
Waterfront holiday rentals in Siesta Key
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Top-rated waterfront rentals in Siesta Key
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals
Welcome to our 3 Bedroom 2 Bathroom Siesta Key Beach House. Full kitchen. Walk to beach. We provide chairs & towels for the Beach Walk to Beach access #12 on Siesta key Lots of places to eat and drink, close by. Free WIFI Daily, Weekly rentals. Swimming Pool on site King Bed in Master bedroom, Bedroom 2 and 3 both have Queens This home is in a great location and it is only a short walk to shops , restaurants and Beach. This home has 2 x 1 bedroomed units attached and is great for families

Crystal House on Siesta Key Beach
This is an updated and renovated two bedroom suite on Siesta Key. Complete with marble dining table, stainless appliances and large televisions. There is a computer in the spare bedroom for your convenience along with an Xbox and DVD player. We tried to think of everything so please feel free to make suggestions after your stay. Your satisfaction is our number one concern. The sofa is a Laz-Y-Boy and is not a sleeper but is very comfortable!!! There is a set of twin-twin bunks in the main room!

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.

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.

Summer House longboat key
Luxurious waterfront home with bay and and canal view, new custom kitchen with a view to the pool and your own private tiki bar, dock that can accommodate up to 21 ft boat , whole house just received a complete inside and out make over. Tropical coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach. minutes from St Armand’s circle. feel free to reach out with any questions or requests

Beachwalk Townhouse with view of Gulf of Mexico
Townhouse with 1550 sq. ft. Private elevator, all new flooring, quartz countertops, sinks, faucets, shower. View of the Beach and Gulf of Mexico from Lanai and Master Bedroom. Only a few steps to Siesta Key Beach Heated Pool, garage, grill, all beach accessories. Relax on the lanai with a view of the beach/gulf or in the downstairs Florida room by the pool. Walking distance to the village of Siesta Key to the many restaurants and amenities. Have a relaxing stay on a wonderful island.

Siesta Key Escape: Sleeps 10 - Pool - Gated Beach!
Unwind in this spacious 4BR/2BA Siesta Key getaway, set on a quiet street steps from gated, private beach entry. Enjoy a resort-style shared pool when you're not at the shore, then head out to Siesta Key Village restaurants, shops, and the island's top attractions. ✔ 4 Bedrooms (Sleeps 10) ✔ Private Beach Access ✔ Open Design Living ✔ Renovated Chef's Kitchen ✔ Private Patio & Shared Outdoors (Pool, BBQ, Games, Fire Pit, Lounges) ✔ Smart TVs ✔ Wi-Fi ✔ Laundry ✔ Parking Learn more below!

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!

Island Time!
This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! 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 secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

Gulf Front! Sunset Deck! + Walk to Bridge St Pier!
🌊🏄Welcome to The Surof House - where panoramic views of the Gulf of Mexico welcome you from almost every corner! 🏖️Experience the ultimate beachfront retreat at this unique & stunning property nestled across from one of the top beaches in the world. A perfect blend of luxury, comfort, & unparalleled views awaites. With an upstairs loft featuring 3 single beds & 2 downstairs rooms with king beds, it's an ideal getaway for families, friends, or anyone seeking a slice of paradise.

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. If we are booked check out our additional units under our profile.

Palm Bay Club! Resort 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.
Popular amenities for waterfront rentals in Siesta Key
Waterfront apartment rentals

Beachfront Corner Condo | Sunset Gulf Views

Sweet Retreat at Shorewalk!

Pass a grille Gulf Way Beachfront Parking WiFi 13

Siesta Key - Poolside Suite - Studio - Free kayaks

Longboat Key-OCEAN FRONT- on the beach

Wave Whisper in Siesta Key

New Modern Longboat Key*5 Steps to Sand*Heatd Pool

Serenity on the Manatee
Waterfront house rentals

AMI/IMG/Boat/Bikes/Golf/Hottub/Kayak/Beach/pool

NEW Saltwater Pool + Spa | Mins to AMI Beaches/IMG

Luxury Waterfront Home in Sarasota w/ Pool & Dock

Walk to beach/village, boat lift, monthly discount

Heated Pool, Elevator, Waterfront, Fire Pit, Dock

Beachfront 180-Degree View, Walk to Village!

Oceanfront home w/sunset views of Sarasota Bay

Sarasota Serenity - Minutes to Beach
Waterfront apartment rentals

Bayside Sunrise Cottage on Siesta Key!

Siesta Dunes 1st Floor Beach Front Retreat + Bikes

The Beach Condo #107 Beachfront Full View

Siesta Key For Me @ The Palm Bay Club

KING Bed + Anna Maria Island Beaches + Beach Gear!

Sunset and beach view from your balcony Unit 403

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool
When is the best time to visit Siesta Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 242 | € 328 | € 357 | € 288 | € 220 | € 219 | € 230 | € 197 | € 178 | € 188 | € 205 | € 230 |
| 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 510 holiday rentals in Siesta Key

Nightly prices starting at
Siesta Key holiday rentals start at € 102 per night before taxes and fees

Verified guest reviews
Over 12,500 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 70 rentals that welcome pets

Holiday rentals with a pool
460 properties feature pools

Rentals with dedicated workspaces
230 properties have a dedicated workspace

Wifi availability
510 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!
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- Anna Maria Island
- Siesta Beach
- Raymond James Stadium
- Crescent Beach
- John's Pass
- Anna Maria Island Beach
- Bean Point Beach
- Coquina Beach
- Turtle Beach
- Vinoy Park
- Lido Key Beach
- Amalie Arena
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- River Strand Golf and Country Club
- Englewood Beach
- North Beach At Fort DeSoto Park
- Tropicana Field
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