Anna Maria Vacation Rentals, Private Rental Homes & Cottages.

Anna Maria Vacation Rental 4.7 Star Review

This large home was constructed in 2009. It is a decorator furnished, pool home and considered top of the line in vacation rental homes. With approximately 3200 square feet of conditioned space and over 2000 square feet of covered balconies, poolside dining and lounging areas, there is plenty of room for a family to spread out and relax in this Fl.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Anna Maria

Anna Maria Cottage 4.9 Star Review

The Ballyhoo is a ground floor rental on historic Bean Point in Anna Maria City. 200 feet to the beach, the Rod & Reel Pier/restaurant/bar and its great food and world class fishing . Enjoy panoramic views of Tampa Bay, the Skyway Bridge, historic Egmont Key and lighthouse, and Passage Key. Our beach offers beautiful blue water, with soft white san.......read more

2 Bedrooms - Sleeps 6
Cottage in Anna Maria

Anna Maria Vacation Rental 4.9 Star Review

Last Minute Deals
Nov 11 - 18, 2023 now $290/nt or $2,030/wk*
Dec 2 - 9, 2023 now $290/nt or $2,030/wk*
Dec 9 - 16, 2023 now $290/nt or $2,030/wk*
*plus fees and taxes.
Hurry Book Now!

Recently Renovated!

- putting green
- master bathroom upstairs
- master balcony enlarged and with seating
- metal roof
- ex.......read more

4 Bedrooms - Sleeps 10
Vacation Rental Home in Anna Maria

ANNA MARIA Vacation Rental 4.8 Star Review

Welcome to Sea Waves, our newly renovated home with 3 bedrooms / 2 bathrooms, a private dock, and an unobstructed, natural view of Bimini Bay. Smart TV, WiFi, free access to Netflix, washer/dryer, and a full kitchen with cooking essentials. Sea Waves cottage is located at the North End of Anna Maria Island, sailboat direct to Bimini Bay, walking di.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in ANNA MARIA

Anna Maria Vacation Rental 4.9 Star Review

Last Minute Deals
- Nov 11 - 18, 2023 now $350/nt*
- Nov 26 - Dec 1, 2023 now $350/nt*
- Dec 2 - 9, 2023 now $350/nt*
- Dec 9 - 16, 2023 now $350/nt*
*plus fees and taxes.
Hurry Book Now!

Newly Renovated 2023!

- New putting green
- New kitchen including coffee bar and wine fridge
- All 5 new bathrooms
- New .......read more

5 Bedrooms - Sleeps 12
Vacation Rental Home in Anna Maria

Anna Maria Cottage 4.7 Star Review

Welcome to Sea Breeze, our newly renovated home with 2 bedrooms / 2 bathrooms, a private dock, and an unobstructed, natural view of Bimini Bay. Smart TV, WiFi, free access to Netflix, washer/dryer, and a full kitchen with cooking essentials. Sea Breeze cottage is located at the North End of Anna Maria Island, sailboat direct to Bimini Bay, walking .......read more

2 Bedrooms - Sleeps 6
Cottage in Anna Maria

Anna Maria Vacation Rental 4.6 Star Review

709 North Bay Blvd., Anna Maria, FL 34216

What You'll Love About This Home:

Location! North End of AMI and 500 Steps To The Beach!
3 Bedrooms / 2 Bathrooms
1 King ,1 Queen, & 2 Twins
Private Heated Pool
Outdoor Shower
Fully Equipped Kitchen
Gas BBQ Grill
Washer & Dryer & Complimentary WIFI
Beach Chairs & Beach .......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 5.0 Star Review

Beautiful elevated Beach House with a private heated pool situated in the sought after residential north end of Anna Maria Island. Superbly located, only 2 minutes walk to the best beaches, only in the north end do you have access to the Gulf and Bay beaches, watch the dolphins, see the huge variety of birds and watch the glorious sunsets. The loca.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 4.9 Star Review

Welcome to Seahorse Cottage, your cozy 2-bedroom, 2-bathroom vacation rental on Anna Maria Island! Located north of Pine Avenue, this cottage offers the perfect combination of privacy and convenience. With a 2-minute walk to the beach access, you can spend your days soaking up the sun and surf at the Gulf of Mexico.

But that's not all – Se.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 4.8 Star Review

We welcome you to stay in our family beach house located on beautiful "Bean Point"; the most beautiful spot on Anna Maria Island, Florida. We have owned this beach house for 20 years now and have made so many wonderful memories!

THE BEACH has changed due to the storm. The last picture is the beach from the last time I was there.

Whe.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 5.0 Star Review

Beautifully decorated and furnished home located an easy walk from Gulf beaches and Tampa bay. Includes a master suite with king size bed, two additional queen bedrooms, lower level playroom off the pool, porch off of kitchen, large heated pool, Weber Gas grill, Smart HDTV, High Speed Wireless Internet, phone service with free calls to US and Cana.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 4.9 Star Review

235 Oak Ave, Anna Maria, FL 34216

What You'll Love About This Home:
Location! On a Canal! 2 Blocks to the Beach!
4 Bedrooms / 3 Bathrooms
California King, King, Queen & Twin, Twin over Full Bunkbeds
Private Heated Pool & Spa
Pool Loungers & Umbrellas
Outdoor Shower
Private Dock with Canal Access
Gas Grill
Pool Tabl.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 4.9 Star Review

Last Minute Deals
Nov 11 - 18, 2023 now $250/nt or $1,750/wk*
Nov 25 - Dec 2 now $250/nt or $1,750/wk*
Dec 2 - 9, 2023 now $250/nt or $1,750/wk*
plus fees and taxes.
Hurry Book Now!

Many new items not shown in photos;

- New exterior Polywood dining table
- New interior dining table set
- New screened lanai conve.......read more

4 Bedrooms - Sleeps 12
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 4.6 Star Review

Bay View Beauty by AMI Locals
Home in Anna Maria, FL

Highlights:
• Ocean Front with Private Beach Access
• Private Pool
• 4 Bicycles are Provided for Guest Use
• Putting Green
• Dog Friendly with Host Approval and $250 Fee

Room Details
-Primary Bedroom: King bed with ensuite bathroom that has a walk-in.......read more

7 Bedrooms - Sleeps 16
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 4.7 Star Review

Island Pearl Oasis by Anna Maria Island Locals
Home in Holmes Beach, FL

Just steps away from the beautiful beaches of Anna Maria Island!

Highlights:
• Heated pool with waterslide and Splash n' Shoot Basketball Hoop
• Pop-a-Shot Basketball Game, Foosball, Ping Pong and Xbox Gaming System
• Keurig Coffee and Cappuccino.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 4.9 Star Review

Just 5 houses from the white sandy beach of the Gulf. Near the heart of Anna Maria village sits this spacious home with a relaxed island feel. This ideal location allows you to walk to the beach, restaurants, bars, pier, trolley stop and Pine Avenue shopping. There's plenty of room to sit back and enjoy your surroundings in this 4 bedroom, 3.5 ba.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 4.8 Star Review

Villa La Concha by Anna Maria Island Accommodations
Home in Anna Maria, FL

Welcome to Villa La Concha, a marvelous vacation home with a private pool, hot tub, game room, and a fabulous outdoor area, all steps away from one of the most beautiful beaches in the world! This exciting rental has six bedrooms and four and a half bathrooms, .......read more

6 Bedrooms - Sleeps 12
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 5.0 Star Review

Located on the "best" street on Anna Maria Island, this two-bedroom, one-bath second floor vacation rental with a spectacular view was completely renovated at the end of 2015. The renovation included basically everything from floor to ceiling. Notice the pictures and reviews, they speak for themselves.

Growing up about 15 minutes off the i.......read more

2 Bedrooms - Sleeps 5
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 5.0 Star Review

Welcome to Once Upon a Tide!

Once Upon A Tide is a fabulous custom design home located on the prestigious North end of Anna Maria Island. Featuring 4 bedrooms and 3.5 bathrooms. Guest will feel relaxed under the palms and mature landscaping. With private heated pool, ping-pong table, bikes and tons of beach gear, Once Upon a Tide is the idea.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 4.9 Star Review

Slip into "island time" immediately and surround yourself with elegance and luxury in this waterfront beauty. This stunning one-level home is situated on the island's coveted north end, on a quiet cul-de-sac and canal with one of the widest open water views on the island.

*Features include*

* Private tropical yard with sparkling wat.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 4.8 Star Review

Seaside Magnolia by Anna Maria Island Locals
Home in Anna Maria, FL

Features:
• Private pool and spa
• newly installed Putting Green
• large backyard area great for your family to get together
• a short 3 block stroll to the gorgeous Anna Maria Island beach
• Beach chairs and a beach cart for guest use
• Was.......read more

7 Bedrooms - Sleeps 16
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 4.7 Star Review

Harbor Haven by Anna Maria Island Locals
Home in Holmes Beach, FL

Just steps away from the beautiful beaches of Anna Maria Island!

Highlights:
• Large heated pool with spa and a waterslide
• Gas grill for BBQs
• Dog friendly with host approval and $250 pet fee

Home Layout
• Bedroom 1: King Bed, balcony, .......read more

4 Bedrooms - Sleeps 14
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 4.5 Star Review

322 Tarpon Ave, Anna Maria FL, 34216

What You'll Love About This Home:
Location! On a Canal. 4 Blocks to the Beach! 2 Blocks to Bay!
3 Bedrooms / 2.5 Bathrooms
California King, 2 Kings, 1 Set of Twin over Queen Bunkbeds
Private Heated Pool
Pool Loungers
Outdoor Shower
Covered Poolside Lounge with Bar & Seating & TV
Pr.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 4.9 Star Review

Anna Maria Beach House by AMI Locals
Home in Anna Maria, Florida
VR19-000061

Welcome to Anna Maria Beach House, a breathtaking five-bedroom and six and half-bathroom vacation home that is just a quick walk from the shimmering sands and warm waters of the Gulf of Mexico! This ultimate beach vacation house has a private pool that is sur.......read more

5 Bedrooms - Sleeps 8
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 5.0 Star Review

Situated on the north end of Anna Maria Island, The Sandy Rose is the perfect location for your next getaway! This 4 bedroom 3 bath property is a beautiful escape from the daily grind. The gorgeous pool, large patio with tv and sectional, and putting green create a picturesque outdoor space for the entire family to enjoy. The open concept design br.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Anna Maria

Anna Maria Cottage 5.0 Star Review

Great 1 bedroom, 1.5 bathroom cottage on the quiet north end of island. The house is conveniently located and within walking distance (two short blocks) to the beach and close to the intersection of Fern Street/Alamanda Road. This great getaway sleeps up to 4.

The cottage has an open floor plan and it is about 900 sq ft. There is a bedroom .......read more

1 Bedrooms - Sleeps 4
Cottage in Anna Maria

Anna Maria Vacation Rental 4.9 Star Review

3 short blocks to the sugar sand beaches of the Gulf of Mexico and 5 blocks to Tampa Bay. This traditional Florida home is on a canal, with bikes and kayaks for your recreational use. 2 bedrooms, 3 bathrooms, living room, kitchen and traditional Florida room overlooking a large patio and pool and our dock on the canal. We also have a screened porc.......read more

2 Bedrooms - Sleeps 5
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 4.8 Star Review

Welcome to La Buena Vida!
On Anna Maria Island (Anna Maria, FL)

The waterfront 3-bedroom home has a private heated pool, spa, and dock! This home's location is second to none, just steps to the bayside beaches and easy walking distance to Bean Point gulf side beaches & Pine Avenue.

We invite you to explore this well taken care of c.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 5.0 Star Review

Welcome to Luxe Island Escape! A next-level, brand new construction tropical retreat.

*Features include*

* Huge heated pool and spa
* Swim up bar seating
* Rooftop deck with sweeping water views
* 4 bedrooms, 4 ½ baths
* 3 king master suites with attached baths
* Indoor/outdoor living on all 3 levels
* Patio.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 4.9 Star Review

Adorable beach cottage on the north end of Anna Maria Island! The beach access trail to the famous Bean Point beach is right by the house. This 3 bedroom 2 bathroom home is situated on a corner lot on a quiet street and is located just steps to the beaches of the Gulf of Mexico. The main level of the home has an open kitchen and dining room, a larg.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 5.0 Star Review

Discover an Anna Maria little secret --BAYFRONT HOMES WITH A WHITE SANDY BEACH -- offering the best of both worlds. Nestled among sea oats, this newly renovated and intimate property is ideal for families or couples looking for an Island escape. Enjoy a quiet, private-like beach experience only a short walk or bike ride to Pine Avenue's shops .......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 4.8 Star Review

Welcome to The Happy Hibiscus!
We are located in a perfect location where we can catch the sunrise and sunset, less than 100 yards to the beautiful, Passage Key Inlet and a short walk to the white sand beaches on Bean Point!

This 4 BR home comfortably sleeps larger groups. Seven beds and a Pack and Play provide lots of options! With larg.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 4.8 Star Review

Looking for the perfect waterfront home for your next vacation? Bella Vista is a beautiful Bayfront home with gorgeous views of Tampa Bay.
Enjoy one of the many outdoor spaces where you can spot dolphins, manatees, Egmont Key, and view the Skyway Bridge light show in the evenings! Cook meals in the fully stocked kitchen and enjoy in one of the.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 4.7 Star Review

Looking for the perfect canal front home for your next vacation? Come enjoy Bellablu! This beautiful, newly renovated property is the perfect space for your next getaway! The large living space provides two separate living rooms that are connected by a spacious galley style kitchen! The ground level is home to two bedrooms, each including king beds.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 5.0 Star Review

It's all about location on vacation, and Reef Romance does not disappoint! Sail away to this beautiful four-bedroom, four-and-a-half-bathroom custom-built home for a dose of luxury at the beach. Located on the prestigious north end of Anna Maria Island, you're just a few houses away from the beach with no busy road to cross.

Stunning inside .......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Anna Maria

Anna Maria Vacation Rental 4.5 Star Review

Aquaville B by AMI Locals
Home in Anna Maria
VR18-000018

Welcome to Aquaville B, a three-bedroom and one bath beach-style cottage, nestled in a quaint, coastal neighborhood that is just a quick stroll from Anna Maria Island Beach and Palmetto Ave Beach! The backyard has lush landscaping that surrounds the pool and outdoor seating to .......read more

3 Bedrooms - Sleeps 5
Vacation Rental Home in Anna Maria