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Siesta Key Vacation Rentals

Siesta Key Waterfront Beach Rentals, Vacation Rentals & More - 365 Rentals Available.

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Air conditioning (159)
Balcony or terrace (92)
DVD player (104)
Dishwasher (153)
Fireplace (1)
Garden (18)
Grill (151)
Heated pool (146)
High Speed Internet (161)
Hot tub/Jacuzzi (8)
Private pool (120)
Sauna (3)
Swimming pool (152)
Washing machine (147)
Wi-Fi available (66)

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Apartment (90)
Condo (19)
Cottage (4)
House (48)
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365 Vacation rentals

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Distance calculated in a straight line, road distances may differ. Confirm exact location with the property owner/manager.

1 / 24

Midnight Cove #532 in Siesta Key, FL- Sun, Sand & Save 20% to 45% per Week

Siesta Key Condo

2 bedrooms 2
2 bathrooms
sleeps 4 4
7 nights min

Nearest beach 0.25 mi
Swimming pool
Child friendly

“Excellent property with lot of parking, laundy on site and warm water in the pool, which was really appreciated on the cooler dates, speacially by the kids. Close walk to a white sandy beach was on asset. Condo was very spacious and full equipped. We...”

- Review left on 01/02/2013

$85.00

Excellent (38 reviews)

from $85.00 / night

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1 / 24

Midnight Cove #714 in Siesta Key, FL- Sun, Sand & Save 20% to 45% per Week

Siesta Key Condo

2 bedrooms 2
2 bathrooms
sleeps 4 4
7 nights min

Nearest beach 0.25 mi
Swimming pool
Child friendly

“Had an excellent time! Unit was clean and precisely as described. Great location on Siesta Key with a short walk for Groceries, Food and Libations. Beach was a 5min walk across the street (using the signaled crosswalk) through the beachside section...”

- Review left on 03/13/2017

$85.00

Excellent (5 reviews)

from $85.00 / night

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1 / 24

Siesta Breakers #603 in Siesta Key, FL- Sun, Sand & Save 20% to 45% per Week

Siesta Key Condo

2 bedrooms 2
2 bathrooms
sleeps 6 6
7 nights min

Nearest beach 0.1 mi
Swimming pool
Child friendly

“This was our first trip to Siesta Key, but not our last! We are already booking another stay at Siesta Breakers for next year. It is a great location on the Beach and great access to the mainland...”

- Review left on 07/14/2014

$147.00

Excellent (26 reviews)

from $147.00 / night

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1 / 17

Siesta Key Beachfront Condo with Gulf View!

Siesta Key Condo

1 bedroom 1
1 bathroom
sleeps 4 4
7 nights min

Beach/lakeside relaxation
Child friendly
Air conditioning

“We stayed in Crescent Royale #409. Condo was extremely clean and well supplied. We had flown in and was thrillled to see beach chairs, umbrellas, towels and etc. that we couldn't bring along. The property was peaceful and quiet. Only problem was RED...”

- Review left on 10/04/2016

$120.00

Very Good (13 reviews)

from $120.00 / night

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1 / 38

Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa

Siesta Key House

5 bedrooms 5
4 bathrooms
sleeps 13 13
7 nights min

Swimming pool
Child friendly
Car not necessary

$516.00

Excellent (7 reviews)

from $516.00 / night

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1 / 40

Beautiful Condominium In Great Location !

Siesta Key Condo

2 bedrooms 2
2 bathrooms
sleeps 6 6
14 nights min

Swimming pool
Child friendly
Air conditioning

“Great place! Everything was wonderful,beach was a short walk away. Love all the new addition to public beach. Pool was heated,we went swimming every day. Unit was very clean and comfortable,couldn't ask for a better place. Took the free taxi to...”

- Review left on 01/06/2017

$89.00

Excellent (12 reviews)

from $89.00 / night

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1 / 33

Siesta Key Beachfront 3 Bedroom Home, Sarasota

Siesta Key House

3 bedrooms 3
3 bathrooms
sleeps 9 9
min stay varies

Beach/lakeside relaxation
Nearest beach 0 mi
Child friendly

$453.00

Excellent (4 reviews)

from $453.00 / night

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1 / 16

Beautiful Crescent Beach on Siesta Key One of the

Siesta Key Condo

2 bedrooms 2
2 bathrooms
sleeps 4 4
7 nights min

Beach/lakeside relaxation
Child friendly
Air conditioning

“Siesta Key is the best beach I ever been so far and this place that Jack and Darlene provide is a dream. Everything is clean and in perfect working condition. The beach is very nice (and I have visited many being a South Floridian), crystal clear and...”

- Review left on 09/19/2016

$193.00

Excellent (2 reviews)

from $193.00 / night

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1 / 33

Tropical Escape 1 Br Siesta Key Inn

Siesta Key Condo

1 bedroom 1
1 bathroom
sleeps 4 4
min stay varies

Nearest beach 0.09 mi
Swimming pool
Ask about children

$228.00

from $228.00 / night

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1 / 40

The Canopy Cottage – 4/3 Private Pool and Spa, Near Siesta’s North Village

Siesta Key House

4 bedrooms 4
3 bathrooms
sleeps 8 8
min stay varies

Child friendly
Pet friendly

Responds fast! Avg. 3 hours 42 minutes

$235.00

from $235.00 / night

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1 / 24

Tropical Beach Getaway at Sandy's Siesta!

Siesta Key Condo

2 bedrooms 2
2 bathrooms
sleeps 4 4
min stay varies

Beach/lakeside relaxation
Nearest beach 0.01 mi
Swimming pool

“We recently spent a week in Siesta Key, our fourth year in a row making this our Fall vacation spot. This year, we we fortunate to find an available week at Sandy' Siesta that matched out travel plans. What a great spot! A short walk to the...”

- Review left on 12/16/2016

$125.00

Excellent (9 reviews)

from $125.00 / night

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1 / 24

Gorgeous Views of the Gulf Sea Turtle Unit Sunset Beach Resort

Siesta Key Apartment

3 bedrooms 3
2 bathrooms
sleeps 8 8
min stay varies

Child friendly

Responds fast! Avg. 3 hours 50 minutes

$567.00

Excellent (1 reviews)

from $567.00 / night

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1 / 23

Luxury Siesta Key Four Bedroom,Five Bathroom Pool Home,180 Yards to Siesta Beach

Siesta Key House

4 bedrooms 4
5 bathrooms
sleeps 12 12
7 nights min

Nearest beach 0.2 mi
Swimming pool
Child friendly

$630.00

Excellent (2 reviews)

from $630.00 / night

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1 / 39

Sophie’s Cottage- Waterfront 2/2 with Heated Pool Near Beach Access [Sleeps 8]

Siesta Key House

2 bedrooms 2
2 bathrooms
sleeps 8 8
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 3 hours 42 minutes

$200.00

from $200.00 / night

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1 / 22

Charming Siesta Key Village Unbeatable Location

Siesta Key Condo

1 bedroom 1
1 bathroom
sleeps 4 4
min stay varies

Nearest beach 0 mi
Swimming pool
Child friendly

Responds fast! Avg. 1 hour 59 minutes

“We stayed for a week and had the best time ever. The accommodations are top notch, locals are very friendly, food delicious and breathtaking beaches. Definitely looking forward to coming back”

- Review left on 12/15/2015

$146.00

Excellent (6 reviews)

from $146.00 / night

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1 / 39

Casa Junonia - 4BR/3BA Private Home, Heated Pool, Private Cabana, Walk to Beach

Siesta Key House

4 bedrooms 4
3 bathrooms
sleeps 12 12
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 3 hours 42 minutes

$380.00

Excellent (1 reviews)

from $380.00 / night

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1 / 10

Siesta Key Beach Vacation

Siesta Key Condo

1 bedroom 1
1 bathroom
sleeps 4 4
14 nights min

Beach/lakeside relaxation
Swimming pool
Child friendly

“FIVE STARS!!!!! Terry the owner is a great guy that insured our stay in his condo went well. The condo has a great location just a couple of blocks from the Siesta Key Beach. The condo has everything you need for a great beach experience. The...”

- Review left on 01/24/2017

$87.00

Excellent (2 reviews)

from $87.00 / night

Inquire

1 / 14

Gateway to Siesta Key 1/2 mile Walk Siesta Key Beach

Siesta Key Condo

2 bedrooms 2
2 bathrooms
sleeps 4 4
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 3 hours 56 minutes

$114.00

from $114.00 / night

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1 / 24

A Tropical 1Br Retreat on a Florida Isle

Siesta Key Condo

1 bedroom 1
1 bathroom
sleeps 4 4
min stay varies

Swimming pool
Ask about children
Air conditioning

“Thank you for a wonderful week! The room was beautiful and Mary Ann and staff were all so accommodating to anything that you may need! We would highly recommend Siesta Palms to everyone! We are looking forward to coming back as soon as possible,...”

- Review left on 07/13/2016

$228.00

Excellent (5 reviews)

from $228.00 / night

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1 / 31

Villa Vista Mare - Luxurious 3BD/3BA Beachfront, Heated Pool

Siesta Key House

3 bedrooms 3
3 bathrooms
sleeps 8 8
min stay varies

Beach/lakeside relaxation
Swimming pool
Child friendly

Responds fast! Avg. 3 hours 42 minutes

$380.00

Excellent (1 reviews)

from $380.00 / night

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1 / 40

Casita Bayou – Completely Renovated 2/1 Heated Pool Home On Canal [Sleeps 6]

Siesta Key House

2 bedrooms 2
1 bathroom
sleeps 6 6
min stay varies

Child friendly
Pet friendly

Responds fast! Avg. 3 hours 42 minutes

$170.00

from $170.00 / night

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1 / 25

Honey Mango Cabana – 2/1, Shared Heated Pool, Near Beach Access

Siesta Key Cottage

2 bedrooms 2
1 bathroom
sleeps 6 6
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 3 hours 42 minutes

$153.00

Excellent (1 reviews)

from $153.00 / night

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1 / 29

Coral Reef Casita- 2 BR Casita, Heated Pool, 4 Min Walk to Beach [Sleeps 6]

Siesta Key House

2 bedrooms 2
2 bathrooms
sleeps 6 6
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 3 hours 42 minutes

$170.00

from $170.00 / night

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1 / 17

WOW!! ONLY STEPS FROM THE POOL AND BEACH IN THIS NEWLY UPDATED CONDO!

Siesta Key Condo

2 bedrooms 2
2 bathrooms
sleeps 6 6
7 nights min

Beach/lakeside relaxation
Nearest beach 0 mi
Swimming pool

$236.00

Excellent (6 reviews)

from $236.00 / night

Inquire

1 / 21

Gorgeous Condo directly on #1 Beach in USA - #111

Siesta Key Condo

1 bedroom 1
1 bathroom
sleeps 3 3
min stay varies

Beach/lakeside relaxation
Swimming pool
Child friendly

“We actually stayed in unit #113 and it was simple but clean with updated kitchen. The grounds, pool, and amenities were well maintained and clean. The Gulf view was amazing! We have visited many beaches but this was the most beautiful with a quiet...”

- Review left on 07/07/2016

$200.00

Excellent (6 reviews)

from $200.00 / night

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1 / 24

Juicy Mango Cabana – 2/2, w/ Shared Heated Pool, Near Beach Access

Siesta Key Cottage

2 bedrooms 2
2 bathrooms
sleeps 6 6
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 3 hours 42 minutes

$170.00

from $170.00 / night

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1 / 41

2 BR, 2 Bath, Siesta Key Village Condo with Pool

Siesta Key Condo

2 bedrooms 2
2 bathrooms
sleeps 4 4
min stay varies

Nearest beach 0.1 mi
Swimming pool
Child friendly

$144.00

Excellent (3 reviews)

from $144.00 / night

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1 / 27

Floritas Key is an encaptivating 3 BR + 2 BA Private Home, Heated Pool w/Spa

Siesta Key House

4 bedrooms 4
2 bathrooms
sleeps 8 8
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 3 hours 42 minutes

$150.00

from $150.00 / night

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1 / 28

Amazing Views of the Gulf Sea Gull unit Sunset Beach Resort

Siesta Key Apartment

2 bedrooms 2
2 bathrooms
sleeps 8 8
min stay varies

Child friendly
Car not necessary
Air conditioning

Responds fast! Avg. 3 hours 50 minutes

$567.00

from $567.00 / night

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1 / 26

Mango Manor - Vibrant 4/3, W/Heated Pool, Right By Beach Access #13 [Sleeps 12]

Siesta Key House

4 bedrooms 4
3 bathrooms
sleeps 12 12
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 3 hours 42 minutes

$310.00

Excellent (1 reviews)

from $310.00 / night

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1 / 18

2 BR, 2 Bath, Siesta Key Village Condo with Pool

Siesta Key Condo

2 bedrooms 2
2 bathrooms
sleeps 4 4
min stay varies

Nearest beach 0.1 mi
Swimming pool
Child friendly

“Great property, beautiful pool, super close to the beach and the village - will totally be back! Awesome property management as well...”

- Review left on 06/13/2016

$143.00

Excellent (9 reviews)

from $143.00 / night

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1 / 43

Villa Cascada- 4BR, 2 Kitchens, Heated Pool, Near Beach Access [Sleeps 12]

Siesta Key House

4 bedrooms 4
4 bathrooms
sleeps 12 12
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 3 hours 42 minutes

$310.00

from $310.00 / night

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1 / 30

Renovated 1st Floor Condo with WIFI, HDTV & w/d

Siesta Key Condo

2 bedrooms 2
2 bathrooms
sleeps 4 4
7 nights min

Nearest beach 0.25 mi
Child friendly
Air conditioning

“My husband & I chose this condo on-line. It was immaculate, very nicely renovated, had a wonderful view of the boat docks and pool, and an owner who could not have been nicer. Midnight Cove II community is a gem. People & staff are friendly, the...”

- Review left on 01/30/2017

$121.00

Excellent (8 reviews)

from $121.00 / night

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1 / 33

Casita Morning Star – 3BR/3BA Private Heated Pool, Screened Lanai, Walk to Beach

Siesta Key House

3 bedrooms 3
3 bathrooms
sleeps 10 10
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 3 hours 42 minutes

$240.00

from $240.00 / night

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1 / 33

Peacock Villa – Gulfview, 3/3, Heated Pool, Near Village

Siesta Key Townhouse

3 bedrooms 3
3 bathrooms
sleeps 8 8
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 3 hours 42 minutes

$240.00

from $240.00 / night

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1 / 40

The Conch – 8BR/6BA Private Home, Heated Pool, Private Cabana, Walk to Beach

Siesta Key House

8 bedrooms 8
6 bathrooms
sleeps 12 12
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 3 hours 42 minutes

$713.00

from $713.00 / night

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1 / 14

Sand Dollar Unit at Sunset Beach Resort Beach Front property

Siesta Key Apartment

1 bedroom 1
1 bathroom
sleeps 4 4
min stay varies

Child friendly
Car not necessary
Air conditioning

Responds fast! Avg. 3 hours 50 minutes

$229.00

from $229.00 / night

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1 / 27

Villa De Paradisio- 4BR Waterfront Home on Canal, Heated Pool, w/Boat [Sleeps12]

Siesta Key House

4 bedrooms 4
2 bathrooms
sleeps 12 12
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 3 hours 42 minutes

$235.00

from $235.00 / night

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1 / 39

Buccaneer’s Hideaway – 4BR/2.5BA Heated Pool, Dock, Canal, MInutes to Siesta Key

Siesta Key House

4 bedrooms 4
3 bathrooms
sleeps 12 12
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 3 hours 42 minutes

$175.00

from $175.00 / night

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1 / 25

Large 1br/1ba vacation rental condo (780 Sq.Ft.)

Siesta Key Condo

1 bedroom 1
1 bathroom
sleeps 4 4
1 night min

Swimming pool
Ask about children
Air conditioning

“This place is absolutely great. Me and my girlfriend spent two nights over the weekend at this condo. First of all this place has more stuff that we could imagine. It literally includes everything you need for having a pleasant and comfortable stay....”

- Review left on 07/26/2016

$104.00

Very Good (4 reviews)

from $104.00 / night

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This is the estimated nightly price based on a weekly stay. Contact the advertiser to confirm the price - it varies depending on when you stay and how long for.

This is the estimated nightly price based on a weekly stay.

This is the total cost of the stay for the dates and number of guests that you entered.

This price is an estimate based on the latest rate information available to us. Contact the advertiser to ask for the exact price, including any additional fees.

Rates for this rental are unknown, please contact the homeowner to confirm the rate.

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