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

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2,033 Vacation rentals

(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

$1,350 / week

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avg. 2 hours 36 minutes

from $193 / night

(27) Excellent 

28

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 $236 / night

$1,650 - $2,500 / week

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avg. 1 hour 32 minutes

from $236 / night

(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 $202 / night

$1,010 - $1,900 / week

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avg. 1 hour 54 minutes

from $202 / 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

30

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 $115 / night

$800 / week

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from $115 / 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

$1,500 - $2,000 / week

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avg. 3 hours 31 minutes

from $235 / night

(6) Good 

36

Siesta Key Vacation apartment 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
What a great location! walk to Siesta Key village or relax on your small Gulf Beach or fishing on the pier at Sandy Cove. This 2 bedroom 2 bath unit is a 2nd level condo with pool views from the balcony. Enjoy breakfast after a short walk at one of the villages' qu …see more

from $100 / night

$700 - $1,250 / week

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avg. 3 hours 33 minutes

from $100 / night

(2) Excellent 

12

Apartment rental in Siesta Key

Florida / Siesta Key

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
Luxury King 1 bedroom condo King Size - Double pillow top bed Ground floor Air conditioning Daily, Weekly, Monthly rates. Everything new 2017 Kitchen Coffee maker Toaster Microwave Stainless Steel fridge with ice maker 21 Years and over Heated swimming poo …see more

from $129 / night

$900 / week

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avg. 1 hour 46 minutes

from $129 / night

45

Siesta Key Vacation condo rental

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This is a large, bright and clean 2 bedroom and 2 bath first floor Condo. Being first floor gives you extra entrance through patio or lobby. Also one of the few condos with a private patio with new furniture to enjoy the beautiful weather and view. Condo clean and brigh …see more

from $93 / night

$650 - $1,300 / week

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avg. 2 hours 13 minutes

from $93 / night

30

Siesta Key Vacation apartment rental

Florida / Siesta Key

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Enjoy an incredible sunset on Siesta Key's Crescent Beach and walk back to your private villa on Siesta Key in Polynesian Gardens. Plan your get-a-way at our two bedroom, two bath villa where you have a screened-in lanai looking into the grassy back yard with your ow …see more

from $170 / night

$910 - $1,500 / week

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avg. 3 minutes

from $170 / night

23

Apartment rental in Siesta Key with shared pool

Florida / Siesta Key

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Over 1600 sq. ft. of spacious living space and ceramic tile throughout; beautifully decorated The living area features a large flat screen TV and DVD player, the kitchen is adorned with granite counter tops and stainless steel appliances. The master bedroom features a k …see more

from $236 / night

$1,650 - $2,950 / week

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from $236 / 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 $90 / night

$625 - $1,350 / week

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from $90 / night

(3) 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 $255 / night

$1,700 - $2,555 / week

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avg. 2 hours 52 minutes

from $255 / night

(11) Very Good 

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 0.1 mi
  • Swimming pool
GREAT Value !!! MVPROPERTIES AT SIESTA KEY Renovated and very conveniently located duplex villas at the beautiful Crescent Beach section of Siesta Key beach. We have (2) 2 bedroom 1 bath apartments. Each apartment sleeps up to 5 persons. Rent 1 apartment or both. Th …see more

from $140 / night

$895 - $1,605 / week

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avg. 1 hour 40 minutes

from $140 / night

(2) Very Good 

13

Vacation apartment in Siesta Key

Florida / Siesta Key

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
A Luxury 1 bedroom ground floor condo King size double pillow top bed 55 Inch HDtv in living room 50 Inch HDtv in bedroom Kitchen, Microwave, Coffee maker, Toaster. Stainless Steel fridge with ice maker. Adults only 21 years and up Heated swimming pool. Free internet (h …see more

from $129 / night

$900 / week

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avg. 1 hour 46 minutes

from $129 / night

(3) Excellent 

49

Siesta Key Vacation apartment rental

Florida / Siesta Key

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
**** Newly Renovated (Jan 2018) **** 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 …see more

from $149 / night

$999 - $1,599 / week

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avg. 1 hour 49 minutes

from $149 / night

(11) Excellent 

31

Siesta Key Vacation apartment rental

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Our Fisherman's Cove condo description Paradise awaits - GORGEOUS, totally renovated in 2016, two bedroom, beach front condo on the Gulf of Mexico with sunset views overlooking the and sunrise views of the lagoon, expansive water views from every window. Beach was r …see more

from $153 / night

$1,065 - $10,765 / week

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avg. 2 hours 19 minutes

from $153 / night

16

Condo rental in Siesta Key

Florida / Siesta Key

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
Siesta Dunes gated complex directly on the Gulf of Mexico. Beautiful complex with gated security. Parking next to the front door of this first floor garden unit with easy access to unit. Unit has everything you need for your stay. Washer and dryer in the unit for your …see more

from $193 / night

$1,350 - $1,500 / week

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avg. 1 hour 58 minutes

from $193 / night

(15) Very Good 

28

Vacation townhouse 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
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 $109 / night

$763 / week

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avg. 1 hour 7 minutes

from $109 / night

(1) Very Good 

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 beach at access 13, a more secluded area and away from the more crowded beaches. The king sized bed is extra comfortable with a flat screened tv, dressers, n …see more

from $119 / night

$833 / week

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from $119 / night

(1) Excellent 

19

Vacation condo rental

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $165 / night

$1,295 - $1,435 / week

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avg. 1 hour 56 minutes

from $165 / night

(3) Excellent 

20

Condo rental in Siesta Key with tennis court

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • 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 - $1,000 / week

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from $115 / night

13

Vacation apartment rental

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Updated and beautifully decorated 2 bedroom/2 bath 4th floor unit. Overlooks gulf side pool, Crescent Beach and Gulf of Mexico. Washer and dryer in unit. Living room includes a sofa sleeper, TV, DVD player. Master bedroom offers King bed, TV, DVD. Master bath has walk-i …see more

from $220 / night

$1,540 - $2,500 / week

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from $220 / night

(1) Excellent 

43

Vacation home in Siesta Key

Florida / Siesta Key

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
1BR (sleeps 4)- Perfect for travelers in search of uncomplicated seclusion. Brought to you by Gertrude Rentals! Located in the most “private” non-private beach neighborhood in Siesta Key, The Old Man and the Sea Inn can accommodate up to 24 guests and is a four unit K …see more

from $100 / night

$1,400 / week

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avg. 34 minutes

from $100 / night

(4) Excellent 

12

Vacation apartment in Siesta Key

Florida / Siesta Key

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Jamaica Royale condo #92. Located at the #1 BEACH IN THE USA, this 2 bedroom, 2 bath garden view unit has everything you need! It is located in the garden area of our beautifully landscaped property. It has new furniture and is freshly painted, with tile floors in the …see more

from $251 / night

$1,757 / week

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avg. 1 hour 44 minutes

from $251 / night

(3) Excellent 

21

Vacation condo in Siesta Key

Florida / Siesta Key

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
Our 2nd floor, end unit condo was completely renovated over the winter of 2012– 2013. The floor plan was opened up to provide a nice airy feel and to enjoy the water view. All furniture, flooring and fixtures are new. The entry hall has a bench to store your flip-flo …see more

from $143 / night

$1,000 - $1,250 / week

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from $143 / night

22

Apartment rental in Siesta Key with shared pool

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Beautifully decorated first floor 2 bed/2 bath 1400+ sq. ft. bay front unit. Glassed enclosed lanai makes an extra family room and overlooks the intra coastal waterway. Step out the back door to stroll the lush, tropical grounds of island paradise! Living room offers …see more

from $147 / night

$1,030 - $1,910 / week

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from $147 / night

22

Apartment rental in Siesta Key with shared pool

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
NEWLY FURNISHED!! Ground floor unit Bay side. Extended living room area. Unit has large tile throughout. The unit will comfortably sleep 6 people. Master has a King bed , guest bedroom has two twin beds and a new queen sofa sleeper in the living room. Kitchen has been u …see more

from $125 / night

$875 - $1,690 / week

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from $125 / night

(1) Excellent 

25

Vacation apartment in Siesta Key

Florida / Siesta Key

2 3 nights min

  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Air conditioning
Relax, get away and enjoy Siesta Key's laid back lifestyle! Nestled in a quiet residential neighborhood, you'll love this large and comfortable 500 square foot studio apartment. It has a king bed and comfortably sleeps 2. The studio is attached to the owners' home, and …see more

from $172 / night

$1,200 / week

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from $172 / night

(2) Excellent 

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 $128 / night

$900 / week

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from $128 / night

(5) Excellent 

38

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 with 2 Queen Beds is beautifully furnished, all new, and super clean! WALK RIGHT OVER TO THE #1 BEACH IN AMERICA, you do not need a car on this vacation stay. And if you want to see the rest of Siesta Key you can take the free shuttles, and …see more

from $99 / night

$693 / week

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from $99 / night

41

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
Beautiful and newly remodeled three bedroom/two bath unit with ceramic tile in living areas and wood laminate in master bedroom and 2nd bedroom. Spacious with over 1800 sq. ft., fourth floor overlooking the intracoastal waterway. Large glassed in lanai makes additional …see more

from $179 / night

$1,250 - $2,080 / week

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from $179 / night

(9) Excellent 

27

Vacation villa in Siesta Key

Florida / Siesta Key

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Beach and water front on Gulf Of Mexico. A block from Siesta Key Village for lite and fine dinning, fun, shopping and nightlife. Two Master Suite King Bedrooms with Master Bath for each. Sauna, four Mexican tiled decks with panoramic views of the Gulf and beaches. …see more

from $500 / night

$2,790 - $4,950 / week

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avg. 2 hours 30 minutes

from $500 / night

(11) Excellent 

Certificate of Excellence

30

Siesta Key Vacation condo rental

Florida / Siesta Key

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
All new! This spacious, 2 bedroom/2 bath has everything you need for a relaxing and fun vacation in Sarasota, just minutes to Siesta Key. Relax in comfort with all the amenities: - Fully equipped Kitchen with all new appliances, dishes, glassware, etc. - Top quality …see more

Certificate of Excellence

from $130 / night

$850 - $1,300 / week

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Responds fast!
avg. 1 hour 50 minutes

from $130 / night

23

Siesta Key Vacation condo rental

Florida / Siesta Key

2 6 6 nights min

  • 2 bedrooms
  • Sleeps 6
  • 6 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
1st floor condo/ 40 yards from the beach/ go out lanai door directly to the beach. Condo was completely re-furbished just a few years ago/ considered one of the very best siesta key condos/ guest need food that is all/ the condo is fully equipped. Considered the best co …see more

from $180 / night

$1,400 / week

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from $180 / night

(1) Excellent 

21

Vacation villa in Siesta Key

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • 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 $141 / night

$987 / week

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avg. 1 hour 47 minutes

from $141 / night

27

Vacation cottage in Siesta Key

Florida / Siesta Key

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
The Beach Place is a small group of tropical garden Floridian beach cottages located at Siesta Key Beach - 30 seconds to the sand and 10 - 15 minute walk to Siesta Village. We have a heated pool, tiki cabana wet bar for the guests to entertain at, beachfront picnic an …see more

from $150 / night

$900 - $1,700 / week

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from $150 / night

30

Siesta Key Vacation condo rental

Florida / Siesta Key

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Got Paradise!? Well now you do..... This oasis on Siesta Key is just that. The condo is only a block or so away from famous Siesta Key beach and rests in Siesta Key Village where you will find lots of great dining, amazing shops, coffee houses and more, all a short wa …see more

from $137 / night

$847 - $2,723 / week

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avg. 3 minutes

from $137 / night

30

Vacation apartment in Siesta Key

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
New furnishings (11/17) complete an already fabulous condo! Be the first to enjoy this newly painted, newly furnished adorable & quaint ground floor two bedroom, one bath condo with water views and all of the amenities you are looking for in a fun yet relaxing atmosphe …see more

from $107 / night

$623 - $1,652 / week

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avg. 3 minutes

from $107 / night

(6) Very Good 

26

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
ZERO HURRICANE DAMAGE IN OUR AREA - This is a Luxurious Villa on Siesta Key Beach Florida on Crystal Sands - Experience why Siesta Key, Sarasota Florida has been rated the #1 beach in the USA (#5 in the world by TravelAdvisor) for so many years. Siesta Key is one of the …see more

from $180 / night

$1,700 / week

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avg. 2 hours 49 minutes

from $180 / night