Vacation Rentals & Apartments in Longboat Key

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3,034 apartments

31

LaPlaya 109A

Florida / Longboat Key

Longboat Key condo

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Ask about children

Price per night from

$311

Price per night from

$311

(3) Excellent 

18

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

Florida / Longboat Key

Longboat Key house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.02 mi
  • Swimming pool

Price per night from

$263

Price per night from

$263

21

Beautiful Private condo on the beach

Florida / Longboat Key

Longboat Key condo

2 6 14 nights min

  • 2 bedrooms
  • sleeps 6
  • 14 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$230

Responds fast!
avg. 1 hour 58 minutes

Price per night from

$230

(4) Very Good 

17

Spacious Gulf Front beach condo on Longboat Key

Florida / Longboat Key

Longboat Key apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Price per night from

$227

Price per night from

$227

(14) Excellent 

7

Las Hermanas/Starfish #3 Beach front Longboat Key

Florida / Longboat Key

Longboat Key apartment

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Ask about children
“Little Piece Of Paradise” Everything you could want in a vacation rental. We wanted to be right on the beach and this place offers that and more. Great kitchen,stocked with everything you need. Beach views from almost every room. We really enjoyed ea
…see more

Price per night from

$164

Responds fast!
avg. 2 hours 56 minutes

Price per night from

$164

24

Longboat Key Condo w/ Pool Access- Walk to Bay!

Florida / Longboat Key

Longboat Key apartment

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$229

Responds fast!
avg. 10 minutes

Price per night from

$229

(12) Excellent 

38

Beachfront Condo on the Beautiful Gulf of Mexico

Florida / Longboat Key

Longboat Key apartment

2 4 4 nights min

  • 2 bedrooms
  • sleeps 4
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Child Friendly
“Great place to Relax!” This is my 2nt time renting this property and I highly recommend it. It is the perfect place to relax & unwind. Beach is great & Ramona makes the whole renting process easy & painless. Looking forward to staying here again soon!
…see more

Price per night from

$344

Responds fast!
avg. 1 hour 59 minutes

Price per night from

$344

(2) Very Good 

8

Longboat Key Retreat

Florida / Longboat Key

Longboat Key house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$148

Price per night from

$148

111

Longboat Key: Dolphins & Sunsets

Florida / Longboat Key

Longboat Key house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child Friendly

Price per night from

$412

Responds fast!
avg. 43 minutes

Price per night from

$412

(2) Very Good 

29

Outrigger Resort unit #3

Florida / Longboat Key

Longboat Key apartment

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Price per night from

$246

Price per night from

$246

13

Little Gull Cottages

Florida / Longboat Key

Longboat Key cottage

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$144

Price per night from

$144

(11) Excellent 

7

Las Hermanas/Starfish #2 Beachfront Longboat Key

Florida / Longboat Key

Longboat Key apartment

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Ask about children
“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.
…see more

Price per night from

$163

Responds fast!
avg. 2 hours 56 minutes

Price per night from

$163

(1) Excellent 

13

Gulf of Mexico Paradise

Florida / Longboat Key

Longboat Key apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.16 mi
  • Swimming pool

Price per night from

$164

Responds fast!
avg. 3 hours 54 minutes

Price per night from

$164

(1) Excellent 

12

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

Florida / Longboat Key

Longboat Key apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$313

Price per night from

$313

(8) Excellent 

6

Beachfront Longboat Key Studio #1

Florida / Longboat Key

Longboat Key apartment

4 7 nights min

  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Ask about children
“Location! Location! Location!” The listing description and photos were accurate, this rental property is amazing. Studio #1 was tastefully decorated and very clean. We had beautiful views of the ocean from the living area. It was very spacious with pl
…see more

Price per night from

$142

Responds fast!
avg. 2 hours 56 minutes

Price per night from

$142

(1) Excellent 

28

Renovated Beachfront Condo with Spectacular Ocean View unit 403

Florida / Longboat Key

Longboat Key apartment

1 6 2 nights min

  • 1 bedroom
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$204

Price per night from

$204

(10) Excellent 

11

Beachfront Unit 4, Cozy Getaway for two

Florida / Longboat Key

Longboat Key apartment

2 7 nights min

  • sleeps 2
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Child Friendly
“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 crowd
…see more

Price per night from

$130

Responds fast!
avg. 2 hours 56 minutes

Price per night from

$130

5

Two Story Condo on the Gulf of Mexico

Florida / Longboat Key

Longboat Key condo

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$541

Price per night from

$541

12

55+ Community with pool and club house

Florida / Longboat Key

Longboat Key villa

2 6 90 nights min

  • 2 bedrooms
  • sleeps 6
  • 90 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$81

Price per night from

$81

18

30% off Designer Villa on canal next to secluded beach

Florida / Longboat Key

Longboat Key house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 3 mi
  • Child Friendly
  • Air conditioning

Price per night from

$167

Price per night from

$167

(6) Very Good 

19

225* BEACH FRONT APARTMENT *

Florida / Longboat Key

Longboat Key apartment

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child Friendly

Price per night from

$160

Responds fast!
avg. 2 hours 30 minutes

Price per night from

$160

(1) Excellent 

28

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

Florida / Longboat Key

Longboat Key apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child Friendly

Price per night from

$306

Responds fast!
avg. 3 hours 30 minutes

Price per night from

$306

(4) Very Good 

28

~ The Beach on Longboat Key ~ * OCEAN FRONT DLX STUDIO - SPECIAL *

Florida / Longboat Key

Longboat Key studio

Studio 3 min stay varies

  • Studio
  • sleeps 3
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“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.
…see more

Price per night from

$148

Responds fast!
avg. 2 hours 30 minutes

Price per night from

$148

54

761 Penfield

Florida / Longboat Key

Longboat Key house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly

Price per night from

$267

Price per night from

$267

23

LaPlaya 201C

Florida / Longboat Key

Longboat Key condo

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Ask about children

Price per night from

$415

Price per night from

$415

20

Beautiful Gulf Front, Newly Renovated #319 Sand Cay on Longboat Key, Sarasota

Florida / Longboat Key

Longboat Key apartment

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$282

Price per night from

$282

19

STUDIO - DIRECT BEACH FRONT CONDO

Florida / Longboat Key

Longboat Key apartment

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child Friendly

Price per night from

$149

Responds fast!
avg. 2 hours 30 minutes

Price per night from

$149

15

Private Bungalow on Canal a block from Beach

Florida / Longboat Key

Longboat Key house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$165

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$165

12

Newly renovated 2/2 w/ private beach access!

Florida / Longboat Key

Longboat Key condo

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$122

Price per night from

$122

19

LaPlaya 104E

Florida / Longboat Key

Longboat Key apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Ask about children

Price per night from

$220

Price per night from

$220

(8) Excellent 

29

1 BEDROOM ON THE BEACH ,LAST MINUTE CANCELATION DISCOUNTED RATES FOR JAN/FEB

Florida / Longboat Key

Longboat Key apartment

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“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
…see more

Price per night from

$150

Price per night from

$150

35

Amazing views of the Gulf and beach from your own balcony unit 301

Florida / Longboat Key

Longboat Key apartment

1 6 2 nights min

  • 1 bedroom
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$205

Price per night from

$205

(1) Excellent 

28

Paradise Cottage at Longboat Key

Florida / Longboat Key

Longboat Key cottage

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Car not necessary
  • Pet Friendly

Price per night from

$229

Price per night from

$229

12

Florida Ocean Front Condo April 13-20, 2019

Florida / Longboat Key

Longboat Key condo

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$493

Responds fast!
avg. 43 minutes

Price per night from

$493

6

Beach Front 1 Bedroom Condo on Gulf of Mexico #10

Florida / Longboat Key

Longboat Key apartment

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask about children

Price per night from

$182

Price per night from

$182

17

Honeysuckle Cottage in North Village of Longboat Key, Fla

Florida / Longboat Key

Longboat Key cottage

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$108

Responds fast!
avg. 2 hours 11 minutes

Price per night from

$108

(6) Very Good 

15

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

Florida / Longboat Key

Longboat Key house

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly
“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 arou
…see more

Price per night from

$121

Responds fast!
avg. 2 hours 11 minutes

Price per night from

$121

(1) Excellent 

44

Zilli Ocean Front 101

Florida / Longboat Key

Longboat Key condo

1 6 7 nights min

  • 1 bedroom
  • sleeps 6
  • 7 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child Friendly

Price per night from

$224

Price per night from

$224

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.