Anna Maria Island 2-bedroom Vacation Rentals, Beach Rentals & More - 41 Rentals Available.
41 Vacation rentals
Filters applied: 2+ Bedrooms

The Cannon- A two bedroom adorable cottage minutes walking to beach
Bradenton Beach Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 5 5
- 2 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Child friendly
$373.00
from $373.00 / night

Songbird Cottage
Anna Maria Island Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Beach/lakeside relaxation
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 16 minutes
$147.00
from $147.00 / night

Beach Dreams " Sweet Dreams Villa"
Anna Maria Island Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- 2 nights min
- Child friendly
- Car not necessary
$458.00
from $458.00 / night

Beach House on Anna Maria Island-Rental Openings
Holmes Beach Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$458.00
from $458.00 / night

"Island Oasis" A single family North end canal home with pool
Anna Maria House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 2 nights min
- Beach/lakeside relaxation
- Swimming pool
- Air conditioning
$745.00
from $745.00 / night
The Anchor- A two bedroom cottage minutes walking to beach.
Bradenton Beach Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 2 nights min
- Beach/lakeside relaxation
- Child friendly
- Air conditioning
$373.00
from $373.00 / night
Sandy Pointe #205
Holmes Beach Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Beach/lakeside relaxation
- Child friendly
- Air conditioning
$155.00
from $155.00 / night
Family Reunion Villa on Anna Maria Island, Florida
Bradenton Beach Villa
- 4 bedrooms 4
- 4 bathrooms
- sleeps 12 12
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$458.00
from $458.00 / night
Your search has been expanded 19.6 miles to include more rentals
2 BR, 2 BA Surf Song Resort Townhouse #343 -- Aug 14-21 Special $800/wk + fees
Madeira Beach Townhouse - 18.2 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 30 mi
- Swimming pool
Responds fast! Avg. 2 hours 51 minutes
$164.00
from $164.00 / night
Enjoy a Florida Vacation in a beachfront condo!
Madeira Beach Condo - 19.4 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 14 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
Responds fast! Avg. 3 hours 59 minutes
$229.00
from $229.00 / night
BAY VIEW. SUNSETS. CLOSE TO ANNA MARIA ISLAND AND IMG ACADEMY
Bradenton House - 6.6 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 4 4
- 7 nights min
- Beach/lakeside relaxation
- Child friendly
- Air conditioning
$367.00
from $367.00 / night
LUXURY WATERFRONT CONDO ON ISLA DEL SOL/St.Pete's
St. Petersburg Condo - 12.5 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 1 mi
- Swimming pool
Responds fast! Avg. 1 hour 25 minutes
$258.00
from $258.00 / night
Pool & Hot Tub-Pine Bay Forest 3-Bedroom Condo, Near AMI Beaches 3 month min
Bradenton Condo - 6.3 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 120 nights min
- Beach/lakeside relaxation
- Nearest beach 1 mi
- Swimming pool
$107.00
from $107.00 / night
Luxury Water Front Condo - Intercoastal Waterway
Treasure Island Condo - 16.6 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$205.00
from $205.00 / night
Lovely 3 BR Home with Office & Heated Pool at Tara
Bradenton House - 17.2 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 20 mi
- Swimming pool
$167.00
from $167.00 / night
Waterfront 2BR 2 Bath Suite at the Sara Bay Marina
Sarasota Condo - 12.7 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 10 mi
- Swimming pool
Responds fast! Avg. 3 hours 28 minutes
$171.00
from $171.00 / night
ULTIMATE ST PETE BEACH FRONT RENTAL CONDO #101
St. Pete Beach Condo - 14.6 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$210.00
from $210.00 / night
IMG golf private 3 bed home
Bradenton House - 10.2 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 4 4
- 12 nights min
- Beach/lakeside relaxation
- Nearest beach 10 mi
- Swimming pool
$201.00
from $201.00 / night
Madeira Norte - Across from John's Pass Village - Ask about our Specials!!!
Madeira Beach Condo - 18.2 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
Responds fast! Avg. 2 hours 40 minutes
$262.00
from $262.00 / night
Tara Golf & Country Club Condo
Bradenton Condo - 17.1 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Beach/lakeside relaxation
- Nearest beach 12 mi
- Swimming pool
Responds fast! Avg. 3 hours 42 minutes
$144.00
from $144.00 / night
SUNSHINE HOLIDAY
St. Petersburg Manor house - 18.9 miles away
- 5 bedrooms 5
- 6 bathrooms
- sleeps 10 10
- 30 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
Responds fast! Avg. 3 hours 44 minutes
$1,145.00
from $1,145.00 / night
Gulf Beach Condo! 3 BR, Handicap & Tall equip'd
Madeira Beach Condo - 19.2 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 5 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
$264.00
from $264.00 / night
Artsy Sarasota,FL. Palm-Aire CC 2bd/2 bath Condo
Sarasota Condo - 16.8 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Beach/lakeside relaxation
- Nearest beach 20 mi
- Swimming pool
$115.00
from $115.00 / night
Kima 503 Madeira Beach Front 2bd/2bath Condo Top Floor WHITE SANDY BEACHES!
Madeira Beach Condo - 19 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$197.00
from $197.00 / night
Kima 102 2bed/2bath Gulf Front Condo in Madeira Beach READY TO ENJOY!!
Madeira Beach Condo - 19 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Air conditioning
$197.00
from $197.00 / night
Kima 403 2bedroom Gulf Front Condo PRICELESS SUNSETS!
Madeira Beach Condo - 19 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$197.00
from $197.00 / night
Kima 205 Spacious 2bd/2bath Madeira Beach Gulf Front Condo Endless Views
Madeira Beach Condo - 19 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$197.00
from $197.00 / night
Kima 101 BEACH FRONT with PRIVATE CABANA 2BR/2Bath
Madeira Beach Condo - 19 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$197.00
from $197.00 / night
BAY BEAUTY
St. Petersburg House - 17.9 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- 3 nights min
- Child friendly
- Air conditioning
Responds fast! Avg. 3 hours 44 minutes
$1,374.00
from $1,374.00 / night
502 Beach Place top floor condo view of bridge, water/John's Pass
Madeira Beach Apartment - 18.1 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 10 10
- 3 nights min
- Swimming pool
- Child friendly
- Air conditioning
$338.00
from $338.00 / night
Madeira Bay Enjoy Sunrise Views from Balcony Overlooking Intracoastal Waterway
Madeira Beach Condo - 18.4 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$229.00
from $229.00 / night
Starfish Gulf Front Two Bedroom Cottage
Madeira Beach House - 18.7 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 6 6
- min stay varies
- Child friendly
- Air conditioning
- Pet friendly
$201.00
from $201.00 / night
Starfish Cottages One Bedroom
Madeira Beach Cottage - 18.7 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Child friendly
- Air conditioning
- Pet friendly
$131.00
from $131.00 / night
Kima 204 Direct Gulf Front in Madeira Beach
Madeira Beach Condo - 19 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$254.00
from $254.00 / night
Spectacular Beachfront Condo-Private Beach/No Fees
St. Pete Beach Condo - 13.1 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
Responds fast! Avg. 1 hour 58 minutes
$344.00
from $344.00 / night
Sunsets and Surf Sounds: Breezy Gulf-Front Condo on Sunset Beach
Treasure Island Condo - 15.4 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$300.00
from $300.00 / night
Historic Pass-A-Grille, Literally Seconds to Beach
St. Pete Beach House - 12.1 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 7 7
- 30 nights min
- Beach/lakeside relaxation
- Nearest beach 1 mi
- Child friendly
$264.00
from $264.00 / night
103 Beach Place condo across from John's Pass sleeps 10
Madeira Beach Apartment - 18.1 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$327.00
from $327.00 / night
Renovated and beachy Sandy Shores Condo- Across from Famous John's Pass!
Madeira Beach Condo - 18.1 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$135.00
from $135.00 / night
Family Fun Poolside Stay! Walkable To Madeira Beach & Local Favorites!
Madeira Beach Condo - 19.6 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$118.00
from $118.00 / night
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