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Waterfront holiday rentals in Siesta Key

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Top-rated waterfront accommodation in Siesta Key

Guests agree: These waterfront accommodation options are highly rated for location, cleanliness and more.

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Cottage in Siesta Key

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

*5 STAR Aug 20 % SALE Sarasota #1 Lux BEACH 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

Condo in Siesta Key

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

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

Condo in Siesta Key

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

@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.

Condo in Siesta Key

The Key to a Great Vacation!

Welcome to our one bedroom, one bath (4 piece) main floor condo. Recently renovated. Freshly painted with new furniture, a brand new king size memory foam mattress with contemporary decoration (with queen size pull out couch). Easily accessible with no steps to climb and close, convenient parking right outside the front door. Quiet, peaceful and near both Siesta Key Beach and the condo pool ensure a wonderful vacation. Walk across the street and enjoy one of the best beaches in the world.

Guest favourite

Cottage in Bradenton

Historic Private King Bed Suite-Near Beach-D’Town.

Your relaxing vacation is here! Private Cottage with a huge deck. Wonderfully furnished with plush linens, beach towels/chairs. A great nights sleep with a king-size bed and pull-out couch which serves as 2nd bed. Private kitchen and bath. TV and fast WIFI. We are located in a historic and quiet neighborhood in DT Bradenton. There are 3 villas on our large corner property. Off street parking. Quiet times are between 10PM until 7:30AM. Please respect others. Walk to many great restaurants!

Guest favourite

Condo in Longboat Key

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf of Mexico and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

Guest favourite

Condo in Longboat Key

Relax on LBK!

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!

Guest favourite

Home in Siesta Key

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!

Guest favourite

Condo in Siesta Key

Siesta Key Condo. Checkout our great rates!

Our beautiful Siesta Key condo is located a short stroll from the famous Siesta Key beach with its beautiful quartz sand and amazing sunsets. The Midnight Cove II condominium complex has private beach access with outstanding amenities and is very family friendly, come and enjoy the natural beauty this complex and all Siesta Key has to offer.

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Siesta Key waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment accommodation

Guest favourite

Rental unit in Ellenton

Serenity on the Manatee

Rental unit in Bradenton Beach

"Dream Away" at The Beach Dreams Resort

Rental unit in Sarasota

· King bed . Pool. Daily rentals

Guest favourite

Rental unit in Longboat Key

Ocean Front Studio Special From $99/night

Rental unit in Siesta Key

Siesta Key Condo. Sit by the water !

Guest favourite

Rental unit in Ruskin

Sunset Del Mar (Studio with view of Tampa Bay)

Guest favourite

Rental unit in Bradenton Beach

Las Palmas Beach Rentals Unit 1

Rental unit in Bradenton Beach

Tortuga Inn Beach Resort # 229 Island Condo, 2Bdrm

Waterfront house rentals

Guest favourite

Home in Myakka City

Charming Country Stay (Near Lakewood Ranch)

Guest favourite

Home in Bradenton

Peaceful Braden River Oasis: Cottage

Home in Siesta Key

Spacious & Modern Gem ~ Walk to Gated Beach ~ Pool

Guest favourite

Home in Englewood

Charming & Comfy Waterfront Oasis ~ Views ~ Dock!

Guest favourite

Home in Bradenton

My Peaceful place on the bay.

Home in Siesta Key

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

Guest favourite

Home in Longboat Key

Summer House longboat key

Guest favourite

Home in Anna Maria

Private 30' Pool and Boat Dock - Rated best on AMI

Waterfront condo accommodation

Guest favourite

Condo in Sarasota

Best Gulf Coast Condo in Siesta Key

Guest favourite

Condo in Venice

The Studio at the Beach 56

Guest favourite

Condo in Venice

Updated beachy condo - ready for you!

Guest favourite

Condo in Longboat Key

The Beach Condo Unit #107 Beachfront

Guest favourite

Condo in Longboat Key

SRQ/Longboat Key Beach - kid friendly/romantic B1

Guest favourite

Condo in Bradenton Beach

Beachfront condo in paradise

Guest favourite

Condo in Siesta Key

Siesta Key Studio - on the BEACH!

Guest favourite

Condo in Siesta Key

One of Best Locations on Siesta Key Beach!!

Quick stats about waterfront rentals in Siesta Key

Total rentals
300 properties
Rentals with a pool
250 properties have a pool
Pet-friendly rentals
60 properties allow pets
Family-friendly rentals
240 properties are a good fit for families
Total number of reviews
8.3K reviews
Nightly prices starting at
$145 NZD before taxes and fees

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