Updating...

Enter dates for more accurate prices

Vacation Rentals & Apartments in Longboat Key

Filter

Vacation Rentals & Apartments in Longboat Key

About Longboat Key

2,831 apartments

Beachfront Condo on the Beautiful Gulf of Mexico

Longboat Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Seclusion and Privacy Steps away From Paradise” Check-in was simple. This gem is located directly on the beach with multiple private houses to the north and a small condo to the south. This made for a private beach setting as there were never more than 10 people on the neighboring properties. Having access to the private garage as well as all the beach furniture and gas grill made the stay that much more enjoyable. The porch was a great setting for breakfast each morning watching the sea life playing in the surf. The location is just a minute from the new Publix as well as a few minutes from St armand's Circle. Plenty of fine dining choices nearby, including Dry Dock Waterfront Grille, Chart House, and Tommy Bahamas. This was our second stay within the past 12 months at this location and it was even better than the first. We definitely plan on returning.

Responds fast! avg. 1 hour 59 minutes

Price per night from

$301

1 / 38

Beautiful Private condo on the beach

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$200

1 / 21

Spacious Gulf Front beach condo on Longboat Key

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$197

1 / 17

NEW! 2BR Longboat Key Condo - Walk to Bay!

Longboat Key apartment

2 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 13 minutes

Price per night from

$250

1 / 24

Las Hermanas/Starfish #3 Beach front Longboat Key

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 4

“Beach front relaxation!” Lovely apartment, clean and well maintained with all the facilities you could need. Nice patio area leading straight onto the beach. A short walk away from Publix - I wish our UK supermarkets were as nice as this one - and a post office nearby too. Stayed here for the first time last year with my parents who are regular visitors. We rented two apartments next door to each other in the block of four, and can't wait to return again in 2015.

Responds fast! avg. 3 hours 9 minutes

Price per night from

$142

1 / 7

Charming Beach House in Longboat Key/ pool/pet/dock

Longboat Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$229

1 / 18

Longboat Key Gulf-front 2 BR/2 BA, amazing views

Longboat Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$272

1 / 12

Gulf of Mexico Paradise

Longboat Key apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$142

1 / 13

Beachfront Unit 4, Cozy Getaway for two

Longboat Key apartment

/ 1 bathroom / sleeps 2

“Relaxing Beachfront Studio” My wife and I stayed here over Spring Break, and had a wonderful time. The unit was clean, updated, and had all the amenities we needed. The beach, which was just steps out the back door, was quiet and away from the crowds (we go on vacation to relax, not fight over beach chairs and get trampled by people). And the building's location is close to St Armand's Circle, great for dining and shopping. We will definitely be back, thank you Jim and Cindy for a great stay!

Responds fast! avg. 3 hours 9 minutes

Price per night from

$113

1 / 11

Outrigger Resort unit #3

Longboat Key apartment

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$214

1 / 29

55+ Community with pool and club house

Longboat Key villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$71

1 / 12

Village of Longboat Key, 1 BR & 1 BA Comfortable Cottage Very Clean

Longboat Key house

1 bedroom / 1 bathroom / sleeps 4

“VERY Pretty” When they say Luxury Log Cabin, that is exactly what you get. This home was beautiful!! Everything you need to stay all night or a week. Living room with couch chair tv, kitchen with everything. 1 bed and full bath upstairs, wrap around deck. Loft with beds too. Downstairs, laundry, 2 bedrooms, couch tv full bath walk out basement to the deck looking right at the water. Best part.. one minute to the strip and you could travel anywhere in short amount of time.

Price per night from

$105

1 / 14

Steps to the Sand! Longboat Key 2 Bed 2 & 1/2 Bath Gulf Front Condo with Den.

Longboat Key apartment

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 21 minutes

Price per night from

$301

1 / 28

Beach Front 1 Bedroom Condo on Gulf of Mexico #10

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$158

1 / 6

** DIRECT OCEAN FRONT SPECIAL MONDAY TO FRIDAY **

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 6 minutes

Price per night from

$139

1 / 29

Las Hermanas/Starfish #2 Beachfront Longboat Key

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 4

“Paradice on the beach” We really enjoyed our stay at Las Hermanas/ Starfish, right on the beach, nice sand and great view of the ocean and sunsets. Very clean and well appointed rooms. Good parking. Handy laundry room.

Responds fast! avg. 3 hours 9 minutes

Price per night from

$142

1 / 7

Sand Cay #310 Luxurious 2/2 on the Beach $150.00. RED TIDE IS GONE!

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$151

1 / 27

Gulf Breezes, Soft Sand! Your Place on the beach!

Longboat Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Brillant” This was the best place I ever stayed in - it was just on the beech and even though the water was chilly the pool is heated- the grounds are a delight for plant lovers , and included an orchid garden- the staff are top class - always there and always more than helpful - there is a security fellow in charge at night - Justin- he is more than helpful - and the service over teh 24 hrs is just great if you arrive late at night and are lost - Justin will keep you on the phone until you arrive !!! thanks for that Justin. We will definitly be returning and the sooner the better , in all a great place and it included the lovely apartment with all mod cons and spotlessly clean - Patricia Bowler

Price per night from

$172

1 / 55

Longboat Key Retreat

Longboat Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$129

1 / 8

LaPlaya 109A

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$258

1 / 31

Beachfront Longboat Key Studio #1

Longboat Key apartment

/ 1 bathroom / sleeps 4

“If you are looking for a quiet and quaint place stay here” Very clean and nicely decorated. Beautiful kitchen, comfortable bathroom and the views and the beach are amazing!! Great service by Jimand Cindy

Responds fast! avg. 3 hours 9 minutes

Price per night from

$124

1 / 6

July SPECIAL Designer Villa on canal next to secluded beach

Longboat Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$145

1 / 18

Beach Castle Resort 6

Longboat Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$270

1 / 28

BBB on Marbury lane-Beach, boating, BBQ!

Longboat Key house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 6 minutes

Price per night from

$250

1 / 19

Longboat Key FL Seaplace 2Br 2Bth 2 Month Min Rent

Longboat Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$68

1 / 24

Honeysuckle Cottage in North Village of Longboat Key, Fla

Longboat Key cottage

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$89

1 / 17

761 Penfield

Longboat Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$233

1 / 54

Longboat Key: Dolphins & Sunsets

Longboat Key house

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 1 hour 39 minutes

Price per night from

$286

1 / 111

** OCEAN FRONT DLX STUDIO - SPECIAL FROM $99/NIGHT **

Longboat Key studio

Studio / 1 bathroom / sleeps 3

“Nice Beachfront Location” We stayed there in late June and found it very suitable for our needs. The beach was very accessible. View was awesome. The unit was clean and comfortable for 2 adults.

Responds fast! avg. 3 hours 6 minutes

Price per night from

$109

1 / 27

Two Story Condo on the Gulf of Mexico

Longboat Key condo

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$515

1 / 5

Private Bungalow on Canal a block from Beach

Longboat Key house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 57 minutes

Price per night from

$176

1 / 15

Florida Ocean Front Condo April 13-20, 2019

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$431

1 / 12

LaPlaya 104E

Longboat Key apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$183

1 / 19

LUXURIOUS 1 BEDROOM ON THE BEACH , $150.00 PER NIGHT. RED TIDE IS GONE!

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 4

“beautiful condo & wonderful stay” My wife & I just returned from a 4 night stay at this property in Longboat Key and had a wonderful vacation. The condo is beautifully and tastefully decorated, making us feel at home immediately. Everything we needed was furnished in the condo. You are steps away from the beach, walking right out of the unit on the 2nd floor to the balcony and down a flight of stairs. The condo faces east/west , so you can see the sun rising through the bedroom in the front, and the sun setting through the open living room/kitchen area or out on the balcony where there are chairs. Spectacular water views all day long. This is a very spacious 1 bdr unit with a nice open floor plan. The office staff was also very helpful and gracious and the grounds are kept in great shape. The property does not have the amenities of a hotel; there is no bar or restaurant, and that suited us just fine. This is a very quiet and relaxing property. Overall, a great stay and we plan on returning for getaways hopefully once or twice a year.

Price per night from

$151

1 / 29

Lovely Tropical Longboat Town house

Longboat Key townhouse

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 20 minutes

Price per night from

$128

1 / 24

Renovated Beachfront Condo with Spectacular Ocean View

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$168

1 / 28

LaPlaya 201C

Longboat Key condo

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$344

1 / 23

~OCEAN FRONT SPECIAL ~ Please inquire about special rates

Longboat Key apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 6 minutes

Price per night from

$167

1 / 16
Viewing 38 of 2,831

About Longboat Key

×

With warm weather year-round and some of the best beaches in the region, Longboat Key has become one of the premiere vacation destinations in the Florida area. Longboat Key has several major festivals and events held throughout the year, so try to plan your trip around one of them. Some of the major events in the area include the St. Armand's Circle Art Festival, held in late January; the Say I Do Again Festival on Valentine's Day, where couples can renew their vows on Siesta Public Beach; and the Siesta Fiesta, an annual arts and crafts fair held in early May.

While you're on vacation in the Longboat Key area, be sure to make time for some of these main attractions and destinations:

  • Sarasota Jungle Gardens: There are five shows at the gardens that feature both animals and rare plants.
  • Historic Palm Avenue: This is known as downtown Sarasota's "Best Walk in Town."
  • Bolletieri Tennis Academy: Located in nearby Bradenton, see the academy where champions like Andre Agassi and Monica Seles got their start.
  • Go shopping: St. Armand's Circle has a huge selection of unique shops and fine dining.
  • Catch a baseball game: If you're in the area during the spring, the Baltimore Orioles train in nearby Sarasota.
  • Historic Spanish Point: Take a guided tour here and learn more about the history of Southwest Florida.

No matter what time of year you visit, you'll be able to find a vacation rental in Longboat Key to suit your needs. In addition to villa rentals with all the amenities and comforts of home, you can also book a beachfront condo rental with white sand beaches right outside your door.

There are also several excellent day-trip options from Longboat Key. Tampa is a short drive via I-75 North. Disney World is also a short distance by car and offers an unforgettable experience for the whole family.

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more