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Vacation rentals with outdoor seating in Siesta Key

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Top-rated outdoor seating rentals in Siesta Key

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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

G$19,288 GYD per night

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!

Aug 10 – 17

G$22,647 GYD per night

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

Sep 17 – 24

G$94,753 GYD per night

Guest suite in Sarasota

4.88 out of 5 average rating, 339 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

Aug 27 – Sep 3

G$22,361 GYD per night

Guesthouse in Sarasota

4.93 out of 5 average rating, 455 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

G$17,130 GYD per night

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!

Jan 1 – 8

G$31,036 GYD per night

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 18 – 25

G$25,781 GYD per night

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 .

Apr 25 – May 2

G$23,938 GYD per night

Guest suite in Siesta Key

4.93 out of 5 average rating, 134 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**

Aug 7 – 14

G$38,703 GYD per night

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 :-)

Nov 29 – Dec 6

G$20,120 GYD per night

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

G$120,794 GYD per night

Guesthouse in Sarasota

4.97 out of 5 average rating, 233 reviews

Casita Lantana, a 1925 cottage in a Tropical Oasis

Welcome to my original 1925 Casita, built in the heyday of the John Ringling era. We are centrally located between Sarasota, Lakewood Ranch, and Bradenton, making it an ideal place to explore all the area offers. Getting around is easy since we are located very close to the Ringling Museum of Art. Plus, it is only a short 15-minute drive to downtown Lido Beach and St. Armands Circle.

Sep 20 – 27

G$25,250 GYD per night

Vacation rentals for every style

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Villas

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Bungalows

Intimate homes. inviting architecture

Houses

A space thats all yours, with room for everyone

Popular amenities for Siesta Key outdoor seating rentals

Free parking on premises

Air conditioning

House rentals with outdoor seating

Home in Sarasota

5.0 out of 5 average rating, 279 reviews

Stunning Luxe Casita- Gateway to Siesta Beach

Dec 6 – 13

G$58,705 GYD per night

Home in Siesta Key

4.92 out of 5 average rating, 141 reviews

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

Jun 6 – 13

G$113,371 GYD per night

Home in Sarasota

4.89 out of 5 average rating, 103 reviews

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

Nov 25 – Dec 2

G$35,206 GYD per night

Home in Sarasota

4.96 out of 5 average rating, 111 reviews

Newly Renovated Ranch Minutes From Beach/Downtown

Jul 14 – 21

G$25,372 GYD per night

Home in Sarasota

4.96 out of 5 average rating, 128 reviews

Sarasota Florida -Wild Orchid Creek Cottage Home

Sep 2 – 9

G$30,245 GYD per night

Home in Sarasota

4.87 out of 5 average rating, 204 reviews

The Pineapple Suite.Teal tropical home in Sarasota

Oct 25 – Nov 1

G$19,878 GYD per night

Home in Sarasota

4.88 out of 5 average rating, 109 reviews

Coral Cottage - near Siesta Key & Lido Beach

Sep 14 – 21

G$26,271 GYD per night

Home in Siesta Key

4.87 out of 5 average rating, 119 reviews

"Safe & Clean" Palm Oasis - Relax in comfort!

Apr 28 – May 5

G$172,660 GYD per night

Apartment rentals with outdoor seating

Apartment in Sarasota

4.96 out of 5 average rating, 139 reviews

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

Aug 30 – Sep 6

G$29,011 GYD per night

Apartment in Sarasota

4.88 out of 5 average rating, 137 reviews

Pets friendly modern studio 5 mi to Siesta Key

Jun 1 – 8

G$22,284 GYD per night

Apartment in Sarasota

4.96 out of 5 average rating, 206 reviews

Private 2 Bedroom Suite with Kitchenette

Jun 14 – 19

G$27,823 GYD per night

Apartment in Sarasota

4.97 out of 5 average rating, 201 reviews

Modern Private Apartment 1 Block from Sarasota Bay

Oct 24 – 31

G$20,122 GYD per night

Apartment in Sarasota

4.98 out of 5 average rating, 160 reviews

Near Siesta Key Beaches - Quiet 1 BR apt

Mar 30 – Apr 6

G$31,060 GYD per night

Apartment in Sarasota

4.94 out of 5 average rating, 133 reviews

Super Clean! 2/2 condo Walk to SKey!

Jun 5 – 12

G$30,885 GYD per night

Apartment in Sarasota

4.97 out of 5 average rating, 166 reviews

Gillespie On The Park, Walk to Downtown

Apr 1 – 8

G$18,464 GYD per night

Apartment in Venice

4.99 out of 5 average rating, 384 reviews

Hales Corner, Cozy & Private Beach Town Getaway

Sep 2 – 9

G$33,509 GYD 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

Aug 19 – 26

G$45,391 GYD per night

Condo in Siesta Key

4.95 out of 5 average rating, 148 reviews

Walk to Siesta Key Village and Beach

Jul 30 – Aug 6

G$73,514 GYD per night

Condo in Siesta Key

4.96 out of 5 average rating, 275 reviews

On the Beach; Siesta Key SunBum Studio

Jan 11 – 18

G$95,703 GYD per night

Condo in Sarasota

4.95 out of 5 average rating, 187 reviews

Newly Renovated + Washer/Dryer- Walk everywhere!

Sep 11 – 18

G$36,317 GYD per night

Condo in Siesta Key

4.96 out of 5 average rating, 105 reviews

Siesta Key Condo. Checkout our great rates!

Aug 29 – Sep 5

G$32,647 GYD 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

G$35,036 GYD per night

Condo in Sarasota

4.95 out of 5 average rating, 123 reviews

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

Sep 13 – 20

G$42,743 GYD per night

Condo in Siesta Key

4.92 out of 5 average rating, 130 reviews

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

May 26 – Jun 2

G$59,763 GYD 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
G$18,817 GYD before taxes and fees

Destinations to explore