
Beachfront vacation rentals in Casey Key
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Top-rated beachfront rentals in Casey Key
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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.
4.95 out of 5 average rating, 146 reviews
Gulf front romantic cottage in paradise
Gated and surrounded by lush scenery you will feel like you have suddenly escaped to the caribbean! The pressures of the world melt away as you get your first glimpse of the Gulf of Mexico. Eclectic design with mostly Caribbean influences. Marble floors, tile counter tops and a large shower with a sit down bench. Walk the custom pathways which reveal beautiful orchids and exotic plants. Go kayaking, fish off the beach or look for sharks teeth. Take a swim in the pool or work on your tan.
4.91 out of 5 average rating, 307 reviews
LG Beach Bungalow on Gulf w/Bay Access & deck too!
Welcome to Golden Girl. Our 3 bedroom 2 bath home is totally renovated with all new furniture. A 2nd level observation deck, private hot tub, bunkroom sleeps 6, two bdrms with kings, queen sleeper sofa in LR, laundry, high speed WIFI, all new appliances, smart TV's, so much more! Lanai opens up to semi private beach and a quiet neighborhood of single family homes. There is Bay access too. Kayaks available for rent. There is a separate apartment above not included. The location cannot be beat!
4.83 out of 5 average rating, 122 reviews
Heated Pools & Spa · Private Beach + Bay Views
Perfect for family and group beach stays, with reliable Wi-Fi and a dedicated workspace for flexible remote work. This oversized renovated 2‑bed, 2‑bath condo sleeps six: a king in the master and two queens in the second bedroom; both bathrooms serve the group for privacy and convenience. Enjoy full gulf-to-bay living with private beach access and supplied chairs, umbrella, cooler and wagon, plus two heated pools, a heated spa, gym, courts, bay views, free parking and keypad self check-in.
4.97 out of 5 average rating, 137 reviews
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!
4.94 out of 5 average rating, 143 reviews
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!
4.91 out of 5 average rating, 130 reviews
High Tides, Low Rates: Open Tomm - Wed!
This sublime oceanfront studio condo is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the ground floor, overlooking the heated pool and ocean, this dreamy studio 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...!
5.0 out of 5 average rating, 124 reviews
Beachfront Siesta Key | Gulf View + Private Beach
Sun Bum Studio is your Siesta Key Beachfront Escape Wake up steps from the white quartz sand of world-famous Siesta Key. Sun Bum Studio is located in the beachfront tower at Palm Bay Club, with a south-facing view of the beach and Gulf from the floor-to-ceiling glass doors and patio. Enjoy private Crescent Beach access with complimentary beach loungers, two heated pools, hot tub, fitness center, tennis and pickleball courts, fishing pier, boat docks, grills and free covered parking.
4.97 out of 5 average rating, 397 reviews
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.
4.98 out of 5 average rating, 128 reviews
Gulf Views | Walkable | Spacious
Spacious Gulf-view 2BR condo perfect for families & groups—featuring a rare 2-queen guest room, king master, and plenty of room to spread out. Walk to the beach, restaurants, coffee, and more—no car needed. Easy beach access + FREE loungers make beach days effortless. Heated pool, fast WiFi & fully stocked with beach gear. Clean, spacious & comfortable in a prime, walkable location. (Daytime weekday construction nearby may cause intermittent noise in 2026.)
4.92 out of 5 average rating, 166 reviews
Manasota Key
Direct Ocean Front Unit. Imagine having a glass of wine at sunset overlooking world class views of the Gulf of Mexico. Steps to the beach and unsurpassed views. Excellent restaurants and Tiki Bars within walking distance. This unit is a 1 bedroom 1 bath spacious unit that can comfortably sleep 4. It includes a King bed & Full size sleeper sofa. It also has a beautiful kitchen with granite countertops and tile floors throughout. No Pets.
4.91 out of 5 average rating, 235 reviews
Siesta Key Beach Front Condo
Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 2 bedroom/2 bath PRIVATELY OWNED vacation condo is steps away from world famous, breathtaking Siesta Beach - consistently VOTED #1 BEST BEACH IN THE USA year after year! This condo is nicely situated on the 2nd floor. The large screened lanai provides spectacular gulf coast views.
4.91 out of 5 average rating, 137 reviewsPopular amenities for Casey Key beachfront rentals
Pet-friendly beachfront home rentals

Penthouse Oceanview Mermaid Villa
4.88 out of 5 average rating, 116 reviews
Studio - On the sand! Right on the beach. Sunsets
4.92 out of 5 average rating, 157 reviews
The Mermaid: Heated Pool, 4 Houses to Beach
4.94 out of 5 average rating, 149 reviews
AMI Sunset Beach - Gulf View Retreat w/ Pool+Decks
4.82 out of 5 average rating, 119 reviews
Do you love the beach?
4.94 out of 5 average rating, 105 reviews
Sea Biscuit - walk to the beach!
5.0 out of 5 average rating, 16 reviews
Venice Island Escape • Steps to Beach • Workspace
5.0 out of 5 average rating, 32 reviews
Manasota Key Beachfront Oasis w/ Private Jacuzzi
4.94 out of 5 average rating, 18 reviewsBeachfront home rentals with a pool

Beach studio 56
4.87 out of 5 average rating, 159 reviews
Beachwalk Townhouse with view of Gulf of Mexico
4.79 out of 5 average rating, 110 reviews
Sarasota Surf & Racquet Club Siesta Key Condo
4.83 out of 5 average rating, 151 reviews
Super Clean Cozy and Quaint steps from the beach
4.9 out of 5 average rating, 133 reviews
Private Beach Siesta Key Resort Jamaica Royale
4.86 out of 5 average rating, 154 reviews
Siesta Key For Me @ The Palm Bay Club
4.98 out of 5 average rating, 139 reviews
Beachfront Resort, Ocean View, Pool, Tennis, Gym
4.9 out of 5 average rating, 241 reviews
Entire Beachside Condo! Don’t worry Beach Happy!
4.8 out of 5 average rating, 174 reviewsPrivate beachfront home rentals

Sunset Hideway steps from beach-stand alone condo
4.81 out of 5 average rating, 47 reviews
Private Beachfront Casey Key Cottage B
4.77 out of 5 average rating, 30 reviews
Beach House Barcelona D- 3 min walk to the beach
5.0 out of 5 average rating, 5 reviews
2 BR/2 BA Beach Front Suite-Kayaks-SUPs-Bikes-Pets
5.0 out of 5 average rating, 5 reviews
Venice Villas Luxury Beachfront – Steps to Sand
5.0 out of 5 average rating, 4 reviews
Beachhouse w/ Pool&Spa-WALKtoBEACHinLESSthan 1MIN
4.99 out of 5 average rating, 72 reviews
Hidden Gem in Punta Gorda
4.98 out of 5 average rating, 57 reviews
Siesta Key Village Home
5.0 out of 5 average rating, 20 reviewsDestinations to explore
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