Vacation Rentals with Pool in Sarasota

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Filtering by: Swimming pool

1,788 vacation rentals
28

1 bedroom cottage with pool and walk to the beach

Sarasota / Lido Key

Lido Key cottage

1 6 1 night min

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

Price per night from

$104

Price per night from

$104

36

Walk to Crescent Beach, Wifi, Community Pool, Pool, Large Townhouse, Private Lau

Southwest Gulf Coast / Sarasota

Sarasota house

3 5 min stay varies

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

Price per night from

$94

Responds fast!
avg. 8 minutes

Price per night from

$94

(1) Excellent 

35

Fido Friendly w/Fenced Yard, Spa/Swimming Pool, Wifi, Large Ranch Home, Large L

Southwest Gulf Coast / Sarasota

Sarasota house

3 7 7 nights min

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

Price per night from

$111

Responds fast!
avg. 8 minutes

Price per night from

$111

(1) Excellent 

37

Oceanfront home w/sunset views of Sarasota Bay

Southwest Gulf Coast / Sarasota

Sarasota house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 10 mi
  • Swimming pool
  • Child Friendly

Price per night from

$148

Responds fast!
avg. 1 hour 19 minutes

Price per night from

$148

31

EATON PLACE

Sarasota / Lido Key

Lido Key house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 16 mi
  • Swimming pool
  • Child Friendly

Price per night from

$174

Price per night from

$174

27

3BR/3BA w/ Fenced Pool, Hot Tub, Patio & Outdoor Kitchen - 1 Block to Bay

Southwest Gulf Coast / Sarasota

Sarasota house

3 6 3 nights min

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

Price per night from

$232

Price per night from

$232

(4) Excellent 

13

Siesta Beach Cottage

Southwest Gulf Coast / Sarasota

Sarasota apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Beautiful place!” Enjoyed our stay in Sarasota on this property! We were not there much but when we were it felt like home. Very clean inside and out. The owner Kimberly showed us were everything was when we got there. Had a nice pool but too cold out
…see more

Price per night from

$189

Price per night from

$189

(4) Excellent 

28

Pet Friendly Pool Home Close to Beaches & Town

Southwest Gulf Coast / Sarasota

Sarasota house

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$174

Responds fast!
avg. 3 hours 41 minutes

Price per night from

$174

13

FLORIDA POOL HOME FOR RENT

Southwest Gulf Coast / Sarasota

Sarasota house

3 6 7 nights min

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

Price per night from

$128

Price per night from

$128

(1) Very Good 

17

Spectacular Vacation Experience

Southwest Gulf Coast / Sarasota

Sarasota house

3 7 29 nights min

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

Price per night from

$239

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$239

(25) Excellent 

44

Canal Pool Home (15 mins to Siesta Key Beach)

Southwest Gulf Coast / Sarasota

Sarasota house

4 8 6 nights min

  • 4 bedrooms
  • sleeps 8
  • 6 nights min
  • Beach / lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool
“Canal pool home” The home was wonderful. Plenty of space for everyone. Kids loved the pool & adults too. Fabulous time on Siesta Key, Longboat Key & Venice beaches.
…see more

Price per night from

$142

Responds fast!
avg. 1 hour 39 minutes

Price per night from

$142

26

House 3 miles to Siesta Key - Walk to Gulf Gate!

Southwest Gulf Coast / Sarasota

Sarasota house

2 6 min stay varies

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

Price per night from

$139

Responds fast!
avg. 10 minutes

Price per night from

$139

(12) Excellent 

58

Luxury Condominium at Siesta Dunes Beachside Pool Hot Tub Tennis Sun Deck

Southwest Gulf Coast / Sarasota

Sarasota apartment

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Very comfortable lodgings” Loads of extras in this unit. Well cared for, updated very nicely. Disappointed that the large deck was taken out of service, possibly for a year! It seems to me that usage could have been sustained by posting signs that cau
…see more

Price per night from

$223

Responds fast!
avg. 3 hours 31 minutes

Price per night from

$223

30

Huge 4BR/4BA w/ Screened Pool, BBQ, Ping-Pong, & Sunroom - Walk to Lido Beach

Southwest Gulf Coast / Sarasota

Sarasota house

4 8 3 nights min

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

Price per night from

$318

Price per night from

$318

(2) Very Good 

29

Family friendly house with pool/spa

Sarasota / Lido Key

Lido Key house

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$174

Responds fast!
avg. 2 hours 11 minutes

Price per night from

$174

(1) Excellent 

21

Renovated ! Heated pool! House Close To USA's Best Beach! Great Rates!

Southwest Gulf Coast / Sarasota

Sarasota villa

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child Friendly

Price per night from

$185

Responds fast!
avg. 3 hours 28 minutes

Price per night from

$185

(1) Excellent 

22

Beautiful 3 bedms/2 bathms with pool close to Downtown

Southwest Gulf Coast / Sarasota

Sarasota house

3 6 7 nights min

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

Price per night from

$125

Price per night from

$125

34

Walk to Siesta Key, No Car Needed, Newly Renovated, Views of Pool, WiFi

Southwest Gulf Coast / Sarasota

Sarasota apartment

2 4 min stay varies

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

Price per night from

$61

Responds fast!
avg. 8 minutes

Price per night from

$61

(1) Excellent 

13

Deluxe Bungalow on Lido Key by St. Armands

Southwest Gulf Coast / Sarasota

Sarasota apartment

1 4 1 night min

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

Price per night from

$75

Price per night from

$75

(4) Excellent 

25

New in Southgate:Lovely remodeled 3 bedroom pool villa 2.5 Miles from Siesta Key

Southwest Gulf Coast / Sarasota

Sarasota villa

3 6 min stay varies

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

Price per night from

$139

Responds fast!
avg. 3 hours 20 minutes

Price per night from

$139

28

4BR Casa Azul w/ Private Pool, Fire Pit, Covered Pergola - Near Bay, Downtown

Southwest Gulf Coast / Sarasota

Sarasota house

4 12 7 nights min

  • 4 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$484

Price per night from

$484

(1) Excellent 

16

Newly Updated 3 Bedroom Pool Home - Close to Beach

Southwest Gulf Coast / Sarasota

Sarasota house

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 13 mi
  • Swimming pool

Price per night from

$100

Responds fast!
avg. 40 minutes

Price per night from

$100

(7) Very Good 

9

St.Armands Circle condo ( Kingston Arms )

Southwest Gulf Coast / Sarasota

Sarasota apartment

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$124

Price per night from

$124

(1) Excellent 

35

Gulf Beach, Pool And Walk To Siesta Key Village

Southwest Gulf Coast / Sarasota

Sarasota apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child Friendly

Price per night from

$114

Price per night from

$114

16

Beach Bungalow on Lido Key near St. Armands

Southwest Gulf Coast / Sarasota

Sarasota apartment

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.4 mi
  • Swimming pool

Price per night from

$80

Price per night from

$80

(1) Excellent 

14

Lido Beach Front Condo

Sarasota / Lido Key

Lido Key apartment

3 6 30 nights min

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

Price per night from

$139

Price per night from

$139

(1) Excellent 

50

Sarasota's Shangri La for family getaways, weddings and more!

Southwest Gulf Coast / Sarasota

Sarasota house

3 10 2 nights min

  • 3 bedrooms
  • sleeps 10
  • 2 nights min
  • Nearest beach 8 mi
  • Swimming pool
  • Child Friendly

Price per night from

$248

Responds fast!
avg. 2 hours 43 minutes

Price per night from

$248

(2) Very Good 

19

Walk to Crescent Beach, Upgraded Sea Winds Condo

Southwest Gulf Coast / Sarasota

Sarasota apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Price per night from

$114

Responds fast!
avg. 2 hours 52 minutes

Price per night from

$114

(12) Excellent 

16

Midnight Cove: Living on the Water

Southwest Gulf Coast / Sarasota

Sarasota apartment

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Having a fabulous time!!” This is our 2nd year in a row and plan on staying again next year. This is our favorite place by far. Fishing only yards from the Lanai, restaurants, stores, bait shop, gulf beach, all within a few minutes walk. The pool is
…see more

Price per night from

$85

Responds fast!
avg. 2 hours 19 minutes

Price per night from

$85

(5) Very Good 

20

Sarasota exquisite vacation home

Southwest Gulf Coast / Sarasota

Sarasota house

3 8 29 nights min

  • 3 bedrooms
  • sleeps 8
  • 29 nights min
  • Beach / lakeside relaxation
  • Nearest beach 7 mi
  • Swimming pool
“Nice House in Sarasota” Stayed in this house in Sarasota. Its in a quiet neighbourhood which really suited us. The house was very clean and had lovely quality furnishings. Angel, the owner was excellent to deal with - responded very quickly to em
…see more

Price per night from

$190

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$190

(16) Excellent 

11

bring A Boat, 12 Minutes To Sarasota Bay

Southwest Gulf Coast / Sarasota

Sarasota house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Nearest beach 4 mi
  • Swimming pool
  • Air conditioning
“Great Spot: Helpful Host, Attractive Accommodations, Relaxing Hot Tub” Nestled within the first golfing/housing development in Florida (c. 1924),Whitfield Estates, Jim's renovated1960s house is an especially easy place to stay. It has a very large liv
…see more

Price per night from

$123

Responds fast!
avg. 2 hours 32 minutes

Price per night from

$123

35

Water Views on Siesta Key, Wifi, Close to Beach, Listen to the Waves Splash Gent

Southwest Gulf Coast / Sarasota

Sarasota apartment

3 6 14 nights min

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

Price per night from

$152

Responds fast!
avg. 8 minutes

Price per night from

$152

24

Sarasota Home w/ Private Pool & Patio Near Beach!

Southwest Gulf Coast / Sarasota

Sarasota house

3 6 min stay varies

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

Price per night from

$132

Responds fast!
avg. 10 minutes

Price per night from

$132

39

New Listing: Dawson House, "A kitchen that is truly warm at heart"

Southwest Gulf Coast / Sarasota

Sarasota house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 5 mi
  • Swimming pool
  • Child Friendly

Price per night from

$230

Responds fast!
avg. 1 hour 16 minutes

Price per night from

$230

25

Well Appointed Home with Heated Pool Just Off Siesta Key Close Gulf Gate Area

Southwest Gulf Coast / Sarasota

Sarasota house

3 6 min stay varies

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

Price per night from

$115

Price per night from

$115

(3) Very Good 

17

Sarasota 2BR 2BTH Condo Close to Siesta Key Beach

Southwest Gulf Coast / Sarasota

Sarasota apartment

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$99

Responds fast!
avg. 3 hours 28 minutes

Price per night from

$99

(7) Excellent 

Certificate of Excellence

35

Heated pool home near Siesta Key

Southwest Gulf Coast / Sarasota

Sarasota house

2 6 min stay varies

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

Certificate of Excellence

Price per night from

$139

Responds fast!
avg. 2 hours 28 minutes

Price per night from

$139

(2) Excellent 

27

Beautiful gated community near Siesta Key beach and downtown Sarasota

Southwest Gulf Coast / Sarasota

Sarasota house

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Swimming pool
  • Air conditioning
  • Private garden
“Great location and community” We loved our stay here. The location suited us. The community is clean and quiet. The people are friendly. Everything worked out for us, our first time renting. We would stay here again. Thank you.
…see more

Price per night from

$99

Responds fast!
avg. 3 hours 37 minutes

Price per night from

$99