Holiday rentals with a kayak in Holmes Beach

Waves on Anna Maria Island

Welcome to Waves — the ultimate beachside vacation home for your perfect Anna Maria Island getaway! Enjoy breathtaking views and easy access to the beach just steps away. A contemporary yet comfortable living area with modern amenities and plenty of natural light. Plus, four inviting bedrooms, a full-equipped gourmet kitchen, and desirable outdoor features like bikes, SUP, and a kayak. Four adult bikes , paddle boards, kayak, beach wagon, beach chairs and a 6 passenger golf cart all included

Heated saltwater pool home - turf putting green

Private 3 bedroom single family home 4 miles to white sand gulf beaches Longboat Key and Anna Maria Island. HEATED SALTWATER POOL home with access to ride bikes to the beach. Spread out in the oversized backyard with your own private pool and sitting area, featuring artificial turf yard and putting green, and beautiful landscaping. All hurricane damage has been repaired. The fence is fixed and the backyard is again completely private. The pergola pictured in photos was lost in the storm.

King Bed/Private Pool/Game Room/Fire Pit/Near AMI

Casa Sol is your private retreat just 10 minutes from the famous Anna Maria Beaches. Splash in your private pool, then head inside to the game room with arcade games for family tournaments. 🛏️ 3 stylish bedrooms, 3 baths with smart bidet toilets 💦 Huge private pool & fenced backyard ⛱️ Kayaks, beach gear & BBQ grill 🎱 Pool Table / Arcade/ Lawn Games, toys, and baby items 🛜 Smart TVs, high-speed Wi-Fi, office for WFH/workout Dates are filling fast. Send us a message for fall discounts

Hibernate in our Bear Creek Home

This 3 bedroom 2 bath home is located in beautiful Bear Creek. Don't worry, no bears! Great place to relax and enjoy the pool, in a quiet, safe neighborhood. Next to Pinellas Trail, a 40 mile paved trail. Great for walking, running and biking. You can bike downtown 6 mi or 4.6 miles to beaches. We have bikes and for those more adventuresome we have kayaks you may use. House features stable, high speed internet. Close to great restaurants, drugstores, supermarkets and coffee shops.

Waterfront Pool Oasis •Kayak, Games & Sunset Views

Relax at your waterfront oasis in Apollo Beach with a private pool, kayaks, and sunset views. Spot dolphins and manatees from the backyard or unwind on loungers with outdoor dining and games. Inside: full kitchen, dining area, 2 bedrooms, 2 baths, plus an extra living room with sleeper sofa and closet that serves as a 3rd bedroom. Close to Tampa, beaches, dining, and family attractions — ideal for families, friends, or a romantic getaway in a spacious private home. LIC# DWE3913431

Waterfront Townhome w/ Heated Pool & Balconies

Relaxation awaits you the moment you step in to Bahia Bungalow, a 2 Bedroom, 1.5 Bath town home nestled in Little Harbor Resort. Little Harbor is located on a partially private guest reserved beach in Ruskin, a short drive from Tampa, Sarasota & St. Pete. The resort overlooks Tampa Bay & features a heated outdoor pool, basketball and pickleball courts, fitness area, a playground & a marina. Dining within the Resort include a bay-view restaurant, a poolside bar/grill.

Villa Al Golfo Pristine Waterfront Oasis

Pristine villa in the lovely seaside Gulf town of Indian Rocks Beach, 2 short blocks to the beach & the Intracoastal in your backyard. All newly renovated, both inside and out, enjoy unobstructed water views, private entrance, personal patio & your own indoor/outdoor fireplace. When you aren't lounging outside or taking a glide on our paddle board, you'll love the gourmet kitchen, comfy living room, two large TV's, cable/wifi, luxe memory foam king bed & secured safe.

Waterfront Gem/ Pool Spa+ Dock/ Near Bridge Street

Anna Maria Waterfront oasis! **5 min walk to beach, private dock, pool heat included!!** 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!

Steps 2 Beach-Island Cottage w/king bd+2bike+parki

Welcome to the Seashell rental, a hidden gem on Pass-a-Grille Island in St. Pete Beach! Just steps from the beach and crystal-clear waters. Relax in our well-appointed space with a King bed, living room, full kitchen. smart TVs, a step-in shower, and dining nook. Indulge in indoor or outdoor dining on the garden patios. A BBQ grill, 2 beach chairs+ 2 bikes are yours to enjoy! Unwind after beaching, shelling, fishing. Experience Pass-a-Grille's charm with us!

Discounted October Stays w/Private 30' Dock & Pool

* It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the beach. * Enjoy the large 16' x 30' private pool in a picturesque tropical landscape along with a 30' fishing/boat dock. * Within walking distance of Pine Avenue, City Pier, Two Scoops, Waterfront Restaurant, Galati's Marina, and Island Ocean Star Restaurant. *Less than a 3 minute walk to Bay Beach and a 15 minute walk to Bean Point.

Las Palmas Beach Rentals unit 2

Unit 2 Ground floor;800 sq ft; patio; limited beach view . Steps to the white sandy beach across the street Free parking to registered guest. Fully equipped kitchen with markets nearby, Restaurants and shopping, within walking or hop free trolly. Trolly stop nearby. Linens and basic supplies are included. Overnight guest are welcome to arrive early to adventure the island, stay parked until after sunset on departure day.

Castaway Cove - Short stays! AMI gem!

Relax with friends and family at Castaway Cove, a true piece of paradise located at the north end of Anna Maria Island near fabulous restaurants, boutiques, AMI city pier, and close to Bay and Gulf of Mexico beaches. Nicely appointed with three bedrooms and two bathrooms, this vacation home has a serene backyard with a private pool, hot tub, and plenty of entertainment space. Rental agreement to be signed before check in.