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Siesta Key Vacation Rentals

Siesta Key 2-bedroom Beach Rentals, Vacation Rentals & More - 304 Rentals Available.

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Air conditioning (151)
Balcony or terrace (15)
DVD player (14)
Dishwasher (141)
Garden (17)
Grill (61)
Heated pool (137)
High Speed Internet (147)
Hot tub/Jacuzzi (6)
Private pool (117)
Sauna (1)
Swimming pool (141)
Washing machine (61)
Wi-Fi available (60)

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Apartment (86)
Condo (12)
Cottage (4)
House (49)
Townhouse (3)
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304 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

Siesta Breakers #603 in Siesta Key, FL- Sun, Sand & Save 20% to 35% 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 / 24

Midnight Cove #532 in Siesta Key, FL- Sun, Sand & Save 20% to 35% 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 (36 reviews)

from $85.00 / 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. 1 hour 48 minutes

$380.00

Excellent (1 reviews)

from $380.00 / night

Book

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

$450.00

Excellent (7 reviews)

from $450.00 / night

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1 / 24

Midnight Cove #714 in Siesta Key, FL- Sun, Sand & Save 20% to 35% 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

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 / 17

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. 1 hour 48 minutes

$240.00

from $240.00 / night

Book

1 / 24

CocoBayou Cottage 3/2 Heated Pool, Near Beach, Intercoastal, Village, Sleeps 10

Siesta Key House

3 bedrooms 3
2 bathrooms
sleeps 10 10
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 1 hour 48 minutes

$240.00

from $240.00 / 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

$495.00

Excellent (1 reviews)

from $495.00 / night

Book

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
min stay varies

Nearest beach 0.2 mi
Swimming pool
Child friendly

$550.00

Excellent (2 reviews)

from $550.00 / 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. 1 hour 48 minutes

$175.00

from $175.00 / night

Book

1 / 38

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. 1 hour 48 minutes

$235.00

from $235.00 / night

Book

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

$99.00

from $99.00 / night

Book

1 / 36

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

Siesta Key House

4 bedrooms 4
3 bathrooms
sleeps 12 12
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 1 hour 48 minutes

$380.00

from $380.00 / night

Book

1 / 25

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. 1 hour 48 minutes

$380.00

Excellent (1 reviews)

from $380.00 / night

Book

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

$186.00

Excellent (2 reviews)

from $186.00 / night

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1 / 38

Casa Eulimia – 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. 2 hours 20 minutes

$380.00

from $380.00 / night

Book

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. 1 hour 48 minutes

$713.00

from $713.00 / night

Book

1 / 31

Casa Coquina – 4BR/3BA Private Home, Heated Pool, Private Cabana, Walk to Beach

Siesta Key House

4 bedrooms 4
3 bathrooms
sleeps 14 14
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 1 hour 48 minutes

$380.00

from $380.00 / night

Book

1 / 30

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. 1 hour 48 minutes

$170.00

from $170.00 / night

Book

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

Inquire

1 / 33

Casa Antilles – 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. 1 hour 48 minutes

$380.00

from $380.00 / night

Book

1 / 43

Casa Tegula – 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. 1 hour 48 minutes

$380.00

from $380.00 / night

Book

1 / 35

Casa Stolida - 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. 1 hour 48 minutes

$380.00

from $380.00 / 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

$495.00

from $495.00 / 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
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 1 hour 48 minutes

$380.00

from $380.00 / night

Book

1 / 37

4 Bd Waterfront Home w/Pool, Close to Siesta Beach

Siesta Key House

4 bedrooms 4
4 bathrooms
sleeps 8 8
7 nights min

Beach/lakeside relaxation
Nearest beach 1 mi
Swimming pool

“House was newly renovated, nicely funnies and clean. Short walk to Siesta Key Beach and 1 mile to town. Very sweet neighborhood...”

- Review left on 03/05/2017

$395.00

Excellent (9 reviews)

from $395.00 / night

Book

1 / 24

Sandy Cabana- 3BR, Heated Pool, Near Beach Access [Sleeps 8]

Siesta Key House

3 bedrooms 3
3 bathrooms
sleeps 8 8
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 1 hour 48 minutes

$205.00

from $205.00 / night

Book

1 / 22

Casita Playa- Playful 2BR, Private Beach Access, Communal Heated Pool [Sleeps 4]

Siesta Key House

2 bedrooms 2
1 bathroom
sleeps 4 4
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 1 hour 48 minutes

$170.00

Very Good (1 reviews)

from $170.00 / 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

$143.00

Excellent (3 reviews)

from $143.00 / night

Inquire

1 / 32

Moonmist Waterside - 3BR on the Intracoastal Waterway Minutes from Siesta Beach

Siesta Key House

3 bedrooms 3
2 bathrooms
sleeps 7 7
min stay varies

Child friendly
Air conditioning

Responds fast! Avg. 1 hour 48 minutes

$225.00

from $225.00 / 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

Responds fast! Avg. 1 hour 48 minutes

$153.00

Excellent (1 reviews)

from $153.00 / night

Book

1 / 29

Seahorse Cabana offers 3BR, Heated Pool, and is Near Beach Access [Sleeps 8]

Siesta Key House

3 bedrooms 3
3 bathrooms
sleeps 8 8
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 1 hour 48 minutes

$205.00

from $205.00 / night

Book

1 / 36

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

Siesta Key House

8 bedrooms 8
6 bathrooms
sleeps 24 24
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 1 hour 48 minutes

$713.00

from $713.00 / night

Book

1 / 10

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. 1 hour 48 minutes

$255.00

from $255.00 / night

Book

1 / 37

Admirals Watch - Stunning Beachfront 3/3 with Panaromic Views of Siesta Beach

Siesta Key House

3 bedrooms 3
3 bathrooms
sleeps 8 8
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 1 hour 48 minutes

$450.00

from $450.00 / night

Book

1 / 29

Pura Vida Oasis - 5BR Waterfront, Heated Pool, Spa near Village/Beach, Sleeps 13

Siesta Key House

4 bedrooms 4
3 bathrooms
sleeps 13 13
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 1 hour 48 minutes

$270.00

from $270.00 / 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

Responds fast! Avg. 1 hour 48 minutes

$310.00

from $310.00 / night

Book

1 / 27

Casita Mar- Beautiful 2 BR, Heated Pool, w/Spa, Private Beach Access [Sleeps 4]

Siesta Key House

2 bedrooms 2
1 bathroom
sleeps 4 4
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 1 hour 48 minutes

$170.00

from $170.00 / night

Book

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

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.

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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