Siesta Key Vacation Rentals on the Water - Waterfront Rentals in Siesta Key

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)

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from $450.00 / night

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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)

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from $85.00 / night

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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)

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from $85.00 / night

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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)

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from $147.00 / night

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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)

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from $380.00 / night

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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)

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from $120.00 / night

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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

$127.00

Excellent (6 reviews)

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from $127.00 / night

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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

$395.00

Excellent (4 reviews)

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from $395.00 / night

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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)

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from $495.00 / night

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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

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from $713.00 / night

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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

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from $310.00 / night

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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

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from $240.00 / night

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636ontheKey - The "Belle of the Beach"

Siesta Key House

4 bedrooms 4
5 bathrooms
sleeps 14 14
min stay varies

Beach/lakeside relaxation
Child friendly
Air conditioning

“We used this house as a work retreat and a celebration! Overall, the house was perfect. Plenty of space, the views were awesome, the living room was great for a work meeting (5 people). The balconies were great. A good location...away from the town...”

- Review left on 01/23/2017

$500.00

Excellent (7 reviews)

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from $500.00 / night

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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. 1 hour 48 minutes

$170.00

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from $170.00 / night

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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

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from $495.00 / night

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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)

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from $380.00 / night

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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

$199.00

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from $199.00 / night

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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

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from $240.00 / night

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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)

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from $89.00 / night

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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

Responds fast! Avg. 1 hour 48 minutes

$175.00

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from $175.00 / night

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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)

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from $143.00 / night

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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)

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from $236.00 / night

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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)

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from $550.00 / night

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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)

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from $153.00 / night

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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)

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from $395.00 / night

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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

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from $255.00 / night

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

Siesta Key Condo

1 bedroom 1
1 bathroom
sleeps 3 3
7 nights min

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)

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from $200.00 / night

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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)

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from $125.00 / night

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