Vacation Rentals on Anna Maria Island Florida

Anna Maria Private vacation home 9.6

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 Bedroom(s)
3 Bath(s) Sleeps 8

Vacation Home

Anna Maria Cottage 9.8

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 Bedroom(s)
1 Bath(s) Sleeps 6

Vacation Home

Anna Maria Private vacation home 9.8

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 Bedroom(s)
4 Bath(s) Sleeps 10

Vacation Home

ANNA MARIA Private vacation home 9.6

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 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Anna Maria Private vacation home 9.8

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 Bedroom(s)
6 Bath(s) Sleeps 12

Vacation Home

Anna Maria Cottage 9.6

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 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Anna Maria Private vacation home 9.6

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 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Anna Maria Private vacation home 9.8

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 Bedroom(s)
3 Bath(s) Sleeps 8

Vacation Home

Anna Maria Private vacation home 9.8

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 Bedroom(s)
3 Bath(s) Sleeps 12

Vacation Home

Anna Maria Private vacation home 9.0

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 Bedroom(s)
8 Bath(s) Sleeps 16

Vacation Home

Anna Maria Private vacation home 9.8

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 Bedroom(s)
5 Bath(s) Sleeps 8

Vacation Home

Anna Maria Private vacation home 10.0

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 Bedroom(s)
1 Bath(s) Sleeps 5

Vacation Home

Anna Maria Private vacation home 9.4

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 Bedroom(s)
3 Bath(s) Sleeps 8

Vacation Home

Anna Maria Private vacation home 10.0

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 Bedroom(s)
2 Bath(s) Sleeps 8

Vacation Home

Anna Maria Private vacation home 9.4

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 Bedroom(s)
3 Bath(s) Sleeps 8

Vacation Home

Anna Maria Private vacation home 9.8

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 Bedroom(s)
3 Bath(s) Sleeps 8

Vacation Home

Anna Maria Cottage 10.0

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 Bedroom(s)
3 Bath(s) Sleeps 4

Vacation Home

Anna Maria Private vacation home 10.0

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 Bedroom(s)
3 Bath(s) Sleeps 5

Vacation Home

Anna Maria Private vacation home 9.8

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 Bedroom(s)
3 Bath(s) Sleeps 8

Vacation Home

Anna Maria Private vacation home 9.4

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 Bedroom(s)
5 Bath(s) Sleeps 8

Vacation Home

Anna Maria Private vacation home 10.0

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 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Anna Maria Private vacation home 9.8

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 Bedroom(s)
2 Bath(s) Sleeps 8

Vacation Home

Anna Maria Private vacation home 9.6

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 Bedroom(s)
4 Bath(s) Sleeps 8

Vacation Home

Anna Maria Private vacation home 9.0

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 Bedroom(s)
4 Bath(s) Sleeps 8

Vacation Home

Anna Maria Private vacation home 9.4

Bay Happy by Anna Maria Island Locals
Home in Anna Maria, FL

Highlights
• 1-minute walk from the Beach
• Private Pool

Room Details
-Primary Bedroom: King Bed and an ensuite bathroom with a walk-in shower and tub.
-Second Bedroom: Queen Bed
-Third bedroom: Queen Bed
-Fourth Bedroom: 2 Twins

Welcome .......read more

4 Bedroom(s)
3 Bath(s) Sleeps 8

Vacation Home

Anna Maria Cottage 10.0

Great 1 bedroom, 1 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 Gladiolus Street/Alamanda Road. This great getaway sleeps up to 4.

The cottage has an open floor plan and it is about 800 sq ft. The bedroom has.......read more

1 Bedroom(s)
2 Bath(s) Sleeps 4

Vacation Home

Anna Maria Private vacation home 10.0

Come slip away to this luxurious island retreat where all of your cares will drift away! This beautiful, professionally decorated, and newly remodeled home has every modern luxury you can think of.

The two spacious king bedrooms are sure to provide you with a great night's sleep! The also spacious third bedroom offers a queen sleeper sofa a.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Anna Maria Villa 10.0

Pine Ave and Northshore Drive adorable beach home. Anna Maria Island vacation beach house located at the north end of the historic village of Anna Maria, Anna Maria Island. Just steps to Pine Ave, the beach, restaurants, and shopping. Walk conveniently everywhere. We have another 2 bedroom 1 bath villa to offer as well, visit VRBO listing # 394722.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Anna Maria Private vacation home 9.0

513 Loquat Drive, Anna Maria, FL 34216
What You'll Love About This Home:
Location! North End Canal Home! 1 Block to Bay!
6 Bedrooms / 3.5 Bathrooms
2 Kings, 3 Queens, 2 Sets of Twin over Twin Bunkbeds
Private Heated Pool & Spa
Pool Loungers & Umbrella
Poolside Covered Lounge with Patio Seating
Outdoor Shower
Gas Grill
.......read more

6 Bedroom(s)
4 Bath(s) Sleeps 14

Vacation Home

Anna Maria Cottage 9.8

Welcome to Anna Maria Island ''paradise without an attitude''. Our ground level newly renovated unit is located in the village of Anna Maria on a quiet residential street, a short stroll to the sugar white sand beach. Free trolley stop, shopping, a variety of restaurants, both fishing piers, the island community center are all within walk.......read more

2 Bedroom(s)
1 Bath(s) Sleeps 4

Vacation Home

Anna Maria Private vacation home 10.0

AMI Memories by Anna Maria Island Locals
Home in Anna Maria, FL

Highlights
• 5-minute walk from the Anna Maria Island Beach
• Private Pool
• Roof Top Deck
• Two houses from restaurants and boutiques on Pine Ave
• Elevator

Welcome to AMI Memories! This absolutely gorgeous home is located on the north end o.......read more

5 Bedroom(s)
4 Bath(s) Sleeps 8

Vacation Home

Anna Maria Private vacation home 9.6

307 Spring Ave, Anna Maria, FL 34216

What You'll Love About This Home:
Location! 3 Blocks to the Beach! 2 Blocks to Bay & AMI Pier!
3 Bedrooms / 2.5 Bathrooms
2 Kings, Two Sets of Twin over Twin Bunkbeds
Private Pool
Pool Loungers
Outdoor Shower
Patio Dining Seating for Six
Gas Grill
Ping Pong Table
Professional.......read more

3 Bedroom(s)
3 Bath(s) Sleeps 8

Vacation Home

Anna Maria Private vacation home 9.8

Welcome to Beach N Bay 204! A honeymooners delight or a couple’s retreat! Enjoy a romantic getaway! Don't miss your chance to stay at the North end of Anna Maria Island in the highly desirable village of Anna Maria, one of Coastal Living Magazine's Top 10 Happiest Seaside Towns! Located right in the middle of all that happiness, Beach N Bay is .......read more

2 Bedroom(s)
1 Bath(s) Sleeps 4

Vacation Home

Anna Maria Private vacation home 9.6

We only rent thru VRBO! Your safety is our priority.

We are writing here as the owners of this lovely cottage. If you find pictures of this cottage on other websites or in social media (e.g. Facebook) all these offerings are scam and published by people how are not our representatives or the owner of this cottage. We recommend to do bookin.......read more

2 Bedroom(s)
1 Bath(s) Sleeps 4

Vacation Home

Anna Maria Private vacation home 9.6

This beautifully spacious home sits on a very large waterfront lot on the northern tip of AMI. The house is embedded in a natural landscape.
The fully air-conditioned house has two air conditioners and parking spaces in front of the house. It was completely renovated in 2015. You have 4 bedrooms with 2 baths, large open kitchen, French doors fro.......read more

4 Bedroom(s)
2 Bath(s) Sleeps 8

Vacation Home

Anna Maria Private vacation home 9.8

Take a break from the hustle and bustle, and relax in the calm and serene atmosphere of this spotless vacation home. Jacaranda Gem offers every amenity you need to have the vacation you have been dreaming of on Anna Maria Island.

*Features include*

* Brand new, completely renovated house from top to bottom
* Huge Saltwater heate.......read more

3 Bedroom(s)
3 Bath(s) Sleeps 6

Vacation Home

Anna Maria Private vacation home 9.6

At A Glance

South-facing private heated pool with a spa
Steps to the beach
Loft and bonus rec room by the pool
Part of our Professional Linen Program
Six bikes, beach wagon, chairs, and toys provided

Overview

Ocean Walk
117 Willow Avenue
Anna Maria, FL 34216

Enjoy your vacation to the fullest when you s.......read more

4 Bedroom(s)
8 Bath(s) Sleeps 10

Vacation Home

Anna Maria Private vacation home 9.8

Sign of the Mermaid by AMI Locals
Home in Anna Maria, Florida
VR17-000054
Welcome to Sign of the Mermaid, a luxurious four bedroom, four and a half bathroom vacation home with a bonus loft that is just four houses from the sugary white sands of Anna Maria Island Beach. With inviting balconies, a large sparkling pool and hot tub, lushly la.......read more

4 Bedroom(s)
5 Bath(s) Sleeps 12

Vacation Home

Anna Maria Private vacation home 10.0

Welcome to A Wave From It All!
On Anna Maria Island (Anna Maria, FL)

HIGHLIGHTS:
- Open layout and spacious Kitchen, Dining, Living w/ TV
- 1 King Bedroom w/ TV, En-Suite Full Bathroom w/ Shower/Tub
- 1 Queen Bedroom w/ TV, En-Suite Full Bathroom w/ Shower
- 1 Queen Bedroom w/ TV, Twin over Full with Twin Trundle Bunk Bed
-.......read more

3 Bedroom(s)
3 Bath(s) Sleeps 8

Vacation Home

Anna Maria Cottage 10.0

This charming Sea Garden Cottage is a true island gem and escape. Sea Garden Cottage is located on North Shore Drive at the north end of the island. It’s charming decor and garden oasis are sure to make you lose yourself in your future get-a-way.

This home rests on a 1.23 acre lot directly on the Gulf, a rarity on the island. The lot is s.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 5

Vacation Home

Anna Maria Private vacation home 9.6

"Remember the first time you fell in love? Prepare for the butterflies again!

We are delighted to present the South Bay Beach House where it is all about family, friends and being happy. Togetherness, little soirees and everything in between. Any reason is a good reason to celebrate life at it's best.

From the moment you arrive at th.......read more

4 Bedroom(s)
3 Bath(s) Sleeps 8

Vacation Home

Anna Maria Private vacation home 9.8

This 2 bedroom, 2 bathroom home certainly lives up to its name. This sweet cottage is as adorable at is it comfortable. Located just steps from the beach on the Northern End of Anna Maria Island, Pure Bliss will leave you feeling relaxed and rested. Spend your afternoons on the lanai and take a stroll and catch the sunset at one of the finest beach.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Anna Maria Private vacation home 9.4

Location, Location, Location.... recently remodeled, surrounded by multi million dollar homes.....and three great beaches and the Rod and Reel Peir......this house contains 4 bedrooms, 2 baths. This four bedroom house - boasts 2 king bedrooms, two queens and a pull out couch-. Large heated pool w/sun shelf- large hot tub spa. TWIN FAMILY ROOMS, p.......read more

4 Bedroom(s)
2 Bath(s) Sleeps 8

Vacation Home

Anna Maria Private vacation home 9.6

What more could you want from a vacation rental then a beautiful Mediterranean inspired canal home nestled into the private North End of Anna Maria Island? Mediterranean Canal Retreat is the perfect escape for those looking to relax enveloped in the simplicity and peacefulness that is Anna Maria. This four bedroom, two bathroom home has a spacious .......read more

4 Bedroom(s)
2 Bath(s) Sleeps 8

Vacation Home

Anna Maria Private vacation home 9.8

You'll fall in love with Mermaid Cove the second you step inside. This beautifully refurbished property boasts all the modern updates without sacrificing any of its original charm. This three bedroom, three bathroom home has a comfortable living space, huge master suite, a gourmet kitchen and is decorated impeccably. Step out back to the pool area .......read more

3 Bedroom(s)
3 Bath(s) Sleeps 6

Vacation Home

Anna Maria Private vacation home 10.0

Location!!! North end of Anna Maria Island . Steps to the Bean Point Beach and everything you need for your perfect Anna Maria Vacation. The Blue Dolphin Inn consists of four units surrounding a free style heated pool. Rent one unit or all. Perfect for a group of extended family and friends who want their own place but still be right together as a .......read more

2 Bedroom(s)
1 Bath(s) Sleeps 4

Vacation Home

Anna Maria Private vacation home 9.8

125 Crescent Drive, Anna Maria, FL 34216

What You'll Love About This Home:

Location! AMI North End Canal Home! 3 Blocks to Beach!
4 Bedroom / 2 Bathroom
3 King Beds / 2 Twin Beds
Private, Heated Pool
Pool Loungers & Hammock
Outdoor Shower
Tropically Landscaped Fenced Backyard
Dock on Canal with Ladder Access for (.......read more

4 Bedroom(s)
2 Bath(s) Sleeps 8

Vacation Home

Anna Maria Private vacation home 10.0

SPOIL YOURSELVES ON THE GULF OF MEXICO BEACH!
Let’s talk Beach House? Whether you're building sand castles with the little ones or falling asleep to the sound of crashing waves, life is quite simply better at the beach. This tranquil, cool and super-styled designer pad in Anna Maria has everything from decks and balconies off every bedroom, m.......read more

5 Bedroom(s)
6 Bath(s) Sleeps 8

Vacation Home