Resort vacation rentals near Anna Maria Island

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Top-rated resort rentals near Anna Maria Island

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Top guest favourite
A modern kitchenette is equipped with a stainless steel sink, a black coffee maker, and a built-in flat top electric stove. A microwave is mounted above, and textured tile backsplash adds a subtle design element.
Resort in Ruskin
4.89 out of 5 average rating, 64 reviews

Little Harbor Hideaway

Welcome to Little Harbor Hideaway! Enjoy the Beach, 2 pools,Hot Tub & Kayaking on Cabbage Creek. We also have 2 restaurants on property. * New PickleBall courts & CornHole boards Our Unit has a very nice king bed as well as a sectional couch with pull out full bed. This unit has a full refrigerator and also has a built in flat top electric stove. 50in Sony Smart TV for Netflix etc +cable New A/C in late 2023 This is a 2nd FL unit w/ large Balcony new Washer & Dryer in common area near steps.

Top guest favourite
A vibrant sunset fills the sky with hues of orange, pink, and blue, reflecting on the water's surface. Silhouettes of wooden piers extend into the water, and tables with umbrellas are positioned in the foreground, creating a serene scenic view.
Resort in Dunedin
4.94 out of 5 average rating, 64 reviews

Best of Beso Suite Water View ADA 2Balcony/1BR/2BA

Stay in the heart of it all at this one-of-a-kind, unique double unit condo, which boasts views from 2 balconies, has 2 full bathrooms & a private bedroom suite. This upscale, tropical oasis is located right off the Gulf of Mexico’s St. Joseph Sound! RELAX & ENJOY the jacuzzi, dolphin watching & barbecuing, from Beso Del Sol Resort’s Waterfront Guest Pool Deck. Bask in the splendor of Delightful Dunedin’s Premier Resort’s Spectacular Sunset with a complimentary shot from Marker 8 Tiki Bar!

A spacious living area features a round glass dining table surrounded by wicker chairs. A cozy seating arrangement is visible, with a large television positioned strategically. Natural light enters through large windows, offering views of palm trees and the outdoor balcony.
Resort in Holmes Beach

Palm Penthouse @CedarCove Resort

What more can be said about the Palm Penthouse, it has a private balcony with panoramic views of the Gulf of Mexico. Watch the most glorious sunsets in the entire world fall before your eyes. The Palm Penthouse is perfect for honeymooners or those just looking for the perfect retreat. The spacious living room of the Palm Penthouse features a large wrap around pull-out sofa, four person dining table and a full kitchen. Full bath off living room and ensuitenBedroom bath with soaking tub.

This beachfront guest room features two spacious beds with crisp linens. A seating area includes two red chairs paired with a small table. Large windows overlook palm trees and the beach. Artwork on the walls adds a pop of color, while a ceiling fan enhances comfort.
Resort in Treasure Island
3 out of 5 average rating, 3 reviews

Beachfront Traditional

Located in the Shells building. Enjoy breathtaking sunset views from your large picture window which overlooks Treasure Island’s wide sandy beaches along the Gulf of Mexico. This 297 Sq. Ft. beachfront guest room features (2) Queen Pillow Top Beds. Other features include: * 55” LCD Flat Panel TV * Mini Refrigerator * Microwave * Coffee Maker * Toaster * AM/FM Clock Radio * Hairdryer * Iron, Ironing Board * Electronic Safe * Ceiling Fan * Beach Towels

Resort in Siesta Key

#1 Twin Palms-Deluxe King Suite

The Deluxe King Suite at our Siesta Key hotel sleeps 2-4. It offers a separate bedroom furnished with a King size bed, 42 inch flat screen TV, large walk-in closet and full bathroom. In the separate living room, there is a Queen size sleeper sofa, a second full bathroom and another 42 inch flat screen TV. This suite has a stainless steel kitchenette, fully stocked for your convenience. You may also enjoy the complimentary Wi-Fi Internet access throughout the resort.

Guest favourite
Resort in Holmes Beach
4.91 out of 5 average rating, 23 reviews

"The Royal " at Palm Tree VIllas Resort

The Royal Villa on Anna Maria Island offers a relaxing quiet getaway for up to six guests. Our heated pool is only steps away from your villa and the beach is a few minutes walking distance. This villa can be adjoined to "the Lady" villa and can then accommodate eight guests total. Please ask for availability in advance for this feature. The trolley is a few minutes walking if you decide to not bring a car. Rent a bike for the stay and get lost exploring the island.

Guest favourite
Resort in Holmes Beach
4.95 out of 5 average rating, 43 reviews

The Lady/Studio 21

Palm Tree Villas offers a portfolio of eight unique 1950's resort rooms ranging from small studios to three bedroom villas with three bathrooms. We would love to host you for a wonderful quaint island getaway vacation. Conveniently close to the trolley line for a quick bite at many great eating spots around the island and close enough to walk to the beach in a few minutes. Park your car and enjoy the island. This offering is an extremely private popular studio.

An aerial view captures the vibrant coastal landscape, highlighting the long stretch of white sandy beaches and turquoise waters. The layout of the small island showcases various buildings and neighborhoods, with roads and waterways interspersed throughout the scene.
Resort in Clearwater
4.62 out of 5 average rating, 21 reviews

Adorable Affordable Beach Efficiency

A Beach Adventure Awaits You..Come Play Or Relax @ the Coral Resort Clearwater Beach, Fl This small , lovely island is all water, beaches, restaurants and fun. NO CAR NEEDED. Bike or walk the beach. Visit: Winter the dolphin is right here... White sand will surround you on all these public beaches . Free parking/ internet. Managers onsite. 24 hr Fishing Pier on site. Rent jetski/boats in walking distance. YOLO Note: Unit A5 is a second floor/no elevator.

Top guest favourite
A serene pool area is surrounded by lush palm trees and tropical landscaping. Lounge chairs are arranged beside the pool, with large umbrellas providing shade. A paved patio offers ample seating and space for relaxation.
Resort in Siesta Key
4.98 out of 5 average rating, 45 reviews

The Nook, with heated pool.

The Inn is conveniently located on Siesta Key directly across the street from the Beach. Its guests enjoy beach access right across the road ( access #9 ). Siesta Village is also just a 5-minute walk from the Inn. If walking is not an option there is a trolley that is free of charge to ride and get around the Key. We have 6 individual Cottages in total that range from a one bedroom units to a three bedroom individual units.

Guest favourite
Resort in Siesta Key
5 out of 5 average rating, 40 reviews

Beach house W/Heated Pool across street from beach

The Inn is conveniently located on Siesta Key directly across the street from the Beach. Its guests enjoy beach access right across the road ( access #9 ). Siesta Village is also just a 5-minute walk from the Inn. If walking is not an option there is a trolley that is free of charge to ride and get around the Key. We have 6 individual Cottages in total that range from a one bedroom units to a three bedroom units.

Guest favourite
A serene beach scene is captured, showcasing fine white sand and gentle waves. Colorful beach umbrellas dot the shoreline, while a wooden walkway leads to the beach from the grassy dunes. The clear blue sky enhances the tranquil atmosphere over the coastal view.
Resort in Treasure Island
4.93 out of 5 average rating, 74 reviews

Treasure Island Beachfront Resort with pool

Amazing beach views from your vacation condo unit and from your private balcony. Newly refreshed privately owned condo at the Island Inn Beach Resort in Treasure Island Florida. Treasure Island is next to St. Pete Beach, south of John's Pass, Madeira Beach, Indian Rocks and Clearwater beaches. Pool bar, heated pool on beach, kitchen with two burner hot plate, pots, pans, coffee maker, microwave and more.

A bright bedroom features a spacious bed adorned with colorful floral bedding and decorative pillows. Flanking the bed are two bedside lamps and a mirrored nightstand. A piece of beach-themed artwork is displayed on the wall, while a door leads to a marble-finished bathroom.
Resort in Anna Maria
4.78 out of 5 average rating, 9 reviews

Suite 1 - Rod and Reel Resort

2 Guests - Queen Bed; Marble European Oversized Shower, Dual Wardrobe and Built-in TV, Keurig Coffee Maker, Hairdryer, Outdoor Refrigerator for Drinks, Complimentary Toiletries, Complimentary Coffee and Condiments, Beach Towels, Spa Robes Secure WI-FI, and Cable Rm Temp Control, Fan, Dual Dark/Light Shades, and Complimentary Bicycles.

Popular amenities for resort rentals near Anna Maria Island

Quick stats about resort rentals near Anna Maria Island

  • Total vacation rentals

    Explore 20 vacation rentals in Anna Maria Island

  • Nightly prices starting at

    Anna Maria Island vacation rentals start at $212 CAD per night before taxes and fees

  • Verified guest reviews

    Over 220 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space and kid-friendly amenities

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    20 of Anna Maria Island vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Anna Maria Island rentals

  • 4.9 Average rating

    Anna Maria Island stays are highly rated by guests—averaging 4.9 out of 5!

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