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Waterfront holiday rentals in Siesta Beach

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Top-rated waterfront rentals in Siesta Beach

Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

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Cottage in Siesta Key

4.88 out of 5 average rating, 217 reviews

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

*Siesta Key elevated villa at Solitude Suites on Siesta Key. *Your own detached private villa, located in a small resort. *Waterfront resort w/ FREE pool, kayaks, stand up paddle boards & Tiki Hut. * Just a 10-12 min walk to award winning beach. *1 Bedroom w/King bed. *1 full bathroom w/shower. *Large kitchen, open living room, fully furnished inc towels & linens. *Private screened lanai w/ table & chairs. *Beautiful shared pool w/ sun shelf & waterfall. *2 min car ride to beach. *Updated!

Guest favourite

Island in Sarasota

4.97 out of 5 average rating, 303 reviews

*NEW May 17 CX 30% OFF! Sarasota #1 Luxury Villa*

Check our nearby sister properties for 2024 dates by clicking our host picture, then click picture again or "contact host". Or BOOK 2024 NOW, stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

Guest favourite

Home in Bradenton

4.94 out of 5 average rating, 154 reviews

Peaceful Braden River Oasis: Cottage

Come get away to this river retreat just outside of Lakewood Ranch. This property has three separate rental units on it including this charming single bedroom cottage with access to the river. It comes with everything you need to enjoy a wonderful vacation! The other units on this property are the Guest House, a larger studio unit 1 bed/1 bath sleeps 2 (Search Peaceful Braden River Oasis: Guest House) and the Main House, a 2 bed/2 bath sleeps 7 (search Peaceful Braden River Oasis: Main House).

Guest favourite

Apartment in Siesta Key

4.96 out of 5 average rating, 276 reviews

On the Beach; Siesta Key SunBum Studio

STEPS TO YOUR OWN PRIVATE BEACH!! NO TRICKS or GIMMICKS LIKE OTHER LISTINGS on the KEY. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, new gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. Enjoy 2 free bikes day rental with booking! You are sure to enjoy your time here on the #1 U.S. Beach.

Home in Siesta Key

4.91 out of 5 average rating, 122 reviews

Sea Club II Garden House

This surprisingly spacious 1200sf beach bungalow has been completely renovated in February 2020 from floor to ceiling. You will enjoy 3 spacious bedrooms with a private Master suite, spacious updated eat in kitchen and large family room. The unit is unique with a private deck to relax on at night. Walking distance to private beach access as well as a newly renovated heated salt water Community pool (Shared) on the intercoastal with breath taking views. This is a one of a kind experience.

Guest favourite

Apartment in Siesta Key

5.0 out of 5 average rating, 18 reviews

Amazing beach view! Entire unit renovated!

The entire unit is completely renovated! Brand new furniture, appliances, and 2 55-inch smart TVs, etc. It comfortably sleeps 4 people. This 1 bedroom/1 bath unit include a California king bedroom set in the bedroom, queen and full sleeper sofas in the living room, and pack-n-play for infants. Big lanai area, enjoy amazing views of the ocean. This 3rd-floor unit steps away from #1 Siesta Key beach. This unit is a short distance to siesta key village for restaurants, shops, & entertainment.

Guest favourite

Tiny home in Sarasota

4.9 out of 5 average rating, 173 reviews

@Tiffanythetinyhome| island | netflix|bike|hammock

You are about to book a famous HGTV 270ft² / 25m² tiny home on a private 1.5-acre island! ☆ Walk to dining, nightlife, and shopping ☆ Fully equipped kitchen (K-cup) ☆ Backyard fire pit + BBQ ☆ Screened-in outdoor lounge w/ hammocks ☆ 415Mbps ☆ Smart TV w/ Netflix ☆ Memory foam bed ☆ FREE Bikes + kayaks + beach gear 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing) We use a compost toilet. Please read house rules for info.

Guest favourite

Apartment in Longboat Key

4.97 out of 5 average rating, 150 reviews

Charming Condo on the Coast!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located on the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and onward to the secluded beach with complimentary chairs and umbrellas. Enjoy a relaxing vacation at our peaceful condo at The Beach on Longboat Key Resort!

Home in Siesta Key

4.89 out of 5 average rating, 100 reviews

Spacious & Modern Gem ~ Walk to Gated Beach ~ Pool

Step into the spacious and modern 4BR 2Bath getaway in a tranquil area just a few steps from the gated beach. It offers a relaxing retreat from which you can easily explore local restaurants, shops, exciting attractions, and natural beauties. The stylish design and rich amenity list will leave you in awe. ✔ 4 Comfortable Bedrooms ✔ Open Design Living ✔ Full Kitchen ✔ Patio ✔ Smart TV ✔ High-Speed Wi-Fi ✔ Free Parking ✔ Building Amenities (Pool, BBQ, Lounges) See more below!

Guest favourite

Guest suite in Sarasota

4.91 out of 5 average rating, 274 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 :-)

Cottage in Siesta Key

4.84 out of 5 average rating, 133 reviews

Adorable Cozy Silver Sands Cottage on Siesta Key!!

Adorable one bedroom "Old Florida Cottage" on the intracoastal bay side of Siesta Key. This is a stand alone cottage, ground floor, no elevators or flights of stairs to mess with. New Pool with a tiki hut, fishing dock, boat basin (up to 24'), beach access 4 min. walk across Midnight Pass Rd. to the #1 beach with the whitest, softest sand you'll ever see! Hi Def TV in LR , Wifi, TV in BR, stocked with everything but your clothes and toothbrush.

Guest favourite

Home in Siesta Key

5.0 out of 5 average rating, 126 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!

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Popular amenities for waterfront rentals in Siesta Beach

Free parking on premises

Air conditioning

Waterfront apartment rentals

Flat in Siesta Key

4.67 out of 5 average rating, 169 reviews

Siesta Key Condo. Sit by the water !

Guest favourite

Flat in Longboat Key

4.82 out of 5 average rating, 124 reviews

Ocean Front Studio Special From $99/night

Flat in Sarasota

4.74 out of 5 average rating, 305 reviews

King bed. Pool. Daily rentals

Guest favourite

Flat in Bradenton Beach

4.92 out of 5 average rating, 263 reviews

Las Palmas Beach Rentals unit 3

Guest favourite

Flat in Bradenton Beach

4.87 out of 5 average rating, 123 reviews

Low Tide @ Tides Inn

Flat in Bradenton Beach

4.89 out of 5 average rating, 118 reviews

Beachfront Studio right on the beach, Free Parking

Guest favourite

Flat in Siesta Key

4.94 out of 5 average rating, 83 reviews

Siesta Premier Location - The 'Calm of Siesta'

Guest favourite

Flat in Siesta Key

5.0 out of 5 average rating, 6 reviews

Sunset Sensation

Waterfront house rentals

Home in Siesta Key

4.79 out of 5 average rating, 117 reviews

3BR Unit with Pool & Hot Tub, 2 min walk to Beach

Guest favourite

Home in Myakka City

4.98 out of 5 average rating, 134 reviews

Charming Country Stay (Near Lakewood Ranch)

Guest favourite

Home in Longboat Key

4.87 out of 5 average rating, 106 reviews

Summer House longboat key

Guest favourite

Home in Sarasota

4.93 out of 5 average rating, 106 reviews

Lake Front House with a Pool

Guest favourite

Home in Bradenton

4.98 out of 5 average rating, 198 reviews

My Sunny home on the Bay.

Guest favourite

Home in Siesta Key

4.99 out of 5 average rating, 67 reviews

Siesta Key Quaint Beach House

Guest favourite

Home in Siesta Key

5.0 out of 5 average rating, 22 reviews

Beachfront 180-Degree View, Walk to Village!

Guest favourite

Home in Siesta Key

5.0 out of 5 average rating, 12 reviews

New Villa on Siesta Key! Pool & Walkable to Beach

Waterfront apartment rentals

Guest favourite

Apartment in Longboat Key

4.92 out of 5 average rating, 146 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Guest favourite

Apartment in Sarasota

4.83 out of 5 average rating, 147 reviews

Best Gulf Coast Condo in Siesta Key

Guest favourite

Apartment in Longboat Key

4.8 out of 5 average rating, 213 reviews

SRQ/Longboat Key Beach - kid friendly/romantic B1

Apartment in Longboat Key

4.82 out of 5 average rating, 159 reviews

Updated Beachfront Condo at Prestigious Long Boat

Guest favourite

Apartment in Venice

4.87 out of 5 average rating, 142 reviews

The Studio at the Beach 56

Guest favourite

Apartment in Longboat Key

4.86 out of 5 average rating, 155 reviews

The Beach Condo Unit #107 Beachfront

Guest favourite

Apartment in Venice

4.82 out of 5 average rating, 219 reviews

Updated beachy condo - ready for you!

Guest favourite

Apartment in Bradenton Beach

4.91 out of 5 average rating, 132 reviews

Beachfront condo in paradise

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