
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.

NO Stairs, Siesta beachfront. Walk to the village!
Welcome to your own private getaway directly on Siesta Beach! This ground floor unit is just steps from the powdery sands of Siesta Key. NO STAIRS Enjoy the updated bathroom with quartz countertops, new fixtures, paint, new furnishings, and décor. You literally walk out your door and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedrooms 1.5 bathroom beachfront home with Gulf views that sleeps 6.

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.

Siesta Premier Location - The 'Calm of Siesta'
My place is right across the street from Siesta Key beach, family-friendly activities, and nightlife. You’ll love my place because of the location, the ambiance, the outdoors space, and the neighborhood. My place is good for couples, adventurers, business travelers, and families. Walking distance to the village and is at less crowded section of the public beach which equals perfect location!! Updated and beautifully decorated condo with breathtaking view of the beach, You will LOVE it!

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 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.

Siesta Key - Poolside Suite - Studio - Free kayaks
Poolside Suite is a hotel room style suite. There is a king sized bed & a 65” smart TV. Free Wifi. A private en suite bathroom features a walk in shower, toilet and large vanity with sink & mirror. Also provided in a walk in closet space is a fridge, microwave, freezer, blender, cups, plates, silverware, keurig, iron, mini ironing board & hangers. Simple & stylish! No frills, yet all the necessities! The a/c is a centralized system, set to 71-73 degrees. Fan provided.

Oceanview on Longboat Key!
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 loungers. Enjoy a relaxing vacation at our peaceful condo at The Beach on Longboat Key Resort!

On the Beach; Siesta Key SunBum Studio
Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta 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, 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!

Palm Bay Club! Resort Style Living on Siesta Key!
Meticulously Renovated Oversized, 2 Bedroom 2 Bath, Beach to Bay unit! Walk to the Famous Siesta Key beach, voted #1 beach in the US, with the worlds softest sand! This complex spans from the magnificent Bay with yachts and boats to the private beach with free access to Chairs and loungers, Cabanas are available to rent. Nearby Siesta Key Village has great shopping and restaurants. Access to free transportation around the island is right outside your door.

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 :-)

Bradenton Beach Sunsets 1, Anna Maria Island, FL
Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

Relaxing 3BR Retreat+ Hot Tub + Pool +Beaches +IMG
🌴Welcome to Beachway Haven! This 5-Star ⭐️ hideaway is just mins from Anna Maria Island's Pristine Beaches & the Gulf of Mexico. Dive into relaxation with your own Heated Saltwater Pool & Spa Hot Tub, nestled in a tropical oasis. Only a skip away from Golf Courses, Nature Parks, IMG Academy, & Palma Sola Causeway's Beach Access – your gateway to Horseback Riding, Kayaking, & endless sandy adventures. Shopping & dining are only a few mins away too!

2BR/2BA home w/ heated pool, 5 min to Siesta Key!
Charming 2BR/2BA Lakefront Home with Heated Pool – Just 2 Miles to Siesta Key Beach! Escape to this picturesque lakefront retreat, only 2 miles from the world-famous Siesta Key Beach. Perfect for families or groups, this spacious and beautifully furnished home offers a relaxing and memorable getaway. Lounge by the heated pool, soak in stunning lake views, or explore nearby attractions—this home is your ideal Sarasota vacation base.
Popular amenities for waterfront rentals in Siesta Key
Waterfront apartment rentals

Newly Remodeled Beachfront Studio - On the sand!

Condo Kokomo - stay ON the beach in Siesta Key!

Sweet Retreat at Shorewalk!

Las Palmas Beach Rentals Unit 1

Longboat Key-OCEAN FRONT- on the beach

Trendy brand new condo w/ garden

Beachfront Studio Retreat on Anna Maria Island

Serenity on the Manatee
Waterfront house rentals

Peaceful Braden River Oasis: Cottage

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

Bradenton Gem near IMG & AMI King Ste & Beach Gear

Spacious & Modern Gem ~ Walk to Gated Beach ~ Pool

Tranquility on the bay.

Lake Front House with a Pool

Sea Club II Garden House

Sarasota Serenity - Minutes to Beach
Waterfront apartment rentals

Best Siesta Key Condo

Best views of the beach from your balcony Unit 301

Sea Shell Ocean view On Beach Walk everywhere Pool

Bayside Sunrise Cottage on Siesta Key!

The Beach Condo #107 Beachfront Full View

Crystal House on Siesta Key Beach

Sarasota Surf & Racquet Club Siesta Key Condo

Luxury 3/3 Margaritaville Resort
When is the best time to visit Siesta Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £202 | £265 | £312 | £256 | £196 | £195 | £188 | £164 | £152 | £152 | £165 | £189 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 18°C |
Quick stats about waterfront rentals in Siesta Key

Total holiday rentals
Explore 380 holiday rentals in Siesta Key

Nightly prices starting at
Siesta Key holiday rentals start at £61 per night before taxes and fees

Verified guest reviews
Over 11,380 verified reviews to help you choose

Family-friendly holiday rentals
310 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 70 rentals that welcome pets

Holiday rentals with a pool
330 properties feature pools

Rentals with dedicated workspaces
230 properties have a dedicated workspace

Wifi availability
380 of Siesta Key holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Siesta Key rentals

4.8 Average rating
Siesta Key stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- Saint Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Havana Holiday rentals
- Fort Lauderdale Holiday rentals
- Four Corners Holiday rentals
- Tampa Holiday rentals
- Kissimmee Holiday rentals
- Rentals with an EV charger Siesta Key
- Family-friendly rentals Siesta Key
- Rentals with lake access Siesta Key
- Rentals with a kayak Siesta Key
- Flat rentals Siesta Key
- Beachfront rentals Siesta Key
- House rentals Siesta Key
- Pet-friendly rentals Siesta Key
- Rentals with a washing machine and dryer Siesta Key
- Rentals with a patio Siesta Key
- Rentals with outdoor seating Siesta Key
- Cottage rentals Siesta Key
- Beach house rentals Siesta Key
- Rentals with a hot tub Siesta Key
- Rentals with breakfast Siesta Key
- Villa rentals Siesta Key
- Rentals with beach access Siesta Key
- Rentals with a firepit Siesta Key
- Mansion rentals Siesta Key
- Rentals with a sauna Siesta Key
- Bungalow rentals Siesta Key
- Townhouse rentals Siesta Key
- Fitness-friendly rentals Siesta Key
- Apartment rentals Siesta Key
- Luxury rentals Siesta Key
- Rentals with a fireplace Siesta Key
- Rentals with pools Siesta Key
- Beach apartment rentals Siesta Key
- Waterfront rentals Sarasota County
- Waterfront rentals Florida
- Waterfront rentals United States
- Anna Maria Island
- Siesta Beach
- Crescent Beach
- John's Pass
- Raymond James Stadium
- Turtle Beach
- Caspersen Beach
- Coquina Beach
- Cortez Beach
- Anna Maria Public Beach
- Lido Key Beach
- Vinoy Park
- Amalie Arena
- Bean Point Beach
- Jannus Live
- Gulfport Beach Recreation Area
- North Beach
- Manasota Key Beach
- River Strand Golf and Country Club
- Splash Harbour Water Park
- Englewood Beach
- North Beach At Fort DeSoto Park
- Point Of Rocks
- Don CeSar Hotel