Siesta Key Vacation Rentals, Villas, & More

1-50 of 140 Siesta Key Rentals

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Siesta Key Florida Vacation Rentals - Villa
1 / 14

Siesta Key Villa
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”15 Reviews

from

$100

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 24

Siesta Key Condo
2 Bedrooms / 1.5 Bathrooms / Sleeps 4

“ Excellent ”4 Reviews

from

$97

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 33

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 4

“ Excellent ”3 Reviews

from

$111

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 32

Siesta Key Condo
2 Bedrooms / 3 Bathrooms / Sleeps 5

from

$190

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 21

Siesta Key Condo
1 Bedroom / 1 Bathroom / Sleeps 4

“ Excellent ”1 Review

from

$199

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 13

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 4

“ Excellent ”14 Reviews

from

$100

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 16

Siesta Key Condo
1 Bedroom / 1 Bathroom / Sleeps 4

“ Excellent ”4 Reviews

from

$163

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 29

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 5

“ Excellent ”17 Reviews

from

$149

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 15

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 5

“ Excellent ”7 Reviews

from

$145

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 21

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”6 Reviews

from

$158

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Home
1 / 24

Siesta Key Home
4 Bedrooms / 3 Bathrooms / Sleeps 12

from

$415

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 20

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$150

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 19

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 4

from

$100

/ night

Email Owner
152 Beach Aerial view
1 / 28

Siesta Key Home
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”2 Reviews

from

$322

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 41

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 5

from

$272

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 15

Siesta Key Condo
1 Bedroom / 1 Bathroom / Sleeps 5

“ Excellent ”14 Reviews

from

$100

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Home
1 / 51

Siesta Key Home
3 Bedrooms / 2.5 Bathrooms / Sleeps 7

from

$395

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 19

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”3 Reviews

from

$118

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Townhouse
1 / 10

Siesta Key Townhouse
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$295

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 19

Siesta Key Condo
3 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”1 Review

from

$221

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Townhouse
1 / 21

Siesta Key Townhouse
3 Bedrooms / 2.5 Bathrooms / Sleeps 8

“ Excellent ”1 Review

from

$214

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 20

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”2 Reviews

from

$83

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 16

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”2 Reviews

from

$122

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 21

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$167

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Home
1 / 45

Siesta Key Home
4 Bedrooms / 2.5 Bathrooms / Sleeps 8

from

$329

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 14

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”5 Reviews

from

$190

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 22

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$175

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Home
1 / 24

Siesta Key Home
4 Bedrooms / 2.5 Bathrooms / Sleeps 12

from

$450

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 8

Siesta Key Condo
1 Bedroom / 1 Bathroom / Sleeps 4

“ Excellent ”3 Reviews

from

$135

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Townhouse
1 / 19

Siesta Key Townhouse
4 Bedrooms / 3.5 Bathrooms / Sleeps 12

“ Excellent ”9 Reviews

from

$90

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Home
1 / 35

Siesta Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 7

“ Excellent ”28 Reviews

from

$172

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 20

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$150

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Apartment
1 / 5

Siesta Key Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$340

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Villa
1 / 18

Siesta Key Villa
2 Bedrooms / 2 Bathrooms / Sleeps 4

“ Excellent ”16 Reviews

from

$143

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 13

Siesta Key Condo
1 Bedroom / 1 Bathroom / Sleeps 4

“ Excellent ”2 Reviews

from

$150

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Townhouse
1 / 10

Siesta Key Townhouse
4 Bedrooms / 4 Bathrooms / Sleeps 10

from

$395

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Apartment
1 / 16

Siesta Key Apartment
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$205

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 16

Siesta Key Condo
2 Bedrooms / 1 Bathroom / Sleeps 6

“ Excellent ”8 Reviews

from

$225

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 7

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”3 Reviews

from

$125

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 20

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 4

“ Excellent ”2 Reviews

from

$100

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Villa
1 / 10

Siesta Key Villa
2 Bedrooms / 1.5 Bathrooms / Sleeps 6

“ Excellent ”2 Reviews

from

$139

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Townhouse
1 / 11

Siesta Key Townhouse
3 Bedrooms / 2.5 Bathrooms / Sleeps 6

from

$295

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 11

Siesta Key Condo
2 Bedrooms / 3 Bathrooms / Sleeps 5

from

$300

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Apartment
1 / 3

Siesta Key Apartment
Studio / 1 Bathroom / Sleeps 2

from

$185

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 7

Siesta Key Condo
2 Bedrooms / 3 Bathrooms / Sleeps 6

from

$295

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Home
1 / 34

Siesta Key Home
4 Bedrooms / 4 Bathrooms / Sleeps 12

from

$229

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 6

Siesta Key Condo
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

from

$295

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Home
1 / 12

Siesta Key Home
4 Bedrooms / 3 Bathrooms / Sleeps 10

from

$258

/ night

Email Owner
Gulf View of Condo (corner unit; 2nd floor)
1 / 15

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$178

/ night

Email Owner
Siesta Key Florida Vacation Rentals - Condo
1 / 24

Siesta Key Condo
2 Bedrooms / 1.5 Bathrooms / Sleeps 4

“ Excellent ”43 Reviews

from

$97

/ night

Email Owner
1  2  3 
If you're planning a vacation to this island paradise, you may want to consider Siesta Key vacation rentals. This beautiful barrier island spans eight miles just off the coast of Sarasota in the Gulf of Mexico. Many resorts and hotels can be found here, but popular accommodations also include Siesta Key condo rentals that provide privacy and access to the island's world-renowned white sand beaches.

Resorts can be overcrowded and overpriced, but Siesta Key vacation home rentals are always private and generally quite affordable. This destination is known as a great romantic getaway, and there are plenty of cozy little cottages for two that will set the perfect mood for your honeymoon or other romantic rendezvous. Regardless of your lifestyle and budget, there is something here to meet your needs.

We couldn't call it an "island paradise" if it didn't offer warm breezes, cool water, swaying palm trees, and some of the world's finest beaches, including Turtle Beach and Palmer Point Beach. Relaxing on the pure quartz beaches with family and friends is certainly a favorite pastime here, and visitors enjoy the charming beach hideaways and ample bird-watching opportunities. You might also spot some friendly dolphins and manatees dotting the surrounding gulf and bay waters.

If you visit the island during the beginning of May, the beach literally comes alive with figures made of sand during the island's unique sand sculpture contest that draws in world-class artists. Of course, anyone can try their hand at a sandcastle or sand sculpture any time of year.

If staying on dry land sounds like a bore, you'll find almost 50 miles of waterways and canals inside the island, not to mention the surrounding Gulf of Mexico and Sarasota and Roberts Bays. Many Siesta Key, FL vacation rentals by owner provide boat docks, and boat rentals are available for you to get out and explore the waters. Other water sports are popular here as well, including fishing, snorkeling, parasailing, and sailboarding.

If you'd rather not captain your own ship, plenty of local charter companies offer guided tours. Many of the local restaurants also offer temporary docking, so that you can go to dinner straight from your afternoon on the water. What better way to work up an appetite for some fresh seafood than a day spent in the sand, sun, and surf?

Of course, the beaches are just the beginning of all there is to see and do in Siesta Key. This tropical island also offers plenty of events and attractions, including unique shopping, dining, and entertainment options. The atmosphere is refreshingly laid-back, and you'll find lots of charming local establishments rather than the chain restaurants and retailers characteristic of other resort areas. All of this and more can be found within walking distance or a leisurely drive of Siesta Key vacation rentals, so start planning your trip today!
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