Anna Maria Island Vacation Rentals With a Pool

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Looking for a refreshing vacation? Explore these fantastic Anna Maria Island rentals with pools! After a day at the beach, a relaxing swim in your pool is the perfect way to unwind.

A vacation rental with a pool adds significant value to your getaway. A private pool offers a relaxing escape from crowded beaches, providing a convenient way to cool off with a refreshing swim whenever desired. It also creates a safe and enjoyable space for family fun, especially for children. It grants you a personal area to unwind and soak up the Florida sunshine in complete privacy.

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SPRINGBREAK10 Special

Spring Break: Save 10%—Plus Exclusive Deals 📞 Call 941-757-8226 TO SAVE Up to 20%!

Your perfect Spring Break getaway awaits on Anna Maria Island! Save 10% off at checkout using promo code: SPRINGBREAK10 or call us directly for special discounts up to 20% off on select rentals!

• Save 10% OFF on select rentals with promo code: SPRINGBREAK10
• Want Up to 20% Off? Call our reservations team for special discounts on select rentals.
• Hurry! This special promotion runs 1/31/2025 – 2/9/2025 at 11:59 PM EST.
• Travel Window: Book for stays now through 4/30/25.
• Subject to availability—our most popular rentals fill fast!
• Cannot be combined with other offers or applied to existing reservations.
• Other terms and conditions may apply.

Moku

House

5 Bedrooms
5 Full, 1 Half Bathrooms
Sleeps 15

SPRINGBREAK10 Special

Spring Break: Save 10%—Plus Exclusive Deals 📞 Call 941-757-8226 TO SAVE Up to 20%!

Your perfect Spring Break getaway awaits on Anna Maria Island! Save 10% off at checkout using promo code: SPRINGBREAK10 or call us directly for special discounts up to 20% off on select rentals!

Villa Rayo Del Sol

House

5 Bedrooms
5 Full, 1 Half Bathrooms
Sleeps 13

SPRINGBREAK10 Special

Spring Break: Save 10%—Plus Exclusive Deals 📞 Call 941-757-8226 TO SAVE Up to 20%!

Your perfect Spring Break getaway awaits on Anna Maria Island! Save 10% off at checkout using promo code: SPRINGBREAK10 or call us directly for special discounts up to 20% off on select rentals!

Nautical Situation

House

8 Bedrooms
8 Full, 2 Half Bathrooms
Sleeps 8

SPRINGBREAK10 Special

Spring Break: Save 10%—Plus Exclusive Deals 📞 Call 941-757-8226 TO SAVE Up to 20%!

Your perfect Spring Break getaway awaits on Anna Maria Island! Save 10% off at checkout using promo code: SPRINGBREAK10 or call us directly for special discounts up to 20% off on select rentals!

Island Life

House

3 Bedrooms
2 Bathrooms
Sleeps 6

SPRINGBREAK10 Special

Spring Break: Save 10%—Plus Exclusive Deals 📞 Call 941-757-8226 TO SAVE Up to 20%!

Your perfect Spring Break getaway awaits on Anna Maria Island! Save 10% off at checkout using promo code: SPRINGBREAK10 or call us directly for special discounts up to 20% off on select rentals!

Anna Maria Grand Beach House

House

9 Bedrooms
9 Full, 1 Half Bathrooms
Sleeps 22

SPRINGBREAK10 Special

Spring Break: Save 10%—Plus Exclusive Deals 📞 Call 941-757-8226 TO SAVE Up to 20%!

Your perfect Spring Break getaway awaits on Anna Maria Island! Save 10% off at checkout using promo code: SPRINGBREAK10 or call us directly for special discounts up to 20% off on select rentals!

Beach Time AMI

House

5 Bedrooms
3 Bathrooms
Sleeps 10

SPRINGBREAK10 Special

Spring Break: Save 10%—Plus Exclusive Deals 📞 Call 941-757-8226 TO SAVE Up to 20%!

Your perfect Spring Break getaway awaits on Anna Maria Island! Save 10% off at checkout using promo code: SPRINGBREAK10 or call us directly for special discounts up to 20% off on select rentals!

Blue Oasis East

Duplex

3 Bedrooms
2 Full, 1 Half Bathrooms
Sleeps 6

SPRINGBREAK10 Special

Spring Break: Save 10%—Plus Exclusive Deals 📞 Call 941-757-8226 TO SAVE Up to 20%!

Your perfect Spring Break getaway awaits on Anna Maria Island! Save 10% off at checkout using promo code: SPRINGBREAK10 or call us directly for special discounts up to 20% off on select rentals!

Coconut Palm Paradise

House

3 Bedrooms
3 Bathrooms
Sleeps 8

SPRINGBREAK10 Special

Spring Break: Save 10%—Plus Exclusive Deals 📞 Call 941-757-8226 TO SAVE Up to 20%!

Your perfect Spring Break getaway awaits on Anna Maria Island! Save 10% off at checkout using promo code: SPRINGBREAK10 or call us directly for special discounts up to 20% off on select rentals!

Villa #6 Starfish

Villa

1 Bedroom
1 Bathrooms
Sleeps 4

SPRINGBREAK10 Special

Spring Break: Save 10%—Plus Exclusive Deals 📞 Call 941-757-8226 TO SAVE Up to 20%!

Your perfect Spring Break getaway awaits on Anna Maria Island! Save 10% off at checkout using promo code: SPRINGBREAK10 or call us directly for special discounts up to 20% off on select rentals!

Coconut Cottage #2

Condo

3 Bedrooms
2 Bathrooms
Sleeps 6

SPRINGBREAK10 Special

Spring Break: Save 10%—Plus Exclusive Deals 📞 Call 941-757-8226 TO SAVE Up to 20%!

Your perfect Spring Break getaway awaits on Anna Maria Island! Save 10% off at checkout using promo code: SPRINGBREAK10 or call us directly for special discounts up to 20% off on select rentals!

Freckled Fin

House

4 Bedrooms
4 Full, 1 Half Bathrooms
Sleeps 8

SPRINGBREAK10 Special

Spring Break: Save 10%—Plus Exclusive Deals 📞 Call 941-757-8226 TO SAVE Up to 20%!

Your perfect Spring Break getaway awaits on Anna Maria Island! Save 10% off at checkout using promo code: SPRINGBREAK10 or call us directly for special discounts up to 20% off on select rentals!

Sea Grape Escape

Condo

2 Bedrooms
2 Bathrooms
Sleeps 4