Vacation Rentals
44 properties available
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
Anna Maria Island Runaway Tropical Dream-One Minute Walk To The Beach-Heated Pool
2 BR 2BA Condo
$167.00 - $538.00 / per night
2
bedrooms
2
baths
6
guests
5
(5)
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 - $4,791.00 / per night
1
bedrooms
4
guests
Relax on the lanai, sip your morning coffee or freshly squeezed citrus juice. The sea breeze is scented with jasmine and frangipani. Fresh air and the sounds of the surf will lower your blood pressure and make you glad to be alive! Anna Maria Island Coquina Tropics is a second-floor, 2br/2ba condo in the seashell-pink Coquina Moorings development,
Coquina Tropics-3 Bedrooms- Bathroom-Water Views From Every Room
3 BR - 2BR Condo
$212.00 - $717.00 / per night
3
bedrooms
2
baths
6
guests
5
(12)
The Sunshine Kissed Villa has everything you need for a complete holiday! Our villa has all you need for staying in, and when you are ready to get out you are moments away from anything that sparks your interest. Your dream tropical getaway awaits on Anna Maria Island, Florida! Located on the Gulf of Mexico, less than 1-hour from Tampa or Sarasota
Anna Maria Island Sunshine Kiss Villa
2 BR 2BA Condo
$111.00 - $442.00 / per night
2
bedrooms
1
baths
6
guests
5
(10)
Relax on the 3rd-floor veranda, and gaze out across the serene aquamarine waters of the Gulf of Mexico. The sea breeze is scented with jasmine and frangipani. Fresh air and the sounds of the surf will lower your blood pressure and make you glad to be alive! This elegant, sunshine-yellow, 4br/3ba vacation home will help you to cherish every sunrise
Anna Maria Island Sun's Up B
4BR 3BA House
$3,000.00 - $7,931.00 / per night
4
bedrooms
3
baths
8
guests
5
(11)
?Hurricane Update:The entire complex is built on pillars more than 20 feet off the ground. The condo sustained no damage, we have been accepting guests for several weeks, the pool has been completely drained, acid washed, refilled and we have installed a new pump, a new filter and all new equipment. The pool has never looked better, the beaches are
Anna Maria Island Retreat
2 BR 2BA Condo
$168.00 - $564.00 / per night
2
bedrooms
2
baths
6
guests
4.9
(90)
Hurricane Update:The condo is built on pillars more than 20ft. off the ground and sustained no damage. The beaches are open, the restaurants are open and the weather is fantastic. We are accepting guests. The owner has stayed onsite and made the following improvements post hurricane:Upstairs:-Replaced the porch fan (light was not working)- Replaced
Bradenton Beach Club Bliss-2 Bedroom-2 Bathroom Condo-2 Pools-HotTub-Private Beach Access
3 BR - 2BR Condo
$192.00 - $655.00 / per night
3
bedrooms
2
baths
6
guests
4.8
(8)
The coastal morning is serene; white sand beaches glow golden at sunrise. The aquamarine Gulf of Mexico sparkles with crystals of sunlight. Dolphins breach along the horizon. Sailboats and yachts drift along Florida’s Intracoastal Waterway. Relax on your screened-in lanai balcony; sip coffee, tea, or fresh-squeezed citrus juice, as palm fronds danc
AM Island Beach To Bay Bliss
2 BR 2BA Condo
$132.00 - $478.00 / per night
2
bedrooms
2
baths
6
guests
5
(6)
?Hurricane Update:The entire complex is built on pillars more than 20 feet off the ground. The condo sustained no damage, we have been accepting guests for several weeks, the pool has been completely drained, acid washed, refilled and we have installed a new pump, a new filter and all new equipment. The pool has never looked better, the beaches are
Anna Maria Island Beach View 207
2 BR 2BA Condo
$132.00 - $478.00 / per night
2
bedrooms
2
baths
6
guests
4.9
(18)
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
$131.00 - $478.00 / per night
2
bedrooms
2
baths
6
guests
5
(8)
Discover your perfect getaway at Runaway Bay, an award-winning condominium development of 186 one- and two-bedroom units at the south end of picturesque Anna Maria Island. Located between where the Gulf of Mexico meets Anna Maria Island’s west beaches and the island’s eastern side of Anna Maria Sound and Palma Sola Bay, this prime location allows g
Runaway Tropical Waves-Pet Friendly
2 BR 2BA Condo
$114.00 - $430.00 / per night
2
bedrooms
2
baths
4
guests
The fourth bedroom is located in the adjoining cottage. This property has a maximum occupancy of eight people including the adjoining cottage. Violation of this policy will result in immediate eviction without compensation. Welcome to the good life. This custom-built, waterfront, 4bd/4ba island palace is nestled by Bean Point at the north end of An
Anna Maria Beach Serenity
4BR 4BR House
$5,000.00 - $13,067.00 / per night
4
bedrooms
4
baths
8
guests
5
(7)
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