Holiday rentals with a hot tub in Longboat Key

Beautiful Island Beach House

Beautiful Island Beach House with pool/hot tub and private beach access on Longboat Key. The large light-filled spacious home is close to everything that you want for a fun, yet relaxing beach vacation: restaurants, bars, shopping, nature walks, and sandy white private beaches. Due to island restrictions, a 28-day stay is the shortest rental period allowed. Please note that this property is not available for young children given the surrounding water. Ages over 6 are welcome with supervision.

Waterfront 2BR 2BA | Pool - 10 min walk to Beach

A spacious first-floor 2-bedroom, 2-bathroom condo with direct pool access and stunning bayfront views. Located just a 10-minute walk to the beach, this beautifully appointed retreat offers the perfect blend of comfort, relaxation, and convenience. Enjoy a private patio overlooking the bay, a fully equipped kitchen, and a bright, open living space. With resort-style amenities, including a pool, hot tub, and tennis courts, it’s an ideal escape for couples, families, and remote workers.

Beachfront Condo Resort on Treasure Island

Be among the first to experience this new condo resort. 992 sq ft of beachfront luxury with full resort amenities. These upper-floor corner units have gorgeous views of the ocean, and each room has a window with beach views. With 2 bedrooms and 2 bathrooms and a pullout couch in the living room, these units can comfortably house 6 people. After arriving in your open concept living area, you will access your private balcony through retractable sliding doors that let the ocean air in.

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.

Casa Bella-5BR/Waterfront/Pool/Spa-9 Min AMI

Beautiful 5 bedroom home renovated in 2023. Located 3 minutes from beach access and 9 minutes to Anna Maria Island. A massive waterfront patio with heated pool and spa encompass this house. Master bedroom with walk-out to spa. Custom double walk-in shower in master suite. Family room with 86" television, decorative fireplace, and 15' ceiling. Roku TV’s in every bedroom. Outdoor propane grill. Beach chairs, umbrella, and cart. We welcome you to Casa Bella.

The Peachy Beach House, steps to the gulf

Rent two weeks from Aug- Dec receive 15% off Hurricane season refunds possible. Two bedroom, 2 full bathroom, new heated private pool Steps from semi-private gulf beach, this 3 story on a quiet street in N. HB Well-stocked kitchen, 2 TVs, large master which is more like resort suite with new tempurpedic king bed Gulf views from bedrooms. You’ll find: crib, high chair, beach chairs, wagon, canopy, beach toys and towels!

Turtle Cottage - Anna Maria Island

Great 1 bedroom, 1 bathroom cottage on the quiet north end of the island. The house is conveniently located and within walking distance (two short blocks) to the beach and close to the intersection of Gladiolus Street/Alamanda Road. Spectacular sunrises are just a short walk away at the Rod and Reel Pier, and the sunsets at Bean Point Beach are second to none, just a few blocks away. This great getaway sleeps up to 4.

Canal-Front Retreat w/ Pool, Dock & Beach Access

Canal-front oasis! Relax in the private heated pool, sip coffee on the dock, or walk to the beach. This bright, updated home has spacious living areas, a stocked kitchen, smart TVs, fast Wi-Fi, and cozy beds. Great for families or couples! Grill by the pool, dine under the stars, or fish from the dock. Includes washer/dryer, beach gear, and parking. Your peaceful, sunny getaway awaits—book now!