton Beach

8% off
S$3,236
for 7 nights, 1 apartment
S$462 per night
includes taxes & fees
Perfect 1-bedroom condo with AC in Bradenton Beach
Dining
Private kitchen
Living area
Pool
Exceptional
(65 reviews)

Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home

Bradenton

8% off
S$6,723
for 7 nights, 1 home
S$960 per night
includes taxes & fees
Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home
Bedroom #2- Queen mattress
Terrace/patio
Private kitchen
Bathroom
Exceptional
(21 reviews)

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

Sarasota

8% off
S$2,195
for 7 nights, 1 home
S$314 per night
includes taxes & fees
Charming 2-bedroom house in the heart of Sarasota—A quaint nature escape
Interior
Interior
Exterior
Private kitchen
Wonderful
(9 reviews)

Family Pool Home Near Anna Maria Island & IMG

Bradenton

7% off
S$2,806
for 7 nights, 1 home
S$401 per night
includes taxes & fees
Family Pool Home Near Anna Maria Island & IMG
Private kitchen
Marina
Property grounds
Living area
Exceptional
(41 reviews)

Siesta Key Beachside Condo-direct beach access

Siesta Key

8% off
S$3,527
for 7 nights, 1 apartment
S$504 per night
includes taxes & fees
Siesta Key Beachside Condo-direct beach access
Room
Private kitchen
Living area
Interior
Exceptional
(34 reviews)

Renovated 2-bed 2 bath home with Pool, Garage, just a bike ride to Siesta Key!

Sarasota

7% off
S$2,226
for 7 nights, 1 home
S$318 per night
includes taxes & fees
Renovated 2-bed 2 bath home with Pool, Garage, just a bike ride to Siesta Key!
Marina
Outdoor dining
Fitness facility
Waterfront restaurant on site with live music
Very good
(175 reviews)

Sarasota “Deluxe King Waterfront Suite” #201 At the Hotel at 7150 N TAMIAMI TR

Sarasota

8% off
S$978
for 7 nights, 1 room
S$140 per night
includes taxes & fees
Sarasota “Deluxe King Waterfront Suite” #201 At the Hotel at 7150 N TAMIAMI TR
Entrance for Checkin
Boat rentals
Large, heated swimming pool and Tiki Bar.
Canal, Tiki Bar, pool
Exceptional
(34 reviews)

Suite newly remodeled, numerous resort like amenities. Take a romantic weekend.

Sarasota

8% off
S$1,799
for 7 nights, 1 apartment
S$257 per night
includes taxes & fees
Suite newly remodeled, numerous resort like amenities. Take a romantic weekend.
Private kitchen
Interior
Pool
Room
Exceptional
(26 reviews)

Family Poolside Paradise on Quiet Cul-de-Sac 4.7 Miles from Siesta Key Beach

Sarasota

8% off
S$6,093
for 7 nights, 1 home
S$870 per night
includes taxes & fees
Family Poolside Paradise on Quiet Cul-de-Sac 4.7 Miles from Siesta Key Beach
Fully stocked coffee bar includes: loose coffee, K-cups, sugars, and more.
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

7% off
S$2,245
for 7 nights, 1 home
S$321 per night
includes taxes & fees
Ingram House 2
Exterior
Beach
Private kitchen
Room
Exceptional
(105 reviews)

Low Rider - Bottom Unit -

Bradenton Beach

8% off
S$4,466
for 7 nights, 1 home
S$638 per night
includes taxes & fees
Low Rider - Bottom Unit -
Property grounds
Enclosed patio area with private pool
Interior
Pool
Exceptional
(57 reviews)

Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks

Sarasota

5% off
S$4,492
for 7 nights, 1 home
S$642 per night
includes taxes & fees
Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks
Room
Interior
Living area
Living area
Wonderful
(49 reviews)

🌴 Peaceful Sarasota Home with Patio, 2BR, 2BA Near Lido Beach & Downtown

Sarasota

7% off
S$1,487
for 7 nights, 1 home
S$212 per night
includes taxes & fees
🌴 Peaceful Sarasota Home with Patio, 2BR, 2BA Near Lido Beach & Downtown
  • 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. Lido Beach and Siesta Key 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)
  • University Park Country Club (11.2 mi / 18.1 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)

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:

  • Lido Beach (8.8 mi / 14.2 km)
  • Siesta Key Beach (12 mi / 19.4 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.

More holiday ideas