50 Best Siesta Key Beach rentals on Holiday Lettings - Vacation rentals

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390 Vacation rentals

(2) Excellent 

26

Vacation villa in Siesta Key

Florida / Siesta Key

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Very spacious, air-conditioned 4 bed detached ranch-type Villa on Siesta Key Bayside. Sleeps 8, 1 King, 1 Queen, 2 Full and 2 twin beds. 1 month minimum Jan-March, 2 week minimum April -Dec. Maximum 3 cars . Large Heated Communal pool, Own Outdoor patio area with …see more

from $205 / night

$1050 - $1946 / week

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avg. 3 hours 42 minutes

from $205 / night

(1) Excellent 

24

Home rental in Siesta Key with swimming pool

Florida / Siesta Key

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool
Fabulous home on Siesta Key (Sarasota)( two weeks minimum stay ). Just 2 minutes drive to the beach & village. This home features 3 bedrooms and 2 baths with a large kitchen that opens to the family room. Great pool with southern exposure,and enclosed in a screen lana …see more

from $193 / night

$1350 / week

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from $193 / night

(1) Excellent 

18

Vacation condo in Siesta Key

Florida / Siesta Key

2 6 14 nights min

  • 2 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool
White Sands Village is located on Siesta Key, just few steps from Siesta Beach and directly on the canal across from Philippee Creek. Highlights of White Sands Unit 303: Free high-speed WiFi Ground floor unit More than 200 channel cable TV DVR to watch your favorite s …see more

from $107 / night

$750 / week

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from $107 / night

(18) Excellent 

23

Siesta Key Vacation condo rental

Florida / Siesta Key

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.01 mi
  • Swimming pool
The condo benefits from its own private pool. The living room, master bedroom, and lanai (balcony) all have stunning ocean views. The lanai, with over $10,000 of new doors and windows, is furnished with a table and chairs to enable you to dine al fresco. There is al …see more

from $358 / night

$2500 / week

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from $358 / night

31

Vacation condo in Siesta Key

Florida / Siesta Key

2 5 14 nights min

  • 2 bedrooms
  • Sleeps 5
  • 14 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
This recently renovated, bright and wonderfully furnished residence has panoramic views and opens above the resort's pools and manicured lawns. Wake up to beautiful sunrises and enjoy your morning coffee at the bistro table for two next to the screened lanai area. A 1 …see more

from $171 / night

$800 - $1200 / week

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from $171 / night

(1) Excellent 

38

Vacation townhouse in Siesta Key

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
WELCOME TO PARADISE! -- BEST LOCATION on SIESTA KEY! MAY-OCT SPECIALS - 4 days min stay. 50-60% discount for longer stay. A very clean, cozy TH with a pool view, a few yards to Crescent beach. THIS IS NOT a typical DAILY RENTAL PLACE. There are TWO BEDROOMS upstair …see more

from $235 / night

$1300 - $1750 / week

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avg. 1 hour 37 minutes

from $235 / night

(6) Excellent 

20

Siesta Key Vacation condo rental

Florida / Siesta Key

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
This luxurious two bedroom/two bath condo is located on the beach on Siesta Key, an island off the coast of Sarasota. Siesta Key boasts miles of white sugar sand beaches, and a public beach which was rated number one in the U.S. this year and is regularly rated in the …see more

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33

Vacation villa rental

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
Unlike many rental properties on Siesta Key, Unit #100 was renovated in 2016! This condo is a 2 bedroom, 2 bath garden view unit located in the quiet area of Jamaica Royale Condominiums! Jamaica Royale is located directly on the Gulf of Mexico along the white sands of …see more

from $160 / night

$1120 / week

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avg. 2 hours 47 minutes

from $160 / night

(2) Excellent 

24

Vacation apartment in Siesta Key

Florida / Siesta Key

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 50 mi
  • Swimming pool
I have tried to make this apartment as comfortable as your own home only at the beach. This unit has two bedrooms and two baths. It can accommodate six people with a king bed and two double beds. There are plenty of closet and dresser space, a fully-equipped kitchen, co …see more

from $265 / night

$1490 - $2095 / week

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from $265 / night

(5) Excellent 

24

Siesta Key Vacation condo rental

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
If you are looking for the perfect spot for a family vacation, to escape the cold and snow, or a quiet romantic getaway this is the place for you. Recently updated throughout, this 2 bedroom 2 bath condo sleeps 6 comfortably all in real beds. Just outside your door is C …see more

from $214 / night

$1495 - $2235 / week

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avg. 1 hour 47 minutes

from $214 / night

(14) Excellent 

Certificate of Excellence

30

Vacation apartment rental

Florida / Siesta Key

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“Pristine sand, blue skies - 'Number 1 Beach'” The Best Thing to Come Home to after a Day on the Beach Is... ...a vacation home as comfortable as your own home. Just a walk across the street to Siesta Key's world famous #1 Beach. This spl …see more

Certificate of Excellence

from $155 / night

$851 - $1300 / week

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avg. 3 hours 13 minutes

from $155 / night

(11) Very Good 

21

Siesta Key Vacation apartment rental

Florida / Siesta Key

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
We offer a boutique style property with just 4 units. Close enough to the beach without the congestion of larger properties. Enjoy this newly renovated (2014) apartment, located less than a mile from beautiful Siesta Key Beach. We've fully remodeled in the "Beach Chi …see more

from $199 / night

$1325 - $1995 / week

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avg. 1 hour 5 minutes

from $199 / night

(1) Excellent 

9

Vacation home in Siesta Key

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
This charming tropical 1,320 sq.ft. 2 bedroom 2 bath home is located within the heart of Siesta Key Village and a block away from the famous Siesta Key Beach. Walk to everything, yet have privacy of a home. It is newly renovated with all new furniture and beach house …see more

from $275 / night

$2065 - $2275 / week

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avg. 3 hours 25 minutes

from $275 / night

10

Vacation condo in Siesta Key

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
2 bedroom/2 bath top-floor end unit steps from the #1 beach in the County and #3 in the World (voted by Trip Advisor Feb. 2016). Sarasota County spent almost $30 million renovating all of the public facilities - new concession, bathrooms, SunDeck Restaurant, playgrou …see more

from $121 / night

$851 - $1495 / week

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from $121 / night

(1) Excellent 

29

Vacation home in Siesta Key

Florida / Siesta Key

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Surrounded by lush, tropical garden, our private villa is situated on a quiet cul-de-sac bordered on two sides by Lake Nancy. A birdwatchers and nature lovers delight! Sip your coffee in your PJs on the private, sunny terrace. Enjoy a dip in the large heated pool, o …see more

from $250 / night

$1750 / week

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avg. 48 minutes

from $250 / night

(5) Excellent 

29

Vacation condo in Siesta Key

Florida / Siesta Key

1 3 14 nights min

  • 1 bedroom
  • Sleeps 3
  • 14 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
Spacious Condo on Siesta Key is so centrally located you won't even need a car! 800 square feet, renovated, new, and super clean! King Bed in Bedroom and Sleeper sofa in living room provides 2 separate bed options with spacious closets ready for your things! Screened La …see more

from $75 / night

$875 - $1500 / week

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from $75 / night

15

Condo rental in Siesta Key with tennis court

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
You will feel like you have arrived in Paradise when you enter the lobby. The facility is more like a resort than a condominium. Unit has 2 bedroom, 2 baths, split plan. Both bedrooms and living room open to screened lanai facing the Gulf of Mexico. Perfect setting for …see more

from $115 / night

$800 - $1000 / week

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from $115 / night

25

Siesta Key Vacation home rental

Florida / Siesta Key

6 12 6 nights min

  • 6 bedrooms
  • Sleeps 12
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
NEWLY LISTED SIESTA KEY WATERFRONT ESCAPE!!!! Brand New , Gated Residence steps from Siesta Key Beach . Perfect location between the village and crystal sands of Siesta Beach!! Bar's, Restaurants, Shopping, Sport Rentals……..EVERYTHING is within walking distance…..NO CAR …see more

from $599 / night

$3490 - $4290 / week

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from $599 / night

(18) Very Good 

Certificate of Excellence

14

Siesta Key Vacation apartment rental

Florida / Siesta Key

2 6 14 nights min

  • 2 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
Newly furnished, newly renovated 2BR (one king size & 2 single beds) + convertible sofa bed, 2 Bathrooms 2nd floor condo (sleeps 4-6), and with all the amenities of a comfortable home. Located in White Sands Village with 7 acres of lush tropical surroundings, our air-co …see more

Certificate of Excellence

from $90 / night

$625 - $1075 / week

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avg. 2 hours 47 minutes

from $90 / night

(2) Very Good 

18

Vacation condo rental

Florida / Siesta Key

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Air conditioning
2 bedroom, 2 bathroom on 4th floor, lovely view... Enjoy the best that beautiful Bay Oaks has to offer. This 4th floor corner condo has been remodeled. With 1101 square feet, this 2BR/2BA condo has a living room, dining room, kitchen and screened lanai where you …see more

from $108 / night

$750 - $800 / week

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from $108 / night

(42) Excellent 

Certificate of Excellence

24

Vacation villa in Siesta Key

Florida / Siesta Key

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Very clean, bright, airy 1 bedroom, single- story cottage. Ebb Tide #1 offers all you need for a wonderful vacation at the beach. - Beautiful, large, heated, saltwater pool. - Private, gated access to world renowned Crescent Beach, famous for its powdery, white, quartz …see more

Certificate of Excellence

from $121 / night

$800 - $1350 / week

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Responds fast!
avg. 1 hour 47 minutes

from $121 / night

(1) Excellent 

20

Vacation condo rental

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
Jamaica Royale Condominiums are located directly on the Gulf of Mexico along the white sands of world-famous Siesta Key Beach in Sarasota, Florida. A barrier island on Florida’s West coast, considered the most beautiful of Florida’s barrier islands, Siesta Key’s beach …see more

from $160 / night

$1120 - $1799 / week

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from $160 / night

12

Vacation home in Siesta Key

Florida / Siesta Key

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Siesta Sun Villa Our home is one large house that has a 3 bed 2 bath unit. A 2 bed 1 bath unit and a 1 bed 1 bath unit. All with connecting doors so you can rent the whole house to sleep 12 guests all in beds. It is perfect for large familys, Weddings and reunions. Priv …see more

from $400 / night

$3200 / week

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from $400 / night

(11) Very Good 

31

Apartment rental in Siesta Key

Florida / Siesta Key

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Welcome to our Condo in Siesta Key ! Located on the inter-coastal Waterway and a short walk to the whitest sand and the # 1 beach in the USA. This 1 bedroom Condo is a great retreat for anyone looking for a beautiful Island getaway! Our condo is on the 2nd floor (s …see more

from $100 / night

$650 - $1000 / week

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avg. 2 hours 9 minutes

from $100 / night

(1) Excellent 

20

Siesta Key Vacation condo rental

Florida / Siesta Key

2 4 14 nights min

  • 2 bedrooms
  • Sleeps 4
  • 14 nights min
  • Child friendly
Siesta Key Vacation Condo all new, and an easy walk over to the #1 Beach in America. Complex has Pool, Covered Parking, Clubhouse, Marina. Two Bedrooms, Two full Bathrooms, Completely renovated Kitchen, all new Tile flooring throughout Condo, back Lanai catches glimps …see more

from $108 / night

$750 - $2000 / week

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from $108 / night

(2) Excellent 

42

Vacation condo with swimming pool in Siesta Key

Florida / Siesta Key

2 5 6 nights min

  • 2 bedrooms
  • Sleeps 5
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Cozy Cove is a small condominium complex of six total units, located on the south end of Siesta Key in Sarasota, Florida. The complex sits on the Gulf side of the Key along Blind Pass. The complex itself is on the inlet with a dock at the back of the property where you …see more

from $89 / night

$623 / week

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avg. 3 hours 47 minutes

from $89 / night

(1) Very Good 

32

Siesta Key Vacation apartment rental

Florida / Siesta Key

2 5 14 nights min

  • 2 bedrooms
  • Sleeps 5
  • 14 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Harbor Towers Yacht and Racquet Club Unit 503 provides one of the best views in the building (fifth floor facing south/east). The glass enclosed Lanai with floor-to-ceiling sliding glass doors provides bright sunlight during the morning and afternoon with excellent view …see more

from $86 / night

$600 - $1310 / week

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from $86 / night

(5) Very Good 

Certificate of Excellence

42

Condo rental in Siesta Key

Florida / Siesta Key

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Leave your worries behind... If you're looking for a relaxing beachfront condo that's been totally remodeled you've come to the right place. Our ground-level oceanfront condo is the perfect place to unwind unplug and recharge the batteries. Fisherman's Cove is a quiet …see more

Certificate of Excellence

from $157 / night

$1095 - $2295 / week

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Responds fast!
avg. 1 hour 38 minutes

from $157 / night

(10) Excellent 

17

Vacation townhouse in Siesta Key

Florida / Siesta Key

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
This luxurious one story townhouse was newly renovated and has its own private access to the #1 beach in the US merely steps away from the front door. It boasts all the luxury you'd expect from a beach house! Modern kitchen, contemporary bathroom with walk in rain showe …see more

from $269 / night

$1883 / week

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from $269 / night

(8) Excellent 

24

Condo rental in Siesta Key

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Split floor plan with each bedroom having a private full bath, tv and access to the lanai. New bathroom floors installed in October 2016 and new tile in master bath/tub. New king size mattress as of May 2017. Secure Wi-fi Relaxing lanai with couch, two chairs and thre …see more

from $172 / night

$1305 - $1905 / week

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Responds fast!
avg. 1 hour 47 minutes

from $172 / night

(1) Excellent 

24

Siesta Key Vacation apartment rental

Florida / Siesta Key

2 10 Min stay varies

  • 2 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
***AUGUST 2017 AVAILABILITY*** Steps to Siesta Beach and a Gorgeous Condo, Bring the Entire Family! #1 Beach in the US (2017) : Siesta Key is the United States #1 Beach Boasting Miles of Powder White Sand and a Charming Village loaded Shopping, Dining and Ice Cream …see more

from $125 / night

$950 - $1400 / week

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avg. 31 minutes

from $125 / night

11

Vacation condo in Siesta Key

Florida / Siesta Key

2 4 14 nights min

  • 2 bedrooms
  • Sleeps 4
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Siesta key condo in sarasota Florida West coast of Florida beautiful sunsets and powdered sugar sandy beaches Condo completely tiled thru-out, Elevator, walk to number 1 rated beach, watch boats go by while enjoying your morning coffee Ringing museum, Florida studio th …see more

from $143 / night

$1000 / week

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Responds fast!
avg. 3 hours 26 minutes

from $143 / night

(7) Excellent 

19

Vacation apartment in Siesta Key

Florida / Siesta Key

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
This vacation rental offers a full view of Siesta Key Beach/ The Gulf upon entry; relax and enjoy from your lanai or master bedroom. The property has been newly transformed to accommodate our guests best welcome to Siesta. From the comfort of the home décor to your full …see more

from $150 / night

$1050 - $1830 / week

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Responds fast!
avg. 28 minutes

from $150 / night

(6) Excellent 

Certificate of Excellence

24

Vacation condo rental

Florida / Siesta Key

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
- Expansive, panoramic gulf view from every room of this 6th floor condo. -Crescent Arms is a quiet, beach front, high rise condominium building that is ideally located for maximum fun and relaxation. -Right on the beach with lounge chairs provided. As close as you …see more

Certificate of Excellence

from $158 / night

$1100 - $1701 / week

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Responds fast!
avg. 44 minutes

from $158 / night

17

Siesta Key Vacation apartment rental

Florida / Siesta Key

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Spacious 1600+ sq. ft. 3/2 ground floor unit. Step out lanai and back door to pool and beach! New flat screen tv's in living room and all bedrooms, king bed in master bedroom. Step-in shower/roman tub in master bath. Guest bedroom has queen bed and guest bath has a tub/ …see more

from $235 / night

$1650 - $2865 / week

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from $235 / night

20

Condo rental in Siesta Key

Florida / Siesta Key

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning
Adorable, quiet, and clean home away from home on the South end of Siesta Key. Only a short five minute walk to private beach at access 13, a more secluded area and away from the public beaches. The king sized bed is extra comfortable with a new flat screened tv, dress …see more

from $175 / night

$1225 / week

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from $175 / night

(4) Very Good 

22

Siesta Key Vacation villa rental

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
LAST MINUTE DEALS NOW AVAILABLE AUGUST - JANUARY at our luxurious Villa#4 (on Crystal Sands, 6300 Midnight Pass Rd, Sarasota, Florida) - sleeps 6 and includes everything your family needs for your stay at the #1 beach in the USA. This Villa has easy access to the beach …see more

from $160 / night

$1220 - $1800 / week

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Responds fast!
avg. 1 hour 51 minutes

from $160 / night

(22) Excellent 

16

Siesta Key Vacation apartment rental

Florida / Siesta Key

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
This lovely 2BD/1BA apartment is located just 1 mile from beautiful Siesta Key Beach. Siesta Key was rated the #1 Beach in the United States by Dr. Beach (2011) and the #2 Beach in the U.S. in the 2013 TripAdvisor Travelers Choice Awards. Siesta Key was listed in 2 …see more

from $155 / night

$1000 - $1625 / week

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Responds fast!
avg. 1 hour 5 minutes

from $155 / night

21

Vacation villa in Siesta Key

Florida / Siesta Key

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Siesta Villa Laughing Gull Find yourself in the relaxing comforts of Siesta Villa Laughing Gull. A single-story stand-alone villa, located in the beautiful private community of Polynesian Gardens, on the tropical barrier island of Siesta Key, Fl. The peaceful tranquilit …see more

from $122 / night

$854 / week

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Responds fast!
avg. 1 hour 35 minutes

from $122 / night

(21) Very Good 

Certificate of Excellence

27

Vacation apartment in Siesta Key

Florida / Siesta Key

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Summer/Fall 2017 Special !! 2018- Only April left...Book Now! One Bedroom- TWO (2) BATHROOMS! PRIVACY 2ND floor END unit! No one walking past door all day and night!! TWO (2) OUTDOOR common areas -BALCONY for morning coffee …see more

Certificate of Excellence

from $100 / night

$1150 / week

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Responds fast!
avg. 3 hours 34 minutes

from $100 / night

1