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

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313 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 $207 / night

$1058 - $1961 / week

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Responds fast!
avg. 2 hours 21 minutes

from $207 / 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

(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

(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

Pricing unknown

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Pricing unknown

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 

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

(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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Responds fast!
avg. 2 hours 29 minutes

from $235 / night

(1) Excellent 

19

Apartment rental in Siesta Key with shared pool

Florida / Siesta Key

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
This unit offeres wireless high speed internet connection. Beautifully decorated fifth floor end unit overlooks the bay and only a few minutes walk to the pure white sands of our own private beach! Water views from all main rooms in this bright and sunny spacious 1800 s …see more

from $155 / night

$1085 - $1915 / week

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from $155 / night

22

Apartment rental in Siesta Key with shared pool

Florida / Siesta Key

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • 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 $135 / night

$945 - $1855 / week

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from $135 / night

31

Vacation apartment with shared pool 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
Gorgeous upgraded unit with spectacular bay views from this fourth floor 2 bedroom/2 bath condo! Just like new! Professionally decorated in Florida decor, ceramic tile flooring, slider glass enclosed lanai makes this over a spacious 1600+ sq. ft! Lanai/family room stret …see more

from $147 / night

$1030 - $1855 / week

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from $147 / night

39

Vacation apartment rental

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Very comfortable 2 bed/2.5 bath second floor townhouse overlooks the tranquil waters of the canal and boat docks. Enjoy the Florida lifestyle relaxing on the spacious glassed-in and screened lanai. Tastefully decorated living area offers sofa bed, TV, & VCR. DSL Wireles …see more

from $147 / night

$1030 - $1855 / week

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from $147 / night

(12) Excellent 

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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Responds fast!
avg. 48 minutes

from $199 / night

(3) Very Good 

33

Vacation condo in Siesta Key

Florida / Siesta Key

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Great first impressions are evident from the moment you enter this lovely condo and enjoy the breathtaking ocean views from our private oversized lanai. We know you'll adore our comfortably decorated oceanfront condo and have the relaxing vacation you've been dreaming o …see more

from $233 / night

$1150 - $1975 / week

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Responds fast!
avg. 2 hours 34 minutes

from $233 / 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 - $1435 / week

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from $160 / 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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Responds fast!
avg. 3 hours 53 minutes

from $89 / night

23

Vacation apartment in Siesta Key

Florida / Siesta Key

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Turtle beach was just re-nourished in March 2016!! Come enjoy the great new beach at Fisherman's Cove! 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. (all new photos -just u …see more

from $171 / night

$1195 - $2295 / week

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Responds fast!
avg. 1 hour 54 minutes

from $171 / night

37

Vacation apartment with shared pool 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
ENJOY YOUR BEACH VACATION in this fabulous first floor 1400+ s.f. unit. Step out from the spacious screened lanai to the beautiful tropical grounds, pool and world famous white sugary sands of Crescent Beach! Ceramic tile spread throughout living areas and Island style …see more

from $220 / night

$1540 - $2425 / week

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from $220 / night

19

Vacation apartment with shared pool 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
Gorgeous intra coastal waterway view from this fifth floor two bedroom/two bath unit. Tastefully decorated, light and bright. Over 1400+ s.f. with tiled glassed in lanai over looking the tropical gardens, boats and waterway. Only a five minute walk to our private piece …see more

from $147 / night

$1030 - $1855 / week

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from $147 / night

(1) Excellent 

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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Responds fast!
avg. 2 hours 22 minutes

from $160 / night

38

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
3BR Unit with over 1800 sq. ft of living space! Unique kitchen layout optimizes gulf viewing and includes stainless steel appliances, granite countertops, new cabinets, and a Keurig coffee maker. New flatscreen tv's throughout and wireless internet. Fabulous 180 degree …see more

from $235 / night

$1650 - $2865 / week

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from $235 / night

(5) Excellent 

21

Siesta Key Vacation villa rental

Florida / Siesta Key

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Villa Palma is a stand-alone single story villa located in the beautiful Polynesian Gardens community, on the beautiful barrier island of Siesta Key, Fl. The home is chic and hip in its mid-century modern beach cottage decor and style. The newly renovated kitchen is sle …see more

from $120 / night

$840 / week

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Responds fast!
avg. 2 hours 4 minutes

from $120 / night

23

Apartment rental in Siesta Key with shared pool

Florida / Siesta Key

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $235 / night

$1650 - $2865 / week

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from $235 / night

17

Vacation apartment with shared pool 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
Gorgeous intra coastal waterway views from this fifth floor 2 bed/2 bath condominium unit. Enjoy the tropical breeze from the screened lanai. Living room is furnished with sofa bed, Flat screen HDTV and DVD/CD combo. Master bedroom has king bed, Flat Screen TV and DVD p …see more

from $135 / night

$945 - $1635 / week

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from $135 / night

17

Siesta Key Vacation apartment rental

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Newly redecorated 5th floor unit overlooking the Gulf of Mexico. Ceramic tile throughout, leather sofas in living room with queen size sleeper, large flat panel TV and DVD. Step out on the spacious screened lanai from the living room or master bedroom and watch the Flor …see more

from $220 / night

$1540 - $2425 / week

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from $220 / night

21

Vacation apartment rental

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
***NEWLY REFURNISHED AND REDECORATED! Gorgeous third floor unit with great view of the tropical grounds, crystal white sands and Gulf of Mexico. Spacious screened lanai stretches across living room to master bedroom. Very tastefully decorated; Living room has Smart TV …see more

from $220 / night

$1540 - $2425 / week

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from $220 / 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

(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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Responds fast!
avg. 2 hours 47 minutes

from $90 / night

23

Siesta Key Vacation apartment rental

Florida / Siesta Key

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
2nd Floor with stairs walk up. Living room has sofa bed, TV, VCR, & DVD. Glass enclosed Lanai with great views of canal. Master bedroom has king size bed with TV. Master bath has tub with shower head & glass doors. Guest bedroom has two twin beds. Guest bath is half bat …see more

from $125 / night

$875 - $1640 / week

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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

(2) 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 on the #1 beach in the USA, This 2 bedroom 2 bath garden view unit is located in the garden area of our beautifully landscaped property. This unit is on the first floor and reserved parking is right outside the front door. This unit has a ful …see more

from $251 / night

$1757 / week

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Responds fast!
avg. 2 hours 43 minutes

from $251 / night

16

Siesta Key Vacation apartment rental

Florida / Siesta Key

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Beautifully remodeled and redecorated unit with granite countertops and stainless steel appliances in the kitchen; ceramic tile throughout and updated baths! Gorgeous decor! This 2 bed/2 bath second floor 1400+ s.f. unit overlooks the tropical gardens and Gulf of Mexic …see more

from $220 / night

$1540 - $2425 / week

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from $220 / night

38

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 $178 / night

$1250 - $2020 / week

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from $178 / night

23

Vacation apartment with shared pool in Siesta Key

Florida / Siesta Key

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Fabulously decorated 3/2 corner unit on the seventh floor. Wood flooring and ceramic tile throughout. The updated kitchen and baths adorn granite counter tops. Decorated with soft leather sofa and chairs, the living room comes with TV/VCR/DVD. Step out onto the screene …see more

from $235 / night

$1650 - $2865 / week

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from $235 / night

(6) 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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Responds fast!
avg. 1 hour 44 minutes

from $214 / 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 $119 / night

$833 / week

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Responds fast!
avg. 2 hours 4 minutes

from $119 / night

13

Vacation apartment rental

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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

$1540 - $2425 / week

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from $220 / 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

$850 - $1350 / week

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from $75 / night

33

Siesta Key Vacation apartment rental

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Absolutely gorgeous, newly remodeled beachfront 2BR/2BA that sleeps 6! All new everything as of November 2015! Nice white tile throughout, all new furniture, all new kitchen appliances, recently added 2nd full bathroom, recently added washer and dryer...EVERYTHING NEW!! …see more

from $218 / night

$1530 - $2325 / week

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from $218 / night

19

Vacation apartment with shared pool 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
Great ground floor gulf front 2 bed/2 bath unit. Step out back door of spacious screened lanai that is only steps to pool and the famous white sands of Crescent Beach. Relax on the lanai while enjoying the view of the tropical grounds and beach. Living room offers a le …see more

from $220 / night

$1540 - $2425 / week

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from $220 / night

20

Siesta Key Vacation home rental

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
Description Details Features Inquires Similar Listings google-map-thumb Siesta Key Beach Condo, 2Br/2Ba Direct Beach Front USD 160 Per day 6312 Midnight Pass Rd., Siesta Key slider PreviousNext Property Description Relax in this beautiful f …see more

from $328 / night

$1200 - $2300 / week

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Responds fast!
avg. 3 hours 27 minutes

from $328 / night