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Siesta Key Vacation Rentals

(206 rentals)
Siesta Key is the eight-mile barrier island off Sarasota, with quartz sand so fine and white that U.S. News ranked Siesta Beach the best in the country. Its walkable Village lines a half-mile of Ocean Blvd with shops and dining Condos run a median of $290 a night; homes and villas sit at $351.
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Second floor, 2 bedroom/2.5 bath townhome located in the quiet complex of Bay Oaks. Unit nicely furnished and offers tile flooring kitchen, dining room and living room, 2 TVs, washer/dryer inside, 2 screened lanai's. Small balcony and full kitchen with wireless high-speed internet. Complex offers...

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$194
avg per night
New
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to our home on beautiful Siesta Key. Located within Harbor Towers Yacht & Racquet Club. This spacious two-bedroom, two-bathroom condo offers a premium setting suitable for long stays and just moments from the beach, the village, and the best of island life.This property has been a place...

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$240
avg per night
Siesta Key House
Sleeps 9, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Indulge in a luxurious escape at this contemporary Siesta Key home. Featuring 4 bedrooms, 4 full bathrooms, and an elevator, this stunning property offers the perfect blend of comfort and style. Enjoy a private backyard oasis with a swim/spa, and stay connected with included Wi-Fi. This home is ideal...

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$324
avg per night
Siesta Key House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Escape to paradise in this stunning Siesta Key house! Featuring a private pool, waterfront views, and a prime location near the beach, this 3-bedroom, 3-bathroom home offers the ultimate luxury getaway. Enjoy modern amenities, a fully equipped kitchen, and spacious living areas, perfect for families....

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$401
avg per night
Siesta Key Apartment
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Updated 1 bedroom, 2nd Floor unit in Siesta Village offers great location just two buildings from the beach and 1 block into the village with restaurants and shopping. Peek-a-boo Gulf view from front porch. The unit offers tile floors, leather furniture, updated kitchen and TVs in living room and bedroom....

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Featured review

"Siesta Key paradise"

We had a great vacation here! Condo was very nice, clean and well supplied. Close to Siesta Village, Beach and within walking distance of almost everything. A definite hidden treasure!

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$235
avg per night

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New
Siesta Key Condo
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Gulf views from both bedrooms and your private screened terrace — a half-mile stroll to world-famous Siesta Key Beach.Ocean Views over palm trees visible from both bedrooms and your private screened in terrace! Walk to world famous Siesta Key Beach! 2 bedroom 2 bath is in perfect condition,...

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$294
avg per night
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What staying in Siesta Key actually costs

Owners list their cleaning fees, taxes, and any extra charges up front, and because you book with the owner directly, you skip the booking fee the large travel sites add. Sarasota County adds a 13% tax on stays under six months.

SHORT STAY
3 nights

$1,246

all in
$415/night

$301 × 3 nights$903
Cleaning + damage waiver$200
Tax (13%)$143
Booking fee$0
Total$1,246

WEEKLY STAY
7 nights

$2,528

all in
$361/night

$291 × 7 nights$2,037
Cleaning + damage waiver$200
Tax (13%)$291
Booking fee$0
Total$2,528

MONTHLY STAY
30 nights

$8,803

all in
$293/night

$253 × 30 nights$7,590
Cleaning + damage waiver$200
Tax (13%)$1,013
Booking fee$0
Total$8,803

When to visit Siesta Key

The Gulf here has two busy stretches: Snowbirds fill the cool, dry winter, and families crowd the warm summer months. For swimming weather without the peak-summer heat or the June-through-November hurricane season, aim for April and May or October, when the Gulf sits in the mid-70s to low 80s and the days stay warm and dry. September, at the height of hurricane season, is the quietest and cheapest month.

Peak rates Best value Shoulder Gulf water temperature
MonthMedian nightlyDifference from annualHigh / low air tempAvg. gulf tempWhat’s going on
January$310+8%71° / 51°64°Peak snowbird season; Sunday farmers market in the Village (year-round)
February$393+37%74° / 54°65°Cortez Fishing Festival, 35 minutes north
March$407+42%77° / 58°67°Sarasota Jazz Festival, mainland
April$330+15%81° / 62°73°Run/Walk for the Turtles; Sarasota Film Festival
May$261-9%86° / 68°78°Sea-turtle nesting begins, lights-out rule
June$285-0%89° / 73°82°Summer family crowds arrive
July$285-0%91° / 74°85°Fourth of July fireworks on Siesta Beach
August$250-13%91° / 75°87°Red tide possible along the coast
September$233-19%89° / 73°85°Peak hurricane season, lowest rates
October$232-19%85° / 67°82°Sea-turtle nesting season ends
November$245-14%79° / 60°75°Crystal Classic sand-sculpting on Siesta Beach
December$279-2%74° / 54°69°Christmas Boat Parade of Lights

Based on the median Siesta Key nightly rate on FloridaRentals.com.


Where to stay in Siesta Key

Siesta Key runs about eight miles, and its three beaches each anchor a different part of the island. Public beach accesses are numbered 1 through 13, but for a beach with a lifeguard, head to the main Siesta Public Beach.

Map of Siesta Key, Florida vacation rental areas
SIESTA KEY
Lido Key
Sarasota
Palmer Point
Gulf of Mexico
Roberts Bay
Little Sarasota Bay
Big Sarasota Pass
Midnight Pass Rd.
Stickney Point Rd.
Beach Rd.
Siesta Beach
Crescent Beach
Point of Rocks
Turtle Beach
Gulf Coast
2 km / 1.2 mi
Siesta Key in three areas: Siesta Beach and Siesta Key Village at the north end; Crescent Beach and Point of Rocks in the middle; and Turtle Beach at the south end. Coastline, roads and beaches © OpenStreetMap contributors; Florida outline: US Census TIGERweb.
Siesta Beach & the Village
The island's north end, where Siesta Key Village packs restaurants, bars and a late-night scene into four walkable blocks around Ocean Boulevard and Canal Road. Siesta Beach, named the No. 1 beach in the country by U.S. News & World Report in 2026, is a short walk away, and White Sands Village is five minutes from the sand.
Crescent Beach & Point of Rocks
South of Siesta Beach, Crescent Beach curves down to the rocky headland at Point of Rocks. This is resort country, about 1.5 to 2.5 miles south of the Village: beachfront communities like Crescent Arms sit directly on the sand, and gated resorts such as Gulf and Bay Club keep a private strip of the beach.
Turtle Beach
The quieter south end of the island along Midnight Pass Road, between the Gulf and Little Sarasota Bay, running down toward Palmer Point. Stays here are mostly low-key homes and smaller complexes, farther from the Village's restaurants and nightlife, and a good fit if you want quiet nights.

Popular Siesta Key resorts

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Things worth doing in Siesta Key

Sunday drum circle
Sunday drum circle
A free, drop-in drum circle forms every Sunday about an hour before sunset, just south of the main pavilion between lifeguard stands 3 and 4.
Siesta Beach
Point of Rocks
Point of Rocks
Snorkel the shallow water over the limestone ledges at the south end of Crescent Beach, reached from Beach Access 12. Bring your own gear.
Crescent Beach
Kayak and paddleboard
Kayak and paddleboard
Launch from the Turtle Beach boat ramp into Blind Pass and the calm bay water. Rentals are available on the bay side of the island.
Turtle Beach
Siesta Beach day
Siesta Beach day
The wide, powder-fine quartz sand stays cool underfoot, and the Gulf stays calm and shallow a long way out, which makes it great for kids.
Siesta Beach
Village dining
Village dining
Eat at the Siesta Key Oyster Bar or The Old Salty Dog, two long-running spots on the Village's walkable half-mile of Ocean Blvd.
Siesta Key Village

Know before you book

Fly into Sarasota-Bradenton, about 20 minutes out.

Sarasota-Bradenton International (SRQ) is the close commercial gateway, about 20 minutes from the island. Tampa International (TPA) is about an hour and 15 minutes north with far more flights, worth it only if it fits your route better.

The free 77 Siesta Islander trolley covers the island.

It runs on-island between Siesta Key Village and Turtle Beach, daily from about 8 a.m. to 10 p.m., and everyone rides free. For off-strip stays and quick trips to Turtle Beach, a car helps. Siesta Beach's main lot is free but fills fast.

Dogs aren't allowed on Siesta Key's beaches.

Sarasota County's ordinance bars dogs from the sand, with an exception for service dogs. The nearest off-leash dog beach is Brohard Paw Park in Venice, about 35 minutes south.

Houses may have longer minimum stays.

Sarasota County bars rentals under 30 days except on Residential Multi-Family barrier-island parcels, which is why island condos can host short stays while many single-family homes carry a 30-day minimum.


Siesta Key vacation rental FAQs

Straight answers to what people ask us most.

How much does a vacation rental on Siesta Key cost?

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The median vacation rental on Siesta Key runs about $301/night, or roughly $2,037 for a week and $7,590 for a month. Condos run a median of $290 a night, while homes and villas sit at $351.

What's the cheapest month to visit Siesta Key?

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October is the cheapest month, because it falls at the height of hurricane season, when demand is lowest. For warm Gulf water and drier weather without paying peak rates, April, May, and October are the better value.

Is Siesta Key the same as Siesta Key Village?

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No. Siesta Key is the whole barrier island and the destination. Siesta Key Village is one walkable district at the north end, a half-mile of Ocean Blvd lined with shops, bars, and restaurants. If the Village is where you want to be, book there.

Can I bring my dog, and are dogs allowed on Siesta Key beach?

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You can bring a dog to a pet-friendly rental, but Sarasota County bars dogs from Siesta Key's beaches, service dogs aside. So plan on a dog-free beach day or a drive off the key when the dog needs sand of its own.

Do I need a car on Siesta Key?

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You don't need a car to navigate the island. The free trolley links the Village and Turtle Beach, and the Village is walkable. However, a car is helpful for day trips off the key, like to Sarasota or the Ringling.

Is Siesta Key good for families with young kids?

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Yes. Siesta Beach has a shaded playground, picnic pavilions, and lifeguards, all a short walk from the main free lot. For a quieter day, Turtle Beach at the south end is calmer and good for shelling.

Nearby areas and how they compare

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