Vacation Rentals


Properties Available 44 properties available
Enchanting, seashell-pink, Gulf-front 3br/2ba vacation getaway on Anna Maria Island. This freshly renovated 1,032 sq ft, Key West-style single-family home was originally built in 1940 and still glows with all the charm of a quintessential “old Florida” beach cottage. Yet, it’s been beautifully renovated inside and out; transformed into a sleek, sty
Hot HOT 24
AMI Gulf Lookout-Views Of The Gulf From Every Room-Rooftop Terrace
3BR 2BR House
$325.00 - $972.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (19)
Ready to run away? Seeking an escape to paradise? Come run away to Runaway Bay; an award-winning condominium development beside white sand beaches and the aquamarine Gulf of Mexico on dreamy Anna Maria Island. This stylish, 2br/2ba ground floor unit in Runaway Bay is just steps from the bay and kayak launch, and only one building away from the cros
Hot HOT 33
Anna Maria Island Runaway Tropical Dream-One Minute Walk To The Beach-Heated Pool
2 BR 2BA Condo
$125.00 - $525.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (5)
What's Included:-Full access to all amenities. -Bikes.-Tennis courts.-Tennis rackets.-Jr. size Olympic pool.-Workout facility open 24/7.-Restaurant.-Tiki Bar.-Proshop. -Fishing Pier.-Boardwalks.A Bayside tennis and residential community in the heart of Longboat Key, FL. Sunshine and warm breezes accent the well-appointed tri-level townhouses that s
Longboat Key Cedars Beach House-Pet Friendly-2 Minute To The Beach
2 BR 2 1/2 BA Condo Pet Friendly
$127.00 - $448.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (7)
This sun-drenched 2br/2ba beach cottage centrally located by Holmes Beach in the heart of Anna Maria has been described as one of the “prettiest vacation homes on the island.” This authentic 1947 beach bungalow has been completely (and splendidly!) renovated with raised ceilings, travertine floors, and showers, granite countertops in the kitchens a
Hot HOT 40
Anna Maria Island Edgewater Bungalow
2BR 2BR House
$250.00 - $862.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (8)
The Anna Maria Island Beach Waves is a beautiful 2 bedroom, 2 bathroom first floor condo that sleeps 6, directly overlooking the pool with two balconies west & east. The east balcony is accessed by sliding glass doors off both the living room and master bedroom. The master bedroom with King sized bed offers beautiful views of the pool, Florida'
Hot HOT 20
Anna Maria Island Beach Waves
2 BR 2BA Condo
$125.00 - $575.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (22)
Welcome to Cottage Haven! This charming cottage located in Bradenton Beach is a very short walk to the beautiful white sand beaches. Featuring its own private backyard you can sit back and unwind on one of the loungers as you enjoy a home-cooked meal from the propane grill. The ground level home is nicely decorated and exudes a sunny, quaint “Old F
Hot HOT 22
Cottage Haven-One Minute Walk To The Beach-Private Yards-Keyless Locks
2BR 2 BR Cottage
$124.00 - $582.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (6)
The Anna Maria Island Beach View 207 is a beautiful recently remodeled two bedroom, two bathroom condo that sleeps six, directly overlooking the heated pool and located 75 yards from the beach and the private beach access. The Beach View #207 provides you with a fully stocked kitchen with six Whirpool appliances, with contemporary glass stove top,
Anna Maria Island Beach View 207
2 BR 2BA Condo
$120.00 - $481.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (18)
Escape to this bright, airy, coastal, freshly remodeled second-floor 2BR/2BA gulf-to-bay condo in the quiet Gulf Watch community of Bradenton Beach located on Anna Maria Island.The open-concept interior has a tranquil, beachy ambiance with a palette of soft blue, white and neutrals. Stroll just 400 steps to private beach access. Warm your toes in
Island Time-Private Beach Access-Heated Pool-Water Views
2 BR 2BA Condo
$133.00 - $522.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (2)
The prime location of Runaway Tropical Escape and stress free atmosphere will assure you a relaxing, memorable vacation. This Condo, in Runaway Bay, provides you the very best in vacation accommodations and is full of onsite amenities.You can enjoy your tropical retreat for a week, a month, or longer, in this recently remodelled, 2 bedroom, 2 bathr
Hot HOT 23
Anna Maria Island Runaway Tropical Escape
2 BR 2BA Condo
$150.00 - $522.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (35)
Look in almost any direction, and there are views of the bay, the gulf, and even downtown Sarasota. Steps away from the white sand beaches of Gulf of Mexico, this 2 bedroom/2 bathroom condo at Baywatch is located high up in the treetops near the shore of Anna Maria Sound. Renters can enjoy the peek-a-boo bay views from the oversized open-aired balc
Anna Maria Island Beach Palms 8B
2 BR 2BA Condo
$120.00 - $472.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (15)
Boasting a large, resort style heated outdoor pool with a hot tub, and a prime location on Anna Maria it's easy to fall in love with this island getaway. The private location on the north end of Anna Maria Island, near Bean Point is ideal to give you space and privacy and only a five minute walk to all local food and activities.Perfect for a romant
Serenity Cottage
2BR 2 BR Cottage
$2,000.00 - $5,651.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
What you will surely appreciate about Beach Palms is the unforgettable views of the sunrise in the morning over the water, laying in bed listening to the fish jumping and the waves gently rolling in. The evening sunset views will amaze you.Bed Configuration:-Primary bedroom - one king bed-Second bedroom - one queen bed - one twin bed-Living room -
Anna Maria Island Beach Palms 2A
2 BR 2BA Condo
$120.00 - $472.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (23)

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