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Vacation rentals with outdoor seating in Siesta Key

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Top-rated accommodations with outdoor seating in Siesta Key

Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.

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Condo in Sarasota

4.8 out of 5 average rating, 199 reviews

Near beach. Pool view. King bed. Daily rentals

The ‘pool view’ overlooks the swimming pool & has a private covered porch for shade 1 bed 1 bath w/ private entrance. The bedroom has a king sized Tempurpedic mattress bed. The living room has a kitchenette area with a fridge, freezer, microwave, coffee maker and the essentials. There is a HD smart TV with cable and apps. Separate bedroom with King size Tempurpedic bed 3 mins walk to Crescent beach access You can walk to a great choice of places to eat and drink Max 2 guests No smoking, pets

Jan. 9 – 16

$165 CAD per night

Guest favourite

Guest suite in Sarasota

4.94 out of 5 average rating, 477 reviews

Studio Apartment. Priv Yard. 5 min to Siesta Key!

Self checkin. Includes kayak and bikes! You’ll love my place because of the coziness, the high ceilings, and the location. My place is good for couples, solo adventurers, and business travelers. Converted garage space. Your own private fenced back yard, kitchenette, fridge, private bathroom, Amazon Firestick with Netflix, Hulu and dock/boat ramp just 30 sec from your door and in a beautiful neighborhood. Just a 10 min bike ride to Siesta Key. The #1 beach in America! What more could you ask for!

Jan. 4 – 11

$227 CAD per night

Guest favourite

Apartment in Siesta Key

4.99 out of 5 average rating, 141 reviews

Siesta Key #1 Beach, pickle ball & tennis paradise

Beautiful Apartment w/ Hotel Services, at Siesta Key Beach. Totally remodeled. Fully equipped to spend the best holidays with family or friends. Condo hotel, on the best beach in Siesta. Beach pool, shade pool (heated), gym, 3 tennis courts on site (2 clay, 1 hard) and 2 pickle ball courts. Master bedroom with King bed. The Mattress is a SAATVA ORGANIC. 2nd room with 2 single beds, and a queen sofa bed, in the living room. Pack n Play 600 MB Wifi. HD TV. 70” Smart TV Nesspreso, Keurig Machines

Apr. 12 – 19

$723 CAD per night

Guest favourite

Guest suite in Sarasota

4.88 out of 5 average rating, 338 reviews

Private, cozy, studio 2 miles from Siesta Key!

Welcome home! 2 miles from Siesta Key! This is a private in-law suite with its own entrance. It also has its own private backyard (no access all around to main house). Check yourself in! The bed is king sized with a gel infused memory foam top for great sleep. A 42'' TV with Netflix streaming. High speed wifi included. (There is no cable tv). Full kitchen equipped with pots, pans, silverware, knives etc. There is also an outdoor grill and table to use with heavy duty plastic plates/cups

Oct. 11 – 18

$172 CAD per night

Guest favourite

Guesthouse in Sarasota

4.93 out of 5 average rating, 456 reviews

La Casetta: "the little house" near to the beaches

La Casetta means, in Italian, a tiny house. Set in a private, peaceful, mature Florida tropical garden, a real hideaway. I am proud of the cleanliness of our property, however in this new reality that we live in, we do carry out enhanced cleaning and sanitizing between guests. We also practice social distancing, insofar as guests have their own part of our luscious back garden as well as your own entrance. La Casetta has 1 queen sized bed, bathroom & kitchenette. Wifi & Netflix available.

Aug. 12 – 19

$135 CAD per night

Guest favourite

Guest suite in Sarasota

4.98 out of 5 average rating, 104 reviews

Mid-Century Modern Beach Getaway

Heart of Southside Village 10 minutes from #1 beach in the USA, Siesta Key. Five-minute drive to downtown Sarasota, 10 minutes to St. Armand Circle, Lido & Longboat Key. Enjoy this peaceful space within walking distance to shopping, restaurants & groceries. Charming private guest house offers a queen bed, sitting chairs, table, dresser, large ensuite bathroom with a walk-in shower & private outdoor sunny space and patio. Use the grill to cook your next meal. It's the perfect couple's getaway!

Aug. 26 – Sep. 2

$195 CAD per night

Guest favourite

Home in Sarasota

4.99 out of 5 average rating, 201 reviews

The Key Lime Cottage 2 miles from Siesta Key Beach

Great location. 2 miles from the # 1 rated Beach in America , Siesta Key . The cottage is near several other beaches as well. Close to restaurants and shopping. 1 hour from Tampa and 2 hours from Orlando. The Key Lime Cottage is totally updated with new stainless steel & granite in the kitchen . There are two new beds ..... one is a queen size and the other is a full size. (URL HIDDEN) Linens & towels are all new. New tile and wood floors throughout. Quite neighborhood for walking .

Nov. 8 – 15

$193 CAD per night

Guest favourite

Guest suite in Sarasota

4.94 out of 5 average rating, 113 reviews

Sweet Siesta Suite

Sweet spot with the best of both Sarasota and Siesta Key - your private oasis for relaxing and rejuvenating. Whether you choose to chill or find adventure it is all within reach! Siesta Key beaches, Village with shops, restaurants, and bars; Sarasota culture, arts, and entertainment; quaint Gulf Gate shops and eateries ...the possibilities truly are endless. Regardless of how you choose to spend your time here, you will be sure to create lasting memories to share and leave wanting more.

Jul. 16 – 23

$209 CAD per night

Guest favourite

Cottage in Sarasota

4.94 out of 5 average rating, 138 reviews

Sea-esta Cottage-cheerful 2bd/1ba w/ free parking

Experience ultimate relaxation in this serene and stylish rental. A brand new home in the heart of Amish Village, Pinecraft. Two cozy bedrooms with plush bedding and soothing coastal decor. Sip your coffee on the front porch, immersed in the tranquility of this idyllic neighborhood. Take a short walk to Yoder's Fresh Market & Restaurant, Coastal 98 Cafe, and the Pinecraft Ice Cream Shop. Just 6 miles to Siesta Key and 7 miles to Lido Beach for endless coastal adventures.

Oct. 26 – Nov. 2

$218 CAD per night

Guest favourite

Guest suite in Siesta Key

4.92 out of 5 average rating, 133 reviews

Cozy Studio - 5 min walk to #1 Siesta Key Beach!

Adorable Cabana style studio just steps from Siesta Key Village, and a 5 minute walk to Beach Access #2. Spend your day exploring the key, swimming in the ocean, and experiencing the local restaurants and shops. Enjoy coffee in the mornings on the patio, and use the available bikes to catch a beautiful sunset each night. **Please note: - No excessive noise or Parties/Events will be allowed** - No Smoking inside the unit** - Quiet hours from 10 PM to 7 AM**

Sep. 26 – Oct. 3

$335 CAD per night

Guest favourite

Guest suite in Sarasota

4.91 out of 5 average rating, 272 reviews

Siesta Keys stylish and affordable Airbnb.

Relax while you stay in a colorful and warm Siesta Key/Sarasota neighborhood home that is only minutes from the famous Siesta Key beach. Enjoy your private, safe, and comfortable suite while being in close reach to all that Florida has to offer. Your suite is spacious and accommodating, wether your an individual, couple, family, or group of friends we have the space and amenities for you to maximize both your comfort and fun time while here in Florida :-)

Dec. 18 – 25

$168 CAD per night

Guest favourite

Home in Siesta Key

5.0 out of 5 average rating, 124 reviews

One-of-a-kind*Beach, Village, Dock & Private Pool!

HERE IT IS! This “one of a kind” property is uniquely situated between the beach, canal, village with a private heated pool & dock, one of the best spots on Siesta Key! This charming 1,500 sq. ft. cottage beach home is being offered for the 1st time. If you want a cute, private original bungalow style beach cottage home all to yourself without the shared wall feel of a condo, then you are in the right spot!

Dec. 12 – 19

$934 CAD per night

Vacation rentals for every style

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Popular amenities for Siesta Key outdoor seating rentals

Free parking on premises

Air conditioning

House rentals with outdoor seating

Guest favourite

Home in Sarasota

5.0 out of 5 average rating, 278 reviews

Stunning Luxe Casita- Gateway to Siesta Beach

Oct. 27 – Nov. 3

$385 CAD per night

Guest favourite

Home in Siesta Key

4.92 out of 5 average rating, 141 reviews

Siesta Key Beach & Village 2BR/2BA Steps to Beach

Dec. 30 – Jan. 6

$675 CAD per night

Guest favourite

Home in Sarasota

4.97 out of 5 average rating, 159 reviews

The Palms-Private Heated Pool Hot Tub-5mi to beach

May 9 – 16

$336 CAD per night

Guest favourite

Home in Sarasota

4.96 out of 5 average rating, 111 reviews

Newly Renovated Ranch Minutes From Beach/Downtown

Jul. 14 – 21

$209 CAD per night

Guest favourite

Home in Sarasota

4.87 out of 5 average rating, 204 reviews

The Pineapple Suite.Teal tropical home in Sarasota

Aug. 4 – 11

$166 CAD per night

Guest favourite

Home in Sarasota

4.96 out of 5 average rating, 128 reviews

Sarasota Florida -Wild Orchid Creek Cottage Home

Sep. 22 – 29

$243 CAD per night

Guest favourite

Home in Sarasota

4.89 out of 5 average rating, 103 reviews

Quiet Retreat-5mi to Beach-Hot Tub, Outdoor Shower

Dec. 4 – 11

$292 CAD per night

Home in Sarasota

4.88 out of 5 average rating, 109 reviews

Coral Cottage - near Siesta Key & Lido Beach

Sep. 25 – Oct. 2

$230 CAD per night

Apartment rentals with outdoor seating

Guest favourite

Apartment in Sarasota

4.87 out of 5 average rating, 114 reviews

Updated Old Florida Studio Getaway in Central SRQ

Sep. 8 – 15

$155 CAD per night

Guest favourite

Apartment in Sarasota

4.98 out of 5 average rating, 160 reviews

Near Siesta Key Beaches - Quiet 1 BR apt

May 25 – Jun. 1

$218 CAD per night

Guest favourite

Apartment in Sarasota

4.96 out of 5 average rating, 206 reviews

Private 2 Bedroom Suite with Kitchenette

Jun. 14 – 19

$225 CAD per night

Guest favourite

Apartment in Sarasota

4.96 out of 5 average rating, 139 reviews

★1 BLOCK TO SIESTA DRIVE★KING BED★FULL KITCHEN★

Jan. 4 – 11

$233 CAD per night

Guest favourite

Apartment in Sarasota

4.88 out of 5 average rating, 137 reviews

Pets friendly modern studio 5 mi to Siesta Key

Aug. 9 – 16

$180 CAD per night

Guest favourite

Apartment in Sarasota

4.97 out of 5 average rating, 201 reviews

Modern Private Apartment 1 Block from Sarasota Bay

Apr. 15 – 22

$178 CAD per night

Guest favourite

Apartment in Sarasota

4.94 out of 5 average rating, 133 reviews

Super Clean! 2/2 condo Walk to SKey!

Jun. 5 – 12

$251 CAD per night

Guest favourite

Apartment in Sarasota

4.97 out of 5 average rating, 166 reviews

Gillespie On The Park, Walk to Downtown

Oct. 2 – 9

$147 CAD per night

Condo rentals with outdoor seating

Condo in Siesta Key

4.83 out of 5 average rating, 286 reviews

[Sunny in Siesta] King bed+5 minute walk to beach

Oct. 9 – 16

$380 CAD per night

Guest favourite

Condo in Siesta Key

4.96 out of 5 average rating, 275 reviews

On the Beach; Siesta Key SunBum Studio

Mar. 9 – 16

$730 CAD per night

Guest favourite

Condo in Siesta Key

4.95 out of 5 average rating, 148 reviews

Walk to Siesta Key Village and Beach

Jul. 28 – Aug. 4

$574 CAD per night

Guest favourite

Condo in Siesta Key

4.96 out of 5 average rating, 105 reviews

Siesta Key Condo. Checkout our great rates!

Aug. 29 – Sep. 5

$275 CAD per night

Guest favourite

Condo in Sarasota

4.96 out of 5 average rating, 120 reviews

Lido-Key- Tiny Studio Holiday Cottage-A

Dec. 11 – 18

$251 CAD per night

Condo in Siesta Key

4.82 out of 5 average rating, 233 reviews

Siesta Key 1/1 King bed “Sunset Suite” Pool Kayaks

May 10 – 17

$292 CAD per night

Guest favourite

Condo in Siesta Key

4.92 out of 5 average rating, 130 reviews

*A Stones Throw from #1 Voted Siesta Key Beach*

May 24 – 31

$471 CAD per night

Guest favourite

Condo in Sarasota

4.95 out of 5 average rating, 123 reviews

Cozy Beach Side 1BD/2BA, Walk to Beach & Pool

Sep. 13 – 20

$337 CAD per night

Quick stats about vacation rentals with outdoor seating in Siesta Key

Total rentals
540 properties
Rentals with a pool
400 properties have a pool
Pet-friendly rentals
180 properties allow pets
Family-friendly rentals
410 properties are a good fit for families
Total number of reviews
17K reviews
Nightly prices starting at
$123 CAD before taxes and fees

Destinations to explore