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Siesta Key Vacation Rentals

Siesta Key 2-bedroom Beach Rentals, Vacation Rentals & More - 297 Rentals Available.

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Air conditioning (149)
Balcony or terrace (87)
DVD player (99)
Dishwasher (144)
Fireplace (1)
Garden (16)
Grill (141)
Heated pool (139)
High Speed Internet (149)
Hot tub/Jacuzzi (5)
Private pool (118)
Sauna (2)
Swimming pool (142)
Washing machine (138)
Wi-Fi available (57)

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Apartment (87)
Condo (13)
Cottage (3)
House (46)
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297 Vacation rentals

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Filters applied: 2+ Bedrooms

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

$88.00

Excellent (38 reviews)

from $88.00 / 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

$88.00

Excellent (5 reviews)

from $88.00 / 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 / 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

Inquire

1 / 51

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 / 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 (8 reviews)

from $516.00 / 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

Inquire

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. 2 hours 25 minutes

$602.00

Excellent (2 reviews)

from $602.00 / night

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1 / 24

Tropical Beach Getaway at Sandy's Siesta! April 2019 dates available!!

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

$130.00

Excellent (9 reviews)

from $130.00 / night

Inquire

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

$682.00

Excellent (2 reviews)

from $682.00 / 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
7 nights min

Swimming pool
Child friendly
Air conditioning

$395.00

Excellent (1 reviews)

from $395.00 / 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

$260.00

from $260.00 / 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 27 minutes

$225.00

from $225.00 / night

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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

$114.00

from $114.00 / night

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1 / 31

FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN, UPDATED KITCHEN!

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 / 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

$185.00

from $185.00 / 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

$185.00

from $185.00 / night

Book

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 (4 reviews)

from $144.00 / night

Inquire

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

$325.00

Excellent (1 reviews)

from $325.00 / 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 27 minutes

$185.00

from $185.00 / night

Book

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

$168.00

Excellent (1 reviews)

from $168.00 / night

Book

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 27 minutes

$150.00

from $150.00 / night

Book

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

$325.00

from $325.00 / night

Book

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 27 minutes

$250.00

from $250.00 / 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

Inquire

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

$144.00

Excellent (10 reviews)

from $144.00 / night

Inquire

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

$255.00

from $255.00 / night

Book

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 27 minutes

$255.00

from $255.00 / night

Book

1 / 45

Villa Trinidad – Hidden 4 BR Home on Canal, Heated Pool, w/Dock [Sleeps 10]

Siesta Key House

4 bedrooms 4
2 bathrooms
sleeps 10 10
min stay varies

Swimming pool
Child friendly
Air conditioning

$250.00

from $250.00 / night

Book

1 / 40

Casa Ohana – 4BR/3BA Private Home, Heated Pool and Cabana, in Siesta Key Village

Siesta Key House

4 bedrooms 4
3 bathrooms
sleeps 12 12
7 nights min

Swimming pool
Child friendly
Air conditioning

$395.00

from $395.00 / night

Book

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. 2 hours 25 minutes

$602.00

from $602.00 / night

Book

1 / 31

Siesta Dream House- 4 BR, 3.5 BA Villa W/ Heated Pool, Spa On Siesta Key

Siesta Key House

4 bedrooms 4
4 bathrooms
sleeps 12 12
7 nights min

Swimming pool
Child friendly
Air conditioning

$325.00

from $325.00 / night

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1 / 41

A Tropical 2Br Retreat on a Florida Isle

Siesta Key Condo

2 bedrooms 2
2 bathrooms
sleeps 5 5
7 nights min

Swimming pool
Ask about children
Air conditioning

“Our stay at Siesta Palms was great. The condo was very clean and up to date. We enjoyed the beautiful pool and proximity to the beach. The owners couldn't have been kinder or more accommodating. I highly recommend this condo...”

- Review left on 04/15/2016

$311.00

Excellent (2 reviews)

from $311.00 / 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
7 nights min

Swimming pool
Child friendly
Air conditioning

$728.00

from $728.00 / night

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1 / 40

Monarch 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

$255.00

from $255.00 / night

Book

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

$260.00

from $260.00 / night

Book

1 / 18

Sea the View - 4/3 Waterfront, Heated Pool, w/Spa, Near Beach [Sleeps 10]

Siesta Key House

3 bedrooms 3
3 bathrooms
sleeps 8 8
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 3 hours 27 minutes

$260.00

from $260.00 / night

Book

1 / 76

The Pearl by the Sea -4/3 Waterfront, Heated Pool, w/Spa, Near Beach [Sleeps 10]

Siesta Key House

4 bedrooms 4
3 bathrooms
sleeps 10 10
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 3 hours 27 minutes

$280.00

Excellent (1 reviews)

from $280.00 / night

Book

1 / 28

Three bedroom house directly on beach with gulf vi

Siesta Key House

3 bedrooms 3
4 bathrooms
sleeps 7 7
min stay varies

Beach/lakeside relaxation
Child friendly
Air conditioning

“My husband and I stayed at Tiffany Sands for the months of February and March 2016. We loved the proximity to the beach and Siesta Key Village. The townhouse is well appointed and had nearly everything we needed for a comfortable 2 month stay. The...”

- Review left on 04/28/2016

$262.00

Very Good (2 reviews)

from $262.00 / night

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1 / 34

Casa Costero- Breathtaking 3 BR in Siesta Key Village, w/Gulf Views [Sleeps 9]

Siesta Key Townhouse

3 bedrooms 3
4 bathrooms
sleeps 9 9
min stay varies

Child friendly

Responds fast! Avg. 3 hours 27 minutes

$255.00

from $255.00 / night

Book

Page 1 of 8

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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.

Estimated price per night based on a weekly stay. Owner fees of {FEE} per stay may apply.

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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