Home rentals with a pool near Anna Maria Island

True beach front home - 3 beds/2 bath, heated pool

This lovely 3 bedroom 2 bathroom home is situated on one of the most beautiful beaches imaginable; nestled among the sea oats leading out onto the white sand beaches and crystal clear waters this area is so famous for. As you cross the bridges and gaze at the glittering turquoise water fringed by swaying palms you will quickly realize that you have stepped back into old Florida – a slice of paradise that transports you back to a time when the pace of life was slower, gentler and more carefree.

Manatee Harbour - Heated Pool

Welcome to MANATEE HARBOUR, our spacious 2 Bed / 2 Bath home with canal, and screened, heated pool. This serene North End oasis has everything for the perfect beach vacation. Linens and towels (for bath and beach). Beach chairs, cart, toys, etc. Fully stocked kitchen. Backyard canal - sit and watch the manatees; launch your kayaks. Easy walk to beach - 1 block to Bayfront Beach; 2 blocks to Bean Point area. Walk to City Pier and Pine Ave. This is a Piperbear property. Ready to host your stay!

Brand New Remodeled Villa + Large Private Pool!

Remodeled cottage with a lush tropical backyard, which boasts a Private Heated pool with Waterfall and Swim-up Tiki Table, turf putting green ,Weber Grill, patio bar with 55” Outdoor Smart TV! Calypso is outfitted with a cozy Coastal decor, you feel that vacation vibe as soon as you walk in the door. The kitchen offers quartz countertops with Stainless Steel appliances. Both bedrooms have King size beds, living room has a queen sleep sofa. All furniture was brand new in December of 2024

Bougie Bungalow at the Beach

This newly renovated, completely private, comfortable Anna Maria Island bungalow is super clean & very comfortable. It has an open, split floor plan, 2 king bedrooms, each with private baths, separate dining and Florida room & is only 3 houses from the amazing white sand beach, the bay & Pier. Only 1 block over is Historic Bridge Street with cool restaurants, mini golf, quaint shops & bars with live music. Once here, you never need to drive -everything is within a block walking distance!

Birdsong-Steps to Bean Point Beach Heated Pool!

Welcome to Birdsong, a picture-perfect 2-bed, 2-bath home situated in Anna Maria, Florida. Recently refreshed with coastal décor, this inviting property is ideal for families or small groups seeking a relaxing getaway. With just a short 3-minute walk to the beach, Birdsong provides an excellent blend of comfort & convenience, allowing you to fully immerse yourself in the beauty of Anna Maria Island. The fenced backyard features a heated pool, outdoor dining, BBQ grill, beach chairs, & cart.

Bayfront Beach access with Heated Pool!

Our modern yet beachy retreat is the perfect oasis on the North end of Anna Maria Island w/breathtaking panoramic views of Tampa Bay & the iconic Skyway Bridge. The backyard oasis features a refreshing saltwater pool & fully fenced backyard, complete w/artificial turf & outdoor shower. Just steps away, you'll find full access to a stunning white sandy beach & the crystal-clear waters of Tampa Bay! Conveniences have been carefully considered, creating the most ideal vacation destination!

New Prof Decorated-Pool/Spa 5 minute walk 2 Ocean

This brand new rebuild on Anna Maria Island located within Anna Maria city has 3 Bedroom, 3 Bathroom home plus loft is professionally decorated throughout, with state-of-the art quartz counter tops, JennAir professional stainless-steel appliances, wide plank wood tile floors, bead board ceilings. All bathrooms have basket weave marble and quartz counters and there is a Whirlpool Washer & Dryer. The house has everything necessary for a perfect beach vacation.

Heated Pool & Spacious Deck! Steps from the Beach!

Welcome to Your Dream Beach Escape! Just one block from the sugar-white sands of Holmes Beach, this newly renovated home has everything you need for a perfect getaway. Bikes, paddle boards, and all the beach gear are included for endless fun! Unwind in the shared HEATED pool or soak up the charm of Anna Maria Island. Shops, dining, and attractions are just a stroll, bike, or trolley ride away. Perfect for families, reunions, and couples!

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!