Siesta Key Beach Rentals & Vacation Rentals - 426 Rentals Available
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Siesta Key Condo
1 BR / 1 BA / Sleeps 4 1 4 Min stay varies
Condo / 1 Bedroom / Sleeps 4
1 bedrooms 1 bathroom Sleeps 4
High Speed Internet • Dishwasher • Microwave
Welcome to Siesta Palms by the Beach . . . where we invite you to relax, unwind and enjoy our casual way of life. Resting just one block from the powdery- white sands of Siesta Key's world famous, award- winning Cresce...
(4) Excellent (4 reviews)
You are this close!!
1 / 20

Siesta Key Condo
2 BR / 2 BA / Sleeps 4 2 4 7 night min stay
Condo / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
Ground floor luxurious executive level totally remodeled two bedroom condo with double french doors to your private patio at the world's best beach, Siesta Beach, with full Gulf view for beautiful sunsets. Family orien...
(18) Excellent (18 reviews)
Siesta Key Florida Vacation Rentals - Apartment
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Siesta Key Apartment
3 BR / 3 BA / Sleeps 6 3 6 Min stay varies
Apartment / 3 Bedrooms / Sleeps 6
3 bedrooms 3 bathrooms Sleeps 6
High Speed Internet • TV (Cable/Satellite) • Private Pool
3 BR. - 3 BA - - 6 Person Max. - - Townhouse - - Beachfront View1010 is a Townhouse unit, located approx. 20 yards away from Crescent Beach. 3 Bedroom / 3 Bath unit. Approx. 1400 Sq. Ft. (1500 including the lanai)Be...
Siesta Key Florida Vacation Rentals - Condo
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Siesta Key Condo
2 BR / 2 BA / Sleeps 6 2 6 7 night min stay
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
Dishwasher • Microwave • Washer/Dryer
Sun, Sand & Save 20% To 35% Per Week At Siesta Breakers #603, Direct- With- Owner "all- In Price" Discounted Rental Rates From $1, 152 To $2, 075 /wk & Savings From $409 To $765 /wk Depending On The Season, And If C...
(32) Excellent (32 reviews)
Front of home.
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Siesta Key Home
4 BR / 4.5 BA / Sleeps 14 4 14 Min stay varies
Home / 4 Bedrooms / Sleeps 14
4 bedrooms 4.5 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
4, 000 Sq Ft Beachfront Home 1/2 Mile From Village! 4 Bedroom + Media Room - 5 Bathroom - Sleeps Up To 14 And Is On The Beach! ! ! Note: Our Home Is Not Listed On Craig's List. If It Is Represented There It...
(3) Excellent (3 reviews)
Siesta Key Florida Vacation Rentals - Condo
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Siesta Key Condo
2 BR / 2 BA / Sleeps 4 2 4 7 night min stay
Condo / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
Two 2 BR / 2 bath beautifully furnished units with fully equipped kitchens, cable TV, WiFi, and washer/dryer. Relax by the pool, stroll to shopping and dining in the Village, or enjoy an afternoon at Siesta Beach on...
(6) Excellent (6 reviews)
Siesta Key Florida Vacation Rentals - Home
1 / 19

Siesta Key Home
2 BR / 2 BA / Sleeps 8 2 8 No min stay
Home / 2 Bedrooms / Sleeps 8
2 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Sophie’s Cottage is a smart, sophisticated upscale waterfront retreat with a private heated pool with sunshelf, boat dock, and a short walk to Siesta Key Beach. Ideally, it accommodates 6 but can easily sleep up to...
(1) Excellent (1 review)
Siesta Key Florida Vacation Rentals - Condo
1 / 32

Siesta Key Condo
2 BR / 2 BA / Sleeps 4 2 4 Min stay varies
Condo / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
Siesta Key 611 is the perfect vacation home for your getaway to sun, sand and pure relaxation! Siesta Key rents Saturday to Saturday, for a minimum of one week. To see available dates, please scroll down to the c...
(7) Excellent (7 reviews)
Beautiful Property!
1 / 18

Siesta Key Condo
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Find Your Vacation Getaway On The Island Paradise Of Siesta Key, Florida! Siesta Key Beach Has Been Rated A #1 Beach In America! (see Dr. Beach's Ratings, May 2011 Or The Nbc Today Show 5/27/11, Also On Tripadvisor)...
Siesta Key Florida Vacation Rentals - Home
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Siesta Key Home
4 BR / 2.5 BA / Sleeps 8 4 8 Min stay varies
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 2.5 bathrooms Sleeps 8
High Speed Internet • Air Conditioning • Private Pool
Oh what a great feeling you get when you are looking out over the pool to the relaxing waters of the Grand Canal. This home is special with 180 ft. of canal wrapping the back of the home so you get to enjoy the views fro...
(3) Excellent (3 reviews)
Siesta Key Florida Vacation Rentals - Cottage
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Siesta Key Cottage
5 BR / 4 BA / Sleeps 10 5 10 No min stay
Cottage / 5 Bedrooms / Sleeps 10
5 bedrooms 4 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Starfish Cottage on Siesta Key is a small magical Island lying just off the coast of the City of Sarasota that can boast having the Number One beach in the entire United States as well as placing in the top twenty beache...
(3) Excellent (3 reviews)
Siesta Key Florida Vacation Rentals - Apartment
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Siesta Key Apartment
2 BR / 1 BA / Sleeps 6 2 6 7 night min stay
Apartment / 2 Bedrooms / Sleeps 6
2 bedrooms 1 bathroom Sleeps 6
High Speed Internet • Dishwasher • Microwave
Owner takes pride in this beautifully decorated 2nd floor unit. 2 bedroom 1 1/2 baths. Newly remodeled! Very cozy and comfortable with amazing tranquility and peacefulness courtesy of the laid back, canal- front settin...
Siesta Key Florida Vacation Rentals - Home
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Siesta Key Home
5 BR / 4 BA / Sleeps 12 5 12 No min stay
Home / 5 Bedrooms / Sleeps 12
5 bedrooms 4 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
The Grand Canal Cottage, perhaps one of Siesta Key’s favorite luxury vacation homes, is a highly landscaped canal- front private luxury home featuring a heated pool with sun shelf and a separate 8- person spa. It is ...
(3) Excellent (3 reviews)
Siesta Key Florida Vacation Rentals - Home
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Siesta Key Home
4 BR / 2.5 BA / Sleeps 12 4 12 Min stay varies
Home / 4 Bedrooms / Sleeps 12
4 bedrooms 2.5 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
Quality rental, tastefully furnished and nice open entertaining plan. New private swimming pool. This home is located in a excellent location, very near Siesta Key Public Beach. It is convenient to Siesta Key Village, ...
(7) Excellent (7 reviews)
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Siesta Key Villa
4 BR / 3 BA / Sleeps 8 4 8 No min stay
Villa / 4 Bedrooms / Sleeps 8
4 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Welcome to “Villa Champagne”, one of the most fabulous vacation homes in Siesta Key. It’s also one of the most popular favorites among our many guest families. The magic begins as you enter the foyer of this beaut...
Siesta Key Florida Vacation Rentals - Condo
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Siesta Key Condo
2 BR / 1.5 BA / Sleeps 4 2 4 7 night min stay
Condo / 2 Bedrooms / Sleeps 4
2 bedrooms 1.5 bathrooms Sleeps 4
Dishwasher • Microwave • Washer/Dryer
Sun, Sand & Save 20% To 35% Per Week At Midnight Cove #714, Direct- With- Owner "all- In Price" Discounted Rental Rates From $658 To $1, 389 /wk & Savings From $240 To $573 /wk Depending On The Season, And If Cash Pa...
(4) Excellent (4 reviews)
Siesta Key Florida Vacation Rentals - Condo
1 / 19

Siesta Key Condo
2 BR / 2 BA / Sleeps 5 2 5 7 night min stay
Condo / 2 Bedrooms / Sleeps 5
2 bedrooms 2 bathrooms Sleeps 5
High Speed Internet • Dishwasher • Microwave
Now renting for the summer and fall season. Please check the calendar below for available dates. Minumum stay is 7 nights. Imagine spending your next vacation relaxing on the lanai of a gorgeous, waterfront condo ju...
(9) Excellent (9 reviews)
Siesta Key Florida Vacation Rentals - Apartment
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Siesta Key Apartment
3 BR / 2 BA / Sleeps 6 3 6 Min stay varies
Apartment / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
5th floor 3BR/2BA end unit with beautiful gulf view! King bed in master bedroom, 2 twin beds in guest bedroom, full size bed in 3rd bedroom. Updated kitchen and bathrooms. Cozy alcove in master bedroom! Unit has new ...
Siesta Key Florida Vacation Rentals - Condo
1 / 41

Siesta Key Condo
2 BR / 2 BA / Sleeps 5 2 5 7 night min stay
Condo / 2 Bedrooms / Sleeps 5
2 bedrooms 2 bathrooms Sleeps 5
High Speed Internet • Dishwasher • Microwave
Welcome to Siesta Palms by the Beach . . . where we invite you to relax, unwind and enjoy our casual way of life. Resting just one block from the powdery- white sands of Siesta Key's world famous, award- winning Cresce...
(2) Excellent (2 reviews)
Siesta Key Florida Vacation Rentals - Condo
1 / 14

Siesta Key Condo
1 BR / 1 BA / Sleeps 4 1 4 7 night min stay
Condo / 1 Bedroom / Sleeps 4
1 bedrooms 1 bathroom Sleeps 4
High Speed Internet • Dishwasher • Microwave
Beautiful one bedroom condo on 4th floor. Come to the beach and enjoy a relaxing vacation with plenty to do and see. Recently updated with new furniture. The view from the 4th floor balcony is incredible. Watch the sailb...
(9) Excellent (9 reviews)
Siesta Key Florida Vacation Rentals - Townhouse
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Siesta Key Townhouse
1 BR / 2 BA / Sleeps 4 1 4 Min stay varies
Townhouse / 1 Bedroom / Sleeps 4
1 bedrooms 2 bathrooms Sleeps 4
Dishwasher • Microwave • Washer/Dryer
Siesta Key Beachfront Rentals (1, 2 and 3 bedroom apartments) Please contact us for a different apartments. The Honeymoon Suite (sleeps max. 4) is a luxury townhouse with 850 sqft / feet over 2 floors, 1 king an...
Siesta Key Florida Vacation Rentals - Condo
1 / 19

Siesta Key Condo
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Siesta Key Condo - Siesta Key Paradise Looking for a vacation rental in Siesta Key? Look no further... we have a two bedroom first floor condo located on the spacious, gorgeous landscaped grounds of Midnight Cove ii...
(5) Excellent (5 reviews)
Siesta Key Florida Vacation Rentals - Townhouse
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Siesta Key Townhouse
2 BR / 2 BA / Sleeps 8 2 8 Min stay varies
Townhouse / 2 Bedrooms / Sleeps 8
2 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
This second floor unit is in a deluxe triplex building that was just fully remodeled to near new condition throughout. It will accommodate 6 people in beds and two on a sleeper sofa, but you can add one or two of the la...
(6) Excellent (6 reviews)
Siesta Key Florida Vacation Rentals - Home
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Siesta Key Home
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Home / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Washer/Dryer • TV (Antenna)
Recently refreshed, bright and peaceful garden view unit. Great location for families who spend their day at the beach or pool and night relaxing in the fully equipped, beautiful condo. This unit sleeps 6 people comfor...
Siesta Key Florida Vacation Rentals - Apartment
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Siesta Key Apartment
2 BR / 1 BA / Sleeps 6 2 6 7 night min stay
Apartment / 2 Bedrooms / Sleeps 6
2 bedrooms 1 bathroom Sleeps 6
High Speed Internet • Dishwasher • Microwave
NEW PAINT AND CARPET! Canal front and tropical garden view from this 2 bedroom/1. 5 bath first floor unit. Step out the back door of the spacious screened lanai to walk along the beautiful grounds and boat dock. Living ...
Siesta Key Florida Vacation Rentals - Apartment
1 / 32

Siesta Key Apartment
2 BR / 1 BA / Sleeps 4 2 4 7 night min stay
Apartment / 2 Bedrooms / Sleeps 4
2 bedrooms 1 bathroom Sleeps 4
High Speed Internet • Dishwasher • Microwave
Very nice, spacious first floor 2 bedroom/1. 5 bath unit 1000 s. f. with ceramic tile floors in living area and wood laminate floors in bedroom. TV's in living room and both bedrooms. DVD player in living area. DSL inte...
Siesta Key Florida Vacation Rentals - Condo
1 / 40

Siesta Key Condo
2 BR / 2 BA / Sleeps 6 2 6 14 night min stay
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Ground floor 2BDR/2BA condominium, completely remodeled in Nov 2011. Perfectly located across from the Siesta Key Beach. Luxuriously furnished for our guests memorable vacation, including beach equipment and beach chai...
(3) Excellent (3 reviews)
Siesta Key Florida Vacation Rentals - Condo
1 / 24

Siesta Key Condo
2 BR / 1.5 BA / Sleeps 4 2 4 7 night min stay
Condo / 2 Bedrooms / Sleeps 4
2 bedrooms 1.5 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
Located in beautiful Siesta Key (voted America's Best Beach for 2015 by Tripadvisor's Travelers Choice! ! ! )Total remodel in Midnight Cove 1, this condo spoils its occupant with all the amenities and luxuries needed f...
(2) Excellent (2 reviews)
Siesta Key Florida Vacation Rentals - Condo
1 / 24

Siesta Key Condo
2 BR / 2 BA / Sleeps 6 2 6 7 night min stay
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Enjoy culture & nature at their best! ! 2 luxurious bedrooms, light filled living- dining rooms, 2 baths, corner unit offers glass slider doors opening to two spacious furnished balconies. Master bedroom offers king ...
(17) Excellent (17 reviews)
Siesta Key Florida Vacation Rentals - Condo
1 / 18

Siesta Key Condo
2 BR / 2 BA / Sleeps 6 2 6 3 night min stay
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Location! Location! Location! Walk out the door, across the street and onto the # 1 ranked beaches in America! This beautiful condo is on the ground floor, no steps, with a tropical enclosed lanai. It features 3 t...
(3) Excellent (3 reviews)
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Top 10 Activities in Siesta Key

Top 10 Activities in Siesta Key
A beach lover’s paradise, Siesta Key is packed with stunning stretches of sand and natural beauty. When you’re planning your next vacation to Siesta Key, don’t miss out on these top 10 activities.
 

Siesta Beach

Siesta Beach, one of the most popular beaches in the area, has plenty of soft sand for sunbathing and sparkling water for swimming. The sand here is 99 percent quartz, which means it stays cool even on warm days. There’s lifeguard protection year-round and a playground for young kids. Visitors will find plenty of parking spots here.
 

Ken Thompson Park

This waterfront park features boardwalks, boat access, and fishing areas. Cast your line from the pier, wander along the elevated boardwalk, or canoe through the mangrove forest at Ken Thompson Park. There’s no admission fee, and parking is available.
 

Ringling Museum of Art

For a dose of culture, look no further than the Ringling Museum of Art in Sarasota. With beautiful ...

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Three Day Itinerary: Siesta Key, FL

Three Day Itinerary: Siesta Key, FL
Siesta Key is a barrier island just off the coast of Sarasota, Florida. Famous for its soft white sand, Siesta Key is the ideal destination for vacationers who want to rest, relax, and enjoy a slower pace of life. From water rentals to fresh seafood, everything at Siesta Key revolves around the ocean.

Day 1: Treat Yourself at Siesta Key Village
A Siesta Key vacation is all about sun and sand, but don't hit the beaches ill-equipped. Head to Siesta Key Village for an indulgent day of shopping and dining. With 6,000 square feet of retail space, the Beach Bazaar has everything you could need for swimming, surfing, snorkeling, sunbathing, and otherwise enjoying your beach escape. Other shops in the village, such as Siesta Key Outfitters and Siesta Key University, offer other gear as well as beach-themed souvenirs for you to take home.

Stop at The Lobster Pot for a casual lunch with New England flair. Try a lobster roll or lobster bisque made with lobsters from Bar Harbor and ...

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About Siesta Key

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. 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.

Things to do

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 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? 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.

Climate

As a top Florida vacation destination you can imagine that Siesta Key offers flawless weather all year round. With over 250 sunny days per year, and a July high of 91 degrees, you're pretty much guaranteed a vacation unspoiled by the elements no matter when you visit. Try booking your trip for the "shoulder season" away from peak times or school vacations to keep crowds at bay. Low humidity makes Siesta Key comfortable, as well as warm. 

Events

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. Take part in the Siesta Key drum circle on the Siesta Key public beach EVERY Sunday night. Beginning about an hour before sundown, instruments ranging from drums, flutes, guitars, shakers and cowbells create the circle. Be part of the audience, or participate with music and dance. Enjoy a stroll through the galleries of Palm Avenue on the first Friday of every month. In addition to fine galleries, this area along lower Main Street is known for its unique variety of shops and restaurants. The Siesta Fiesta is in mid-April and celebrates local artisans while fostering a feeling of camraderie around the town. 

Food

After a day out on the beach or screaming while parasailing you're likely to work up an appetite. A place like Senor Siesta. rated #1 on TripAdvisor for Siesta Key restaurants, could fit the bill. With delicious and affordable latin cuisine available such as the empanada appetizer, you will be happy you chose to eat there. If you're looking for a more European flavor, why not try out Bonjour French Cafe & Crepes? For dessert, you should grab a scoop or three at Ciao Gelato or Big Olaf Cremery. Lastly, for a more down home feel, eat at The Cottage Restaurant which has all types of classic American dishes made to perfection. You won't go hungry in Siesta Key, trust us.  

​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!