A minimum stay of one month is required in accordance with Peppertree Bay Association regulations.

37 properties  

$641/night

1045 | 2 BEDROOM | 2 BATHROOM | GARDEN RETREAT

OwnerRez
2 Bedrooms • 1 Bath • Sleeps 1-4
Internet Near Ocean Pool
Settle into the Siesta Key lifestyle at this inviting 2-bedroom, 2-bath garden retreat at Peppertree Bay. Enjoy private Crescent Beach access, two heated pools, tennis and pickleball, a fitness center, and Peppertree Bay’s private fishing pier—all within the community. With a full kitchen, in-unit laundry, Wi-Fi, comfortable living spaces, and tropical surroundings, Unit 1045 is perfectly suited for an extended island stay.

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$374/night

1055-206 | 2 BEDROOM | 2 BATHROOM | MIDRISE

OwnerRez
2 Bedrooms • 2 Baths • Sleeps 1-6
Internet Ocean View Pool
Relax in this beautifully updated 2-bedroom, 2-bath Gulf side condo just 75 yards from Crescent Beach. Enjoy a private lanai overlooking the pond, a remodeled kitchen with stainless steel appliances, covered parking, elevator access, and exclusive access to Peppertree Bay's private beach, heated pools, tennis courts, fitness center, and sauna. Perfect for extended 30-night stays on Siesta Key.

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$374/night

1055-207 | 2 BEDROOM | 2 BATHROOM | MIDRISE

OwnerRez
2 Bedrooms • Sleeps 1-4
Accessible Internet Near Ocean Pool
Relax and enjoy Siesta Key from this comfortable 2-bedroom, 2-bathroom second-floor condo at Peppertree Bay. Perfect for up to four guests, Unit 1055-207 features a full kitchen, in-unit laundry, Wi-Fi, elevator access, and free parking. Guests also enjoy Peppertree Bay’s private beach access, pools, tennis, fitness facilities, marina, fishing areas, and tropical community grounds. An ideal choice for an extended Siesta Key stay.

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$374/night

1055-302 | 2 BEDROOM | 2 BATHROOM | MIDRISE

OwnerRez
2 Bedrooms • 2 Baths • Sleeps 1-4
Accessible Internet Near Ocean Pool
Bedding:
Master Bedroom: 1 King
Guest Bedroom: 1 Queen
Sleeper Sofa: No
Electronics:
Livingroom: 40'' TV
Master Bedroom: 32'' TV
Guest Bedroom: 32" TV
Bathrooms:
Master: bath tub - with grab bars
Guest: walk-in shower - with grab bars - without a shower seat

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$463/night

1055-503 | 2 BEDROOM | 2 BATHROOM | MIDRISE

OwnerRez
2 Bedrooms • 2 Baths • Sleeps 1-4
Internet Pool
Luxurious fifth-floor Gulf-view condo featuring two king bedrooms, a renovated kitchen, expansive lanai, and private beach access. Enjoy Peppertree Bay's heated pools, tennis courts, fitness center, fishing pier, and resort amenities—all just steps from the world-famous white sands of Crescent Beach. Perfect for a relaxing 30-night stay on beautiful Siesta Key.

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$641/night

1055-802 | 2 BEDROOM | 2 BATHROOM | PENTHOUSE

OwnerRez
2 Bedrooms • 2 Baths • Sleeps 1-4
Accessible Internet Beachfront Pool
2BR, 2BA eighth-floor Gulf view condominium featuring an expansive enclosed lanai, updated kitchen, king primary suite, and private beach access. Enjoy breathtaking sunsets, two heated pools, tennis and pickleball courts, fitness center, fishing pier, covered parking, and all of Peppertree Bay's premier resort amenities during your relaxing 30-night stay on beautiful Siesta Key.

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$641/night

1055-803 | 2 BEDROOM | 2 BATHROOM | PENTHOUSE

OwnerRez
2 Bedrooms • Sleeps 1-4
Accessible Internet Ocean View Pool
Luxury 2BR, 2BA eighth-floor Gulf view condominium featuring an expansive enclosed lanai, fully equipped kitchen, king primary suite, twin guest bedroom, and private beach access. Enjoy panoramic sunsets, two heated pools, tennis and pickleball courts, fitness center, fishing pier, covered parking, and all of Peppertree Bay's premier resort amenities during your relaxing 30-night stay on beautiful Siesta Key.

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$463/night

1055-805 | 2 BEDROOM | 2 BATHROOM | MIDRISE

OwnerRez
2 Bedrooms • Sleeps 1-4
Accessible Internet Near Ocean Pool
Spacious and comfortable Siesta Key retreat for up to 4 guests. Enjoy a bright living space, full kitchen, two bedrooms and two bathrooms, plus access to the beautiful Peppertree Bay community and its convenient location near the beach, dining, shopping, and Siesta Key Village.

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/night

1080-403 | 2 BEDROOM | 2 BATHROOM | MIDRISE

OwnerRez
Sleeps 1-4
Allows pets

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$374/night

1080-601 | 2 BEDROOM | 2 BATHROOM | MIDRISE

OwnerRez
1 Bedroom • Sleeps 1-4
Accessible Internet Pool
Condo Summary:
Bedding: Master Bedroom: King - Guest Bedroom: King - Sleeper Sofa: No
Electronics: Living-room: 40" TV - Master Bedroom: 32" TV - Guest Bedroom: No
Bathrooms: Master: Bath tub - without grab bars
Guest: Walk-in Shower - without grab bars
2 Bedroom / 2 Bath unit. Approx. 1250 Sq. Ft. (1375 including the lanai

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$374/night

1080-701 | 2 BEDROOM | 2 BATHROOM | MIDRISE

OwnerRez
2 Bedrooms • Sleeps 1-6
Accessible Internet Beach Pool
Enjoy the Siesta Key lifestyle from this inviting 2-bedroom Gulfside condo at Peppertree Bay. Unit 1080-701 offers a comfortable home-away-from-home just steps from the community’s private beach access, with a full kitchen, in-unit washer and dryer, Wi-Fi, and access to Peppertree Bay’s pools, fitness center, tennis courts, fishing pier, and beautifully maintained Gulf-to-Bay grounds.

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$374/night

1080-702 | 2 BEDROOM | 2 BATHROOM | MIDRISE

OwnerRez
2 Bedrooms • Sleeps 1-6
Accessible Internet Pool
Enjoy an extended Siesta Key stay in this comfortable seventh-floor condo at Peppertree Bay. Featuring a full kitchen, in-unit laundry, Wi-Fi and elevator access, plus access to Peppertree Bay's beach, pool, tennis and pickleball, fitness facilities and beautiful Gulf-to-Bay community.

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1 – 12 of 37 places to stay