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

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1,228 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 50 minutes

from $193 / 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 $224 / night

$1,148 - $2,128 / week

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avg. 1 hour 51 minutes

from $224 / 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

(19) 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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from $358 / 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

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
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 view …see more

from $114 / night

$770 - $1,610 / week

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avg. 3 minutes

from $114 / night

(1) 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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from $129 / 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

(11) 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 $198 / night

$1,386 / week

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avg. 1 hour 12 minutes

from $198 / night

13

Vacation home in Siesta Key

Florida / Siesta Key

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Escape to your own secluded tropical oasis. Lush island landscaping surrounding the property makes this home a unique and private setting. Private dock on protected cove 2 minutes from Sarasota Bay/ICW. Rent a boat at neighboring marina if you choose. Breathtaking large …see more

from $429 / night

$3,000 - $5,500 / week

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from $429 / 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 atmospher …see more

from $107 / night

$742 - $1,505 / week

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avg. 3 minutes

from $107 / 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 $275 / night

$2,065 - $2,275 / week

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avg. 3 hours 51 minutes

from $275 / night

35

Vacation home rental

Florida / Siesta Key

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The Palm Oasis is a 4-bed single family home with 2,000 sq. ft. located only 1 block away from Siesta Key Beach. This home is on one level and has all the amenities including a brand new salt-water pool which is the center of the backyard and a outdoor BBQ grill with …see more

from $358 / night

$2,500 - $3,850 / week

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avg. 1 hour 44 minutes

from $358 / night

(1) Excellent 

20

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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from $160 / night

(17) 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

$850 - $1,300 / week

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Responds fast!
avg. 1 hour 23 minutes

from $155 / 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

$1,000 / week

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avg. 3 hours 36 minutes

from $143 / night

14

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
Owner takes pride in this beautifully decorated ground floor unit featuring ceramic tile floors and extended living room. Slider doors open to screens across the back of the unit and your own private back door. Step out to the serene canal waters, boat docks and swimmi …see more

from $125 / night

$875 - $1,690 / week

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from $125 / 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 own p …see more

from $170 / night

$910 - $1,499 / week

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avg. 3 minutes

from $170 / 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

(1) Excellent 

20

Siesta Key Vacation apartment rental

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The condo is across the street from beautiful white sand Siesta Key Beach, and less than a mile from Siesta Key Village (Restaurants, bars, shopping, etc). You’ll love my place because of the location. The condo is perfect for couples, solo adventurers, and families (wi …see more

from $175 / night

$1,225 / week

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from $175 / night

(23) 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

$1,000 - $2,100 / week

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avg. 59 minutes

from $155 / 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 $97 / night

$675 - $1,350 / week

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from $97 / night

30

Siesta Key Vacation apartment rental

Florida / Siesta Key

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Air conditioning
Bay side of the road, canal-front, ground-level 2BR/1.5BA unit. New to the rental program! Spacious living and dining area, (living room extended out so no patio/lanai.) Rear entrance looks out onto a little inlet/canal with boat docks and nearby pool. King bed in maste …see more

from $120 / night

$845 - $1,480 / week

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from $120 / night

15

Vacation apartment rental

Florida / Siesta Key

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
OUSTANDING VIEW FROM THIS DIRECT BEACHFRONT UNIT! Ceramic tile in living area; carpet in bedrooms. DSL and wireless internet connection available in kitchen area. 2 bedroom/1.5 bath third floor walk-up. Enjoy the Siesta sunsets and the cool tropical breeze while sipping …see more

from $218 / night

$1,530 - $2,395 / week

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from $218 / night

(3) Excellent 

49

Siesta Key Vacation apartment rental

Florida / Siesta Key

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • 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 $179 / night

$999 - $1,299 / week

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avg. 1 hour 53 minutes

from $179 / night

16

Vacation villa in Siesta Key

Florida / Siesta Key

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly
Modern Clean, Well Appointed Stand Alone Villa, 2 bdrm-2bath. Private Hi-speed internet, 3 tv's , Whole house DVR, Sleeps 4. Fully equipped kitchen, computer desk in living room, dual recliner leather sofa, Lazyboy reckliner, HD TV with DVR 280 channels and free Starz m …see more

from $164 / night

$1,150 - $1,686 / week

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from $164 / night

18

Condo rental in Siesta Key

Florida / Siesta Key

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Child friendly
  • Air conditioning
You will have a visit to remember in this elegant three bedroom, two and one half bath vacation condo with a path to the famous Siesta Key white sand beaches just out your door! Two levels with tiles lanais and Gulf views from each level. Enjoy the amazing Gulf Coast su …see more

from $371 / night

$2,595 / week

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from $371 / night

23

Vacation apartment with shared pool in Siesta Key

Florida / Siesta Key

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Newly remodeled! Beautifully and tastefully decorated in a very simple, clean and modern style. Spacious, second floor 3BR/2BA quiet and private corner unit. King bed in master, 2 Twins in the large guest room and a double sized bed in the small guest room. Comfortably …see more

from $235 / night

$1,650 - $2,950 / week

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from $235 / 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

(11) Very Good 

16

Siesta Key Vacation apartment rental

Florida / Siesta Key

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
GREAT Value !!! MVPROPERTIES AT SIESTA KEY Recently renovated and very conveniently located duplex villas at beautiful Crescent Beach on Siesta Key. We have (2) 2 bedroom 1 bath apartments. Each apartment sleeps up to 5 persons. Rent 1 apartment or both. The units ar …see more

from $150 / night

$995 - $1,605 / week

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avg. 1 hour 16 minutes

from $150 / night

38

Siesta Key Vacation apartment rental

Florida / Siesta Key

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • 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

$1,250 - $2,080 / week

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from $178 / 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 - $1,150 / week

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Responds fast!
avg. 2 hours 6 minutes

from $130 / night

12

Vacation condo with swimming pool in Siesta Key

Florida / Siesta Key

2 6 14 nights min

  • 2 bedrooms
  • Sleeps 6
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our high-rise Condo located in Crystal Sands Resort unit #1102, 11th floor, gives our guests a panoramic view of the beautiful Crescent Beach on Siesta Key. Watch the Sun rise in the morning and set in the evening from our unique Southwest balcony view. Our thirty-five …see more

from $315 / night

$2,200 / week

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avg. 3 hours 0 minutes

from $315 / night

(1) Excellent 

35

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
I am happy to report that Hurricane Irma did not crush our beautiful Siesta Key, as it could have. Our complex has a couple of trees down and a few of exterior lamps pushed over; however, we have electricity are putting it all back together! Unlike many rental propert …see more

from $149 / night

$1,043 / week

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avg. 54 minutes

from $149 / night

46

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
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

39

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
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

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

$1,195 - $2,295 / week

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Responds fast!
avg. 1 hour 54 minutes

from $171 / night

20

Siesta Key Vacation apartment rental

Florida / Siesta Key

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
THIS 2 BEDROOM/2 BATH 2ND FLOOR WALK UP UNIT HAS BEEN REMODELED!! Light ceramic tile throughout; updated kitchen with granite counter tops and stainless steel appliances! Beautifully decorated with leather sofa and reclining chair. Flat screen TV in living area; flat sc …see more

from $218 / night

$1,530 - $2,395 / week

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from $218 / night

(9) Excellent 

Certificate of Excellence

27

Vacation villa in Siesta Key

Florida / Siesta Key

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
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

Certificate of Excellence

from $400 / night

$2,750 - $5,000 / week

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avg. 2 hours 36 minutes

from $400 / night