Holiday Rentals in Anna Maria Island
Revenue impacts this sort order. Learn more
Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
2981 rentals in Anna Maria Island.
BAY FRONT HOUSE WITH PRIVATE DOCK
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Best Little Beach House on Anna Maria Island...With a pool
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Completely Renovated! BEACH FRONT with HEATED POOL GulfView #102
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Luxury Suite Near The Beach
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Castaway Cottage + Beach + Heated Private Pool & Spa = R & R! Near Bean Point!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Seaside Sanctuary #1 - World's Greatest Sunsets!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Salty Snapper Beach House, Steps to Beach, Pool Table, Tropical Yard w/Fire Pit
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
Beautiful, Gulf-Front Home on Bean Point--Halcyon House
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Blue Sky: Luxury 5 Bdrm/4 bath with heated pool - 1 block to beach!
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Anna Maria-Villa Tarpon- Ground Level Private Canal/Dock, Saltwater Heated pool
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Dragonfly - Southern charm on the North end of Anna Maria Island
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Calling all water lovers! Plus free bikes+tandem kayaks+beach cart+hot tub+dock
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Sea Pirate #8, Family Friendly Cottage By The Sea on Anna Maria Island
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Seaside Sanctuary #2 - Read Our Reviews - 100% Positive
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Naut 2 Shabby Bungalow | A sweet and cozy getaway on Pine Avenue!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Spectacular Beachfront House with Pool
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Elevator! Luxury Rental w/ Heated Pool & Spa 4-7 nights, 3 min walk to beach
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Sea Garden Cottage with Direct Beach Access,AC & WiFi - North End Anna Maria Fl
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Blue Water Beach House: 5+ bdrm, 4.5 bath, Heated Pool/spa, 1.5 blocks to beach
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Tranquil Anna Maria Island Resort, Unit 1... Only 4 units, all amenities!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Tranquil Anna Maria Island Resort, Unit 3... Only 4 units, all amenities!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
2 BR 2 Full BA on Anna Maria Island just steps to Beach!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Areca Cove On Beautiful Anna Maria Island! 3 Min Walk To Beach!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
SPOIL YOURSELVES AND VACATION DIRECTLY ON THE GULF OF MEXICO BEACH!
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Beautiful, decorated and furnished, spacious Great Room family & kid friendly,
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Steps to Bean Point Beach, Pineapple Breeze is a quaint home with private pool
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Spacious Canal Front Home w/ Private Heated Pool on AMI
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
North Island beach getaway
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
beach - private + sunny + heated pool - clean - PS4 - Solar Energy - pool table
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Bungalow On The Bayou (Best Location on the Island)
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Located steps to the Beach! Heated Pool, Easy Ground floor living, bikes & more!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Spoonbill Hideaway*10% DISCOUNT*Huge Pool/Spa/Across from Gulf Beach*
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
AMI Completely Renovated Sunset Paradise! Direct Beach Front Gulf View Condo#105
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Charming house with private heated pool, lanai. Great location to beach & shops
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Luxury Upscale Beach Home Steps from Gulf of Mexico, Heated Pool, Spa & Golfcart
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Island Living, refreshing outdoor shower and pool , pet friendly if approved
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
AMI North End Private Heated Pool. Great location to beach
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Close To The Beach And Restaurants With Private Heated Pool!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Gulf View Retreat, Beach Views, Pool, Firepit, 2 Kayaks, PaddleBoard, 3BR/2Ba
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Anna Maria Beach Condo 1/1
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
1 BR / 1 BA, Anna Maria Island,Holmes Beach Florida, Gulf Coast, Beach Condo
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Close to Beach Heated Pool & Hot Tub FREE WiFi & Trolley Close to Beach
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Big Luxury 6 bd/pool/spa! Bikes! Kayak! Reviews! Beach! Newly updated!
Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Panoramic bay views! 3 minute walk to beach! Holidays are still open!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Family Fun Close to Beach, Pool Slide Spa & Elevator
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Charming cottage in quiet area, close to beach & bay.
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
LARGE Saltwater heated/cooled pool in a tropical backyard! Near IMG/beach ️
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
VERY CLEAN - ANNA MARIA ISLAND 2B/2B WELL MAINTAINED-FULLY RENOVATED-STOCKED-
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Showing results 1-50 of 2,981
Frequently Asked Questions about Anna Maria Island
- Yes, here are some popular holiday rentals in Anna Maria Island that have a pool:
- A Pearl of a Beach Home - now with luxury Saltwater heated pool and hot tub
- Enjoy our Beach, Pool and Dock! 100 5-Star Reviews!
- Anna Maria Island Beach Palms 5B
- Yes, here are some popular holiday rentals in Anna Maria Island that have internet access:See all holiday rentals in Anna Maria Island on Tripadvisor
- The best pet friendly rentals in Anna Maria Island are:
- AMI Beach Shack
- BAY FRONT HOUSE WITH PRIVATE DOCK
- Beachfront Paradise w/ Private Beach, Dogs Stay Free, Beach in Backyard