Vacation rentals with a hot tub in Longboat Key

Longboat Key-OCEAN FRONT- on the beach

My place is located in a small boutique complex located on Longboat Key. Walk to shops, restaurants and park. You’ll love my place because of Gulf front location with full gulf view from living room, kitchen, master bedroom, and screened lanai. Completely updated in 2015 with full kitchen, two full baths and two bedrooms. A perfect place to relax, listen to the surf and watch amazing sunsets over the Gulf of Mexico. My place is good for couples, solo adventurers, and families (with kids).

Outdoor spaces · Bathroom · Family

Waterfront Coastal Retreat | Steps from LBK Beach

Welcome to paradise— your tropical escape awaits! Wake up to island serenity in our brand NEW STUDIO SUITE where you'll enjoy peaceful lagoon views from your private balcony. This gem, located in the coveted Longboat Key Resort Club, beautifully blends modern touches with coastal charm. Bask under the sun and enjoy private access to Longboat Key Beach and the heated resort pool which is just steps away. Perfectly positioned for relaxation, adventure, and exploring the best of Downtown Sarasota.

Walkability · View · Layout

Stunning beach house with heated pool and hot tub!

Welcome to The Colony, a stunning vacation rental on Anna Maria Island, designed to capture the essence of Palm Beach living. This spacious 4-bedroom, 4.5-bathroom house features elegant decor and modern amenities. Step outside to discover a beautiful backyard oasis, complete with a large pool, hot tub, and a well-appointed patio that invites relaxation. Just a 5 minute walk to the pristine beaches of AMI, The Colony is perfectly situated in charming Holmes Beach for an unforgettable getaway.

Bathroom · Outdoor spaces · Indoor spaces

The Blessing House- Htd Pool/Spa, Close to Beaches

Welcome to The Blessing House, a beautifully curated Sarasota retreat designed for relaxation, comfort, inspiration, and quality time together. Enjoy a heated pool & spa, lush lanai, bright designer interiors, and a peaceful residential setting just 15 minutes from Siesta Key, Lido Key, and downtown Sarasota. Thoughtfully maintained and enjoyed by our family throughout the year, this home is ideal for couples, families, and discerning travelers seeking a restful and memorable getaway.

Hot tub · Bathroom · Pool

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.

Beach · Kitchen · Walkability

Beach Condo with Quiet, Private Beach

Escape to our serene 2-BR beachfront condo on Longboat Key. This corner unit offers stunning Gulf of Mexico views and sleeps 6. Enjoy direct beach access, a heated pool, and a private patio perfect for sunsets. Located in the quiet Beach Castle Resort, it's the ideal beach vacation rental for families or couples seeking a tranquil getaway. Walk to local restaurants and cafes from your peaceful retreat. A guest-loved home, consistently rated top 5% among Airbnb’s homes.

Outdoor spaces · Hot tub · Check-in

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

Beautifully renovated 5 bedroom home. Located 3 minutes from beach access and 9 minutes to Anna Maria Island. A massive waterfront patio with string lights and 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.

Bathroom · Hot tub · Parking

Secluded Bayside Gem with beautiful bay views

Sat to Sat Check in/out 7 day minimum rentals only. Jan-April we do not accept reservations with children of any age. Additional 6% Manatee County tax not included need to collect separately. Newly added Pickleball courts on premises. This secluded, beautifully decorated, bay front condo has expanded views of the Sarasota Bay. 2 min drive to the quiet, unspoiled white sand beaches of the Gulf of Mexico, short distance to great water front dining.

Outdoor spaces · Bathroom · Hospitality

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!

Outdoor spaces · Hot tub · Family

Cozy AF Jungle-House Hideaway

We invite you to the **Cozy AF Jungle House**! Step into the foliage and immerse yourself in the jungle vibes. With every glance, you'll discover something new—from the sabretooth tiger skull to the romantic hot tub and even a crystal hanging banana. Adventurers, dare to play Jumanji if you’re feeling bold! Our goal is not just to provide a place to stay, but an experience you’ll cherish forever.

Hot tub · Outdoor spaces · Kitchen

DEC SALE! Sarasota #1 Luxury Villa w/PRIV BEACH!

BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

Bathroom · Hot tub · Condition

Las Palmas Beach Rentals unit 2

Ground floor; limited beach view . Steps to the white sandy beach. Free parking to registered guest. Furnished rooms, full size kitchen, linens provided. Free trolley stop on the block. GREAT LOCATION! Shopping and restaurants short walking distance. Check out our guidebook for additional island tips. Once booked it will be in your itinerary.

Hot tub · Outdoor spaces · Condition