Holiday rentals with a pool in Florida

Coastal Escape: heated saltwater pool & playground

★ Close to beaches - Honeymoon Island: just 6 miles away. - Clearwater Beach: 15 miles away - crowned the nation's #1 beach Trip Advisor in 2018 ★ Heated saltwater pool ★ Screened-in lanai ★ BBQ grill ★ Large backyard w/ playground ★ Outdoor dining area ★ 3 bedrooms New Mattresses - California king size bed - Queen size bed - Kid-friendly room w/ two bunk beds ★ Renovated kitchen and bathrooms ★ Open living space - great for family gatherings, movie nights ★ Children toys and games

Boater’s Paradise-Stunning Sunsets! Games Room!

Renovated lanai! This 3 bed/4 bath home is on the nicest canal with 200+ ft of frontage & gorgeous views of the canal & sunset. The pool, tiki hut & docks have full sun all day. Each bedroom has a private bath & there's a 2 pc powder room off the laundry. The primary has a king bed & walkout to pool. The 2nd bedroom has a queen bed & pool access. Bedroom 3 has a queen & private bath. Fully equipped kitchen with everything you need. And a games room! Enjoy stunning sunsets under the tiki hut.

LUX Villa w/ Private Salt Water Pool, Lanai, Canal

Are you looking to swim, relax outdoors, fish and take in beautiful sunsets on a wide gulf access canal? If so you will fall in love with this stunning newly constructed custom built home! The 2750 square foot home is bright & airy with two main bedroom on-suites & a separate family wing! The gourmet kitchen, dining room & great room open via large sliders to the lanai & pool w/ views of the canal in much desired SW Cape! Beach inspired villa! Large captains walk & Tiki! Check out our reviews!

LUXE Oasis | 10 min Beach • HTD Pool+5th Ave •Crib

Welcome to Your Naples Getaway! Why our home is perfect for your vacation: 🏖️ Beaches Nearby – Just a quick 10–15 minute drive to Via Miramar and Lowdermilk Beach. 📍Prime Location – Nestled on a peaceful street only 7 minutes from the iconic 5th Avenue. 🏡 Resort-Style Comfort – Relax in our fully screened lanai featuring: • Heated private pool • Luxury chaise loungers • Outdoor TV • Gas grill for BBQ nights Unwind with a cocktail, take a sunset dip, or simply kick back under the stars!

Luxe Riverfront Retreat~Pool~Spa~Bar~Tropical Yard

Luxurious 4BR 3.5Bath villa located in a prime location, directly on the Calosahachee River in a sought-after waterfront area near downtown. Magnificent expansive backyard with high-end amenities and direct river access ✔ 4 bedrooms ✔ Open Design Living ✔ Full Kitchen ✔ Patio (Pool and Hot tub, Bar, Dining, BBQ) ✔ Expansive Tropical Yard ✔ Indoor/Outdoor Surround Sound ✔ 7 Smart TVs ✔ High-Speed Wi-Fi ✔ Large Private pier/dock w/ boat & jet ski lift and a Tiki Hut! See more below!

Amazing View/Oceanfront Retreat/EZ to Pool/Beach

Welcome to LuxuryinCocoaBeach! You stumbled on it. Perfect beach condo. Stunning direct-ocean views, steps to warm sand, heated pool and blazing-fast Wi-Fi await your family. - 2 spacious bedrooms • sleeps 4 in total comfort - Private balcony for sunrise coffee and all-day viewing - Resort pool and FREE beach gear - Smart TVs, premium cable, free parking Book your preferred dates now and wake up to the sound of waves! Note: The community pool will be closed until December 10, 2025.

The Palm House

Escape to The Palm House! Featuring a brand new salt water pool, fountain, and outdoor kitchen oasis! Recently completed pool area is a tropical dream! Located just 15 minutes from the beach. Open concept great room with a chef’s kitchen and tropical views in every direction. Enjoy a true indoor outdoor South Florida experience with 20 foot sliders that open to the patio. Custom and modern touches in every room! You’ll love the lux built in bunkbeds! Stylish bedrooms with room to sleep 8.

Tropical Resort! 1mi BEACH+HTD Pool+SPA+Boat Rntl!

Whether it's to relax or create memories, your ocean access vacation home awaits. Equipped with complimentary paddle boards & kayaks, outdoor wet bar/grill and a giant tiki with hanging egg chairs overlooking the water. The 3 bed and 2 bath split floor plan creates a spacious interior. Come fish on our 70' dock or relax in our hammocks under our many palm trees while the leaves whisper a sweet melody through the air. Ask about our boat rental so you can get the most out of your vacation!

*NEW Vanderbilt Drive - Dream Vacation Home*

Relax in this 4 bedroom + Pool house beachside retreat on coveted VANDERBILT DRIVE, just 1 mile from either Wiggins Pass, Vanderbilt Beach, and Mercato. Enjoy this newly renovated home with luxury finishes, quality furniture, and coastal decor. Located on Vanderbilt Dr! Walk out the front door and go for a jog, bike ride, or a coffee stroll. Come see why we maintain Superhost status across all properties and experience another one of our thoughtfully furnished and decorated retreats.

Luxury Coastal House ON THE BEACH w/Pool & VIEWS

5435 Highway A1A is proudly managed by ‘Happy Palm Stays’, the top vacation rental manager on the Space & Treasure Coasts! Welcome to our beautiful oceanfront oasis! This luxurious 4-bedroom home offers the ultimate retreat, perfect for families or groups seeking comfort, convenience, and unforgettable experiences. Experience the perfect blend of modern luxury and coastal charm at our exceptional property. Whether you’re here for relaxation or adventure, we have everything you need!

Coastal Scandinavian Retreat | Cocoa Beach, FL

Escape into a world of luxury with unprecedented accommodations featuring extraordinary amenities! Our exquisitely designed residence offers a panoramic backyard oasis with various settings including resort style pool with loungers, private hammock, sparkling hot tub, fire pit, kitchen & wet bar, and covered dining. All nestled in a canvas rich in the hues of its natural surroundings, our coastal paradise provides a grand living experience in a gorgeous Scandinavian environment.

Relaxing Island Escape | Cocoa Beach, Florida

Tee up your next vacation with all the sun, sand & surf Cocoa Beach has to offer. Our retreat is the perfect venue for easy breezy coastal living and has amenities to keep everyone entertained - including a one of a kind backyard putting green! From the heated saltwater pool, hot tub under the poolside pergola, outdoor grill, and game room to a nature preserve with boardwalk and gazebo for bird watching, simply arrive, unwind, and call our place home during your visit.