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

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1,540 Vacation rentals

(24) 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 $358 / night

$2,500 / week

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Responds fast!
avg. 3 hours 7 minutes

from $358 / night

(2) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $202 / night

$1,010 - $1,900 / week

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Responds fast!
avg. 1 hour 26 minutes

from $202 / 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

$1,350 / week

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Responds fast!
avg. 3 hours 11 minutes

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

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 $171 / night

$800 - $1,200 / 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

$1,500 - $2,000 / week

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avg. 3 hours 31 minutes

from $235 / night

35

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
Take a look at this beautiful newly remodeled and redecorated unit! Ground floor 2/2 1400+ sq. ft. with slider glass enclosed lanai for a little more privacy. Open the sliders and still get the screened lanai effect and experience the cool tropical breeze from the Gulf …see more

from $220 / night

$1,540 - $2,500 / week

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from $220 / 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
Fabulous beachfront 2/1.5 second floor unit with incredible 180 degree view of Crescent Beach and Gulf of Mexico! The closest you can get to the beach! Sit on the screened lanai and watch the beautiful sunset. Remodeled kitchen and baths and newly redecorated! Serene se …see more

from $219 / night

$1,530 - $2,395 / week

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from $219 / 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 Adults only 21 Years and over Heated …see more

from $129 / night

$900 / week

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Responds fast!
avg. 1 hour 9 minutes

from $129 / night

46

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
On the water and over 1800 sq. ft., this is a beautiful & newly re-decorated canal-front, two-story town home condo on the bay side. Ceramic tile floors on the first level, carpeted stairs and bedrooms on the second level. The town home is a walk-up on the second floor. …see more

from $147 / night

$1,030 - $1,910 / week

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from $147 / night

30

Vacation apartment in Siesta Key

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Enjoy your vacation in this beautifully renovated two bedroom 1.5 bath condo that sleeps 6. Step into the unit and immediately notice the warm open feel, the beautifully tiled floors and the sweeping panoramic views of an inlet off of the intracoastal waterway. The vi …see more

from $114 / night

$800 - $1,610 / week

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Responds fast!
avg. 3 minutes

from $114 / night

21

Siesta Key Vacation condo rental

Florida / Siesta Key

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 $175 / night

$1,400 - $1,700 / week

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from $175 / night

(1) Excellent 

38

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
WHAT A VIEW! Very updated, tastefully modern, Bay Front Condo with AMAZING views of the water! ALL NEW, absolutely BEAUTIFUL Hardwood floors! Newer, Stainless Steel appliances in the fully equipped kitchen with dishwasher, full-size refrigerator, microwave, oven and sto …see more

from $147 / night

$1,030 - $1,910 / week

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from $147 / night

(12) Excellent 

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 $178 / night

$1,246 / week

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Responds fast!
avg. 1 hour 8 minutes

from $178 / night

33

Siesta Key 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
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 $219 / night

$1,530 - $2,395 / week

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from $219 / night

26

Vacation apartment with shared pool in Siesta Key

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
BEAUTIFUL & NEWLY RE-DECORATED 2 BED/2BATH; over 1400 s.f. located on the first floor. Ceramic tile floors in living areas. Dine al fresco or sip a margarita on the spacious screened lanai at the table or high top bar overlooking the lush tropical grounds, crystal white …see more

from $220 / night

$1,540 - $2,500 / week

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from $220 / 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 $165 / night

$1,150 - $1,450 / week

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Responds fast!
avg. 3 hours 35 minutes

from $165 / night

19

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
What a fabulous light and bright 2 bed/1.5 bath third floor unit with ceramic flooring in the living area! Enjoy a cool tropical drink on the open balcony overlooking the white sugary sands of Crescent Beach and the azure blue waters of the Gulf of Mexico! Living room …see more

from $219 / night

$1,530 - $2,395 / week

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from $219 / 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 

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 $131 / night

$917 / week

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Responds fast!
avg. 2 hours 1 minutes

from $131 / night

28

Vacation apartment with shared pool in Siesta Key

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Owner takes pride in this beautifully decorated 2nd floor unit. 2 bedroom 1 1/2 baths. Newly remodeled! Very cozy and comfortable with amazing tranquility and peacefulness courtesy of the laid back, canal-front setting. The unit features ceramic tile floors and a den-li …see more

from $125 / night

$875 - $1,690 / week

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from $125 / night

23

Vacation apartment in Siesta Key

Florida / Siesta Key

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Child friendly
My Condo located in a corner unit on the 6th floor offers a beautiful panoramic view of both the Gulf of Mexico and the Intracoastal Waterway. Decorated in Tropical Tommy Bahama the Condo is clean and comfortable. View Boats and Dolphins traveling the Intracoastal W …see more

from $180 / night

$1,200 / week

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from $180 / night

19

Vacation home accommodation

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Make this beautiful beach cottage your vacation home! It is only a stone's throw from the beach and very short walk to Siesta Key Village. Enjoy the sun, picnics on the beach, exquisite sunsets, bike riding, shopping or just relaxing in your own private yard. Once you …see more

from $180 / night

$1,260 / week

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from $180 / 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

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

33

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
Beautifully updated and redecorated unit on the 2nd floor in the mid-rise building on the Gulf Side with Gulf View! 2 bedroom, 2 full bath with washer & dryer in the unit. The Master bedroom has a king bed with a sliding glass door out to the lanai. The master bath has …see more

from $220 / night

$1,540 - $2,500 / week

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from $220 / night

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
NEWLY REFURBISHED 2 BR, 1.5 BA !! New floors, paint, furniture, decor & appliances in 2012. This light and bright ground floor condo is the closest Bay unit to the pool, office, laundry and beach. The newly furnished screened lanai offers views of the beautiful tropical …see more

from $125 / night

$875 - $1,690 / week

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from $125 / 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

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

$1,030 - $1,910 / week

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from $147 / 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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Responds fast!
avg. 3 hours 50 minutes

from $255 / 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
Sleeps no more than 6. Spacious 2 bedroom 1.5 Bath, Bay Side unit with a nice canal view! Walk out your back door to the heated pool and boat docks! Only about a 5 minute (350yd) walk to your private area of the beautiful white sands of award winning Crescent beach. The …see more

from $125 / night

$875 - $1,690 / week

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from $125 / night

(25) Excellent 

45

Siesta Key Vacation apartment rental

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Our condo is on the second floor and is only 3 doors from the lovely pool, jacuzzi and fishing pier. The private Cresant Beach which is deeded just for the Palm Bay Guests and is just across the street from the Bay side. It is raked every a.m. and loung chairs set out …see more

from $129 / night

$903 - $1,750 / week

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from $129 / night

34

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

$1,540 - $2,500 / week

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from $220 / 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 $131 / night

$917 / week

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Responds fast!
avg. 2 hours 1 minutes

from $131 / 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 $160 / night

$1,295 - $1,435 / week

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Responds fast!
avg. 1 hour 51 minutes

from $160 / night

32

Vacation hotel apartment in Siesta Key

Florida / Siesta Key

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
Imagine Yourself At (Tiny) Home: Beach life is best! Enter through the bright yellow, life-sized replica of a Siesta Key lifeguard stand, and drop your beach bags on the two stools beneath our surfboard-shaped breakfast bar. Passing through the living room, decorated w …see more

from $162 / night

$1,134 / week

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from $162 / night

(10) 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 53 minutes

from $130 / night

(1) Excellent 

28

Vacation home in Siesta Key

Florida / Siesta Key

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Old Man and the Sea Inn - 1 marlin to the sand! 2BR (sleeps 8). Brought to you by Gertrude Rentals! Perfect for travelers in search of uncomplicated seclusion. Located in the most “private” non-private beach neighborhood in Siesta Key, The Old Man and the Sea Inn can …see more

from $140 / night

$1,000 / week

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Responds fast!
avg. 1 hour 26 minutes

from $140 / night

(1) Excellent 

19

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
Enjoy the Florida lifestyle in this 4th Floor, 1400 sq. ft., 2 BDR/ 2 Bath condo overlooking the tranquil waters of the intra coastal waterway. Cross the road and you are just a few hundred feet away from your own piece of the soft white sugary sands of Crescent Beach. …see more

from $147 / night

$1,030 - $1,910 / week

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from $147 / night

(4) Excellent 

14

Vacation apartment 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
PLEASE BOOK THRU ME, CARRIE CAUDILL, FLORIDA, DO NOT SEND MONEY TO ANOTHER PERSON OR STATE. PLEASE CONTACT THE OWNER FOR PRICES AND DATE'S, DON'T GO BY FLIPKEY'S, CARRIE 941-587-4794 siestakeycarrie@gmail.com My ground floor rental is directly on the beach on the …see more

from $211 / night

$1,475 / week

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from $211 / night