Vacation Rentals with Pool in Longboat Key

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Filtering by: Swimming pool

1,717 vacation rentals

(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

(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

$198

Price per night from

$198

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

$229

Responds fast!
avg. 1 hour 58 minutes

Price per night from

$229

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

$358

Responds fast!
avg. 43 minutes

Price per night from

$358

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

$200

Responds fast!
avg. 14 minutes

Price per night from

$200

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

(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

(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

$214

Price per night from

$214

(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

$272

Price per night from

$272

(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

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

$471

Price per night from

$471

(6) Very Good 

29

* OCEAN BEACH FRONT *

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 42 minutes

Price per night from

$160

(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

$142

Responds fast!
avg. 3 hours 54 minutes

Price per night from

$142

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

$106

Price per night from

$106

(4) Very Good 

27

~ 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 42 minutes

Price per night from

$148

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

$178

Price per night from

$178

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

$281

Price per night from

$281

(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

16

DIRECT BEACH FRONT CONDO ** SPECIAL ** April 2 - 6

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

$139

Responds fast!
avg. 2 hours 42 minutes

Price per night from

$139

(5) Excellent 

25

ZILLI VILLA

Florida / Longboat Key

Longboat Key villa

2 10 7 nights min

  • 2 bedrooms
  • sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Price per night from

$228

Price per night from

$228

(5) Excellent 

53

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

Florida / Longboat Key

Longboat Key apartment

2 6 4 nights min

  • 2 bedrooms
  • sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“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
…see more

Price per night from

$209

Price per night from

$209

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

$430

Responds fast!
avg. 43 minutes

Price per night from

$430

(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

$195

Price per night from

$195

(1) Excellent 

24

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

Florida / Longboat Key

Longboat Key apartment

2 4 60 nights min

  • 2 bedrooms
  • sleeps 4
  • 60 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$68

Price per night from

$68

28

JAN 2019 AVAIL Multi-level Private Home LONGBOAT KEY w/elevator. close to beach!

Florida / Longboat Key

Longboat Key house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.4 mi
  • Swimming pool

Price per night from

$150

Responds fast!
avg. 1 hour 41 minutes

Price per night from

$150

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

$158

Price per night from

$158

(1) Average 

13

Beach front condo in Longboat Key

Florida / Longboat Key

Longboat Key condo

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$220

Responds fast!
avg. 2 hours 59 minutes

Price per night from

$220

11

2 bedroom poolside condo steps from ocean beach and dock on bay 4-13 to 4-20

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

$260

Responds fast!
avg. 43 minutes

Price per night from

$260

24

Lovely Tropical Longboat Town house

Florida / Longboat Key

Longboat Key townhouse

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$147

Responds fast!
avg. 7 minutes

Price per night from

$147

24

Longboat Key Cosy 1bed/1bath between white sand beach and Sarasota bay.

Florida / Longboat Key

Longboat Key apartment

1 4 90 nights min

  • 1 bedroom
  • sleeps 4
  • 90 nights min
  • Nearest beach 0.3 mi
  • Swimming pool
  • Air conditioning

Price per night from

$108

Price per night from

$108

45

Sand Cay #310 Luxurious 2/2 on the Beach DISCOUNTED RATES FOR JANUARY

Florida / Longboat Key

Longboat Key condo

2 6 3 nights min

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

Price per night from

$150

Price per night from

$150

28

Holiday Home Directly by Sea - Self Catering

Florida / Longboat Key

Longboat Key apartment

2 6 14 nights min

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

Price per night from

$213

Price per night from

$213

10

1 bedroom single story family friendly resort April 6-13, 2019

Florida / Longboat Key

Longboat Key condo

1 4 7 nights min

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

Price per night from

$213

Responds fast!
avg. 43 minutes

Price per night from

$213

38

Beach Paradise on the Gulf of Mexico, toes in the sand,sunsets, tennis, gym, it

Florida / Longboat Key

Longboat Key condo

3 6 21 nights min

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

Price per night from

$249

Responds fast!
avg. 31 minutes

Price per night from

$249

22

Beautiful Island Sanctuary Best Location in South Longboat Key!

Florida / Longboat Key

Longboat Key house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$425

Price per night from

$425

18

AVAILABLE NOW! 2/1.5 LONGBOAT KEY! PRIVATE BEACH ACCESS! 2 LARGE POOLS!

Florida / Longboat Key

Longboat Key villa

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 0.25 mi
  • Swimming pool
  • Child Friendly

Price per night from

$100

Price per night from

$100

20

Awe-inspiring Views of Sarasota Bay

Florida / Longboat Key

Longboat Key condo

2 5 30 nights min

  • 2 bedrooms
  • sleeps 5
  • 30 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$150

Price per night from

$150

11

2 bedroom Florida condo at family friendly resort 3-21 to 3-28

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

$257

Responds fast!
avg. 43 minutes

Price per night from

$257