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311 vacation rentals

(4) Excellent 

13

Siesta Beach Cottage

Southwest Gulf Coast / Sarasota

Sarasota apartment

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • 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
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Price per night from

$190

Price per night from

$190

31

EATON PLACE

Sarasota / Lido Key

Lido Key house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 16 mi
  • Swimming pool
  • Child Friendly

Price per night from

$380

Price per night from

$380

(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

$101

Responds fast!
avg. 41 minutes

Price per night from

$101

(1) Excellent 

26

Tropical Escape Sarasota

Sarasota / Lockwood Ridge

Lockwood Ridge house

3 15 min stay varies

  • 3 bedrooms
  • sleeps 15
  • min stay varies
  • Nearest beach 13 mi
  • Child Friendly
  • Car not necessary

Price per night from

$160

Responds fast!
avg. 40 minutes

Price per night from

$160

(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
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Price per night from

$124

Responds fast!
avg. 2 hours 30 minutes

Price per night from

$124

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

(10) Very Good 

23

Superb Village Des Pins Sarasota vacation villa near Siesta Key

Southwest Gulf Coast / Sarasota

Sarasota villa

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool
“Nice stay in Sarasota” Eddie and Wendy great to deal with. Villa in great location. Very clean and comfortable. Excellent facilities in complex - beautiful heated pool and spa. Lovely grounds, very quiet and relaxing. Would recommend.
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Price per night from

$98

Responds fast!
avg. 35 minutes

Price per night from

$98

(14) Excellent 

34

Late SALE Sep/Oct only -Lakeside villa Uni. Park,golf,cycles,pool, beach

Southwest Gulf Coast / Sarasota

Sarasota villa

3 4 30 nights min

  • 3 bedrooms
  • sleeps 4
  • 30 nights min
  • Beach / lakeside relaxation
  • Nearest beach 20 mi
  • Swimming pool
“A perfect setting and location” Everything about this vacation is perfect from start to finish. Joyce guides you through the pre vacation procedure seamlessly. All relevant information is sent concerning local amenities and events occurring duri
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Price per night from

$180

Responds fast!
avg. 1 hour 16 minutes

Price per night from

$180

11

Charming 2 Bedroom House, Fenced and Private

Southwest Gulf Coast / Sarasota

Sarasota house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets

Price per night from

$200

Responds fast!
avg. 2 hours 42 minutes

Price per night from

$200

24

Sarasota, Beaches, Lido, Down Town, Siesta

Southwest Gulf Coast / Sarasota

Sarasota house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Nearest beach 8 mi
  • Swimming pool
  • Child Friendly

Price per night from

$230

Price per night from

$230

24

Stoneybrook Country Club Condo Rental 4TH FAIRWAY

Southwest Gulf Coast / Sarasota

Sarasota villa

2 6 min stay varies

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

Price per night from

$148

Responds fast!
avg. 3 hours 31 minutes

Price per night from

$148

(1) Very Good 

31

Sarasota's best kept secret! Beautiful Rennnovated Villa, 2Br 2 Bath, sleeps 4-6

Southwest Gulf Coast / Sarasota

Sarasota villa

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool

Price per night from

$93

Price per night from

$93

10

#7 Loft Apartment in Historic District Downtown Sarasota

Southwest Gulf Coast / Sarasota

Sarasota apartment

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Pet Friendly

Price per night from

$109

Responds fast!
avg. 1 hour 19 minutes

Price per night from

$109

22

Sarasota golf course home/heated swimming pool

Southwest Gulf Coast / Sarasota

Sarasota house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 15 mi
  • Swimming pool
  • Child Friendly

Price per night from

$156

Price per night from

$156

(5) Excellent 

32

SARASOTA : Paradise for golfers and beach lovers

Southwest Gulf Coast / Sarasota

Sarasota house

4 8 30 nights min

  • 4 bedrooms
  • sleeps 8
  • 30 nights min
  • Beach / lakeside relaxation
  • Nearest beach 13 mi
  • Swimming pool

Price per night from

$168

Price per night from

$168

(1) Very Good 

25

Tennis, Anyone, or is Golf Your Thing?

Southwest Gulf Coast / Sarasota

Sarasota condo

1 4 30 nights min

  • 1 bedroom
  • sleeps 4
  • 30 nights min
  • Nearest beach 16 mi
  • Swimming pool
  • Air conditioning

Price per night from

$94

Price per night from

$94

19

Tropical Charm - Beautifully furnished, pool

Southwest Gulf Coast / Sarasota

Sarasota condo

2 5 90 nights min

  • 2 bedrooms
  • sleeps 5
  • 90 nights min
  • Nearest beach 9 mi
  • Swimming pool
  • Child Friendly

Price per night from

$84

Price per night from

$84

21

Stunning & Bright Sarasota Home

Southwest Gulf Coast / Sarasota

Sarasota house

3 6 min stay varies

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

Price per night from

$161

Price per night from

$161

16

Sarasota Vacation Home! - Cute & Cozy Beach Cottage (Age Restricted)

Southwest Gulf Coast / Sarasota

Sarasota caravan/mobile home

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 6 mi
  • Swimming pool
  • Child Friendly

Price per night from

$74

Responds fast!
avg. 1 hour 59 minutes

Price per night from

$74

(1) Very Good 

10

Nature Coast 2/2+ Home Sleeps 6

Southwest Gulf Coast / Sarasota

Sarasota house

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly
“Sarasota / Bradenton House Near Everything” The location was great for us (close to the airport, Ringling College, and the beach). The house came outfitted with everything we needed to enjoy a week in the Sarasota / Bradenton area. All we needed was
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Price per night from

$100

Responds fast!
avg. 12 minutes

Price per night from

$100

24

Sarasota 19

Southwest Gulf Coast / Sarasota

Sarasota house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Car not necessary

Price per night from

$127

Responds fast!
avg. 3 hours 26 minutes

Price per night from

$127

(1) Very Good 

35

Tranquility at the Preserve

Southwest Gulf Coast / Sarasota

Sarasota house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“very nice and clean” everything worked out great!!! we would stay and recommend this house to anyone coming into town or just get a way.
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Price per night from

$240

Responds fast!
avg. 3 hours 6 minutes

Price per night from

$240

18

Sarasota Pinecraft Cottage 2

Southwest Gulf Coast / Sarasota

Sarasota cottage

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Nearest beach 8 mi
  • Child Friendly
  • Air conditioning

Price per night from

$151

Responds fast!
avg. 2 hours 19 minutes

Price per night from

$151

(20) Excellent 

22

3 Bedroom Family friendly Coastal Manor of Sarasota

Southwest Gulf Coast / Sarasota

Sarasota apartment

3 6 14 nights min

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

Price per night from

$353

Price per night from

$353

17

Sarasota Villa

Southwest Gulf Coast / Sarasota

Sarasota villa

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Price per night from

$99

Price per night from

$99

18

ClubHome in Heritage Oaks Golf & CC

Sarasota / Heritage Oaks Golf and Country Club

Heritage Oaks Golf and Country Club bungalow

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Beach / lakeside relaxation
  • Nearest beach 14 mi
  • Swimming pool

Price per night from

$136

Price per night from

$136

(2) Excellent 

14

Heritage Oaks

Sarasota / Heritage Oaks Golf and Country Club

Heritage Oaks Golf and Country Club condo

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 12 mi
  • Swimming pool

Price per night from

$79

Price per night from

$79

Great rentals within 20 miles that match your search

Distance approx 6.3 km from Sarasota Show on Map

(2) Very Good 

24

Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

Florida / Siesta Key

Siesta Key apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$108

Price per night from

$108

Distance approx 9.28 km from Sarasota Show on Map

(1) Excellent 

31

Sunshine Cove 5-Star Resort Villa near IMG, Golf, Beaches; WiFi, Hot Tubs, Pools

Southwest Gulf Coast / Bradenton

Bradenton condo

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 9 mi
  • Swimming pool
  • Child Friendly

Price per night from

$92

Responds fast!
avg. 1 hour 15 minutes

Price per night from

$92

Distance approx 5.37 km from Sarasota Show on Map

22

Amazing Gulf Beech Rental with Fantastic FREE Amenities!!!

Florida / Longboat Key

Longboat Key condo

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$291

Price per night from

$291

Distance approx 9.29 km from Sarasota Show on Map

24

SHOREWALK VACATION VILLA

Southwest Gulf Coast / Bradenton

Bradenton apartment

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 15 mi
  • Swimming pool

Price per night from

$126

Price per night from

$126

Distance approx 7.52 km from Sarasota Show on Map

9

Waterfront Glamping Sarasota Steampunk Style Cabin

Florida / Braden River

Braden River cottage

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 11 mi
  • Child Friendly
  • Air conditioning

Price per night from

$45

Price per night from

$45

Distance approx 5.21 km from Sarasota Show on Map

25

Siesta Key Beach Townhouse with Heated Pool and Accommodates up to 8 Guests

Florida / Siesta Key

Siesta Key condo

2 8 min stay varies

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

Price per night from

$117

Price per night from

$117

Distance approx 13.68 km from Sarasota Show on Map

27

Runaway Bay 250

Florida / Cortez

Cortez condo

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$181

Responds fast!
avg. 3 hours 43 minutes

Price per night from

$181

Distance approx 16.12 km from Sarasota

16

Pool Party North Side

Anna Maria Island / Holmes Beach

Holmes Beach house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$173

Responds fast!
avg. 3 hours 6 minutes

Price per night from

$173

Distance approx 5.97 km from Sarasota Show on Map

(26) Excellent 

24

Siesta Breakers #603 in Siesta Key, FL- Sun, Sand & *Save 20% to 45% per Week*

Florida / Siesta Key

Siesta Key condo

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child Friendly

Price per night from

$147

Price per night from

$147

Distance approx 7.75 km from Sarasota Show on Map

16

IMG golf private 3 bed home

Southwest Gulf Coast / Bradenton

Bradenton house

3 4 min stay varies

  • 3 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 10 mi
  • Swimming pool
  • Child Friendly

Price per night from

$136

Price per night from

$136

Distance approx 7.15 km from Sarasota Show on Map

16

Villa with golf course view with solar heated pool

Florida / Lakewood Ranch

Lakewood Ranch villa

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Nearest beach 19 mi
  • Swimming pool
  • Ask about children

Price per night from

$134

Responds fast!
avg. 3 hours 42 minutes

Price per night from

$134