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Vacation Rentals in Anna Maria Island
Find the perfect Cheap Vacation Rentals, Vacation Rental Deals and Luxury Villas in Florida, Colorado, California, Hawaii, South Carolina, Outerbanks and more! Get Last Minute Deals on Beach Houses, Ski cabins, Family Vacation Rentals and Pet Friendly Vacation Rentals now at How2Vacation.com!
Featured Vacation Rental Companies
Anna Maria Island's #1 destination for all of your Sales and Vacation Rental needs. We specialize in luxury waterfront properties. Make your dreams a reality. Contact the island experts at Sato Real Estate Inc.. We are "Island Faces Renting Island Places".Phone Number: 941-778-7200
Vacation Rentals in Anna Maria Island
Sunset Landings #5
- 2 Bedrooms, 2.5 Bathrooms, Sleeps 4
- 703 Gulf Dr. So., #5 Sunset Landings #5 Imagine a Florida getaway: white sandy beaches just a few feet from…
- from
- $1000
weekend
Bayou 4D
- 2 Bedrooms, 1 Bathroom, Sleeps 4
- Conveniently located on the north end of Anna Maria, sandwiched between the historic Roser Church and Tampa Bay, is this…
- from
- $3100
monthly
Bayou 1B
- 2 Bedrooms, 1 Bathroom, Sleeps 4
- 522 Pine Ave., #1B BAYOU CONDO...Conveniently located on the north end of Anna Maria, sandwiched between the historic Roser Church…
- from
- $2200
weekend
Bayou 3B
- 2 Bedrooms, 1 Bathroom, Sleeps 4
- Beautiful 2 bedroom, 1 bath condo at the Bayou Condos on Pine Ave. This ground level unit offers a queen…
- from
- $700
weekend
Tiffany Place #207
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Tiffany Place Located just steps away from the sparkling waters and fine white sand beaches of the Gulf of Mexico,…
- from
- $1200
weekend
Tiffany Place #201
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Tiffany Place Located just steps away from the sparkling waters and fine white sand beaches of the Gulf of Mexico,…
- from
- $1325
weekend
Tiffany Place #113
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Tiffany Place Located just steps away from the sparkling waters and fine white sand beaches of the Gulf of Mexico,…
- from
- $1200
weekend
Tiffany Place #103
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Tiffany Place Located just steps away from the sparkling waters and fine white sand beaches of the Gulf of Mexico,…
- from
- $1200
weekend
Tiffany Place #102
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Tiffany Place Located just steps away from the sparkling waters and fine white sand beaches of the Gulf of Mexico,…
- from
- $1325
weekend
Tiffany Place #117
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Tiffany Place Located just steps away from the sparkling waters and fine white sand beaches of the Gulf of Mexico,…
- from
- $1325
weekend
Tiffany Place #215
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Tiffany Place Located just steps away from the sparkling waters and fine white sand beaches of the Gulf of Mexico,…
- from
- $1200
weekend
Tiffany Place #106
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Tiffany Place Located just steps away from the sparkling waters and fine white sand beaches of the Gulf of Mexico,…
- from
- $1200
weekend
Westbay Point and Moorings 166
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- WBPM #166 6500 Flotilla Dr., #166 Charming 2 bedroom, 1 bath duplex located in a quiet neighborhood in Holmes Beach.…
- from
- $3000
monthly
Water's Edge
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Looking for a relaxing rental with breathtaking views of the Gulf of Mexico? Then Waters Edge is the place for…
- from
- $1100
weekend
Shore Walk
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Right out the doorway and down a couple steps?.gorgeous, white sandy beach. Relax in this beautiful two bedroom, two bath,…
- from
- $4000
monthly
Sunbow Bay Sunflower
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- A holiday at Sunbow Bay Condominiums just off Manatee Avenue Bridge, a narrow, sun-bleached road bridge connection between the mainland…
- from
- $1000
weekend
Sunset Terrace
- 2 Bedrooms, 2 Bathrooms, Sleeps 4
- Sunset Terrace There is no better place to spend your Anna Maria Island vacation than in a beautifully decorated gulf-front…
- from
- $1100
weekend
Summer Sands
- 2 Bedrooms, 2.5 Bathrooms, Sleeps 4
- Summer Sands With its beautiful views of the Inter-coastal waterway, Summer Sands is the perfect condo for your relaxing trip…
- from
- $3200
monthly
Bean Point Beach Shack
- 5 Bedrooms, 3 Bathrooms, Sleeps 10
- 5BR/3BA Beach Front Pricing is listed below. January $2500 weekly February-March 10 $2950 weekly March 10-April 14 $3250 weekly April…
- from
- $2500
weekend
All Decked Out
- 5 Bedrooms, 3 Bathrooms, Sleeps 10
- Take in the lights of the Skyway Bridge at night or watch an early morning sunrise over Tampa Bay from…
- from
- $2750
weekend
Perfect Family Getaway
- 4 Bedrooms, 2 Bathrooms, Sleeps 8
- Enjoy the view from your wonderful open porch or swim in the gulf, only steps away. Bring the whole family…
- from
- $1000
monthly
The Salty Dog
- 4 Bedrooms, 3 Bathrooms, Sleeps 8
- Kick off your shoes and promise yourself not to put them on again. Take off your watch and tell time…
- from
- $1799
weekend
Kaleidoscope
- 4 Bedrooms, 2.5 Bathrooms, Sleeps 8
- Giddy! This 4 bedroom is sooooo beautiful, so beachie, so colorful and so close to the beach, it will make…
- from
- $2750
weekend
Lemonfish
- 4 Bedrooms, 3.5 Bathrooms, Sleeps 8
- Welcome to Lemonfish! Lemonfish is far too pleasant to be reserved only for a week. With the feel of an…
- from
- $2500
weekend
Queen's Channel
- 4 Bedrooms, 3.5 Bathrooms, Sleeps 8
- Welcome to Queen's Channel, an elegant, spacious, custom built elevated house located on deep sailboat water on the Northern tip…
- from
- $2750
weekend
Mintfish
- 4 Bedrooms, 4 Bathrooms, Sleeps 8
- Stay in your bathing suits from breakfast to bedtime. Start a party that can last all week. Watch the sailboats…
- from
- $2800
weekend
Casa-Linda
- 4 Bedrooms, 3 Bathrooms, Sleeps 8
- Close your eyes and think of your best ever beach holiday. What do you see? We bet there is a…
- from
- $3000
weekend
Honeyfish
- 4 Bedrooms, 4 Bathrooms, Sleeps 8
- Sea grape trees, tropical flowering bushes and swaying palm trees surround this beautiful ocean-blue-colored beach villa on the north end…
- from
- $2500
weekend
Good Life
- 4 Bedrooms, 2 Bathrooms, Sleeps 8
- Tropical 4 bedroom 2 bath home with heated pool is a mere 350 yards from the sugar sand beaches located…
- from
- $1600
weekend
Palm Perch
- 4 Bedrooms, 3 Bathrooms, Sleeps 8
- Imagine the most elegant and accommodating beach home. One without compromise. Combining stylish design, expansive floor plan, sparkling windows, open…
- from
- $2400
weekend
Mango Tango
- 4 Bedrooms, 3.5 Bathrooms, Sleeps 8
- Mango Tango, with it's relaxed ambiance, is a home offered for rent in the true Anna Maria Island tradition. Elegantly…
- from
- $2200
weekend
Key Lime Cove
- 4 Bedrooms, 3.5 Bathrooms, Sleeps 8
- A unique Anna Maria Island retreat can be discovered at a Key Lime Cove. Nestled in Holmes Beach and only…
- from
- $1800
weekend
Casa Playa West
- 4 Bedrooms, 3.5 Bathrooms, Sleeps 8
- Casa Playa If you are looking to relax on Anna Maria Island in luxury and elegance then Casa Playa is…
- from
- $2250
weekend
Casa Playa East
- 4 Bedrooms, 3.5 Bathrooms, Sleeps 8
- Casa Playa If you are looking to relax on Anna Maria Island in luxury and elegance then Casa Playa is…
- from
- $2250
weekend
Heavenly Sunset
- 3 Bedrooms, 2 Bathrooms, Sleeps 6
- This beach house was built in the 1950's and renovated and expanded in 1992 and again in 2003. The original…
- from
- $1750
weekend
Calico Cottage
- 3 Bedrooms, 2 Bathrooms, Sleeps 6
- Steps to the beach! Just walk outside and stroll across the street to the Gulf from this charming 3 bedroom,…
- from
- $800
weekend
Cherryfish
- 3 Bedrooms, 3 Bathrooms, Sleeps 6
- Welcome to Cherryfish! Imagine the most elegant and accommodating beach home. One without compromise. Combining stylish design, expansive floor plan,…
- from
- $3500
weekend
The Smiling Mermaid
- 3 Bedrooms, 2 Bathrooms, Sleeps 6
- Come here to get away from it all! This cottage is all about beach life - simple wooden floors, comfy…
- from
- $1400
weekend
Kathy's Starfish Bungalow
- 3 Bedrooms, 2 Bathrooms, Sleeps 6
- You've asked for real beach house: steps from the sand, with character and comfort. Look no further! You?ve just found…
- from
- $700
weekend
Batley's Beach Hotel
- 3 Bedrooms, 2 Bathrooms, Sleeps 6
- Located in the "heart" of Anna Maria City, sits this ground level, 3 bedroom, 2 bath home just waiting for…
- from
- $1000
weekend
California Dreamin'
- 3 Bedrooms, 2 Bathrooms, Sleeps 6
- California Dreamin? 211 Palm In need of a vacation to excite the senses and soothe the spirit? Near to the…
- from
- $3000
monthly
Citrus Junction
- 3 Bedrooms, 3 Bathrooms, Sleeps 6
- Beach Bound Conveniently located, casually designed and decked-out for a family. This waterfront home opens directly onto a shady big…
- from
- $3400
monthly
Papa Dukes
- 3 Bedrooms, 2 Bathrooms, Sleeps 6
- Privately located, casually designed and stylishly decked-out waterfront cottage opens directly onto a dock and the intercoastal with direct boaters?…
- from
- $1100
weekend
Seven Palms
- 3 Bedrooms, 2 Bathrooms, Sleeps 6
- This spacious and immaculate 3 bedroom, 2 bath home is located just steps from desirable Bayfront Park and the City…
- from
- $1200
weekend
Beach Music
- 3 Bedrooms, 2 Bathrooms, Sleeps 6
- You'll feel like you've stepped into the quintessential beach house when you walk through the doors of Beach Music. This…
- from
- $1100
weekend
Bayou Getaway
- 3 Bedrooms, 3 Bathrooms, Sleeps 6
- Bayou Getaway Nestled on a quiet street just a couple of blocks from the gulf beaches, Bayou Getaway is the…
- from
- $1600
weekend
Coastal Castaway
- 3 Bedrooms, 3.5 Bathrooms, Sleeps 6
- Two houses from the beach, this Key West jewel is beautifully decorated in harmony with the island with the colors…
- from
- $1800
weekend
The Royal Nut
- 3 Bedrooms, 2 Bathrooms, Sleeps 6
- Both practical and exotic. The Royal Nut is conveniently located near restaurants, shopping and across the street from some of…
- from
- $1500
weekend
The Tropical Hibiscus
- 3 Bedrooms, 3 Bathrooms, Sleeps 6
- Lovely 3 bedroom, 3 bath, canal front, pool home w/ fabulous view of Tampa Bay and Skyway Bridge. NO PETS,…
- from
- $4800
monthly
Azure Dreaming
- 3 Bedrooms, 2 Bathrooms, Sleeps 6
- Welcome to Azure Dreams, a striking blend of Mediterranean and Florida style in a peaceful natural setting. Simply and truly…
- from
- $4800
weekend
