Waterfront holiday rentals near Siesta Beach

4.88 out of 5 average rating, 111 reviews

Beachfront Escape – Private Balcony, Gulf Views

Beachfront Bliss — No Streets to Cross, Just Steps from the Sand! Enjoy breathtaking Gulf and sunset views from your private balcony in this spacious, newly updated condo. Featuring a brand-new bathroom and new flooring throughout, this 4th-floor unit (with elevator access) is the perfect retreat for your Longboat Key escape. The condo comfortably sleeps up to 6 guests. Sip your morning coffee or catch dolphin sightings and stunning sunsets from the balcony with 180° view of the Gulf. Elevator.

4.88 out of 5 average rating, 100 reviews

Townhouse in Siesta Key

Quiet Siesta Key | Gated Beach Access – Steps Away

Stay, relax, and play-your Siesta Key retreat is here. Make lasting memories at this cozy Siesta Key townhouse, just steps from the famous white sands. Private beach access and no roads to cross, it’s safe and stress-free for the whole family. Relax in spacious living areas, cook in the full kitchen, or enjoy games and movie nights after a day in the sun. Highlights include 2 bedrooms, private parking, nearby shops and dining, and the free Siesta Key Breeze Trolley for easy island exploring.

4.98 out of 5 average rating, 222 reviews

Oceanfront LBK: Open Tuesday, $175/nt + Fees!

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...!

4.93 out of 5 average rating, 122 reviews

The enclosed Lanai features large bay windows showcasing views of the Gulf of Mexico. A seating area includes wicker chairs and a coffee table. Light-colored walls are contrasted by wooden accents and a ceiling fan, creating a bright and airy atmosphere.

Flat in Siesta Key

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!

A light-filled living area features a comfortable white sectional sofa with decorative pillows, complemented by a wooden coffee table. Large glass doors lead to an outdoor space, while a television and two lamps enhance the room's functionality and warmth.

4.85 out of 5 average rating, 117 reviews

The Palm Bay Club on Siesta key Beach

Welcome to The Palm Bay Club on Siesta Key Beach Enjoy sunrise to sunset from our great resort that has private bay to beach access . Updated 2 bedroom 2 Bath ground floor with walk out balcony .Each bedroom offers private en-suite, Clean and bright open floor plan, well appointed kitchen ,Central A/C . Resort features 2 heated pools , enjoy the tranquility of the bay from the large hot tub or pool . Fishing pier, tennis & pickle ball courts, gym, laundry area we also offer boat slips

4.87 out of 5 average rating, 282 reviews

An open living space features a fully equipped kitchen with wooden cabinetry, a dining table, and seating area. A flat-screen TV is mounted on the wall. Light-colored flooring enhances the spacious feel, while natural light brightens the room through multiple windows.

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/ heated pool, kayaks, table tennis & 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!

A screened lanai offers poolside views, with vibrant orange and blue chairs positioned to enjoy the scenery. Lush greenery borders the area, while palm trees sway in the gentle breeze. Glimpses of the Gulf of Mexico and a heated pool are visible through the railing.

4.9 out of 5 average rating, 202 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 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.

A tranquil pool area is surrounded by palm trees, reflecting the clear blue sky. Lounge chairs are positioned around the pool's edge, inviting relaxation. The sun casts a warm glow over the scene, enhancing the peaceful ambiance of the resort.

4.98 out of 5 average rating, 125 reviews

Siesta Key For Me @ The Palm Bay Club

🏖️ Newly Renovated Siesta Key Condo | Ocean + Bay Views | Sleeps 6 📍 Bayside Suite at The Palm Bay Club | Walk to Beach ✨ ALL-NEW RENOVATIONS MAY 2025! Brand new bathrooms, flooring, doors, trim, granite countertops & more—be among the first to enjoy our stylish upgrade! Welcome to Condo #310 at The Palm Bay Club—a 2BR/2BA bright and breezy bayside condo with water views, modern upgrades, and private beach access just a short walk away. Sleeps up to 6 guests comfortably.

4.9 out of 5 average rating, 136 reviews

Flat in Bradenton Beach

Newly Remodeled Beachfront Studio - On the sand!

ONE SHELL COVE on Anna Maria Island has been totally remodeled after Hurricanes Helene and Milton. Wonderful studio floor plan with amazing kitchen. Beautiful view of the waves and the beach right outside your window. Grab your towel, take a few steps and you're on the beach. The sand comes right up to your door in this ground floor unit. Amazing Location Walk to some restaurants Free Trolley goes up and down the Island Rent Kayaks and Paddleboards and enjoy the Beach

5 out of 5 average rating, 154 reviews

Home in Siesta Key

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

Fully Restored Post-Hurricane and Ready to Welcome You!! RCC in Siesta Key is a one-of-a-kind coastal cottage perfectly located between the beach, canal, and village. Enjoy a private heated pool, private dock, and one of the best locations on the island. This 1,500 square foot standalone bungalow has been fully restored with fresh post-hurricane updates. If you want a charming, private beach home with no shared walls and no condo feel, you have found the right place!

A private patio with a round wooden table and two chairs overlooks a manicured lawn leading to the beach. Palm trees sway gently beside the outdoor seating area, offering a serene view of the Gulf waters in the background.

4.97 out of 5 average rating, 355 reviews

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!

4.88 out of 5 average rating, 125 reviews

Sunset and beach view from your balcony Unit 403

A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you check into this fabulous unit. This unit has been completely renovated. The best 1 bed/1 bath in Longboat Key for a great price. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in.

Popular amenities for waterfront rentals near Siesta Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

5 out of 5 average rating, 22 reviews

Flat in Bradenton Beach

Beachfront Corner Condo | Sunset Gulf Views

4.98 out of 5 average rating, 126 reviews

A spacious living room features a large grey sectional sofa with teal accent pillows, a wooden coffee table, and a light blue area rug. Large glass doors provide access to an outdoor area, while a vibrant seascape painting adorns the wall.

Flat in Bradenton

Sweet Retreat at Shorewalk!

4.89 out of 5 average rating, 227 reviews

A dining table showcases a glass top with intricately woven placemats. Each setting features decorative plates and neatly folded napkins secured with decorative rings. Sheer curtains frame the window, offering glimpses of lush palm trees outside.

Flat in Bradenton Beach

Las Palmas Beach Rentals Unit 1

4.96 out of 5 average rating, 114 reviews

Tall grasses gently sway in the foreground, framing a serene beach scene. Soft waves lap against the shore, reflecting hues of orange, pink, and purple from the sunset sky. Cloud formations add depth to the view, enhancing the tranquility of the coastal landscape.

Flat in Longboat Key

Longboat Key-OCEAN FRONT- on the beach

5 out of 5 average rating, 12 reviews

Flat in Siesta Key

Siesta Beach Front Suite

4.97 out of 5 average rating, 423 reviews

A serene view of the Manatee River showcases calm waters reflecting the sky. Lush greenery surrounds the area, accompanied by a covered dock nearby. An American flag flutters gently, and a hint of a charming structure with a porch is visible to the right.

Flat in Ellenton

Serenity on the Manatee

Superhost

A large heated swimming pool is visible in the foreground, surrounded by lounge chairs and umbrellas. The water appears inviting under a clear blue sky, with a view of the inter-coastal waterway in the background. Tropical vegetation adds to the serene atmosphere.

Flat in Siesta Key

4.7 out of 5 average rating, 188 reviews

Siesta Key Condo. Sit by the water !

4.85 out of 5 average rating, 347 reviews

A vibrant blue exterior of the studio is surrounded by lush greenery. Two chairs are positioned on a gravel patio area, providing a welcoming spot outside. The entrance to the studio is framed by palm trees, emphasizing a serene and inviting setting.

Flat in Sarasota

· King bed . Pool. Daily rentals

Waterfront house rentals

4.95 out of 5 average rating, 116 reviews

A comfortable living area is furnished with a gray sofa and decorative pillows. A large beanbag sits on the textured rug, while a medium-sized TV is positioned on a light-colored console. Natural light fills the space through sliding glass doors, adorned with sheer curtains.

Home in Bradenton

Waterfront View Mins To AMI Beaches

4.78 out of 5 average rating, 534 reviews

An inviting beach scene features a sun umbrella providing shade over a wooden lounge chair, set upon soft, sandy shores. The clear blue sky contrasts with the tranquil turquoise waters, creating a peaceful atmosphere near the shoreline.

Home in Siesta Key

Beachfront Getaway in Siesta Key

A heated pool is framed by a screened enclosure, allowing for sunlit swims while providing shade. Comfortable lounge chairs are lined along the poolside, and greenery is visible in the background, creating a serene atmosphere for relaxation.

4.94 out of 5 average rating, 108 reviews

2BR/2BA home w/ heated pool, 5 min to Siesta Key!

A screened lanai encloses a private saltwater pool, featuring a shallow entry and a vibrant pink float. Two lounge chairs are positioned nearby, surrounded by greenery that enhances the serene pool area.

4.94 out of 5 average rating, 104 reviews

Minutes to Siesta Key, heated pool & tiki on water

4.86 out of 5 average rating, 114 reviews

Trendy & Relaxing: Close to Beach ~ Pool ~ Hot Tub

4.9 out of 5 average rating, 152 reviews

A serene beach scene is captured with gentle waves lapping against the shore. The clear water displays various shades of blue and green, while a sandy coastline extends into the distance. People can be seen enjoying the beach, with a bright blue sky overhead.

Home in Siesta Key

Sea Club II Garden House

4.97 out of 5 average rating, 115 reviews

Two bright turquoise adirondack chairs are positioned on a pebbled shoreline, facing a calm canal. Lush palm trees and greenery surround the area, while distant houses line the opposite bank under a clear blue sky.

Home in Bradenton Beach

Waterfront Pool Home Steps to Beach

A serene outdoor seating area features several lounge chairs with cushions, positioned on a brick patio overlooking tranquil water. The setting is complemented by a soft sunset in the background, with lush greenery visible across the bay.

4.89 out of 5 average rating, 106 reviews

Oceanfront home w/sunset views of Sarasota Bay

Waterfront apartment rentals

The open-concept kitchen and dining area feature modern furnishings, with a spacious table for six and bar seating along the kitchen island. Floor-to-ceiling windows provide unobstructed views of the beach, allowing natural light to brighten the room.

5 out of 5 average rating, 9 reviews

2BR Penthouse - Stunning Beach Views on Siesta Key

A modern kitchen features white cabinetry and a spacious counter. Stainless steel appliances, including an oven and microwave, are visible. A decorative beach sign adorns the wall, and a bowl of fresh fruit sits on the counter, adding a pop of color to the bright space.

4.86 out of 5 average rating, 188 reviews

Best Siesta Key Condo - Rarely available

A spacious rooftop sun deck features lounge chairs arranged around a glass table, offering partial views of the ocean and beach. Sunlight brightens the area, while nearby palm trees add to the coastal atmosphere.

4.9 out of 5 average rating, 52 reviews

Sundeck, 20ft to Beach Access, 500ft from Village

A detailed map highlights the location of Siesta Key, showcasing nearby points of interest and roadways. The Gulf of Mexico is indicated to the southwest, while the surrounding areas and other keys are marked, providing context for travel and exploration.

4.87 out of 5 average rating, 104 reviews

Bayside Sunrise Cottage on Siesta Key!

An aerial view captures a picturesque community along the inter-coastal waterway, showcasing a cluster of condos with terra-cotta roofs. The lush greenery surrounds the buildings, and the serene blue waters reflect the sky, with the distant coastline visible beneath a sunny atmosphere.

4.83 out of 5 average rating, 53 reviews

Relaxing Siesta Key 3rd Floor Condo

A view from above showcases the lush, landscaped grounds of the condo complex, featuring curving pathways and palm trees. In the foreground, a heated pool is visible, with beach access just beyond. The serene beach and expansive ocean create a welcoming atmosphere.

4.82 out of 5 average rating, 137 reviews

Sarasota Surf & Racquet Club Siesta Key Condo

A modern living space is showcased with a comfortable dark sofa and a round coffee table on a textured area rug. A dining table with four chairs is positioned nearby, while a large window offers a view of the ocean and natural light fills the room.

5 out of 5 average rating, 47 reviews

Amazing beach view! Entire unit renovated!

A dining area is presented with a large wooden table surrounded by blue upholstered chairs. Sunlight pours through expansive windows, revealing views of the turquoise waters and sandy beach beyond. A beach-inspired artwork decorates the wall, adding a touch of coastal charm.

5 out of 5 average rating, 75 reviews

Breathtaking Beachfront Views in Siesta Key

Other waterfront holiday rentals

4.98 out of 5 average rating, 93 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

A spacious patio provides a serene view overlooking Whitaker Bayou, with boats moored along the water. A round dining table, surrounded by white chairs, offers an inviting spot for meals while enjoying the scenery. The area is complemented by a colorful artwork piece on the wall.

5 out of 5 average rating, 12 reviews

Modern 1/1.5 Waterfront at The Strand

A bright living area features a spacious white sofa centered beneath a large woven light fixture. Tropical plants are situated near large windows that allow natural light to fill the space. A neutral rug complements the light-colored furniture and decor.

4.93 out of 5 average rating, 30 reviews

Coastal Retreat near Siesta Key Beach and Downtown

5 out of 5 average rating, 8 reviews

Spectacular 2B Condo on Siesta Key Beach

A curved swimming pool is set against a backdrop of lush tropical foliage and palm trees, with water views extending to a nearby dock. Brightly colored pots with plants are placed around the pool area, enhancing the serene outdoor setting.

4.96 out of 5 average rating, 75 reviews

True Island Living House/beach/water views

An expansive view showcases the Gulf waters and sandy beach from a fourth-floor corner unit. Lounge chairs are visible on the beach, while a balcony railing frames the scene. Bright skies are complemented by gentle waves rolling onto the shore.

4.93 out of 5 average rating, 75 reviews

Beach & Pool Open! Direct Beachfront Condo! Sunset

4.95 out of 5 average rating, 20 reviews

Sarasota Serenity - Minutes to Beach