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Waterfront holiday rentals in Siesta Key

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Siesta Key

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

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Apartment 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

9–16 Jan

€ 113 per night

Guest favourite

Island in Sarasota

4.97 out of 5 average rating, 301 reviews

NEW MAY CX! last min SALE Sarasota #1 Luxury!

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!

8–15 Jan

€ 682 per night

Apartment in Siesta Key

4.82 out of 5 average rating, 233 reviews

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

We pay your AIRBNB service fees for you! Updated & inviting coastal getaway, located on the island of Siesta Key in a small resort called Solitude Suites on Siesta Key. The “Sunset Suite” has a living/dining/kitchenette area w/ 65” TV, a separate bedroom & a separate bathroom. Off the bedroom is a private open wood deck. Table & chairs allow you to enjoy the perfect view of a Siesta Key sunset. New shower in Dec 2023! 2 min drive or 10 min walk to beach! Enjoy FREE Kayaks, SUPs & Tiki Huts!

10–17 May

€ 200 per night

Guest favourite

Home in Bradenton

4.94 out of 5 average rating, 153 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).

27 Mar – 3 Apr

€ 124 per night

Guest favourite

Flat in Longboat Key

4.82 out of 5 average rating, 124 reviews

Ocean Front Studio Special From $99/night

This complex is a 2 story bldg with only 14 condos, beautifully landscaped, with sophisticated charm and a casual beach atmosphere. The pictures are taken from the condo, so what you see is what you get, direct beautiful Ocean views. Sip your beverage of choice as you enjoy the sunsets and the balmy breezes on your large walkout private patio with a table, chairs, chaise lounges which faces the aqua waters of the Gulf of Mexico. This is a condo that you will want to return to year after year.

11–18 Aug

€ 236 per night

Guest favourite

Apartment in Siesta Key

4.96 out of 5 average rating, 275 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.

9–16 Mar

€ 499 per night

Guest favourite

Tiny home in Sarasota

4.89 out of 5 average rating, 171 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.

2–9 Jul

€ 201 per night

Apartment in Siesta Key

4.82 out of 5 average rating, 131 reviews

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.

2–9 Nov

€ 231 per night

Guest favourite

Apartment in Longboat Key

4.93 out of 5 average rating, 144 reviews

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.

14–21 Dec

€ 322 per night

Guest favourite

Apartment in Longboat Key

4.97 out of 5 average rating, 148 reviews

Sunset Views - Open May 13 & 14 - $175/nt!

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!

14–21 Dec

€ 349 per night

Guest favourite

Apartment in Tierra Verde

4.96 out of 5 average rating, 237 reviews

Natural Beauty on Tierra Verde, Waterfront Condo

Feels like the Florida Keys! Fully renovated & well appointed second floor, 1 bed, 1 bath condo in Holiday Island condo resort. The condo features a beautiful waterfront & pool view, tennis, bicycles, hot tub, dock with grills, gym, and more. Remodeled in 2015 the condo features a fully equipped kitchen, Keurig coffee maker, beautiful views from the living room, dining room, kitchen, balcony. Walking distance to many local restaurants & minutes away from St. Pete Beach & Fort DeSoto.

14–21 Dec

€ 145 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 :-)

18–25 Dec

€ 115 per night

Holiday rentals for every style

Get the amount of space that is right for you

Flats

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Houses

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

Popular amenities for waterfront rentals in Siesta Key

Free parking on premises

Air conditioning

Waterfront apartment rentals

Flat in Siesta Key

4.67 out of 5 average rating, 168 reviews

Siesta Key Condo. Sit by the water !

18–25 Aug

€ 238 per night

Guest favourite

Flat in Ellenton

4.96 out of 5 average rating, 320 reviews

Serenity on the Manatee

6–13 Oct

€ 140 per night

Flat in Saint Pete Beach

4.77 out of 5 average rating, 199 reviews

Steps from Sand & Pool

23–30 Oct

€ 139 per night

Guest favourite

Flat in Ruskin

4.84 out of 5 average rating, 102 reviews

Sunset Del Mar (Studio with view of Tampa Bay)

4–11 Dec

€ 156 per night

Guest favourite

Flat in Bradenton Beach

4.88 out of 5 average rating, 204 reviews

Las Palmas Beach Rentals Unit 1

11–18 Dec

€ 293 per night

Flat in Bradenton Beach

4.89 out of 5 average rating, 118 reviews

Beachfront Studio right on the beach, Free Parking

28 Dec – 4 Jan

€ 614 per night

Flat in Siesta Key

5.0 out of 5 average rating, 4 reviews

Sunset Sensation

4–11 Sep

€ 523 per night

Guest favourite

Flat in Siesta Key

4.94 out of 5 average rating, 83 reviews

Siesta Premier Location - The 'Calm of Siesta'

5–12 Jan

€ 366 per night

Waterfront house rentals

Home in Siesta Key

4.91 out of 5 average rating, 121 reviews

Sea Club II Garden House

10–17 Nov

€ 407 per night

Guest favourite

Home in Myakka City

4.98 out of 5 average rating, 134 reviews

Charming Country Stay (Near Lakewood Ranch)

15–22 Jul

€ 158 per night

Guest favourite

Home in Longboat Key

4.87 out of 5 average rating, 106 reviews

Summer House longboat key

9–16 Aug

€ 620 per night

Guest favourite

Home in Englewood

4.96 out of 5 average rating, 103 reviews

Waterfront Cottage by Manasota Key

12–19 Sep

€ 166 per night

Guest favourite

Home in Sarasota

4.93 out of 5 average rating, 106 reviews

Lake Front House with a Pool

13–20 Oct

€ 250 per night

Guest favourite

Home in Anna Maria

4.93 out of 5 average rating, 152 reviews

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

6–13 Nov

€ 567 per night

Guest favourite

Home in Siesta Key

5.0 out of 5 average rating, 22 reviews

Beachfront 180-Degree View, Walk to Village!

21–28 Sep

€ 630 per night

Guest favourite

Home in Siesta Key

4.9 out of 5 average rating, 21 reviews

Paradise Retreat

1–8 Nov

€ 591 per night

Waterfront apartment rentals

Guest favourite

Apartment in Siesta Key

4.9 out of 5 average rating, 203 reviews

Sea Club 2 Condo Siesta Key

5–12 Feb

€ 398 per night

Guest favourite

Apartment in Longboat Key

4.8 out of 5 average rating, 212 reviews

SRQ/Longboat Key Beach - kid friendly/romantic B1

13–20 Nov

€ 212 per night

Guest favourite

Apartment in Venice

4.82 out of 5 average rating, 219 reviews

Updated beachy condo - ready for you!

12–19 Dec

€ 149 per night

Apartment in Longboat Key

4.82 out of 5 average rating, 159 reviews

Updated Beachfront Condo at Prestigious Long Boat

7–14 Dec

€ 662 per night

Guest favourite

Apartment in Siesta Key

4.97 out of 5 average rating, 110 reviews

Siesta Key For Me @ The Palm Bay Club

13–20 Dec

€ 355 per night

Guest favourite

Apartment in Venice

4.83 out of 5 average rating, 174 reviews

Venice Beach Studio 71

18–25 Aug

€ 145 per night

Guest favourite

Apartment in Bradenton Beach

4.91 out of 5 average rating, 129 reviews

Beachfront condo in paradise

20–27 Apr

€ 423 per night

Guest favourite

Apartment in Longboat Key

4.86 out of 5 average rating, 154 reviews

The Beach Condo Unit #107 Beachfront

22–29 Oct

€ 347 per night

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
€ 84 before taxes and fees

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